Be a Startup Superstar Ignite Your Career Working at a Tech Startup - Steven Kahan

Be a Startup Superstar
Be a Startup
Superstar
Ignite Your Career Working
at a Tech Start-Up
Steven Mark Kahan
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10 9 8 7 6 5 4 3 2 1
Contents
Foreword by David Meerman Scott
Introduction
PART I:
Chapter 1:
ix
xiii
THE BEST OPPORTUNITIES ARE IN
START-UPS
1
Use the Tech Start-Up Boom to Zoom
3
The Unprecedented Opportunity in Tech Start-Ups
Why Work for a Start-Up Over a Big Corporation?
Fewer Barriers to Entry
Versatility in Roles
Access to Leaders
Financial Rewards
Culture
Upward Mobility
v
5
9
10
11
11
13
14
16
vi
Chapter 2:
CONTENTS
Pick the Right Start-Up for You
19
How to Find Start-Up Opportunities
Research Posted Jobs Online
Explore Technology Accelerators
Attend In-Person Entrepreneur Events
Engage with Start-Up Leaders Online
Attend Hiring Parties
Be Willing to Intern (Preferably for Pay)
Seek Mentors
Five Criteria to Choose a Start-Up
Quality People Who Share Your Values
The Concept Fills a Big Market Need
A Great Product You Believe In
A Role You Can Fill Today with More Opportunities Tomorrow
The Start-Up Is Well-Funded
Getting Hired
20
21
21
21
23
23
24
25
26
27
28
30
31
31
33
PART II:
35
Chapter 3:
SEVEN KEYS TO THE C-SUITE
Develop Your Leadership Skills and
Self-Confidence
37
Visualize Your Success Until It’s Real
Use “Co-Opetition” and Competition to Stand Out
Become an Expert and a Constant Learner
Develop Strong Communication Skills
Embrace Accountability
Show Humility
Believe in Yourself
38
40
41
44
47
49
50
Chapter 4:
53
Stand Out from the Herd
Differentiate Yourself
Ask More Questions
Take Calculated Risks and Challenge the Status Quo
Find the Courage to Make Tough Decisions
Call Out the Elephant in the Room
Be Known as an Idea Person Who Executes
53
56
59
63
65
66
Chapter 5:
Contents
vii
Act Like a Leader (Even If You Don’t Have
the Title Yet)
69
Set Clear, Inspiring Goals
Three Pillars of Goal-Setting
The Baby Steps
Keep Your Goals in Sight
A Final Thought on Goals
Everything Can’t Be a High Priority
Create Order Out of Chaos
Make Fact-Informed Gut Decisions
Earn Your Stripes
70
70
71
72
73
74
77
80
82
Chapter 6:
85
Adopt Winning Work Habits
Work Hard without Feeling Overworked
Show You Know Your Customers
Be Part of the Solution
Pay Attention to Details (without Being a Control Freak)
Add Value Through Simplicity
Persist and Be Patient
Chapter 7:
Choose Carefully the Company You Keep
85
88
91
93
96
97
101
Surround Yourself with A-Plus Talent
Find the Right Mentors
Choose Your Mentors
Mentor/Mentee Relationship Guidelines
Know When to Stay and When to Go
When to Go
When to Stay
Leaving the Right Way
Trust Your Unique Path
101
106
107
108
109
110
111
112
113
Chapter 8:
117
Embrace the Power of Kindness
Walk in Others’ Shoes
How to Develop Empathy
Get to Know Your Team
Say Thank You and Mean It
Gratitude Is Contagious
How to Show Gratitude
Create Fun and Joy
118
120
121
123
124
124
126
viii
CONTENTS
Exude Energy and Optimism
Keep Your Surroundings Positive
How to Foster Optimism in Yourself and Your Environment
128
129
130
Chapter 9:
133
Take Care of What Matters
Protect Your Calendar
Meetings
The Should-Dos Trap
Be Your Own Top Priority
Put Your Family First
Make Health and Fitness a Priority
Work Out
Eat Right
Sleep More
Live Life to the Fullest
133
135
137
139
140
142
143
145
145
147
Acknowledgements
About the Author
Index
149
151
153
Foreword
What Are You Waiting For?
It’s Time to Change
the World!
I
had been eagerly awaiting my first day at an enormous and very
famous Wall Street investment bank. I had hit the big time!
Through a family connection, I had landed an entry-level position as my first job after college. Sure, I would be starting at the
ground floor, but I was confident that I had the chops to succeed
and move my way up the corporate ladder. I was super excited that
morning as I introduced myself to my new manager, a grizzled Wall
Street veteran.
However, with one simple action upon meeting me, the manager seemed to delight in crushing my enthusiasm. With his power
move, my morning went from the wide-eyed, first-day excitement
and dreams of a promising career, to imagining mind-numbing
ix
x
FOREWORD
drudgery for the next four decades. Did this guy, who must have
seen hundreds of eager, fresh graduates just like me over the years,
do this to everyone?
Before I was introduced to my new colleagues, before I knew
what my initial role would be, heck, before I was even told where
to pee, I was shown how to use the time clock. A time clock! Like
you see in movies when they depict old-time factories. The manager
smirked as he gave me my very own punch card with my name on
it within 10 minutes of the first day of my career. I was told I had to
punch in when I arrived in the morning, again when I went to lunch,
when I returned from lunch, and finally when I left in the evening.
A time clock? Really? Did they not trust me? Yikes, I thought,
what have I gotten myself into? At that moment, I knew I had to
plot my exit from the Fortune 500 company world of work.
It wasn’t long before I became the sixth employee of an economic consulting company. What a fantastic career move that was.
This was an environment where I was able to carve out my own path
based on how my skills and interests aligned with the company’s
goals.
At the age of 26, I moved to Tokyo to start the company’s Japan
office. I went from literally punching a time clock at a massive corporation to being the sole employee of my start-up company outside
the home office. Soon I was doing business at a high level and making a difference. And I was having an absolute blast! The fact that
I was located 6,500 miles away from the management team, plus the
12-hour time difference, meant I was working when the rest of the
team back in New York was asleep. And this meant that I had total
and complete autonomy. I couldn’t have been happier.
What a remarkable difference between the drudgery of my work
as a tiny part of an enormous Fortune 500 company compared to
my new work as a huge part of a small entrepreneurial venture. The
lessons I learned about myself and what matters in my life have led
me to continue chasing that start-up culture to this day.
Now, I serve as an advisor to select emerging companies that
are working to transform their industries by delivering disruptive
products and services. My advisory clients include HubSpot,
Foreword
xi
a company I started working with in 2007 when they had a handful
of customers and fewer than 10 employees. I helped the HubSpot
team grow the company to more than 60,000 customers in 90
countries, and more than $500 million in annual revenue. My
current portfolio of advisory clients in the start-up world also
includes Mynd, Expertfile, YayPay, SlapFive, and InstaViser. I’m
also a Go-To-Market Limited Partner at Stage 2 Capital, a venture
capital firm that invests in start-up companies.
Be a Startup Superstar is the book I wish I had when I was in
college and considering a career in business. It’s a deep dive into
start-up culture and includes wonderful stories about what life is
like on the inside of successful, high-growth organizations. I found
myself nodding in understanding and appreciation on each page.
This is no academic tome written by somebody who simply studies what others do. Steve Kahan is a highly successful entrepreneur
himself. He’s been in a number of successful start-up ventures and
has also been in the trenches in the huge-company world. Steve
delivers valuable insights on every page. He’s your personal mentor
as he guides you through the start-up world.
The stories you read in these pages show you how to be successful working at a start-up. In my experience, there is a huge difference
in how to approach work at a mega-corporation versus a start-up,
and Steve tells you exactly how to navigate those differences. In a
big company, politics rule. Pleasing the boss is often more important than serving the customer. In the start-up world, the opposite
is true: Success comes from what you do to grow the business, not
from what you do to serve the egos of the muckety-mucks with big
titles. Steve uses real-world examples to point out those differences
so you can navigate your career with skill.
Start-up companies represent an enormous opportunity for
smart self-starters. And these entrepreneurial ventures are always
on the lookout for talent, for people like you. CEOs tell me all the
time that the most difficult part of their job is finding the passionate
people who will make a difference in their companies.
If you want to work for a company where everybody at the cocktail party will recognize the name on your business card, this is not
xii
FOREWORD
the book for you. If you want somebody else to tell you what to do
at work, look elsewhere. However, if you’re eager to have fun, make
a difference, and change the world, read on! We’re counting on you.
— David Meerman Scott, entrepreneur, business growth
strategist, and bestselling author of 11 books, including
Fanocracy and The New Rules of Marketing and PR
www.DavidMeermanScott.com @DMScott
Introduction
Life is no brief candle to me. It is a sort of splendid torch which I have
got a hold of for the moment, and I want to make it burn as brightly
as possible before handing it on to future generations.
—George Bernard Shaw, playwright
I
invite you to imagine you and I are meeting for a dinner
appointment. It’s a warm evening and we are seated at an
outdoor rooftop restaurant overlooking a bright, big city. As the
sun sinks into a soft orange glow, and the lights from the buildings
illuminate the deepening blue of the streets below, we talk about
your college experience. Your face lights up as you tell me about
the recognition you received; the camaraderie you experienced
with professors, classmates, and friends who challenged your
thinking. You express a longing for the structure of the educational
framework where success surely comes to those who work hard.
And then our conversation shifts to your current job situation.
You inhale deeply. During college, you had imagined so much
success and income in your future, but here you are, full of
xiii
xiv
INTRODUCTION
knowledge and ready to put it to use, ready to prove yourself—but
you’re stuck. You’re stuck in a job where advancement seems long
and far away, and your life lacks the richness you desire and expect.
You think about your peers, and while there are a few lucky ones
who already seem rich and happy (according to their social media
posts, anyway), you and most others are still getting by, trying to
mitigate risk due to those aforementioned student loans you can
no longer defer. You’re hoping for a big break or a lucky streak,
or a mentor to take an interest in you and help you to navigate
through this career conundrum in which you and other young
professionals are caught.
I am that mentor, and I’m taking an interest in you. This book
provides the insider perspective of a mentor who has been in your
exact situation and found a way forward, not just to a great job, but
to a great career and massive success, both financial and personal. I
want to help you discover your own path to becoming a brave leader
in a world that you might have previously overlooked or written off
as too risky: the tech startup world.
While working for a startup might seem riskier than working
for a large corporation, the potential rewards far outweigh the risks.
And, if you’re smart, you can mitigate the risk. I will show you where
the opportunities lie, how to take advantage of them, and how to
choose a start-up with the best chance for success—whether you’re
aiming for a tech or nontech role.
Have you ever felt stuck in your job? Have you wondered how
you will ever reach the level of success you imagined for yourself?
You’re not alone. In 2019, amid a robust economy and low unemployment, college graduates struggled to get hired. Upon graduation, 75% didn’t have a job lined up at all. It took the average college
graduate almost eight months to find a job—all against a backdrop
where the average student loan debt was $41,810. Add to that the
fact that in the same year, only 31% of employees in the US and
Canada felt engaged at work, and I believe this means we have a
serious epidemic on our hands.
This epidemic is not new. It nearly infected me.
Introduction
xv
Many years ago, after graduating college and landing my first
job processing claims in a large bureaucratic corporation, I realized
that the traditional “safe” path from school to climbing the corporate ladder was not only high risk for my career, it almost felt like a
death trap.
I dared to question my plan and ask myself, “What if I could earn
a great living and love the work I do?”
Even though I had no skills or experience in technology, I left my
boring, low-paying analog job and went to work for a tech start-up,
and it afforded opportunities that would have never been available
to me had I remained in a traditional corporate environment.
Since then, I have spent more than 30 years building my career
within the tech start-up world. From my first start-up job as marketing representative at Database Design to my current role as CMO
of Thycotic, I have been blessed to work for seven tech start-ups.
All six of my prior employers have either successfully sold or have
gone public, generating more than $3 billion in shareholder value.
I’ve had the privilege of working with hundreds of amazingly talented start-up entrepreneurs. I’ve learned about how they think,
what they do, and the attitudes they hold that have helped them
achieve extraordinary success.
My mission, and the purpose of this book, is to offer the underemployed, college-educated young person a way out of the death
trap. If this is you, keep reading, because I’m about to reveal some
of the massive opportunities available in tech start-ups today, even
if you aren’t a “techie.” This book arms you with the knowledge
of how to choose the right start-up, and how to succeed once you
get hired.
If you carry a huge student loan debt, the reality is that you
can’t afford not to work for a start-up. At a big corporation, pay is
limited to incremental annual raises according to the company’s
well-entrenched salary policies. On the other hand, in working
for a start-up, the big payoff comes through stock options. Often,
a start-up will offer you a relatively modest starting salary and an
opportunity to own a piece of the pie for yourself. This could lead
xvi
INTRODUCTION
to extremely high compensation later on, assuming the company
grows and eventually has a successful exit. I experienced this six
times as of this writing, and it’s worked out very well, like millions
of dollars well.
Working for a start-up won’t just help your bank statement—it
will also help you grow professionally at a quicker pace than would
be possible at a large corporation. Most start-ups don’t hire with a set
idea of your potential or career path. It’s the perfect environment to
try on different roles and find your zone of genius, and then move
up quickly from there. You can come in at an entry-level position
and end up working on big, world-changing projects alongside the
founders where your contributions can be seen and noted. At the
right start-up, you can quickly stand out and gain more responsibilities and opportunities to advance, both in your position of authority
and compensation.
Finding exceptional opportunities is only the beginning—you
need to be ready to seize them. This book provides you with the
seven traits of successful start-up entrepreneurs—how they act and
the attitudes they share in common—and how you can develop and
practice the art of leadership until these traits become a part of your
own success story.
Be a Startup Superstar is divided into two parts. I recommend
that you read the book in its entirety from start to finish, and then
go back and reread and dog-ear the pages you need the most at any
given time.
In Part I, I explain the opportunity: tech start-ups need new and
exciting talent of all kinds. Beyond tech skills, these companies seek
people with all kinds of talents and creativity who have bold ideas
and the leadership skills to bring them to fruition. Of course, the
best opportunities often come with a side of risk. Most start-ups fail,
so to give the reader the best chances for success, Part I wraps up
with a chapter on the five key traits to look for when selecting a tech
start-up before you apply for a job.
In Part II, I share the seven keys to the C-suite, which include
dozens of golden nuggets about what you need to do to ignite your
career in the start-up world, and how they are vastly different from
Introduction
xvii
the traditional corporate norms. You can begin to practice these
leadership attributes and entrepreneurial mind-sets that can propel
you to the top and keep you there. These are the traits they don’t
teach you in college or in on-the-job training by a corporation’s
learning and development team. These are the lost leadership skills
that will help you break out from the pack and rise to the top. They
will turn your potential for success into reality. They will help you
learn the lessons that will empower you to make better decisions
and get better outcomes in work and in life itself.
In short, forget climbing the corporate ladder; I’m going to show
you how to rocket past every rung and land in the C-suite in record
time. Never before has there been a greater opportunity to rise to the
top at great speed. Now is the time to go for it.
Part I
The Best
Opportunities Are
in Start-Ups
Tech start-ups are popping up all over and they need talent—
desperately. You don’t have to be a techie nerd to succeed in a tech
firm. These companies need all kinds of talent and creativity from
people with bold ideas and the leadership skills to bring them to
fruition.
1
Chapter 1
Use the Tech Start-Up
Boom to Zoom
A start-up is “the largest group of rebels, rule-breakers, and unconventional thinkers that you can find to create breakthrough change
in the world.”
—Chris Kane, co-founder and CEO of Munchmoney
Picture this: a lecture hall crammed with students in their last
semester. The professor asks for a show of hands—who is planning
on applying to a Fortune 500 company, or a top five tech giant?
A sea of hands rises. A start-up? Merely a smattering. This was the
scene that my friend, Josiah Sternfeld, professor at the McCombs
School of Business at the University of Texas at Austin, described
to me.
I was surprised. I’d spent my entire career working for a string
of tech start-ups, making millions of dollars, countless friends, and
indelible memories in the process. It seemed nonsensical to me that
so few business school students had considered start-ups, while at
the same time so many young companies found themselves in talent droughts. With so many unemployed and underemployed young
3
4
B E A S TA RT U P S U P E R S TA R
people, I tried to imagine why so few had raised their hands to apply
for a job at a start-up in tech. Maybe because so many are carrying
student loan debt, they fear it would be too risky to work for a company with no track record.
But I had to wonder if all those eager undergrads gunning for
the Fortune 500 gigs ended up employed. I thought not—as my
friend discovered, everyone wants to work for these companies. The
big corporates have the name, the prestige, they offer stability, and,
because they receive so many applications, they can afford to be
highly selective.
I did some research, and, as I suspected, many of the “Big
Company or Bust” grads weren’t enjoying smooth success in the
professional world. Fourteen percent of young adults with bachelor’s degrees (or higher),1 and 43% are underemployed, according
to a report by the labor analytics firm Burning Glass Technologies.2
So, what’s happening here? Why are so many bright, energetic, and
creative young people having trouble finding gainful work? Why
is it so many recent grads send out hundreds of applications that
yield little more than an interview or two?
I read more articles and found out that many of these
once-hopeful grads become resigned, defeated, and end up taking
jobs in the service sector and living with their parents, licking their
wounds before making a charge at an MBA. Or, like me when I first
got out of college, they fall into some dead-end, miserable job, and
wait for the day they can quit.
If this scenario sounds familiar, if the person I’m describing
is you, take heart. It doesn’t have to be like this. I once was in
your predicament, and I found a way out and never looked back.
You have other options. Lots of them. Today, you can find massive
opportunities in technology start-ups, and you don’t have to be
a techie.
1
IES National Center for Education Statistics. Employment rates of 25- to 34-year-olds in 2017,
https://nces.ed.gov/fastfacts/display.asp?id=561.
2 Melissa Korn, “Some 43% of College Grads Are Underemployed in First Job,” Wall Street
Journal (October 26, 2018), https://www.wsj.com/articles/study-offers-new-hope-for-englishmajors-1540546200.
Use the Tech Start-Up Boom to Zoom
5
The Unprecedented Opportunity in Tech Start-Ups
First, let’s examine what a start-up even is. According to the US
Small Business Administration, a start-up is a firm that’s less than
one year old. That, however, provides a poor picture of what actually
defines a start-up. My friend Doug Erwin, chairman and principal of
RedHouse Associates and a serial tech entrepreneur, offers a more
instructive definition. According to him, start-up is a stage. He says,
“A company is still in the start-up stage if it operates like it’s the last
frontier for outlaws, a world where nonconformists can live and create and sell their ideas.”
Who doesn’t want to be involved in that? At a start-up, you get
to play the rough riding rebel on the run, the freewheeling upstart
pestering the lumbering, flat-footed law. If you go to work for any
of the Fortune 500 or Big Tech, you become one of those bumbling
lawmen—a cog, punching in to pass the days pushing papers in
a daze.
“Sure,” you say, “this sounds great. But how do I get in?” Well,
the good news is, start-ups are proliferating at an unprecedented
pace. According to the Global Entrepreneurship Monitor, worldwide,
three new start-ups open every second. That comes out to 100 million
a year.3 In 2017, in the US alone, entrepreneurs created 404,000 new
start-ups.4
The growth in start-ups, and the potential for upward mobility,
is particularly strong in the technology sector where I have spent
my career. My first tech start-up experience began more than 30
years ago—long before the boom. If anything, that sector is an even
more lucrative opportunity now, as new technology permeates
every aspect of our world—how we work, communicate, travel,
eat, exercise, buy things, manage our health, move money around,
consume entertainment, and even interact with our pets.
3
Manoj Madhusudanan, “Fast-Growing, Emerging Firms are Great Targets for B2B Sales,” Ziligence Blog (July 16, 2018), https://ziligence.com/blog/2018/07/16/fast-growing-emerging-firmsare-great-targets-for-b2b-sales/.
4 U.S. Small Business Administration Office of Advocacy, Annual Report of the Office of Economic
Research, FY 2017, https://www.sba.gov/sites/default/files/OER_2017_Annual_Report.pdf.
6
B E A S TA RT U P S U P E R S TA R
Naturally, the tech sector has become one of the largest components of the US economy. According to CompTIA’s Cyberstates
2019 report, nearly 503,000 tech businesses were operating in the US
in 2018, marking six consecutive years of growth. Fueled by small,
emerging tech businesses, employment in the US technology sector
reached 11.8 million workers in 2018, increasing by an average of
200,000 new jobs every year since 2010.5 The tech boom is on, and
there’s a massive opportunity to reap the rewards for anyone who is
willing to rise to the challenge.
This is particularly true now, with an extremely high amount of
capital flowing into tech start-ups that shows no signs of stopping.
From 2016 through the first half of 2018, 44,000 start-up businesses
received more than $282 billion in funding. Forty-one percent of
them, nearly half, were technology companies.6
However, life is not all rosy in the start-up world. The market
is saturated with ideas and products, so in order to succeed, tech
start-ups need a lot more than money. They need a unique and valuable product or service, a solid business plan, intelligent advertising,
effective management, and high customer retention. Of course, you
can’t just go out and buy any of these things, which means that
tech start-ups primarily need one thing to succeed: strong teams of
people.
According to a 2018 survey of tech start-up CEOs, 66% said
the number-one issue keeping them up at night is “hiring good
people.” Not acquiring customers, not revenue growth, not raising
more money.7 While this may seem counterintuitive, it’s actually
obvious—a company can only go as far as the people who run it
will take it.
In the same survey, 60% of CEOs said it was harder to recruit
talent in 2018 than it was in 2017. So, finding the right talent is a
5
“Cyberstates 2019” research report, CompTIA, https://www.cyberstates.org/pdf/CompTIA_
Cyberstates_2019.pdf.
6 “These Are the Industries Attracting the Most Venture Capital,” World Economic Forum (February 13, 2017), https://www.weforum.org/agenda/2017/02/these-are-the-industries-attractingthe-most-venture-capital/.
7 “State of Startups 2018,” First Round, accessed December 22, 2018, http://stateofstartups.
firstround.com/2018/.
Use the Tech Start-Up Boom to Zoom
7
problem, and it’s getting worse. Add that to the fact that 45% of tech
start-up CEOs expected to hire 6 to 20 employees in the following
year, with 13% saying they expected to hire more than 51 employees
in the next year, and you get a talent drought.
Now, you might think that all these jobs tech companies are
looking to fill are for software developers and coders. Not so. They
need employees in sales, marketing, operations, finance, design, and
HR, to name a few.
Why is it so hard for start-ups to find good people? A large part
of the problem comes from the monomaniac focus recent graduates
have on working for the big companies. Even though tech start-ups
offer a huge number of benefits (discussed later in the chapter),
they still have to compete with the established giants. In the areas
with the largest concentration of tech companies, like New York
and the San Francisco Bay area, leviathans like Google, Facebook,
and Apple swallow up most of the talent. Everywhere else, the Fortune 500 and locally based incumbent giants send representatives
to schools for job fairs where they can sniff out and recruit the talent they need. You’ll never see a start-up at a school’s job fair. They
can’t spare the manpower or the cash from the all-hands-on-deck
needs of their day-to-day operations. Often, start-ups need to hire
people who can work remotely. But can you imagine a start-up in
Silicon Valley or Seattle sending a team to Lawrence, Kansas, and
a thousand other small towns with big schools to hunt for talent?
They can’t.
That means that start-up companies are desperate for smart,
self-motivated, creative, hardworking, visionary people who want
to share their talents in an innovative workplace that’s buzzing with
energy and opportunity. And they’re not just looking for techies.
They need people of all types and levels of experience—artsy, techy,
young and old, experienced and green, in-person and remote.
Note that I didn’t say start-up companies are just looking for
“talented people with Ivy League MBAs and prestigious connections.” Today’s most valuable large companies (such as Apple,
Amazon, Airbnb, or Uber) not so long ago were start-ups with
humble beginnings. Their initial teams didn’t come in with Harvard
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MBAs and years of experience in corporate jobs. In fact, it’s likely
that involving leaders with traditional business backgrounds would
have impeded these companies’ abilities to grow.
Today’s start-ups have big ideas, they’re well-funded, and they
need people who can join the team and help to bring their vision
to fruition. They are looking for you. So, if you’re entrepreneurially
minded, full of energy, and eager to learn and work hard, for the
right start-up, you could be a godsend.
I know what you might be thinking, “This isn’t the right fit. The
start-up world is too risky. What if the company closes? I have student loans. I want to start a family. And, sure, Steve, you’ve made
millions, you have this exciting life, but what’s to say you didn’t get
lucky?”
Or maybe you’re a little older and you’ve been in a boring,
dead-end job for a while and you’re afraid to make the leap. Either
way, the sooner you give up your excuses, the sooner you can get
out of this rut and go find a great opportunity. If you’re serious
about taking the fast track to the C-suite, and you’re ready for a
fast-paced, stimulating work environment, then tech start-ups are
the way to go.
I know I’ve already said this, but I can’t stress enough that you
don’t need to be a tech person to be a valued member of a technology start-up’s team. I’ve held C-level positions in six tech start-ups,
and I can’t write a single line of code. Steve Jobs was a technology
Luddite compared to Steve Wozniak, yet because of his other skills,
he became the face of Apple, which as of this writing is among the
most successful companies in the US, and arguably one of the most
important start-ups of all time.
Let’s remember, too, that while the big corporate job may seem
more stable, there’s never truly a guarantee. And, if you follow the
advice in this book to pick the best start-up for you, it will greatly
reduce the risk of picking a loser. And sure, maybe, if I had done this
once, it would be luck. But twice? Three times? Four? Five? Six? You
get the point. There’s a bit of luck involved in anything, but I believe
most of what others call “luck” is actually the result of focused effort
and accurate thinking. You need to work hard and intelligently take
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9
advantage of opportunities as you create them. And, fine, if you’re
truly happy unemployed and living with your parents, or if you like
your current job because it’s slow-paced and undemanding, then,
by all means, stay where you are. But if you’re bored, if you feel
you have something more to contribute, if you want to play a bigger
game, make the leap. Keep reading.
Why Work for a Start-Up Over a Big Corporation?
A few years ago, Microsoft dangled a senior leadership role in front
of me, which included a high-compensation offer and the chance to
move to Seattle. It was tempting. I had been working for Bindview, a
start-up where I ran marketing and helped to lead. But my role there
was soon to end—Symantec, a much larger company, was acquiring
us. While I could have continued on at Symantec, I didn’t really want
to, which left me with two real options: Microsoft, or find another
start-up.
On the surface, this might seem like an easy choice. This kind of
senior management position at Microsoft is something many people
only dream of. And Microsoft was making a hard push for me. They
flew my wife and me out to Redmond, where I interviewed with several key senior executives. Later, they organized a huge, scrumptious
dinner where I had the chance to meet and break bread with people
who could end up being my peers. They showed me Steve Ballmer’s
and Bill Gates’s offices. They offered to set us up with temporary corporate living right on a lake near their beautiful campus. I met the
people who would be working on my team, and the person I would
be accountable to, and we all hit it off. On top of all this, they offered
an extremely generous compensation package. And, as a remarkable personal touch, they found out that my son loved video games
and sent him an Xbox.
I had spent my entire career working in start-ups. I made more
money faster than anyone I knew who went the traditional route,
and never wanted to change that before. But Microsoft had been so
persuasive, I seriously considered it. I wrote down the pros and cons,
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B E A S TA RT U P S U P E R S TA R
talked with my mentor, and discussed it with my wife and children.
My wife loved the idea, even though it would mean uprooting our
lives and changing schools for the kids. It helped that when we traveled to Seattle to visit the campus, it was unusually sunny, and the
Pacific Northwest seemed like heaven on earth to her. And the kids
were on board as well—the Xbox had seen to that.
Then, early one morning while pondering the offer, I imagined how I would change the company’s website to capitalize
on an urgent market opportunity, and then I thought about the
big-company bureaucracy I’d have to go through, which I imagined
would have been like trying to get a bill through Congress. I called
the hiring manager and asked for an example of his team advocating for such a change, and he confirmed that it would require
jumping in slow motion through layers of hoops.
Prior to that call, I had nearly accepted the offer. But, hearing
about all the big corporate red tape I’d have to wade through, I realized that taking that job would make me miserable. I couldn’t get
myself to leave the high-flying start-up atmosphere where I had the
freedom to move the needle in quantum leaps, not increments.
It’s a big decision to choose to share your talents with a start-up
versus a large corporate incumbent. Both options include benefits
and risks. But if you have an entrepreneurial mind-set, you will discover, like I did, that start-ups can offer huge benefits. Here are what
I see as the top six.
Fewer Barriers to Entry
While big corporations often choose to hire the candidates who went
to Ivy League schools, are well-connected, or have loads of experience at higher-level positions, start-ups are interested in something
else. They choose to hire people who think creatively, show a
willingness to work hard, and demonstrate raw leadership qualities
that, once cultivated, can help the company (and the individual)
achieve breakthrough success. Remember, this is the ground
floor—every early hire plays a vital part in the company’s
construction and development.
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Start-up entrepreneurs are creators, not maintenance workers,
and start-ups need visionaries at every level. In addition, tech
start-ups are so desperate for A-plus talent that they tend to be
more flexible about terms and willing to hire employees to fill
remote positions, regardless of whether they live near a cornfield in
Nebraska, a beach town in Florida, or in the heart of Karachi.
Versatility in Roles
Most jobs in big, old-school companies offer a limited range of
authority, meaning no single individual, besides perhaps the CEO,
has the ability to influence the entire company in a significant
way. When you get hired to fill a role at an established business,
that’s exactly what they expect you to do: fill that role. It’s rare, if
not impossible, to find the freedom to experiment and try your
hand at filling different roles within various departments. Large
companies don’t want you to even think about how or where
you could contribute in new ways, yet this level of agility is the
norm at a start-up.
Most start-ups don’t hire with a set idea of your potential or
career path, because the start-up is young and undergoing massive
change. Founders may find it hard to predict what the company’s
needs will be as it grows. This is the perfect environment to try on
different hats and find your zone of genius—the area where you
work best—then move up quickly from there.
When I began at start-ups, I worked in sales, customer support,
and professional services before finding my zone in marketing.
From there I was able to build deep experience and expertise in
marketing and zoom to the C-suite as CMO.
Access to Leaders
Working for a start-up, you can come in at an entry-level
position and end up working on big, world-changing projects
with the founders where your contributions will be seen and
noted.
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When I was 25 and working with the start-up KnowledgeWare,
I was involved with a high-stakes project and charged with creating a plan to get existing customers to convert, for a small fee, to
the new version of our products on a new operating system. The
founders didn’t want to distract the sales team from attracting new
customers, and so they asked me to lead the initiative. At the time,
I was young and mostly untested. This assignment, however, had me
meeting with the vice president of marketing and the CEO, weekly
at first, and eventually we met daily. I had been given a tremendous
opportunity, and I didn’t want to squander it. I was laser focused,
and they noticed. Toward the end of the assignment, the company
had a dinner in my honor and presented me with a special achievement award.
This was a watershed moment for my career. Beyond the
obvious reasons—winning an award, developing a close rapport
with higher-ups—the experience had put me in a kind of pressure
cooker that spurred rapid growth. I had to create proven results, and
learn how to on the job. The fact that the higher-ups had selected
me to handle this assignment served as a massive confidence
boost, because I felt like the top executives had seen something
in me that I hadn’t yet seen in myself. This, in turn, helped me
take on even more high-stakes projects. This success begot other
successes.
After I delivered on the first project, the company wanted to
build a plan to develop a consultancy service. They hired an external senior consulting executive to handle the implementation. He
bungled it, and because they had the confidence in me after my handling the OS switch, they asked me to lead that team. I had never
done consulting before, but learning once more on the job, I added
another tool to my box, another cross-discipline competency, which
ultimately increased my value as an executive.
Now, let’s imagine: what if I had been a new hire for Google at
the same age with the same shortage of experience? I wouldn’t even
have sniffed a project of that caliber. I’d have been stuck in some
entry-level position, within a tiny scope, and miles of corporate ladder between me and senior leadership. In a pool the size of Google,
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13
with so many other swimmers, it’s easy to drown. But at Knowledgeware, I swam circles in the kiddie pool.
Financial Rewards
If you aspire to work in a big corporate environment because you
think you want the security, predictability, well-defined processes,
and better pay (sometimes) from the start—beware. What you’re
really buying into is limitation. I see it all the time in my dealings
with large corporations: the old corporate mind-set is filled with
bureaucracy, politics, boredom, pigeon-holed roles, and fewer
opportunities for employees to shine. All of this translates to
minimal financial rewards. It’s hard to stand out in a company with
thousands of employees.
Go to work for a big company, and you’ll get a paycheck—a paycheck and a 4% annual raise along with a formal review from a manager who dreads delivering it. The potential upside is far greater at
start-ups. And the initial financial rewards might not be too bad
either. Depending on the size, cash flow, and product launch status, a start-up may offer a competitive salary right off the bat, or it
may start you off with a modest salary with the potential to own a
piece of the pie through stock options. The stock options could lead
to astronomical compensation later on, if the company is successful.
In my opinion, always go for the stock options. A good rule of
thumb: the earlier you get in at a start-up, usually the better. For
example, if someone joined Thycotic in 2019 and took stock options,
they’d get their options at the current fair market value, which, for
the point of this example, let’s say is $10, while if you’d gotten into
Thycotic at the ground floor when the options were valued at, say,
$3, then you would have gained $7 per unit. The earlier you get
in, assuming the company grows, the more money you can end up
making.
The second piece to stock options is just how important they
can be for personal wealth. In my experience, as you grow in your
career and move up the ladder, you have the opportunity to make
more money. And, as you get older, you get new responsibilities.
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You have a family, you want to buy a house, you want to invest
in your children’s education, the list goes on. The point is, you
constantly find new ways to spend money. So, even though your
salary is increasing, and even though your bonuses are increasing,
your actual personal wealth doesn’t grow because your expenses
increase at the same time. And while some people are more diligent
about saving and investing than others, the amount of money even
the most disciplined person can accumulate pales in comparison to
what you can make through stock options, for the simple reasons
that those assets are less liquid, and they can increase in value very
fast, so you may consider holding on and riding the wave of value
creation. In the actual handling of stock options, of course, there
are all sorts of rules and regulations that dictate when and how you
cash them out, so that will vary on a case-by-case basis.
The bottom line is this: when it comes to investing, where I’ve
found the biggest gains, and where I feel the most confident, is betting on myself and the team I work with. When you invest in the
general stock market, picking up stocks in other corporations that
you’re not involved in, you’re betting on things outside of your control, like if the oil prices will hold, or if the CEO, who you don’t
know at all, will run the company well. The smart move is to keep
your money where you can play a direct role in its growth, and you
have direct knowledge in the day-to-day operations. Do note that
not all start-ups offer options, and that is something to consider in
your selection process, but we will handle this in more depth later
in the book.
Culture
Remember that earlier quote about being the last outlaws on the
frontier? About being the freewheeling, quick on the trigger, rebel
with a cause ethos of a start-up? I can tell you from my experience,
it’s true. When you’re working for the right start-up, that’s how you
feel. And like any band of outlaws, you and your co-workers will
develop the kind of community that can only exist in a small company of rebels.
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For example, during the six months I led a team for PentaSafe in
our UK office, I worked with a man named Dave, who never smiled.
He was a good guy, but he was as dry as a brick. One day, someone
saw him smiling for the first time, and they took a photo. Because
we knew he’d be okay with it, we made hundreds of copies of the
picture and hung them all over the offices. When he came in the
next day, he cracked up, and so did everyone else. The environment
and culture of the right start-up will encourage this type of fun and
camaraderie.
This is why it was the culture of the start-up world that first drew
me away from my boring corporate job. I wasn’t even thinking about
the prestigious titles or the promise of a huge payday, and I’m not the
only one who feels this way. The data backs this up. Culture has a lot
to do with employee engagement and happiness. Even in the midst
of long hours and hard work, start-ups, especially well-funded ones,
often know how to help creativity thrive. Where else will you find
a lunchtime ping-pong tournament or a late afternoon kitchenette
kombucha gathering?
It’s all nice and start-up-y when a company offers workplace
amenities for employees to blow off steam, such as ping-pong tables,
billiards, video games, open spaces, and even free snacks—but it all
comes down to the culture of the people, not the amenities. You can
have all that stuff and it could be great, or the environment could
still suck in spite of it. I’ve worked for start-ups with such offerings, and I’ve worked with start-ups, such as Thycotic, where we’re
all cramped in cubicles, but we don’t care. We are motivated and
aligned with a sense of purpose, and that’s a stronger measure of a
company culture than a playspace.
A 2017 survey shows that company culture ranks as the most
important factor in talent taking a new job.8 Yet, culture change
remains elusive to large companies. According to Gallup’s 2017
State of the American Workplace report, only 33% of US employees
across companies of all sizes are engaged at work.9 That means
8
Roy Maurer, “Candidates Choose Jobs Because of Company Culture,” SHRM (February 15,
2017), https://www.shrm.org/resourcesandtools/hr-topics/talent-acquisition/pages/candidateschoose-jobs-company-culture.aspx.
9 “State of the American Workforce” (2017), accessed January 4, 2019, https://www.gallup.com/
workplace/236282/american-workplace-changing-dizzying-pace.aspx.
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that 67% of employees are not engaged, and it’s a safe bet that
many of them are hiding in plain sight at the old guard incumbent
corporations. These employees are only doing what is assigned,
and nothing more. This kills creativity and cuts off any possibility
for growth. Discouraged and bored, workers show up like shadows,
going through the motions and performing the minimum to get
by. If enough people hide out, it slowly kills a company, and shareholder value takes a hit. But to me, the real tragedy is the thousands
of workers whose creativity, ingenuity, and natural drive for growth
get snuffed out over years of being relegated to repetitive tasks in a
tiny, gray cubicle.
Upward Mobility
If you have enough drive, it is possible to climb the old guard
corporate ladder, but be prepared for a slow climb. Incumbent
companies are burdened with incumbent mind-sets. Barriers to
advancement are high, and opportunities are few. If you have set
your sights on making it to the C-suite of a Fortune 500 or even
Fortune 1000 company, your opportunities are severely limited.
Among those companies, there can only be 500 or a thousand CEO
positions, maybe 2,500 to 5,000 in the rest of the suite. That means
your odds of getting a job in the C-suite of a Fortune 500 company
are lower than the odds of being drafted by the National Football
League—way lower considering the NFL drafts 224 new players
each year,10 and people tend to linger in the C-suite quite a bit longer
than that.
Compare these numbers to the 46,500 start-ups in the US,11
and it’s easy to see there are far more executive leadership opportunities at start-up companies. If you believe your corporate destiny
is to become a leader, you can find a start-up with a dynamic,
fast-moving environment that values initiative and offers the
opportunity to move up quickly.
Of course, the best opportunities often come with a side of risk.
When you share your talent with a start-up, you have to be ready to
10
11
As of 2019, 32 teams pick one player each in seven rounds of drafts.
Startup Ranking, https://www.startupranking.com/countries.
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move fast and adapt to constant change. There’s no hiding out. But
with a start-up mind-set and hard work, you can reap the rewards.
And finally, in connection to an earlier point, the kind of versatility a start-up affords helps put you on the fast track to the C-suite.
A New York Times story about the quickest path to becoming a CEO
pointed to evidence that “it helps greatly to have experience in as
many of a business’s functional areas as possible. A person who burrows down for years in, say, the finance department, stands less of
a chance of reaching the top executive job than a corporate finance
specialist who has also spent time in, say, marketing. Or engineering. Or both of those, plus others.”12
When James Legg, now president and CEO of Thycotic, was
fresh out of college, he was thrilled to score a job with a large
company called Computer Associates as an account manager, but
within three years the company acquired other companies, and its
employee numbers swelled from 500 to 5,000. He was fascinated
with the growth but not the behemoth status, so he jumped to
a company called BMC Software where he was offered his first
management role, and moved to California for the job. But soon,
this company also grew to the point where Legg discovered the
problem with large companies and why he didn’t want to stay
in them. “It was great working for a large company, but in that
environment, my ability to make an impact was severely limited.
I like to build things and figure things out, and I was intrigued
by how I could build a company, get ahead, and position it as a
leader. I couldn’t do that at a large company, but I could do that
at a start-up.” He’s since served as a top leader at a succession of
start-ups where his work can directly impact the bottom line and
the world.13
Considering all this, it could seem like a no-brainer to join
up with a tech start-up. I don’t want to give you the wrong idea,
however. There are clear downsides, and the start-up world is not
12
Neil Irwin, “How to Become a C.E.O.? The Quickest Path Is a Winding One,” The Upshot, New
York Times (September 9, 2016), https://www.nytimes.com/2016/09/11/upshot/how-to-becomea-ceo-the-quickest-path-is-a-winding-one.html.
13 Author interview with James Legg, April 2019.
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for everyone. You will experience long hours, and since you’ll be
working on high-stakes projects early, learning on the fly, and
growing with the company, you’ll face a lot of stress. You will carry
a heavier workload and greater responsibility than in a typical
entry-level position at an incumbent company. And for the most
part, you’ll be rewarded for all this extra work with a lower salary,
and less job security—at first.
But, it can have massive rewards.
In the spring of 2018, I sat in a boardroom on the top floor of
a New York skyscraper overlooking Central Park. I saw the bright
green of budding trees under a perfectly blue sky. We were just about
to conclude a successful board meeting. Staring out over this beautiful view, I recalled my first corporate job when I was processing
claims. A job so boring, no one could have paid me enough to get
me to stay there.
But on this day, I thought, “I would do this work for free, but
instead, I’m getting paid more than I ever dreamed of when I was
sitting in my cubicle processing claims 25 years ago. What if I had
never taken a chance on a tech start-up? What if I had not asked
myself if there was another way to create a successful career?” None
of this would have happened. I would have been stuck in that other
job path, and like most people, never gotten out of the rut.
Curiosity took me out of that cubicle and led me to ask questions
and find role models, and ultimately enabled me to carve a path for
myself within the tech start-up world.
You can create a similar story. If you don’t make it your story, it
will be your colleague’s story, your roommate’s story, or a friend of
a friend’s story—because the tech start-up market is in a long-term
boom, and there’s room for you to come in and thrive.
Chapter 2
Pick the Right Start-Up
for You
Don’t worry about failure. You only have to be right once.
—Drew Houston, co-founder and CEO of Dropbox
Are you chomping at the bit, ready to bolt from a corporate desk
to the start-up track? I was, too, when, soon after graduating, I
signed up at my first start-up. I rushed into the first opportunity
that presented itself. This was a mistake. I knew next to nothing
about the company—I didn’t know about its funding, growth
plans, or marketing plans. I didn’t even really know what we
sold. I knew the name, of course, but the product was some sort
of specialized technology and I only had a fuzzy idea of what it
actually did.
Ultimately, the company was successful. It had smart people at
the helm, a strong product, and a compelling story. In many ways,
it’s the luckiest I’ve been in my career. Because in my haste, I made
every possible mistake I could have made. And even though the
company ended up being a success, we experienced long periods
of struggle where we had to lay off swaths of the sales team, and
it looked like the whole thing might fold. Which happens far too
often.
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At a dinner party a few years ago, I met a man who told me he
worked an eight-to-five job for a big company in Austin. I asked him
if he liked what he did, and he shrugged and said, “It’s a job.” He
volunteered to me that years earlier, he had gotten in on the ground
floor of a start-up and loved it, but it tanked after two years, and he
never tried to work for a start-up again. With the way I dove headfirst and blind into my first start-up, I could have very easily ended
up on a sinking ship, just like this guy. I didn’t. I got lucky and picked
a company that turned out to be a winner, and I ended up a millionaire. But you don’t have to rely on luck.
What I didn’t realize at the time was that, with the proper preparation and research, you can avoid this sort of precariousness. In
this chapter, I provide strategies for finding start-up job opportunities, and guidelines for how to choose the start-up to join that will
maximize your chances of success.
How to Find Start-Up Opportunities
As you begin your search, you should keep this in mind—generally
speaking, a start-up handles hiring in two waves: in the first, they’re
just trying to assemble the core team. The start-up usually is brand
new, and as such, the process might not be as efficient. Once the
start-up is beginning to prove it is viable and can scale, then it makes
second-wave hires. These positions tend to be more specialized, the
hiring process is streamlined, and the company already has a bit of
momentum.
Recognizing the difference between first- and second-wave
hiring will help you evaluate each start-up you find to determine
whether you want to apply, as there are advantages and drawbacks
to joining with each wave. If you join in the first wave, the company
will be smaller and in a more precarious position, as they haven’t
proven viability. For the most part, these jobs are hard to find,
and usually go to someone with either a personal connection to
the founder or some sort of a reputation in the start-up world.
For that reason, combined with the precariousness of joining a
Pick the Right Start-Up for You
21
company in the first wave, I recommend that young workers or
people looking to make their transition into the start-up world go
after second-wave positions.
Research Posted Jobs Online
I know, you just rolled your eyes and muttered “obviously.” This is
still the best place to start, but to get results, you’ve got to know how
to look. Start by deciding which area of technology most interests
you (e.g., cybersecurity, health information technology, artificial
intelligence), then add which field or department you want to work
in (e.g., finance, marketing), and finally add phrases like “start-up”
or “early stage start-up.” Mix it up by beginning your search based
on geographical location, whether that’s where you live or in a
city you’re thinking of moving to. Then, look for positions where
you can work remotely. Check LinkedIn and other job websites for
postings by new companies. These early searches will yield a list
of companies and jobs in your area, as well as entrepreneur events
and trade fairs you can attend.
Explore Technology Accelerators
Accelerators (or seed accelerators) are application-only programs
that provide capital, mentorship, and educational opportunities to
start-ups, which often culminate in either a public pitch event or a
demo day. These are a great weeding-out tool, as companies that go
through an accelerator have a greater chance of attracting a lot of
venture funding. Research local accelerators and see which companies are participating.
Attend In-Person Entrepreneur Events
These events might take the form of trade shows, seminars, talks
given by industry leaders, or networking events held by local trade
groups, among many others. For example, in cybersecurity, the
SANS Institute is a cooperative research and education group.
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SANS, true to its mission, hosts a large number of training and
networking events around the country, many of which are open to
the public and could provide useful contacts for breaking into the
cybersecurity field. Once you know which field of tech you want
to work in, figure out what the major trade groups are (like the
SANS Institute) and be on the lookout for upcoming events. Most
local accelerators post calendars on their websites that list industry
events in the area.
When you have selected a list of events to attend, go to them. But
don’t just show up. Go with a plan. Research the event beforehand,
know who will be there, and know who you want to talk to. When
you arrive with your target list in mind, don’t just cruise around
asking CEOs for jobs. Introduce yourself and ask questions. People
love to talk about themselves, so this is the easiest way to establish
rapport. You can start by asking about the technology at hand, but
eventually you should personalize it. Ask them about things like
what they do for the company, what they love about working for the
company, what makes the company special, and what makes them
excited to get up in the morning.
Listen to their responses. Don’t just feign interest. This is the
most important thing—nobody likes insincerity and people can
always detect it. If you’re serious about breaking into whatever the
industry is, you should have a genuine interest in the answers.
Because you will learn, not only about the company, but also
about how to be successful in the industry. Then, once you get
a conversation flowing, if a bridge to asking about employment
or getting your foot in the door materializes, you can use it. You
can say something like, “Wow, it sounds like you have the kind
of position that I would really love to have one day. Do you mind
if I tell you what I do, where I’m at, and would you mind giving
me some pointers?” Then, without having seen your resume, they
already have a sense of your skill set. From there, you can ask if
they know if their company is hiring, and if you could throw your
hat into the ring. This way you don’t come across as desperate, just
genuinely interested in the company’s work.
Pick the Right Start-Up for You
23
If you go in with the mind-set of selling them on hiring you, then
you’re going to get nowhere. People hate to be sold to. They want to
give and get. When it comes to networking, the best way to sell them
on you, is to focus on them.
Engage with Start-Up Leaders Online
When you find the companies you’re interested in, follow them and
their leaders on social media. Read their posts, and when you see
something interesting or that you have questions about, reach out.
A way this might work is if you read a post of theirs on LinkedIn, and
it resonated with you. You could then reach out with a well-written,
specialized, private connection request in response to the post. This
will show that you have done your homework, have thought about
the industry and this person’s role in it, and you want to engage in a
serious manner. Again, you don’t want to come across as someone
just trying to get something or sell them on you.
If there is somebody you want to get in touch with, keep
an eye out for their next speaking engagements, hiring events,
or announcements about their participation in trade shows or
conferences. Go to them, introduce yourself, and ask a couple of
questions. With a little research, usually you can uncover their
email address and send a thoughtful, well-written email.
Of course, it’s important to remember that you’re reaching out to
busy people who probably receive a lot of messages like this. Don’t
get discouraged if you don’t receive a ton of responses—I know that
I ignore most of the LinkedIn messages that I receive. But you can
maximize your chances by preparing a well-written, articulate, and
diligent inquiry.
Attend Hiring Parties
When I worked for PentaSafe, we ran our headquarters out of a
beautiful, redbrick Southern-style mansion. People had their offices
in bedrooms, bathrooms, and closets. It, of course, seemed like the
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perfect place for a party, and at that time we were growing rapidly
and needed to hire more team members.
More than once, we got a few kegs and put them out on the
front lawn, then just spread the word around. At the time, a
much larger competitor was headquartered nearby, so we hired
a banner plane to fly over their headquarters with a sign that said
“We’re Hiring! Check out our website for details about our hiring
party!”
People would come, have a few drinks on the lawn of the mansion with us, listen to music, and talk about the company. Several
start-ups still use tactics like these to attract talent, and if you have
a chance to attend one of these parties, seize it! Not only are they
great for getting you hired, but they also will give you an excellent
opportunity to gauge the company culture.
Be Willing to Intern (Preferably for Pay)
If your resume doesn’t include any experience beyond front-line
retail or foodservice, it won’t garner a lot of attention, even at a
start-up. That’s why, if you’re in school or fresh out, an internship
is a great way to get your foot in the door.
The start-ups I worked for frequently hired paid interns in both
tech and nontech positions. One start-up, The Planet, hired a young
man as a finance intern while he was a junior in college. Since he
had no experience in finance, we would never have hired him as a
full-time employee, but we were willing to give him a paid internship
to assist our finance leader. With us, he made meaningful contributions to our financial analysis efforts and developed his Microsoft
SQL skills at the same time. This is important—not all internships
are created equal, and if you’re about to provide free or cheap labor
for an organization, it’s vital that you get valuable experience in turn.
Make sure to ask what the scope of any potential internship will be,
and don’t be afraid to advocate for yourself as an intern. Remain professional, of course, but remember that nobody will make sure that
you benefit from your internship if you’re not proactive.
Pick the Right Start-Up for You
25
Returning to the example, a year later, another start-up offered
that same student an internship where he could acquire a deeper
level of experience, and he took it. Using what he learned from these
two positions, he landed a good job in finance soon after he graduated. And, if he hadn’t gone to work for them, we would have hired
him back in a heartbeat.
This is not an unusual story. Internships give you the chance
to work in different areas, prove yourself, and develop relationships
with managers so you have a head start when you want to break into
the start-up world.
To score an internship, research companies and reach out to
specific people, describe why you’re interested in an internship,
and offer your talents. Usually, if you show initiative and a genuine interest in the company and the work, people tend to be
receptive.
Seek Mentors
In early 2019, I received an email from a Harvard undergrad. It said,
in short, “I’m interested in tech and cybersecurity, and I wonder if
you can teach me some things to help me on my path ahead.” I’d
never spoken to him before and he had discovered my email while
researching tech start-ups, but his message was well-written and
sincere. So I said yes. Executives, obviously, are busy, but they all
remember the people who helped them achieve the success they
have, and most are on the lookout for opportunities to help the next
generation. If an executive sees a potential fit or mutual benefit,
they’ll make the time to help. I met with the young man a couple of
times for mentor-mentee-type discussions. If he ever asked me for
an internship, I’d say yes, because I already know him. And once
I see how he works, he would be in a plumb position to be hired
as well.
With the glut of start-ups in the market, after even a little bit of
research, you can have a massive list of firms to choose from. So,
time to start sending out resumes, right? Not yet. Next comes the
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most important step to ensure your success—evaluating the companies so that you pick a winner.
Five Criteria to Choose a Start-Up
Yes, there are lots of start-ups, and yes, they all desperately need
talent, but exercise caution when selecting where to work. Not all
start-ups are created equal; a great one can rocket you into a successful future, and a dud can set you back, at least temporarily. Only the
strongest start-ups survive—current calculations show that about
75% of all venture-backed start-ups fail.1 I know what you’re probably thinking, but don’t be daunted. Instead, be savvy enough to pick
a winner. Approach the decision like an investor would, because
going to work for a start-up means you will be investing your time,
energy, and talent. And through stock options, you may even get
company equity. As an investor, find out enough to be sure the company you go to work for is the right fit.
Not only will you want to pick a winner as your first start-up,
but also be ready to find a new one. The time will come when you’re
rocking it with one start-up, and suddenly the leaders announce a
successful exit. This can be great—if you have stock options, their
worth will soar—but just as suddenly, you’re out of the job. Always
have a bit of a head start on a backup plan so you’re better positioned
to leap over to a new start-up if need be.
Then, on the flip side, the company might fold and you might
end up in the same situation of the person I met at that party, suddenly out of the job and tempted to go back to the steady corporate life. That’s what you want to avoid—in the volatile world of
start-ups, the company you work for might suddenly cease to exist.
It’s a reality, but one that you can plan for and ensure that you still
can go on to have a successful career in start-ups.
So, what should you look for? First and foremost, the start-up
must have a good story. The story should describe its mission in the
1
Patrick Henry, “Why Some Startups Succeed (and Why Most Fail),” Entrepreneur (February 18,
2017), https://www.entrepreneur.com/article/288769.
Pick the Right Start-Up for You
27
context of the lives of its customers and how it solves a problem, and
why it was launched in the first place. But a compelling story is not
enough. You want it to have a good story as well as strong indicators
for success. If you find a start-up with both, you will likely get the
outcomes you desire personally, professionally, and financially.
Here are the five criteria to look for to find the best start-up fit
for you, and one that’s likely to succeed as well.
Quality People Who Share Your Values
Doug Erwin, a venture capitalist who evaluated 8,000 companies to
find the 14 that he chose to invest in, says, “The first thing that a VC
invests in is the management team. The second thing is the management team. The third thing is, you guessed it, the management
team.” He continued, “The right leaders can turn a shitty product
into a success, but poor leaders can’t save an exceptional product.
The people are the most important.”
I agree one hundred percent.
Before you apply for a job with any start-up, look at the company’s values and mission statement. Make sure they align with the
values that are important to you. This should give you an early idea
about the leadership and the culture. Then, when you get the chance
to talk with people who work there, ask if they know the company’s
mission. Ideally, every employee in the boat knows the company
mission and is rowing in the same direction.
After you read the values and mission statement, do your
research on the head honcho and other key leaders. Seek to find
a team of leaders you can respect, trust, and admire. Consider:
has the CEO launched a business before? Was it successful? If so,
chances are high that this leader can do it again, and it’s likely
he or she brought other key leaders along to this company. Most
CEOs have great stories to tell, and they often include past failures.
Pay attention to the CEOs’ stories and how they overcame past
challenges. See if their stories inspire you.
Check out interviews and blog posts from company leaders to
learn about their backgrounds, goals, and their abilities to influence
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and inspire. Nothing enhances your odds of winning more than
surrounding yourself with A-plus talent, so choose a start-up where
you are inspired by those who can mentor you and help you become
your best as you grow with the company.
Besides looking at the leadership team, get a feel for the company culture at all levels. You can tell a lot about the culture by
observing what I call “the heartbeat” of the company. You can sense
the heartbeat if you sit in the parking lot at 6:30 a.m. and watch what
time people arrive, and how they look as they enter. Do they walk
in with a pep in their step as they begin another day of important,
exciting work? Or do they look drained as they plod across the lot
and pull open the door that looks heavier than it possibly could be?
Once you get inside for an interview or meeting, use every
moment and notice every detail to gauge the company’s culture,
from the demeanor of the first person who greets you; to the energy
levels of the people coming and going; to the decor, postings, and
office environment itself.
Also, use the interview or meeting to ask direct questions. Ask
your interviewer about the CEO, what they love about their teams,
and what they would be doing if they weren’t building a start-up
right now. All of this will give you a better sense of the type of people
this company attracts.
The Concept Fills a Big Market Need
Cool technology alone doesn’t cut it. No one—not consumers and
certainly not investors—spends money on “nice-to-have” technology; they spend money on the “need-to-haves.” If the company’s
product or service doesn’t fill a genuine market need, then the ship’s
going down, and you’d be a fool to board it.
How can you tell if a start-up’s product or service fills a huge
need in the marketplace? Sometimes it’s fairly obvious. Back in
2013, a company sprouted up around a product called “Vessyl,”
a cup that, in real time, told the users what was in it. Stephen
Colbert picked up the story and quipped, “Finally, a way to get
information that used to only be available on the can I poured
Pick the Right Start-Up for You
29
the drink from.” The product filled no genuine market need—it
was just nifty nonsense. Reading the website, they tried to make
it sound incredible: a “revolution in drinking,” promising data in
“real time.” In short, it was loaded with buzzwords. And, as of 2018,
Mark One, the company behind Vessyl, is no longer operating.2 Not
only is it a good lesson in how important need is to market value,
but it’s also a good rule of thumb—if the website contains more
buzzwords than actual specifics about market need, it’s probably
best to steer clear of what they’re selling.3
It’s not always that easy, however. When you’ve perused the
website and still aren’t sure, research the company online and read
what influencers have to say about its ability to provide a unique
value that sets it apart from competitors. Find the company’s growth
plans online, and compare them to others in the marketplace. Look
for evidence that the start-up is sufficiently ambitious with a solid
business strategy that includes managing future growth. See if you
can find signs that the start-up has every chance for success in what
they offer and how they are structured. Again, you can get a strong
sense of this during an interview. Ask questions about the product,
the customers, and the market.
Good examples include: “Why is now the time for your company
to exist? And why are you the ones to solve this problem? What’s
your biggest threat? What milestones have you achieved?” Ask them
to tell you about a real paying customer, how they found the company, and the customer’s experience. If they can’t give a convincing
answer to any of these questions, you should avoid that start-up.
Finally, look for competition. Are there other companies working on a similar product? Is Google? Apple? Amazon? If so, good.
This might seem counterintuitive, but competition means there’s a
market, and start-ups can run nimble circles around big companies.
You know who didn’t have competitors? Vessyl, and we all know
how that ended. Of course, you need to make sure that the start-up
2
“Mark One,” Crunchbase, 2019, https://www.crunchbase.com/organization/mark-one#sectionoverview.
3 “Vessyl Digital Cup,” The Colbert Report (July 14, 2014), http://www.cc.com/video-clips/9nzwjt/
the-colbert-report-vessyl-digital-cup.
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you work for differentiates itself within the market, but there needs
to be a market.
Besides a market to compete in, the product or service must
have a competitive advantage. Kevin Klausmeyer, financial expert
and independent start-up board member, says the advantage can
be found in a variety of areas, but the company must have at least
one. “It could be product elegance, product features and functions,
a unique partnership with a big player, or speed to market. When
looking to join a company, make sure you understand the competitive advantage and how they plan to win.” He points out that both
Tumblr and MeetUp were wildly successful tech start-ups with
their simple concepts (a blog platform and a social event platform)
because they had the first-to-market advantage.4
A Great Product You Believe In
You want to work toward something you’re passionate about. If not,
why are you even in the start-up world? You can complete rote tasks
for any company, and many will pay you better for it than a start-up.
Before you apply, research a detailed description of the product
or service the company offers, and see if it resonates with you. Do
you believe in it? Would you purchase, use, or recommend it? I’m
not saying that you have to be a target customer of the product or
service, but I am saying you want to be proud of what you help
to produce.
If possible, attend one of the company’s shindigs in person,
such as a marketing event, sponsorship activity, conference, or
trade show. Pay attention to the reaction by the audience or other
outsiders when they are presented with the spiel of the product
or service. Talk with employees to get their insights about what
the company offers. With a little time and energy, you’ll be able to
find out how well the product or service delivers on its core value
proposition.
If you can’t get behind the product with enthusiasm, move on.
4
Author interview with Kevin Klausmeyer, April 2019.
Pick the Right Start-Up for You
31
A Role You Can Fill Today with More Opportunities Tomorrow
Look at the company’s job postings and see if they have needs that
truly match your interests and areas of expertise. Not all opportunities are posted, so a little networking can go a long way toward
finding out what a company actually needs and how you can help.
Don’t settle for a role in which you have zero interest, but keep an
open mind. Allow yourself the room to imagine what taking on
new roles would be like. Be willing to be flexible in how you apply
your skills. Remember, a lot of start-ups haven’t pigeonholed roles
and responsibilities yet, and you need to be ready to step up when
called upon.
Once you get to the interview stage, ask if the start-up aims to
hire people who they can develop and promote. Some start-ups promote from within more than others. It depends on their culture and
their leadership team’s interest in and (usually brief) history of raising leaders through the ranks. Many times, I’ve seen promotions
take place via a tap on the shoulder while someone is filling up a
coffee mug in the kitchenette: “Hey, Courtney, I’d like you to step
into the manager role, starting now.”
Choose a start-up where you can make an instant impact, and
grow into a larger role. It’s best to choose a start-up that’s in it for the
long-haul and working to build a great company. If in the interview
they’re already talking about an exit, then that’s your cue to exit the
interview. What you’re trying to do is find a strong enough start-up
where you can stay long enough to help build a great company
with lots of happy customers and employees, while developing
your own expertise and leadership skills along the way. If the
interview discussion reveals that everyone is focused on selling out,
rather than continuing to build the strongest possible company,
then the selling day will never happen, so avoid wasting your
time there.
The Start-Up Is Well-Funded
It all rides on the money, honey. Before you get too serious about
pursuing a job with a particular start-up, verify that the company
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is properly capitalized so it has the best chance at stability and
growth. Choose a start-up that has a long enough runway for it to
get off the ground. That means there’s enough money to go from
development through marketing and launch and pay its people
well along the way. This is not too much to ask; it’s a non-negotiable
requirement.
Even if they offer stock options, you should never accept stock
options in place of a livable salary, because if they’re making that
offer, it probably means they don’t have enough money to launch,
and those stock options won’t be worth the paper they’re printed
on. A too-short financial runway means the start-up may run out of
tarmac and, at best, putter out, at worst, crash and implode.
During an interview, ask questions such as, “How is the start-up
funded? What’s the five-year plan? How long is the runway? How
tight is the budget right now?”
Find out where the money is coming from. Is it self-funded or
are venture capitalists behind it? Who has skin in this game? The
answers to these questions will give you a good idea about not only
the funding, but whether the leaders are inclined to tiptoe around
the financials. If they lean toward vague answers, it would be hard to
feel confident about their ability to be up front about the company’s
health in the future. Look for transparency and straight-shooting
conversations about financials. Also, VCs often list on their websites the companies they fund, so you can use this bit of research to
confirm that a start-up’s funding is legit.
While funding is technically the start-up’s lifeblood and a
concrete indicator of its chances for success, there is a bit of a
chicken-and-egg scenario at play. If the management team is strong
and the product solves a problem, then the funding will come.
You’re just usually better off to delay making a commitment until
the funding is in place.
Those are the criteria I use to evaluate start-ups. Only go to work
for one that has a combination of all five. Three, even four, won’t cut
it. If you want to zoom to the C-suite, you’ll need an environment
with these conditions to spur you forward.
Pick the Right Start-Up for You
33
Getting Hired
Finding companies to apply to and even get your foot in the door is
only the first part—no matter what, there will be an interview process, and you have to nail it. Going into the interview, make sure
that you’re ready to demonstrate that you have the skills, and more
importantly, the mind-set that they are looking for. As I’ve mentioned, start-ups place less emphasis on your education and prior
experience than large corporations.
Doug Erwin, the serial tech entrepreneur I mentioned earlier
in this chapter, says when he’s hiring at a start-up, “I look for people who want to build solutions to solve problems. People who have
failed and then succeeded, and who aren’t afraid to take chances.
I look for people who are prepared. People who are good communicators and who have a sense of humor and can laugh at themselves.
And, of course, people who have the skills to do the job. I want
people who show they can think outside the box.”
What does this look like? Erwin tells the story about when he
used to have a friendly annual meeting with the head of HR at
Southwest Airlines. On one visit, Erwin waited in the lobby with
a bunch of men interviewing to be pilots. Erwin says, “The lobby
was full of these serious men with cropped hair, obviously military
pilots. Someone came into the lobby and announced, ‘To all of
you interviewing for pilot jobs, we are only interviewing people in
shorts. Thank you very much,’ and then disappeared back through
the door. I saw one guy cut his pant legs off right there in the lobby.
Others ran out to their cars and put on their gym shorts, and came
back in.”
While Southwest Airlines isn’t a start-up anymore, their HR
team demonstrated a start-up mentality in seeking quick-thinking
people who were willing to go all-in and have a sense of humor.
Bring that energy to your interview, and it will make you stand out
to start-up leaders.
Great energy will help, but the single fastest way to snag the
attention of a start-up founder is to have an elevator pitch—for
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yourself. This seems incredibly simple, yet most people don’t do
it. When you go into an interview, you need to be selling yourself,
your brand, and what you will bring to the start-up that nobody else
will. For example, my elevator pitch for myself is, “I deliver plans
for marketing strategy and execution that help start-up companies
achieve breakthrough revenue growth in brutally competitive
marketplaces.”
One sentence that describes what they get when they hire me.
And notice, it’s not shy; it’s bold and concrete. “Breakthrough
revenue growth” operates well because it’s vague (not a specific
numeral), but clearly conveys that I will take revenue to the next
level breakthrough. And notice brutally—I could have said very
or hyper or extremely, but brutally tells you that I am somebody
who’s accustomed to working in fields where the competition can
be cutthroat. You want to create your sentence so that when people
hear it, they say: “Oh, how do you do that?” Once they ask, then
you can follow it up with your story.
Of course, I have years of success to back this statement up. But
this elevator pitch tactic holds up in all situations. No matter where
you are, at any point in your career, you need to be able to succinctly
express what makes you a unique asset. As an example, let’s say
that you’re fresh out of college, looking to join a sales team, and
you don’t have much experience. Your statement might be, “I help
companies I work for to increase sales by listening to customers and
providing them the best solutions to solve their toughest business
challenges.” Then, you tie it into who you are. You might not have
much sales experience, but they’ll ask, “How do you do that?” And
you’ll say, “I’m a hard worker and I learn rapidly. I’ll aggressively
research the product, the market, and the competition. I’ll listen to
our customers’ biggest challenges, and show them how our product
is a solution, if indeed it is.”
Finally, don’t be afraid to tell them how what you bring to the
table is unique. Say that no one else will listen better than you, work
harder than you, or know their products and the advantages over
competitors better than you. If you come in with this level of preparation, a concise explanation of what you provide, and the right attitude and energy, you’ll have a much better chance at getting the
head of a start-up to roll the dice on you.
Part II
Seven Keys
to the C-Suite
Although getting in on the ground floor is a great start, it’s how you
show up that will determine how fast and how high you climb. I’ve
carefully curated the top 35 leadership attributes you need to get
hired, zoom to the top, and stay there, and I’m sharing them with
you in the following chapters.
35
Chapter 3
Develop Your Leadership
Skills and Self-Confidence
Brilliant thinking is rare, but courage is in even shorter supply than
genius.
—Peter Thiel, entrepreneur and co-founder of PayPal
In the small environment of a start-up, the higher-ups see everything you do, and nothing will make you stand out faster than
leadership skills and self-confidence. Often, working for a start-up,
you’ll have a chance to step into a leadership position much
earlier than you would at a large company, and you need to be
comfortable and confident as a leader to eagerly take advantage of
those opportunities. You cannot excel without both of these traits.
I’ve worked with tremendously skilled employees who lacked the
self-confidence to implement their ideas. I’ve also worked with
those who were full of confidence, but couldn’t walk the talk.
Neither made it to the top of their fields. In this chapter, I share
how to develop each one within yourself.
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Visualize Your Success Until It’s Real
If you haven’t, you need to create a vision for what you want, and
visit it often. Write a narrative or make a vision board. I know, it
might sound hokey to tack up a picture of a reclining chair on the
deck of a yacht anchored in a gleaming ocean. Or a composite image
of you on a stage, smiling big, arms raised, as you inspire thousands
in the audience before you. Or a photo of a glass of red wine on a
stone table at a hillside café overlooking Florence, Italy, at sunset.
But wait, those images don’t feel hokey, do they? They feel pretty
incredible. And if those are your goals and you see those images
every day, you’ll be more likely to reach them. Visualization is effective for the simple reason that the first step of getting what you want
is knowing what you want.
And while visualization can sound like a panacea peddled by
self-help gurus, the research shows it works. A 2016 nationwide survey by TD Bank showed that 82% of small business owners using
visualization boards had accomplished 50% of what they had on
their boards.1 More than that, according to psychologist Barbara
Nussbaum, a partner on the study who specializes in the emotional
and psychological implications of money, visualization doesn’t just
help you achieve your goals by seeing them. It actually increases the
emotional connection to those goals because you begin to associate
positive emotions with what you’re imagining, and that emotion
becomes a powerful motivator.2
For me, I achieve this by writing down my vision and revisiting
it and experiencing that vision imaginatively first thing each morning. I have done this since I graduated college. When I visualize,
I aim high, and I don’t just think about what I want. I fill in my
visions with details, picturing the experience and what it will feel
like once I accomplish it, until my visions seem so real, a part of
1 Eilene Zimmerman, “Survey Shows Visualizing Success Works,” Forbes (January 27,
2016), https://www.forbes.com/sites/eilenezimmerman/2016/01/27/survey-shows-visualizingsuccess-works/#625ef796760b.
2 Ibid.
Develop Your Leadership Skills and Self-Confidence
39
me believes they already have happened. I’ve pictured myself in the
C-suite. I’ve seen myself wowing people with my brilliant ideas and
incredible results at a board meeting. I’ve imagined myself making
seven figures as a start-up I’ve worked for gets acquired. And I’ve
accomplished each of those things.
Practicing this in the morning allows me to set the tone for the
rest of the day. I know what I’m moving toward, and it allows me
to constantly ask: what can I do to take a step in the direction of
achieving the outcome I’ve been dreaming about? In my experience,
when I ask myself these questions, I always come up with answers,
and success follows.
My success till date would not have been possible without this
visualization.
Whether you use a digital vision board on your computer, a
physical vision board with pinned-up images, or you visualize
success and capture your ideas in writing—it’s having a vision that
counts. You want to feel so turned on by your future success that
you go through your day hearing the waves gently rolling against
the side of that yacht, feeling the energy of the audience before you,
and tasting the sweetness of life in that red Italian sunset. The key:
be crystal clear and specific about your goals, keep them in front of
you, and always ask how you will get there. This is the first step to
success, and also to developing yourself as a leader and to fortifying
your self-confidence. A leader needs a vision to rally his followers
toward.
Also, when you have a strong vision for your success, it will
make your outlook on life more positive. That way, even when you
experience setbacks, you will be able to remain undeterred and refocus on your vision.
You will experience setbacks. Great success is a journey, and it
never comes by walking in a straight line. If you’re too busy looking
down at the road, you won’t know where you’re going and you won’t
end up anywhere exciting. You will only reach a great place if you
look ahead and keep advancing toward it, even when it seems far
away at first.
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Use “Co-Opetition” and Competition to Stand Out
I’m a Type A personality with an intense desire to compete. Part of
this, I’m sure, comes from growing up the eldest of three boys in a
family without a lot of money. My mom would go and buy three or
four boxes of cereal, and just about two days later, it’d all be gone. My
brothers and I each tried to wake up before the others to get downstairs and then scarf down as much cereal as possible—if you didn’t
get there first, there’d be hardly anything left to eat. Just getting a
meal became a contest.
A lot of people view competitiveness negatively, but without it,
I never would have achieved what I have in my life. I’ve thrown the
full weight of my ruthless competitive energy into leading marketing teams at any given start-up, consistently outsmarting our biggest
competitors. Any good leader will have this drive to compete. It’s
contagious—when you care about outperforming other firms, it sets
the tone in the office and it pushes your co-workers to work together
to outplay the competition.
You should never be remorseful about winning. Remember, at
the end of the day, you need to win to get ahead. And the way I’ve
always seen it, your competitors are trying to take food off your
table and your family’s table. They’re trying to get to the cereal
before you, so you need to try to beat them in every way possible.
This doesn’t mean you should gloat or be rude to your competitors.
In fact, you need to always win with humility and treat your competitors with respect, because in the start-up world, the tables can
turn rapidly.
A strong competitive impulse will help you stand out in the company you work for, but not always for the right reason. As long as
you direct your competitiveness at external companies, you’ll be a
star. But as soon as you compete with co-workers and try to undermine them or make them look worse than you, you’ll be viewed as
an asshole, not an asset.
Nobody likes to reward an asshole, so even if you do compete
with co-workers for promotions and major projects, do it with
grace and by doing your best. Celebrate your co-workers’ successes
Develop Your Leadership Skills and Self-Confidence
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because they are your company’s successes, and as such, they
benefit you.
Channel your competitive energy to move with your co-workers,
not against them. How do you do this? By focusing on the larger
problem (i.e., helping the company succeed), rather than obsessing about who will get the corner office. This healthy competitive
spirit can unite an office and team. When I worked at PentaSafe,
we didn’t just fly banner planes to advertise hiring parties. Whenever we had a great quarter, we would hire a plane with a banner
that said “PentaSafe had another great quarter!” and fly it over the
same competitor’s offices. And we, the team that made that quarter
great, would all celebrate with some beers, watching the plane fly
over their premises. In this way, our shared competitiveness led to
camaraderie and also great success, as we soon took over the market.
This doesn’t mean you have to view every competitor as an
enemy. You can use “co-opetition,” a term coined by authors
Adam Brandenburger and Barry Nalebuff in their 1996 book of
the same name, to channel your success. Co-opetition is when a
start-up cooperates with a competitor to the benefit of both. For
example, I worked with a start-up that provided a large, competing
company with access to our emerging technology. This co-opetition
helped our start-up gain revenue, and the established company
was able to provide better technology solutions to its customers
without having to develop them internally. Both sides won big, but
it required an act of balance to work simultaneously as competitors
and collaborators.
Become an Expert and a Constant Learner
To move up in a start-up environment, you must drink deeply from
the cup of knowledge, rather than just sip at the edges. This applies
to two types of knowledge: deep knowledge in one main area, and
broad knowledge in many. Both are critically important to achieving your vision of success. And both are lifelong processes. There is
no such thing as enough or too much knowledge, and as changes
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in the tech industry whiz by, your formal education becomes less
relevant, and staying on top of industry knowledge becomes even
more crucial.
In my twenties, I worked in customer support at a start-up. It was
okay—I had a more engaging life than before and I found my work
fairly interesting, but at the same time I had two young children
and rapidly growing debt. Worse, I didn’t feel truly passionate about
my job.
I took the time to reevaluate my “whys”—essentially asking
myself what I wanted to achieve personally and then examining
the impact I wanted to make in the world overall. This gave me a
list of objectives and the reasoning behind them. Not too long into
doing this, I realized that my true passion lay in marketing.
I then took a step few people do, and which I recommend for
all who read this: once I had my “whys,” I went through and created a plan for my career. A lot of people are excellent at mapping
out business plans—growth strategies, mission statements, major
milestones. But almost nobody does the same thing for their career.
Now, this kind of plan can get out of hand—it’s very easy to end
up with 30 or more pages. Try to knock it down to a page or two
of what you view as the most essential elements, then keep those
pages folded up in your wallet. Carry them around with you, as
I did, and occasionally pull them out to revisit them and evaluate
your progress.
Part of my personal plan included becoming an expert in marketing. I immersed myself in books, studying marketing operations
from a wide range of companies, taking notes on all the marketing
plans I could get my hands on, and attending seminars. So when an
entry-level marketing job opened up at the start-up where I worked,
I was ready.
Soon, my deep studies paid off: my marketing knowledge went
far beyond my peers’. I was promoted. Here, I had a choice. I could
rest on my laurels, decide that I had learned enough about marketing, and have a perfectly mediocre career, or I could intensify my
investment in learning and go even deeper in my studies. I chose
the latter, and it propelled me to even higher levels.
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You have to go deep to go high. When I hire, one of the most
important factors in my talent evaluation process is deep knowledge. I know that people who have taken the time to become an
expert will perform better, solve bigger problems, and produce
higher value. Besides getting you hired, those three qualities will
get you promoted as well.
Kevin Klausmeyer, as I mentioned earlier, learned early-on
how to distinguish himself through deep and wide knowledge.
“I was a finance guy in a tech space,” Klausmeyer says. “I joined an
industry task force focused on writing software accounting rules,
and the level of knowledge I gained made me unique and helped
me stand out as a finance guy who’s helping to create the rules that
all companies in the tech industry needed to follow. That was my
differentiator.”3 He encourages all employees—whether in or out
of tech fields—to find their own differentiator. Get that additional
certification, join an industry group, and seek a volunteer leadership role in an area you’re passionate about that will distinguish
you from the pack.
Spend time creating your “whys,” find one main area you’re
passionate about, and focus your career in that area. Of course,
make sure it’s a broad enough area to have a growth path to the top
within multiple start-ups. If you acquire too-specialized knowledge,
you won’t be effective in the C-suite. For example, I focused on
marketing and how it contributes to revenue growth, not website
development.
Once you decide to make yourself an expert, it’s easy to find
the information you need. Knowledge is everywhere. Learn from
analysts, industry influencers, and mentors, and take notes on their
insider secrets. Dive into market research, plans, blogs, articles,
websites, and public filings. Say yes to challenging projects and
learn as you go. Seek help as needed, and look for constructive
feedback from people whom you trust and respect.
One of the best places to look for new knowledge is your competitors. Steve Jobs loved the Picasso quote “Good artists borrow,
3
Author interview with Kevin Klausmeyer, April 2019.
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great artists steal,” for a reason. It also applies to business. I once
noticed that another technology leader had built an online tool for
helping organizations assess the need for their product. I thought
this was a great idea. I studied the concept and realized we could
develop a better version that focused more on the customer and less
on our own company. We built it and it was a huge hit. It increased
our sales and propelled our company forward. The key isn’t to just
put out some knockoff of what your competitor is doing—it’s to
improve upon ideas that already exist.
When people ask me how they can move up, I always tell
them to invest in growing their knowledge every day. You need a
beyond-the-basics understanding of the industry and your company. If you’re aiming for a financial position at a tech start-up,
for example, you’ll need to develop deep financial expertise, plus
knowledge of the company’s products, competitors, and customers.
That doesn’t mean you need to know how to code (I don’t). It
means you pay attention to innovations happening around you and
think about how to learn from them to create something better or
contribute bigger ideas.
Create your own learning plan that includes what you will learn,
by when, and with what resources. Then schedule learning times on
your calendar and don’t let anyone take that time away from you.
This is your time to devote to yourself and growing your knowledge
every day, whether you’re working toward a degree in a formal education setting, or engaging in self-guided learning via books, online
courses, videos, or conferences.
We’re all busy, and lifelong learning requires effort, but it’s
an investment that can skyrocket your income, effectiveness,
confidence, communication skills, and ability to lead. If people
know that you’re an expert in the field, they’re much, much more
likely to follow you.
Develop Strong Communication Skills
Warren Buffett said, “The one easy way to become worth fifty
percent more than you are now (at least), is to hone your
Develop Your Leadership Skills and Self-Confidence
45
communication skills, both written and verbal. . . . You can have all
the brainpower in the world, but you have to be able to transmit it.
And the transmission is communication.”4
The data, again, backs this up. A LinkedIn survey of hiring managers in the US revealed that “communication” is the
number-one in-demand soft skill, and it’s the most desired skill
among entry-level individual contributors.5 In my experience, this
is especially true in the start-up world, where change is constant. In
order to be nimble enough to survive, a start-up needs employees
who can adapt to ongoing changes and communicate well on the fly.
Developing strong communication skills will make you a better
persuader, too, which means you’ll be able to convince people to buy
your products, but also convince your co-workers to rally around
your vision.
You need this no matter what field you work in, whether
financial or marketing. Once, in a half-day meeting with our
start-up’s C-suite and leaders from a potential partner company,
our CFO gave a presentation on our financials. The slides were
great, but she couldn’t present them clearly. Our guests grew more
and more doubtful about our capabilities. Sensing catastrophe,
one of our directors with strong communication skills took over
the presentation, saving the partnership. And, a few months later,
the CEO replaced the CFO.
You must develop your public speaking to zoom to the top.
I know—the idea of talking in front of a crowd can be terrifying.
I struggled with stage fright as well. But you have to get over it. I
had to, and it didn’t come easy at first. It will help to remember
that most audiences want you to succeed. Then, the key is this:
preparation + practice = confidence.
Pay attention to the speaking habits of the most effective communicators, and model what they do. The best presentations I’ve
4
Bill Murphy Jr., “Warren Buffett Just Shared His 1 Best Piece of Advice,” Inc. (December
7, 2018), https://www.inc.com/bill-murphy-jr/warren-buffett-just-shared-his-1-best-piece-ofadvice-he-says-its-very-simple-will-boost-your-net-worth-by-at-least-50-percent.html.
5 Guy Berger, “Data Reveals the Most In-Demand Soft Skills Among Candidates,” LinkedIn
Talent Blog (August 30, 2016), https://business.linkedin.com/talent-solutions/blog/trends-andresearch/2016/most-indemand-soft-skills.
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seen are those where the presenter speaks from the heart and starts
the whole thing off with humor, a question, or a comfortable story
to lighten things up from the get-go. The speaker shows engaging
slides that aren’t wordy (if they include slides at all) without reading
the slides, and articulates a clear takeaway.
To fully prepare, you should know the subject and flow of the
presentation “cold,” understanding the audience and what they’re
after, anticipating questions and being prepared with answers.
Practice any presentation in advance on your spouse, partner, your
friend, and/or your co-workers.
Then, during the actual presentation, facilitate two-way dialogue and engagement with the audience (ask them questions and
invite them to present questions to you) and use eye contact to
watch for nonverbal clues for engagement.
Outside of a presentation setting, all of these same rules apply.
Be prepared, and know what you’re talking about before you speak.
And if you don’t, admit to it. The worst thing to do is flounder your
way through some jumbled statement. Finally, proper communication is a two-way street. Just as you need to read the audience when
you give a presentation, when interacting with co-workers, practice
listening more than you talk.
If you can combine expert tech knowledge with precise communication, you will become like a golden unicorn: rare and valuable.
Most people who work in tech are primarily analytical thinkers who
communicate in jargon, making them unintelligible to the uninitiated. Worse, they often have little patience for anything outside of
the realms of tech, so it’s difficult to hold their attention long enough
to effectively communicate. If you’re going to succeed in the tech
start-up world, or in any field, you need to be able to communicate
with these sorts of hyper-analytical people. It will make you stand
out as a leader, too, as you’ll be able to bridge gaps in understanding
and propel the company forward.
So, how do you do that? An important thing to remember is that
techies respond poorly to platitudes (e.g., “If we work together, nothing can hold us back!”). They’re primarily interested in the details
that apply to their work, such as the customer’s experience of the
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47
products they design. Focus on specifics, and show that you have
thought about what they do and that you, too, have an analytical
side. Employ that deep, broad knowledge base you’ve developed.
They want to know that you’re not ignoring them, but nothing will
irk them more than being required to attend meetings they perceive
as unnecessary.
This is one example of what, ultimately, is the most important
aspect of communication: adaptability. Each person prefers to
receive information and be interacted with in a certain way. If you
can find what that is and make subtle adjustments so they feel
heard, seen, appreciated, and included, you’ll make leaps in your
leadership abilities. Leaps that will take you to the C-suite.
Embrace Accountability
According to the Harvard Business Review, one of every two managers is terrible at accountability, and “The single most shirked
responsibility of executives is holding people accountable.” As
the workforce gets younger, the problem gets worse. HBR reports
that millennial workers expect praise and recognition and aren’t
equipped to productively handle constructive criticism.6 This
inability to take responsibility or accountability for your actions
creates problems, especially in the tech start-up space. Receive
constructive feedback with gratitude and grace. Not only that, make
it a point to seek feedback from others about your performance.
Tech start-ups are too small to hide out in. If you drop the ball,
it has major consequences, and, if you don’t take responsibility,
everyone notices. On the other hand, because this trait is so rare, it’s
an amazing opportunity for you to stand out, especially if you’re a
young employee. If you’re comfortable taking feedback and owning
your mistakes, people will notice. It will naturally make them
gravitate toward you as a leader, and it will put you on a fast track
to promotions.
6
Darren Overfield and Rob Kaiser, “One Out of Every Two Managers Is Terrible at Accountability,” Harvard Business Review (November 8, 2012), https://hbr.org/2012/11/one-out-of-everytwo-managers-is-terrible-at-accountability.
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If you don’t take responsibility for your mistakes, it will put you
on the fast track to the can. When I led a team tasked with rolling
out a digital channel to market our product to a new audience, we
had a short deadline. Everyone needed to work hard and meet their
individual deadlines for us to be successful. Most people did, but
we had one employee who never finished his work on time, and
who never gave updates to the rest of us. This held back the project
and sent us scrambling to pick up his slack, but whenever somebody
confronted him, he blew it off like it was no big deal. His teammates,
fed up, bypassed him and stopped inviting him to project meetings.
And I fired him before he had a chance to ask, “Can we shift the
dates again?”
Accountability works two ways. You need to hold yourself
accountable to meet deadlines and produce excellent work. The
best way to do this is to be ultra-clear about project ownership,
goals, timelines, outcomes, and metrics, so that you know your
commitments. If a responsibility isn’t clear, ask for clarity. Then,
as I’ve said before, take it a step further and write down your
personal goals and plans on a sticky note or index card and keep
it readily available. Regularly review them, monitor progress and
performance, and adjust.
The other side of accountability is accepting when other people hold you accountable. There’s a phrase that knocks around the
start-up world, “One throat to choke.” Essentially, it means that, at
the end of the day, there should be one person who is ultimately held
accountable for any given project, and that usually ends up being
the leader. While other workers might have their own responsibilities and tasks, ultimately it falls to one person to make sure that
everything works. And, in my experience, this sort of centralization
is vital. If there’s one central authority delegating those tasks and
then making sure that they’re done well and on time, it frees everyone else up to focus on their specific tasks. If you want to stand out,
lead projects, and eventually land in the C-suite, make sure that
throat is yours. Embrace the role of taking the lead and being the
one responsible to ensure the project’s success. Use that position to
grow as a leader and impress your superiors.
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Show Humility
I once had an open leadership position on my marketing team, and
two internal candidates for the job. Both were highly skilled, knowledgeable, proven leaders. But there was one major difference: one
seemed to credit every good result to his own sage wisdom, while
the other acknowledged contributions from everyone on her teams.
I promoted the second because of that confident humility. I knew
she would share successes with the team, inspire trust and confidence, and admit when she was wrong, all of which are powerful
tools in building camaraderie.
We’ve all known “I people” who are out for themselves,
taking all the credit, hiding the contributions of others, and
decreasing morale. Guess what? No one wants to help them get
to the top. Instead, if you’re a “we person,” giving credit where
it’s due, you’ll bring out the best in others, and inspire trust and
confidence. And people will like you, which, at the end of the day,
is one of the most important aspects of success. People want to see
people they like succeed.
So, what is humility? It is not low self-esteem. In fact, the
opposite. Humble people don’t boast often, instead, they project
quiet confidence. It’s okay to toot your own horn, but mainly as a
tool to establish your credibility. Never, ever, boast just to “impress”
people. Being humble is the ability to stand confidently in what
you know and have accomplished, and remember that you can
always learn more, and that no single accomplishment is yours
alone. It’s the ability to also be listening and seeking out ways to
grow, and to give credit to how other people contribute to your
successes.
Of course, it’s not easy to let go of your ego. Often, people are
afraid to show humility because they think it makes them look
weak. But it doesn’t. As Zachary Feder and Khatera Sahibzada
point out in an article for Entrepreneur, “Humility . . . requires a
substantial inner strength to embody—one that not only welcomes
feedback and criticism but knows that it is one of the fundamental
ways that we grow.”
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I’ve found that when you give credit to others and shine the light
on them, it actually comes back to you tenfold. They will want to
run through walls for you to help you succeed. Those in power and
your co-workers will appreciate that you express humility and recognize others. Make no mistake, people in power know the role you
play—you don’t have to constantly tell them.
Believe in Yourself
Confidence equals security equals positive emotion equals better
performance.
—Tony Schwartz, president and CEO of The Energy Project
Self-doubt is like a frayed string: if you tug on it, it can unravel
your whole sweater.
In my experience, self-belief is the biggest indicator of success
at a start-up. Not intelligence, not opportunity, not resourcefulness.
But the belief that you can make your goals happen—especially in
a start-up scenario where the path will be bumpier than at a major
corporation. You need self-belief to stay steady during the ups and
downs. All of us, myself included, deal with vulnerability, uncertainty, and failure. If you let these things defeat you, you’ll never get
anywhere. Trust that you will move forward and figure it out.
I am fortunate to have a built-in belief in myself. Even growing up poor, I knew that my situation was temporary. On the first
day of sixth grade, I showed up in my worn-out clothes and toting
my worn-out backpack. Right away I noticed that most of my classmates sported new gear from head to toe. Despite lacking all the
external indicators of success (wealthy upbringing, private schools,
high-net-worth family and friends), I was unfazed. Now, if you don’t
have this in-born self-belief, don’t worry. It’s a muscle, and like any
other, you can build it.
When I worked for The Planet, we had a crisis that threatened
to shut down the entire company. Our data center exploded,
sending all our servers up in flames. Those servers held the cloud
data of thousands of our customers, and suddenly, it was all gone.
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When I got the call with the news early on a Sunday morning, for
just a moment, I thought, “We could go out of business. Customers
will leave. This is the worst thing that could happen.” Now, if
I continued to keep tugging at those threads, I would have come
undone. But those potentially unraveling thoughts didn’t last for
long. We called a meeting of all of the leadership—on the same
Sunday. In the meeting, right on a big whiteboard, we developed an
action plan for how we would manage the crisis. We made two big
decisions up front: that we would be completely transparent with
our customers, telling them not only what we knew, but also what
we didn’t know, and when we would know what we didn’t know.
The other: that we would do right by the customer, financially
and otherwise. We shaped our entire approach around these two
principles, sharing updates and photographs on the process and
offering financial compensation when necessary to the clients.
We were able to develop a plan so quickly because the leadership had enough confidence in our ability to bounce back. If they
had succumbed to doubt, we would have never recovered from a
disaster of this scale. But they didn’t, and they organized us to take
that first step. And once we had that first step, that plan in place
gave us even more confidence. We felt that we were doing all the
right things—being proactive and moving in the correct direction.
We had a roadmap and could draw extra assurance from it. Ultimately, we lost very few customers and I attribute it to the positive
self-belief of the company’s leaders.
Of course, this is an extreme example, but it illustrates an important point about succeeding in business. First, that every day in
business, especially at start-ups, is chaos. Something will happen—
a customer will be upset, the competition will make some bold
move, a server will crash that will require a fast response. You
need to trust in your ability to handle that, and it’s much easier
to trust in that ability when you’re prepared. Preparation equals
confidence—whether it’s putting out literal server fires, or just
giving a standard presentation.
Usually, people with low self-esteem practice a lot of negative
self-talk. They think “I’m a failure, nothing goes right, I’m a loser.”
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If you do this, the first step in building your self-esteem is to
eliminate negative thoughts. If you spend hours a day convincing
yourself that you suck, and then try to tack on some positive thinking, those affirmations will come across as lies and it can actually
hurt your self-esteem. Notice when you fall into negative patterns
of thought and then gently correct yourself. Be patient—you’ve
probably spent years developing these negative patterns and it will
take time to unravel them.
Once you’ve eliminated the negative, you can build on that foundation. Start by writing down what you’re great at, what results you
produced, and what beautiful relationships exist in your life. Make a
list of the daily or weekly accomplishments you want to achieve and
reward yourself when you do. Develop your inner voice to be your
champion and avoid negative people and situations. As you increase
your knowledge, take time for self-care and give to others, you will
increase your belief in yourself and this will propel you forward in
business and in life.
The more you demonstrate that you genuinely believe in
yourself and your skills, the value you bring, and your ability to
succeed, the more others will see you in that same positive light and
be more likely to trust you and value your opinion. It will translate
to confidence in the workplace, and nothing draws people to you
like confidence.
Chapter 4
Stand Out from the Herd
If you want to stand out from the crowd, give people a reason not to
forget you.
—Sir Richard Branson, investor, author, founder of Virgin Group
Once you’ve been hired at the start-up, you won’t just float to the
top. It’s a battle and it requires a lot of effort to swim to the surface.
You’ll be competing against everyone else in the start-up world for
leadership positions, and the fact is, many of them will have similar skill sets. To stand out from the crowd, you’ll need to find new
ways to set yourself apart, and one of the best ways to do that is
to develop and display strong leadership attributes. Leadership is a
multifaceted skill that takes time and effort to learn. What we discussed in the last chapter was just a starting place—to really stand
out, you need to develop your ability to ask more questions, take
more risks, make tough decisions, and come up with great ideas and
execute on them.
Differentiate Yourself
As I’ve mentioned before, you need to have an elevator pitch for
yourself that you can roll out in an interview with start-up leaders. It
should take as long as an elevator ride—20 seconds, max, and relay
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right away why they want to hire you. Make sure it conveys how you
provide unique value, and why they should invest in you.
To help you get the content to write this, ask your colleagues,
mentors, and friends to describe your most powerful, unique
qualities and strengths. While we might have our own idea of what
makes us unique, there’s no substitute for knowing what other
people believe makes you stand out. At the same time, ask these
people what your greatest weaknesses are, and force yourself to
listen without getting defensive. Their feedback, if honest, might
help you realize areas where you can improve.
Just as start-ups must create products and services to differentiate themselves in the marketplace where they are competing
with bigger and better-funded companies, you must differentiate
yourself from the herd of people who want the higher jobs that
you are after. A start-up company’s differentiators include the
products, services, distribution, brand image, or specialization
that they offer. Here’s what it looks like when you apply those
concepts to your career: Your product is your performance. Your
service is how you deliver superior solutions and build relationships.
Your distribution is how you communicate and share your performance. Your (personal) brand is the experience of others when they
interact with you. And your specialization is your deep knowledge in one main area that helps you deliver your product better
than others.
In my many years making personnel decisions, I’ve noticed that
the employees who get hired and move up are the ones that make
everyone else realize they are the best at what they do. Even employees with the least amount of experience can move up ahead of those
with seniority by showing their leadership skills.
Following are six specific ways you can separate yourself from
the herd:
1. Take initiative. Are there important tasks on your manager’s
to-do list? Take on a project that no one wants to tackle, but must
get done.
2. Build relationships across the company. People who get big
things done are people who know others who can help.
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3. Show your love for the company. Surprisingly, not enough
people go out of their way to show their commitment to a company and its values and goals.
4. Build your skills. As you grow your knowledge in the area
where you want to move up, you will become an invaluable
asset.
5. Go the extra mile. Ultimately, the one quality most under your
control is your effort. If you slack off, it shows, and you’ll be
canned. But if you push yourself and go further than anyone
else, that will show and help you move up in the company.
6. Sharpen your communication skills. Even a poorly written
email message will reflect poorly on your skills, so keep it sharp,
always.
It’s worth noting that a big opportunity to differentiate yourself
is when you help to differentiate your company in the market.
It’s a double-dip of differentiation—you can improve both your
own standing and your company’s standing. A great example of
this came during my time at PentaSafe. When I joined, we were
a small, private cybersecurity firm competing against three much
larger public companies. The thing was, we were all selling essentially the same product: vulnerability assessment and intrusion
detection.
We needed a way to differentiate ourselves, and because of
our limited resources, we would never be able to do that with the
technology alone. The other companies had much larger and more
impressive R&D departments. So, I took a look at our company
and a look at the field, and what I realized was that while the other
firms focused on the technology alone, nobody was looking at the
other side of the security equation: the people and the policies.
We had this project that one of our creative engineers was working on. We weren’t sure we’d take it to market. It was a tool that
allowed companies to assess how well their employees understand
the security policies, which is huge, because most employees don’t
know these policies at all. Usually, they get a huge dump of papers,
sign them without reading them, and forget about it.
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We went ahead and brought the product to market and we
used that as a main differentiator. It allowed us to sell ourselves as
the only company that addressed all three factors in the security
equation: the technology, the policies, and the people.
The funny thing is, we hardly sold any of the new tools that
would assess how well employees understood the policies. On
that level, it would look like a failure, but the fact that we had
the tool got us into the door at many firms. Once we were in the
door, we were able to sell them on our main product and steal
business from the larger competitors. So, in that way, it was a great
success.
We didn’t stop there. Along with two team members, Chris
Pick and Todd Tucker, the three of us developed a community we
called “the Human Firewall Council.” We gathered thousands of
people from all over the world together in one place to talk about
cybersecurity.
The council really took off. Chris and Todd, after PentaSafe was
acquired and we all cashed out in a big way, both went on to work
for another firm, APPTIO. There, they implemented the same sort
of council and expanded on and improved the idea. This initiative
helped them achieve success and move into executive leadership
positions.
Let’s break down the lessons here, because there are a couple.
The first is that whether you’re a company or an individual, if you
want to succeed, you need to find an area where you stand out.
The second lesson is that many times, you can achieve both of
these goals at once. When you discover vital innovation that helps
the company stand out and act on it, you will stand out in turn,
and then you can leverage your newfound expertise to launch into
success in new ventures.
Ask More Questions
You might think that the most successful start-up CEOs with stellar
track records, huge social influencer platforms, and millions in the
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bank are the ones doing all the talking in a meeting. But it’s the
opposite: they ask thoughtful questions and listen for responses.
They realize that the right questions inspire reflection, and that
reflection inspires action. If you want to move up to the C-suite,
cultivate this skill.
I learned this lesson early. At one of my first start-up positions,
I earned a reputation as someone who delivered, so the leadership
asked me to take on a new function, well outside of my previous
experience. I wanted desperately to impress my new manager, so at
each meeting with him, I barfed-up a nonstop barrage of plans and
solutions. He just listened quietly, and I left each meeting congratulating myself on how smart and clever I was.
Even though my team got impressive results, my relationship
with my manager soured. I couldn’t understand why. Then one day,
a mentor of mine asked how I was doing. I told him I was down
because my manager and I weren’t working together well, and I
couldn’t figure out why. What else would this mentor do, but ask
a bunch of questions? After listening to my responses, he said, “Ask
your manager more of the right questions instead of telling him all
the answers.”
In those days, I carried a notebook wherever I went. My mentor
gestured to it and told me to write a small question mark at the top
of every page to remind myself what to do.
I took his advice. It worked like magic. Turns out my manager
had wanted me to ask for his priorities and feedback so he could
collaborate with my team and me. Our relationship improved, and
so did our team’s results.
I see the same tendency to try to act like an expert all the time
in young, confident professionals. It never works—it’s the rough
equivalent of getting “INEXPERIENCED” tattooed on your forehead. If you want to impress, especially when you’re young, focus
more on asking smart questions than on telling people what you
know. It will show you have the maturity to realize how much you
don’t know, and are eager to deepen your knowledge. This will make
your supervisors and peers trust you and want to give you more challenging projects and responsibility.
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It takes effort to overcome the urge to have all the answers or
to “be right,” but it’s essential for success, especially in the start-up
world. In The Book of Beautiful Questions, published in 2018, innovation expert Warren Berger quotes the venture capitalist Christopher
Schroeder, who says, “he uses the following question to remind himself to keep an open mind: Would I rather be right . . . or would I rather
understand? If you’re adamant about being right,” Schroeder says,
“you lock yourself in your own echo chamber—and that can cause
you to make bad decisions.”1
In a large company with established processes, it’s easy for an
employee to do only what they’re told, without asking questions.
But in a start-up environment, where the company’s processes are
being developed, it’s critical to ask intelligent and useful questions to
comprehend the big picture and find additional creative solutions.
Not only will it make you stand out as thoughtful, but it will also
make you better at your job.
The same concept applies when talking to customers. I’ve
received hundreds of sales calls during my career. Most of the
salespeople can express their value proposition, but only a handful
ask me questions.
Those salespeople who don’t ask questions forget the most
important aspect of sales: listening. How can they pitch a product
to me if they don’t even know what problems I’m currently dealing
with? Maybe I have a problem that I don’t even realize I have yet.
Sure, they can tell me they see a problem, but I’m far more likely
to believe it if I say it myself. The salespeople who ask the most
intelligent questions that make me realize the gaps in my solutions
are almost always the ones I end up buying from.
The big takeaway from this isn’t just to ask more questions. It’s
to ask more thoughtful, higher-quality questions. There’s nothing
more annoying than someone who asks questions just to ask them,
or who asks questions about something that’s already been covered.
If you want to learn how to ask good questions, there’s no better teacher than Socrates. According to his method, you start with
1
Warren Berger, The Book of Beautiful Questions (London: Bloomsbury Publishing, 2018).
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an open-ended, challenging question. Then, follow it up by asking
“Why?” After much discussion, you might land on some sort of an
answer. Then, you ask more questions about that answer, examining
the solution you came up with.
Of course, unlike in philosophy, in business, you must act, so
at a certain point you need to pause the process of reevaluation to
implement a solution. After that, however, you still should continue
to ask questions regarding your solution, and refine your thinking.
While this might seem intellectualized and esoteric, it applies to
business as well. For example, instead of asking, “Are our customers
satisfied?” ask questions like, “How can we help our customers
experience greater satisfaction?” “What is the purpose of this
function?” and “How can we better support customer success?”
From there, it’s a matter of finding the best answer and coming up
with a set of actionable items. Then, carry out those actions but
don’t let the process stop there. Once you have results, continue to
interrogate what happened, asking questions like, “Why did that
occur?” With those sorts of questions, you can refine the steps you
took even further.
There is, however, one question that is more important than
any other in any decision-making scenario, personal or professional.
Asking this question can lead to a deeper understanding, better decisions, and more brilliant outcomes. Those who ask this question are
seen as more strategic and forward-thinking, and those are traits
that zoom leaders to the top. The question: What’s next?
Simple, isn’t it? Try it and see the results for yourself.
Take Calculated Risks and Challenge the Status Quo
When you think of Babe Ruth, what comes to mind? Home runs?
In 1927, Babe Ruth hit his 60th home run of the season and set
a home run record that would stand for 34 years.2 But the Babe
wasn’t just the Sultan of Swat, he was also the King of Strikeouts.
2
“Babe Ruth Hits 60th Homer of 1927 Season,” History.com, https://www.history.com/this-dayin-history/babe-ruth-hits-60th-homer-of-1927-season.
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His risky all-or-nothing batting style sent him on a record number
of triumphant trips around the bases, and a record number of walks
straight back to the dugout.
The lesson: you won’t hit a home run if you don’t take a chance
and swing. Don’t get confused. I’m not advocating for swinging
hard at every opportunity. I’m advocating taking big swings at ripe
pitches, in game-changing moments, after you have prepared and
practiced.
I’ve developed a reputation as a risk-taker, but I don’t see myself
that way. I see myself as a calculated risk-taker, and there’s a big, subtle difference. A risk denotes unnecessary action that’s often impulsive and driven by emotion. A calculated risk means taking a chance
after you’ve done your homework and prepared a Plan B (and Plan
C, if necessary). If you never take a risk, you won’t go anywhere, but
if you take lots of big risks, you’ll likely falter. To create an impact,
you must be willing to take calculated risks.
Even with calculated risks, you’ll still lose occasionally. I did—
while nearly all of my bold moves paid off, a few fizzled. For
instance, I once sunk a huge amount of time and money into a
new marketing campaign. The campaign’s theme was bold and
different, and our team expected that this difference would lead
to greater success. It flopped miserably. Though I dreaded telling
the CEO, I took full responsibility and provided solutions to move
forward. This strikeout hurt, but it also fortified my character,
resilience, and knowledge so I could hit a home run the next time.
Which I did.
Even though I failed on that attempt, I didn’t stop taking risks.
If you’re bent on maintaining the status quo, you won’t last long at
a start-up. To ignite your career, you’ve got to be willing to shine
a light on the important things that must change, and to lead the
effort. This doesn’t mean challenging everything so you’re perceived
as an anti-establishment contrarian. It’s more about challenging the
old ways and creating new, better ways where it counts. Focus on
taking calculated risks and innovating in areas where your special
brand of thinking can make the biggest impact, such as increasing
revenue, lowering costs, and improving customers’ lives.
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One great example: I joined Quest Software, a relatively large
public technology company, to run their marketing. I realized that
our cross-selling was abysmal. Customers would buy one product,
and that’s it. We sold a bunch of different products, some of which
we had developed natively, but we had acquired several from
smaller companies, and our customers weren’t getting the benefit
of all we had to offer.
I undertook the first step of any improvement process: asking a
question. I asked, “Why is the cross-selling of our own products so
poor?”
I did some research. I went down to the sales floor and interviewed our salespeople, asking them to give me the elevator pitch
for the company. Almost none of them could agree on what it was,
and I soon realized that we had so many products, the salespeople
only pushed the ones they knew best. Then I looked at the website.
We had no system to organize our products by type; we organized
them based on how recently we’d acquired them. Imagine if instead
of grouping products by shopping categories (books, food, clothes,
etc.), Amazon had all of their items listed by how recently they’d
acquired them. You’d never buy anything from them!
Well, that’s more or less where we were, so I asked two more
questions: “Why don’t we have an elevator pitch?” And “Why do
we organize our products in this way?” And everyone told me the
same thing—that’s what the chairman wanted.
I went to the chairman and told him everyone had told me that
the reason we had a muddled elevator pitch and a hodgepodge website was that he had wanted it that way, and I asked him why that
was. He, of course, was shocked—he’d never said he wanted that. In
fact, he had wanted the opposite.
What happened was that everyone in the company had become
accustomed to the status quo. They were so used to how things were
that they’d invented a story about why things were like that, which
simply wasn’t true.
After our discussion, the CEO gave me the green light to
revamp the elevator pitch and the website. A few months later,
my team and I rolled out a compelling elevator pitch and product
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reorganization that grouped every product into seven logical and
easily distinguishable categories. Then, we studied which products
would work best together, and designed the website to make
recommendations to customers based on these compatibilities.
These changes didn’t come easy. People had become so comfortable in the status quo that, at first, we encountered resistance
and pushback. A lot of the sales team didn’t buy into the new
elevator pitch right away, and people from different departments
fought us over where their products would be grouped. Eventually,
we got enough support and momentum from the employees and
other stakeholders to make the change successful.
This became a complete overhaul of marketing and sales, so we
risked losing a lot of invested time, money, and training. But it was
a calculated risk and it paid off with a high potential to increase revenue in the long term.
Taking any risk, no matter how calculated, can generate fear.
As we’ve established, even joining a start-up can be a calculated
risk. At the same time, people constantly tell me that when they’ve
taken a calculated risk, they’ve experienced the most success and
happiness.
Test it for yourself: write down three of the biggest calculated
risks you’ve taken in your life. Then, write down the outcome of
each and how it changed your life. This exercise will build your confidence for your next calculated risk.
Remember to pick your risks well—there’s no point risking a
huge chunk of revenue on something that will hardly move the
needle. Once you’ve identified your aim, be prepared. Do your
homework, ask questions, weigh outcomes, consider alternatives, and start with baby steps before going all-in. Recruit other
like-minded leaders to join you in the effort—not for cover, but for
assistance. If a calculated risk turns out to be a dud, owning up
to it and moving on will also help you to stand out as leadership
material.
Bottom line: an effective leader takes calculated risks, and if you
do the same, you will stand out from the herd big time.
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Find the Courage to Make Tough Decisions
In any moment of decision, the best thing you can do is the right thing,
the next best thing is the wrong thing, and the worst thing you can do
is nothing.
—President Theodore Roosevelt
If you can’t make strong decisions along the way to the top, you’ll
never make it to the top. No matter what your job title is, it’s never
good to idle in a cloud of indecision. If you want to zoom up the
start-up ladder, prove from the get-go that you have the guts to confidently assess a situation and make an informed decision. You won’t
start out making the biggest company-wide decisions, of course, but
you should still train your decision-making muscle on your way.
Most people think that tough decisions are restricted to business
matters, but this isn’t true. Life is filled with tough decisions—from
deciding where to focus your expertise, which employer to choose,
how to protect your work/life balance, when to ask for help, how to
spend your company’s money on projects within your realm, whom
you choose to marry, if you choose to marry, whether to have children, etc. Essentially, every aspect of your life, from your daily habits
to your behavior, is a decision.
The only difference is that as you go higher in a company,
the decisions you need to make become more complicated. In a
10-year study by Navalent of more than 2,700 leaders, 57% of newly
appointed executives said that decisions were more complicated
and difficult to make than they had expected.3
If you’re unaccustomed to making big decisions, you can practice and develop the mental toughness by deciding on smaller issues
within your realm. When others are riding the fence between two
tough options, be the one who stands out by advocating for the decision that you think is best and presenting evidence for why. This
leadership quality will be noticed and appreciated. It also can help
you get to and stay in the C-suite.
3
Ron Carucci, “Leaders, Stop Avoiding Hard Decisions,” Harvard Business Review (April 13,
2018), https://hbr.org/2018/04/leaders-stop-avoiding-hard-decisions.
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I’ve always loved being the person on a team who’s held accountable for making tough decisions. Of course, I don’t make them in a
vacuum, but I established myself early in my career as one who was
willing to “make the call.” I’ve since learned to surround myself with
others who have the courage to make tough decisions after doing
their homework on the issues, because having decisive, confident
people on my team makes my job easier.
Of course, effective decision-making is a tricky skill to master
because the outcomes of big decisions rarely exist in black and
white. A strong leader recognizes that a decision might produce
unclear or undesired outcomes, but will decide anyway. Build
your courage to make tough decisions by focusing on the primary
desired outcome. Research the facts, involve others in the process,
and welcome the discomfort.
Put the consequences of the decision into perspective. Ask
yourself, “What’s the worst that can happen?” and “What if I’m
wrong?” Likely, you’ll see that the consequences are not as dire
as you thought. Failure leads to learning, which leads to success.
When a bold decision produces stellar results, internalize them and
use that success to boost your courage.
In the early days of the start-up Thycotic, Becca, a super-talented
individual, ran marketing. At the time, Thycotic focused the majority of its marketing around face-to-face tactics like trade shows,
events, and seminars. When I came on board, I realized there was
no way we could accomplish wild growth through the seminar
approach. We needed to transition to a high-velocity, digital-centric
sales and marketing model. I made a case for capturing buyers at
the point of need with free online tools, free trials, and interesting
content they would want to download.
And this is where Becca’s tough decision-making moment
came into being. She was running marketing at the time, but the
digital-centric approach was not in her skill set. She had to make
a tough decision. She could: (A) get frustrated and leave. (B) Get
frustrated and stay, pretending to go along while resisting and
trying to maintain the old way for as long as possible. Or (C) jump
on board, commit to the success of the company and her own
long-term career growth, and embrace a ton of new learning.
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She chose C.
Though it was difficult at first, Becca took the opportunity to
learn everything possible about digital marketing and high-velocity
online sales funnel models. She made the tough decision to buckle
down and learn, to accept the gaps in her knowledge with grace,
and to realize where the opportunity could take her. She kept her
gaze focused on long-term growth, both for Thycotic and for her
own career. She became an expert in digital marketing. She built
a skill set capable of running the new strategy, and I predict it will
carry her to lasting success and multiple CMO offers. But none of
that would have happened if she hadn’t decided consciously to take
on the challenge and make it work.
Call Out the Elephant in the Room
In a 7:30 Monday morning leadership meeting at a fast-growing
start-up in my past, the CEO suddenly announced that the European leadership team had been let go. There was no explanation, no
discussion, not even a “Does anyone have any questions?” query.
As the meeting continued on to the next topic, everyone glanced at
one another in surprise, and the unanswered questions swirling in
their minds loomed like an elephant in the room—a big, obvious
problem that no one wanted to bring up. Yet the meeting kept
going.
Later that day, I scheduled a private meeting with the CEO
(again, this is the beauty of start-ups where you have greater access
to senior leaders) and asked him point blank about what had
happened. He said the European team had been underperforming,
so he cleaned house.
I asked him what the plan was, and he started answering in
vague, uncertain terms. Eventually, I realized that we had no clear
plan going forward. I got worried—the company was rocketing, but,
if Europe was a mess, all our success was at risk.
My initiative kicked into action, and I offered a solution:
I volunteered to run the European division while he figured it out
in the interim. Two weeks later, I went to Europe with one of our
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top salespeople. I was there for six months, and we turned the ship
around. We actually outperformed the US division in one of those
quarters, mostly because we landed one monster sale.
I was only there for six months, but my decision to call out
the elephant in the room reaped huge benefits. It accelerated the
rebuilding of our European wing, but it also gave me a completely
new experience. In my professional career to that point, I’d never
had success in actual, hands-on sales. I’d always developed my
marketing with an eye toward sales, but it’s not the same thing. In
Europe, however, I got to take part in direct sales and experience
huge success, for the first time.
I agree with Randy Pausch, American professor and author
of The Last Lecture, when he said, “When there is an elephant in
the room, introduce him.” If you look for the elephants, you will
find them. They are the issues everyone else tiptoes around, the
uncomfortable topics others want to avoid. Of course, it’s easier
and less stressful to avoid pointing out big problems or asking
probing questions. But when you are the brave one who calls out
an obvious elephant in the room, you become the stand-out savior
of the speechless, willing to boldly ask what no man or woman has
asked before.
You will get noticed.
One caveat, you don’t want to be seen as bringing up a nonissue.
Before approaching the boss about a perceived elephant, first check
with others to make sure your perception is on target, and that an
elephant of a problem actually exists. And then, assuming it is a big
issue that needs a solution—and this is the crux of my point—offer
to be part of the solution. Because venting or asking about a problem
without any proposed action only lowers your reputation and makes
the elephant grow bigger.
Be Known as an Idea Person Who Executes
There’s no shortage of people with good ideas; there’s a big shortage of people with good ideas who follow up with action that yields
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results. In the highly competitive start-up marketplace, the ability
to think up and execute on good ideas can propel your career and
the company’s growth at the same time.
Great ideas come to people whose brains are constantly open to
them. Think of ideas as the lifeblood of your success in the start-up
environment, where innovation and creativity are critical to staying alive and ahead of the pack. Jumpstart your creative thinking
by asking questions such as: “Is there a better way?” “Why can’t we
do that?” and “What if we do this instead?” Surround yourself with
people interested in the same topics, and mine their thinking to spur
your own. I’ve found that simple ideas often win over complex ones.
Often, executing on a collection of smaller ideas will be more valuable than waiting for that elusive next big idea.
The trick is to allow your mind the space to let your relaxed creativity flow so raw ideas can formulate into actionable ones. Find
your own best quiet time to get into idea-generation mode and go
there often. For me, the best ideas float into my psyche when I’m
just waking up in the morning or when I’m running on a beach.
Around the year 2000, I had been interested in cybersecurity
and I had been hearing over and over how IT security specialists
were drowning in constant alerts from various security products.
I took off running on the beach, my feet pounding out a rhythm
on the sand. I thought about conversations I’d had with influencers,
the solutions I’d studied, and what I had learned about the existing
options that hadn’t worked. And then an idea washed over me: we
could capture and combine the various alerts into a single, meaningful and actionable dashboard!
At this point, I could have decided to document this idea in
a journal and let it stay there, as I went about my full, busy life.
Or I could decide to execute on the idea and make something
happen. I saw its vast potential value, so I further developed the
concept and spent long hours building a business plan. I secured
an entrepreneur to finance it, assembled a team, and in 2003, we
launched eSecurity, the first company to provide the market with
a security information/event management solution. It went on to
become a multimillion-dollar company, and it all started when I
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focused on solving one problem, created the mental space for ideas
to flow, and then took action on the best idea.
For every 10 rough ideas, one brilliant gem might rise to the
surface as worthy of implementing. You will, of course, never know
with 100% certainty which of your ideas are brilliant until after
you’ve tried them out. That being said, there are some ways that
you can gauge where your ideas sit on the gradient of dud to gem.
For one, if you know the metrics of the idea, you will have a sense
of its quality. Using marketing as an example, it’s a lot easier to tell
if an idea has potential if you understand who the target audience
is and what they usually respond to or not. Knowing these things
makes it easier to see where your idea fits.
Second, you can test your idea. This can be both external, with
the specific target audience (for example, holding a focus group),
and internal, like running your idea by your colleagues. Gauge the
reaction you get. Also, dedicate time to testing that’s proportional
with risk. If your idea is a big gamble that requires a large investment, it’s wise to spend more time on testing before you go all-in,
and the inverse is true.
Finally, do a gut check. Sometimes you get a sense that an idea
is a really good one, and, if that happens, follow it. You should still
look at the metrics, do the testing, and refine your idea, but it’s also
important to listen to yourself and trust your instincts.
Too many great ideas whither as a result of inaction. If you have
an idea, no matter how good it is, nothing will happen with it if
you don’t do anything. So, if you get that feeling or a hunch, even
early in your career, make an opportunity to share your idea with the
higher-ups. Be strategic about this, of course, but don’t ever quash
something you believe in because you’re afraid that somebody will
think the idea is stupid. The price of not sharing a great idea far
outweighs the risk of keeping it to yourself.
Chapter 5
Act Like a Leader
(Even If You Don’t
Have the Title Yet)
The only way to think like a leader is to first act: to plunge yourself
into new projects and activities, interact with very different kinds of
people, and experiment with unfamiliar ways of getting things done.
—Herminia Ibarra, professor and author of Act Like a Leader,
Think Like a Leader
Ask a hundred business people what successful leadership looks
like, and you’ll get a hundred different answers. There might be
some overlap, sure, but the truth is that leadership is one of the most
difficult traits to define. Thousands of minds have been exhausted in
an attempt to capture exactly what it means to be a great leader, and,
with so many competing voices offering advice, it’s hard to know
where to look. In my experience, I’ve found five basic habits and
traits to be a great starting place in my development as a leader. They
have helped me quickly go from the ground floor to the C-suite and
I am excited to share them with you now. They are: set clear goals,
prioritize them, remain calm during chaos, make fact-informed gut
decisions, and always work to earn your stripes.
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Set Clear, Inspiring Goals
No one reaches lofty heights without lofty goals. If you want to lead,
then your goals need to inspire you to jump out of bed and give
everything your best each morning. For a goal to be truly attainable, whether it be applied to projects and initiatives, health and
fitness, relationships, or your career, you must give it this level of
enthusiasm.
Far too often, people get stuck in low-level positions because
they let the inertia of a daily workload distract them from their
biggest dreams. Without a larger goal to work toward, years slip by,
and you run the risk of going nowhere. If you don’t set the goal,
then by default, your career goal will become merely to get through
another day. Don’t let this happen to you. Use the opportunity of
working with a start-up to set big goals that inspire you.
With 100% certainty, I would not have achieved anything big
or inspiring without first setting the goal and then asking trusted
advisors for guidance when I found myself beyond my depth. Everything I have achieved in my career has come from setting clear, specific short- and long-term goals, with an overarching “why” that
drives me.
Three Pillars of Goal-Setting
Not every goal is created equal. If you want to see results, master
the skill of crafting goals. I’ve determined that every good goal rests
upon three pillars: specificity, relevance, and competitive attention.
Leave out any one of these, and your goal will crumble.
Specificity means to be precise in the wording of your goals.
“I will sell more than I did last year” is not a goal, it is just a lame
collection of vague words. “I will sell 15% more each month for the
next three months” is a specific goal.
Relevance means that each goal should be difficult to achieve
and directly applicable to your career and path. If you undershoot,
you’ll underperform and never reach your potential. So, here’s the
question: what would you dare to accomplish that would provide
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the most joy and satisfaction? Which mere idea of a goal is so
exciting that it gets your blood moving? Think about your big
achievements as if you were guaranteed to succeed. I like to ask a
team what success looks like if we go a step further, and I call it
“Goals Plus One.” Do the same for all of your goals, and they will
be relevant.
Finally, Competitive Attention means you always aim to
maintain an edge. Pay attention to what the competition is doing,
and set your goals in relation to their actions.
Of course, any goal, no matter how strong the pillars are, will
crumble without a foundation. That foundation is the why, the motivation that drives you. If you don’t understand the larger purpose
you’re working for, you won’t achieve anything. As you set your
goals, give yourself the space and time to think about the why that
motivates each goal.
The Baby Steps
Once you’ve set your goals, the best way to execute on them is to
break them down into baby steps. The system I use to break down
my goals into steps begins by asking the following questions:
What specifically do you want to achieve and what are the milestones along the way?
Who is involved and what are their responsibilities?
Which resources will be required?
How will you measure progress to stay on track?
When will you achieve the goal?
For example, let’s say that I’m setting goals for my marketing
team. For the what, I’ll set very specific marketing metrics about
the amount that marketing needs to contribute to revenue growth.
But deeper than that, I look at it cross-structurally and ask how
much revenue the sales team needs to create. I set very specific
milestones, like I might say that each sales member needs to have
50 or 100 calls in a month, and that the marketing team needs to
deliver new internet ads in a week. I then move on to the who,
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and figure out first what we can do in-house and what we need
to contract out. Then, for the which, I assess which resources we
need—things like materials, money, and time, but again, I get as
specific as possible. For the how, I develop a plan for how people
report on their results, and establish a schedule of meetings to keep
everyone updated and in the loop. And finally, for the when, I create
a master timetable, that, again, gets as detailed as possible about
each individual deadline and milestone. The fact that I’m so clear
about the goals and consistent in holding everyone accountable is
how, at Thycotic, we’ve been able to avoid any major hiccups. For
every single quarter I’ve been there, we’ve hit our revenue goals,
and many times, we’ve exceeded them.
This brings up an important point. To succeed, you can’t just
focus on your own personal goals. Even when you’re just starting
out, it’s better to be seen as a person who helps to ensure that the
project, team, and workplace goals are clear and inspiring. I’ve been
in meetings where a wise person raises a hand and asks, “And why
are we doing this?” because it wasn’t clear. If you don’t have a leader
who shares the inspiring purpose behind the work, proactively ask
him or her for the big “why”—even outside of a meeting, over a cup
of coffee. This is how budding leaders amp up the motivation for
everyone, build meaningful relationships with the boss, and stand
out as potential leadership material in the start-up space.
Keep Your Goals in Sight
Doug Erwin, whom I’ve mentioned, says, “When I speak with
a group of people, I say, ‘Everybody here who thinks you’re a
goal-setter, raise your hand.’ Everybody raises their hand. I say,
‘Keep ’em up. Now how many of you write down those goals?’ And
half the hands go down. Then I say, ‘How many of you write down
those goals and post them so that you see them?’ And most of the
hands go down.” Erwin says that those whose hands are still up
are the ones he wants to hire because they are the ones constantly
focused on what they should be focused on. “You’ve got to be so
damn laser-focused on what your goals are. I’m not just talking
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about having them on your iPad or your phone. You need to post
them in front of you.”
In other words, they need to be visible. When I worked at PentaSafe under Erwin, he created the most powerful visual goal I’ve
ever seen. Just before the year 2000, the start-up was planning for
a big year, and we needed to hire about 15 salespeople so they’d be
ready to go in January. Erwin called a company meeting, and, at the
appointed time, about 50 of us went outside into the front yard of
our building. Erwin sat on the stairs in front of us, and he called up
Eric, a sales guy, to sit on a stool up front. Erwin announced that Eric
had just closed our company’s first million-dollar order, and Eric’s
commission was $280,000.
Right on cue, a Brink’s truck pulled up, two armed guards got
out, and they dumped $280,000 in tens and twenties over Eric’s
head. Erwin said, “That’s what $280,000 looks like.” Then he told
everyone that all of the bonuses he was going to pay out to everyone
would also add up to another $280,000. Everybody was taking
pictures and videos and posting them online. The guards put the
money back in the truck, and we all went back inside while visions
of money stacks danced in our heads. Thanks to all of the employee
posts online, we received more than 100 resumes from salespeople
within the next two days. Attracting quality applicants was part of
Erwin’s purpose for creating this memorable visual, but I guarantee
you that everybody on the sales team got a clear image of their
next sales goal that day, and a powerful sense for the rewards that
awaited them. Keep your goals in front of you, and, whenever
possible, attach a specific image to them so that you can see what
you’re going toward.
A Final Thought on Goals
When you first start setting big goals for yourself, you will probably feel some sort of anxiety or fear. This is natural—you might
doubt your ability to achieve what you set out to do. It’s important
to remember that some of the best benefits of setting big, inspiring
goals aren’t solely in the achievement. Sometimes we don’t reach
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our big goals or we shift gears and adjust to new ones. That’s okay,
because just reaching for a big goal improves your focus, stretches
your capabilities, and helps you grow.
Everything Can’t Be a High Priority
Things which matter most must never be at the mercy of things which
matter least.
—Johann Wolfgang von Goethe, German writer and statesman
Setting clear goals pays another dividend: it provides the barometer to help you decide what to say yes to and what to say no to. In
an intense start-up environment, it’s easy to be overwhelmed by too
many goals when they all seem like high priorities. Don’t be so busy
chasing all the loose dogs that you can’t build a fence. Focus your
energy on the goals that will solve the biggest problems, create the
best results, and propel you the farthest, the fastest.
Early in my career, I had typed up my goals and printed out a
long list to keep in front of me. Just looking at it made me anxious
and jittery. I didn’t know where to start. I asked my manager for
help prioritizing. I handed her my list, halfway thinking she would
be impressed with my willingness to take on such a huge workload.
I thought she would just arrange them in a better order. We spent
about 30 minutes discussing them, and during that time, she crossed
out about half of my goals. She told me that if I tried to accomplish
them all, I would only have a meager pittance of time to spend on
each one, and the results would be equally meager. I’d be going an
inch in every direction without moving a mile. This lesson in prioritization changed my life.
High performers, as I saw myself to be even at that point of my
career, tend to take on massive workloads. This is part of the DNA of
hard-working people, and it’s a trait I respect. But it can also create
significant stress and lead to burnout over the long haul. I’ve learned
that you can be a high performer without being overwhelmed, if you
prioritize your goals. Success isn’t about how much you do. Success
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is about performing the right actions toward the right goals that will
create the biggest impact.
The key is to shift your mind-set. It’s not just about doing
more than everyone else—which, in highly competitive fields of
overachievers, is almost impossible. What will make you stand
out is getting better results than everyone else, and the best way
to do that is to prioritize. I personally like Sheryl Sandberg’s, chief
operating officer of Facebook, idea of “ruthless prioritization,”
which she defines as “only focusing on the very best ideas. It means
figuring out the 10 things on your list and, if you can’t do all 10,
doing the top two really well.”1
I’ve created a framework for ruthlessly prioritizing, and it’s
been my process for 30 years of executive leadership. I start by
creating an annual master list of goals (I hold on to these at the
end of every year and occasionally revisit them to see how my goals
have changed over the years, and what I accomplished or chose not
to accomplish). I break them down into quarterly objectives and
weekly goals, and then I stack each goal into one of three buckets:
Priority A (do these now), Priority B (do these next), and Priority C
(don’t waste my time doing these). From there, I break down my
A and B goals into daily task lists. Every evening, I set aside time
to plan the next day, and I document my top three (only three!)
priorities to focus on for the day. This takes discipline and helps
me focus on the things that matter most so I don’t get caught up
in a sea of distractions. The key is to be realistic about what I can
accomplish each day. When I get to the office in the dark of an early
weekday morning, I concentrate on completing the first priority
before moving on to the next one. This is key—you can’t just go
through the motions of setting goals, you must follow through
with action.
I follow a similar prioritization process for my marketing team’s
goals. We start with the highest-level goal for what we’re trying to
achieve. Using the same example as earlier, our team’s number-one
1
Jeanne Sahadi, “How Sheryl Sandberg Practices ‘Ruthless Prioritization,” CNN.com (October 3,
2018), https://www.cnn.com/2018/10/03/success/sheryl-sandberg-profile/index.html.
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goal might be to contribute a specific amount of revenue to the company’s overall revenue goal. Then, using the aforementioned question, we break it down from there. We make sure each person on the
marketing team knows his or her role, goals, and what specific tasks
to prioritize in order to contribute to our marketing goals and to the
company’s revenue goal.
And we don’t hide our goals and metrics under a bushel.
We blast them out on everyone’s computer dashboard in real
time. We display them on monitors in public spaces throughout
the Thycotic offices. We can pull them up on our phones at any
moment. We literally create a Management by Objectives (MBO)
addendum to the plan, where everyone’s quarterly objectives are
documented and shared with the whole team, and they regularly
report on progress. Everyone in the company can see how the
marketing team is contributing to the attainment of revenue on our
main priority goals daily, quarterly, and annually. This allows us to
adjust as we go, and keeps everyone focused on the highest-priority
goals with no chance of wasting time on fluffy work.
At Thycotic, our senior vice president of international, Simon
Azzopardi, has a cool way of keeping the biggest goal in front of
his team of employees. His teams cover the Middle East, Europe,
Asia, and Africa, and they work with distributors around the world.
To keep everyone aligned, he sets the standard for prioritization by
holding “True North” sessions and gathering diverse teams together
to focus on the most important goal and priority.
He developed his True North process during a 16-hour flight to
Australia years ago. He was sitting in his airplane seat and thinking
about his biggest challenge, which was how to keep so many people
on his international team motivated and pulling the rope in the
same direction. He watched a YouTube video of Stephen Covey
standing in front of a room full of executives. Covey told everyone
to stand up, close their eyes, and point north. Then they opened
their eyes. Everybody was pointing in a different direction. He
explained that this lack of direction caused the highest amount of
wasted resources in companies because everybody was heading for
a different “north.”
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This speech inspired Azzopardi to form the solution to his own
challenge. Starting the next day, he asked his teams to describe their
main goal. “Everybody gave me different answers. I thought it was
amazing that we were even mildly successful without being aligned.
But how much more successful would we be if we were aligned?”
He implemented his own version of a True North strategy, where
everyone on the team is focused on the same goal, and he still uses
it to this day. He later found out there was an existing program, but
it is different than the one he was inspired to create for his teams at
Thycotic.
He starts by defining what True North means for the company,
and then the teams and individuals define their own goals and roles
within the larger context. Every person on his team carries a small
card that is custom for each role, and the cards are updated every
year. The front of the card lists the three main areas of focus, and the
back of the card expands on the three points. This provides the filter
through which the team focuses all of their objectives and activities.
If you want to get promoted, show your value by always moving
toward the True North of your company and team goals. It doesn’t
mean that everything you do every minute has to have a direct tie,
but don’t let busywork, distractions, or obstacles get in the way of
your focused attention on the top goals in front of you. If a senior
executive passes an employee in the hall and thinks, “I wonder what
that person does?” because it’s not clear how the person contributes
to the most important priorities, that employee won’t last long.
Create Order Out of Chaos
Chaos is part of business, especially among start-ups that are trying
to break through in a constantly changing environment. Since
start-ups are more vulnerable, unbridled chaos can lead to disaster.
It’s easy to stay focused when everything is copacetic. But when
chaos reigns, every employee, not just every senior leader, has an
opportunity to step up, lean in, and help to steady the focus on
the big picture, revisit the whys, and initiate clear steps forward.
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It’s demonstrating this kind of leadership that can get you noticed
and accelerate your path to the C-suite.
Chaos can take the form of a financial disaster, a lawsuit, a brand
failure, or a sudden bad reputation. Or, as in the case of PentaSafe
in 2008, it could be a hurricane.
Our company was on the top floor of a downtown building.
When Hurricane Ike hit, flooding rose up in the streets below, and
the city went dark. All of our people were safe, but our servers
were down. We had customers all over the world who relied on our
servers to support them in the use of our products. We presumed
they would not be aware of or sympathetic to a natural disaster in
our city. We knew we couldn’t let our customers down and just
cozy up in our homes and take a surprise staycation.
Everyone went home, but got online and built out a plan for
operating as a team while working remotely. Those of us on the management team navigated the flooded streets and met at our office
building, where city officials allowed us temporary access to our
top-floor offices. We walked up the 25 stories in the dark, humid,
heat of the stairwell, and making several trips, carried out our most
critical servers and equipment.
We moved all of the equipment to a dry location with power,
and our IT team got them all reconnected and fired up so our
customer support could go on. While many Houston companies
shut down during that week, we barely skipped a beat and kept on
providing the same level of support that our customers expected. It
came down to creating order out of chaos. In the midst of the fury,
we had a communication process in place so we could build a game
plan. We focused on a set of priorities and put our customers at the
top of the list.
In another case of mitigating chaos, a hacker launched a DDoS
(distributed denial of service) attack that took down our website
right at the end of a quarter when we were trying to hit our sales
numbers. Again, calmness ruled the day and we assessed the situation, understood what we needed to do, and created priorities. The
employees who demonstrated calm, cool, collectedness came across
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as those who would be able to lead with a steady hand and a plan
when they had a chance to move up to a leadership role.
You can’t control your competitors’ moves, nefarious people, or
the weather. You can, however, have the right principles in place
(individually, as a team, and as a company) so you can handle potential chaos in an orderly way.
This doesn’t mean overanalyzing everything that could go
wrong to the point of fear and overwhelm. That’s counterproductive—if you get stuck thinking about everything that might
not work out, you’ll never be able to get anything done. Instead,
focus on these six ways to build your propensity for creating order
out of chaos, and stand out as a potential leader:
1. Embrace the chaos. While some people shy away from it, great
leaders lean in. They realize that turbulence is part of flying, and
you have to fly through it.
2. Focus on the destination. Chaos is distracting and noisy.
Maintain clarity around where you are headed. When kids are
learning to ride a bike, they quickly realize that they have to
look up ahead. If they stare at their spinning front tire, they will
soon crash, and the crying won’t be pretty.
3. Focus on the must-haves, not on the should-haves. Establish order in the most critical and largest areas first.
4. Be the model. No matter what position you currently hold,
or the level of instability around you, you can demonstrate
your leadership with a clear purpose, determination, and a
sense of calm.
5. Communicate professionally. Take a deep breath before you
speak, and don’t allow your emotions to get the best of you. Others will notice what you say and your body language, even in the
midst of chaos.
6. Properly manage expectations. People naturally want to take
action to quickly eliminate chaos. Resist that temptation. Sometimes, fast action only exacerbates the crisis. You won’t be able
to resolve every crisis instantly or in one fell swoop, and make
sure that you and your team are aware it is a process.
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Make Fact-Informed Gut Decisions
Steve Jobs was famous for bucking conventional wisdom and following his gut, his intuition—and obviously, he scored astronomical
wins. But, you and I are not Jobs, so for us terrestrial types, I recommend a more balanced decision-making leadership style that I call
“fact-informed gut decisions.” Data must drive decisions because
it’s the concrete, proven evidence of a logical, rational set of facts. At
the same time, you need to embrace a bit of Jobs’s cavalier energy
and listen to what’s gurgling in your gut. Part of a start-up’s competitive edge comes from its ability to move fast, and this often means
acting on an opportunity before you have all the data, or before the
data has caught up with reality. Getting too mired in analysis paralysis can negate an important advantage.
One of the times I listened to my gut, and it paid huge dividends,
was when I was one of the leaders of Thycotic, a cybersecurity
start-up that existed before cloud-based security solutions were
popular. The CEO and I were deliberating on exactly if and when
our company would take the giant step to the cloud as a solution
for IT security. We analyzed all the facts about the cloud and
interviewed customers to determine their comfort level with the
idea. The data we got didn’t support the switch—it showed that
most customers didn’t trust the cloud enough to handle all of their
proprietary information. The data indicated that eventually, though
not right away, the cloud would be popular and profitable, and we
should wait three to five years before getting into the game.
But there was this voice in our gut, whispering, You have a
wide-open competitive window; do it immediately.
We listened, and became one of the first companies to offer
cloud-based cybersecurity solutions. That first-mover advantage
put us in a great position to capitalize when the cloud took off in
popularity, and our revenues skyrocketed.
This reminds me of an observation made by Jack Welch, the former chairman and CEO of General Electric, who said, “The best
executive today is the executive that can see around that corner.
[They can see] what’s coming. Not when you’re in the tunnel, and
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the train is coming right at you. Anybody can make change then.
The job is to change before that’s necessary, and it’s the hardest thing
in the world.”2
To become known as a good decision-maker (and therefore a
good leader), you need a great nose for the hard facts and a trusty
gut. It’s okay to trust your instincts—they’re a big part of how you
got to where you are, and will continue to define your life. But,
whenever possible, do your best to support it with data.
There is too much at stake today to overlook the facts, and
they’ve never been more accessible than now. With a few clicks on
business intelligence tools, you can collect raw data and perform an
analysis to help you interpret and contextualize it. Facts improve
the speed and efficiency by which you can predict outcomes. They
give you a clearer picture of the situation and help you understand
what’s working and what isn’t. They can help you understand
what specific tactics drive the most revenue, why sales are up or
down, and if your customers are happy or not. Armed with this
intellectual information and layered with your own intuition, you
can reliably make the best decisions.
We’ve already discussed how you can improve your researching
and data analytical skills. You might be asking: how can I improve
my intuition? It’s possible, but tricky. The first part of this process
we’ve already covered—strive to do your diligence and have as many
facts/metrics at your disposal as possible. Then, get outside opinions
from people you trust so that you’re making more intelligent, educated guesses, instead of just shooting from the hip. After that, the
real growth comes in reflection. Once you’ve seen how each decision you’ve made plays out, review them. What were the outcomes?
How did the factors leading up to the decision affect the outcomes?
Were the results predicted by the data? What surprised you? Was the
decision the right one? Was there a better course of action you could
have taken?
You don’t want to get caught beating yourself up for making
a wrong call. Instead, use these questions to learn from what you
2
Jack Welch and Suzy Welch, Winning (New York: HarperCollins, 2005).
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did, then take the lesson and put the rest behind you. If you do
this enough and are honest enough with how you evaluate yourself, you’ll build up your intuition and it will help you make better
fact-based gut calls in the future.
Earn Your Stripes
In the military, you don’t get stripes on your uniform without hard
work that puts everything on the line. The same thing holds true
in a start-up. You have to earn your stripes, every day, especially if
you want to be promoted. Being seen as a valuable asset is not automatically bestowed upon anyone, even if you arrive with heaps of
success, a resume stuffed with experience, and a vast collection of
knowledge.
This holds true for me, too. When I join a new company,
I never feel worthy of my title until I get a few major wins. Even
then, I never feel 100% comfortable, and, if I catch myself getting
too relaxed in my position, I create discomfort for myself. This
motivates me to keep working hard and proving my worth to my
teammates, and I suggest you adopt this perspective, too.
For example, when I first came on with PentaSafe, Doug Erwin
invited me over to his house for a private meeting, where the executive team told me the challenges that the company faced. Essentially,
we weren’t differentiated enough in the market. I set a goal to overhaul the company’s branding, positioning, website, and marketing
materials—in the first 100 days. Since then, this has become my
calling card and how I earn my stripes whenever I start at a new
company. Just as the first 100 days of a presidency are some of the
most important, I think your first 100 days at a new job are the most
important. It will set the tone for the rest of your time at the company, and show everyone around you what sort of worker you are
and what to expect.
So, I got this team I didn’t know at all, and I came in and said,
“We’re changing everything.” They thought I was crazy—that
there was no way we would be able to pull off all that I wanted to
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accomplish in the first 100 days. I pushed them, hard, and it turned
out that not a single one of them broke under the pressure. They all
were dedicated and talented individuals, and when I pushed them,
instead of stumbling, they ran faster.
At the end of the 100 days, we had a kickoff meeting for the next
quarter and upper management gave me an hour to present what
we had done. As part of the presentation, one of the guys on my
team had created a video that explained how the new logo we’d created encapsulated the company’s mission. I’d never seen it before,
and the video was so incredible that it literally almost brought the
audience to tears (including me).
When I finished presenting all of the work that we had done,
the entire auditorium stood up and applauded. My team all came
onstage and took off their nice button-down shirts. Underneath,
they were all wearing T-shirts with logos that looked like the
“Survivor” logo but it read: “I Survived a Quarter with Kahan.”
The attendees kept applauding my team and me, and, in that
moment I realized two things: my team and I had earned our
stripes and the trust of the company, and I knew that the company
was aligned, united in its mission, and ready to charge forward.
Five years later, we navigated a lucrative exit. If you attack every
situation like it’s an opportunity to display your worth, work
ethic, and creativity, it will pay dividends for your career and
the company.
Be aware that it’s impossible for you to earn your stripes if
you lack clarity on what’s expected of you. The most important
thing you can do is to set clear expectations with your manager
and co-workers. Successful people make sure that expectations
are mutually agreed upon at the outset of their employment, of
their projects, and of their objectives. They revisit expectations
periodically with key stakeholders to ensure they are aligned. When
expectations are mismatched, like it or not, your boss normally
gets the final say. So if you’re not in sync with your boss about
expectations, you may never figure out what it takes to succeed
within your organization and team. Also discuss with your boss
what their expectations are for you in this role.
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Along the same lines, a great way to stand out and show initiative is to go to your boss and say: “Tell me what I need to do to earn
my stripes here.” It will immediately put you on their radar as someone who is dedicated and eager to provide your best work. The key
is to listen to the answer and actually follow through. When you do
that, you’ll put yourself at the front of the pack when the executive
team is looking for new leaders.
Chapter 6
Adopt Winning Work
Habits
We are what we repeatedly do. Excellence, then, is not an act, but a
habit.
—Will Durant, philosopher
Anyone can act like a leader. The true accomplishment is being
a leader. That is what will get you to the C-suite. To be a leader
requires that you live every single day like you are a leader—be sure
your lifestyle and your habits match your ambition. If they don’t,
you’re just lying to yourself. In order to become a successful leader
in the start-up world, develop these six habits until they become
second nature. They are: work hard, focus on end users, present
solutions, pay attention to detail, simplify, and persist.
Work Hard without Feeling Overworked
In start-ups, there’s no easy button. The only way to the top is hard
work. You’ve got to get your hands digitally dirty. Since larger competitors have more people, money, and resources, start-ups compete by outworking them. The same rule applies to you. If another
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person is better educated or better connected than you—how can
you compete? By outworking them. The truth is, the hustle will cost
you. It’s the price for the sustained success, and every accomplished
start-up leader I know has paid.
One of them, Simon Azzopardi, senior vice president of the
international team at Thycotic, says that hard work has bolstered
his success at every step of his start-up journey. Early in his
career, he read a story about John D. Rockefeller that captured his
imagination. The tycoon was asked, “How much money is enough
money?” and Rockefeller replied, “Just a little bit more.” Azzopardi
adopted that mentality and applied it to his work ethic. He says,
“How much work is enough work? Just a little bit more. My ability
to always strive for us to achieve a little bit more has helped me
tremendously in the start-up world. You have to be self-motivated.
Nobody’s giving you ‘atta-boys’ every day. It requires hard work,
and it’s hard when things fail, but when things work, the hard work
and extra effort were all worth it.”
This trait is so important that it’s become one of the primary
things I look for whenever I promote or hire. Early on, one of my
mentors told me to fill my team with workhorses, not showhorses.
The people who end up most successful aren’t always the smartest
in the room—they’re almost always the hardest working.
I’m fortunate in the sense that I’ve been a hard worker my entire
life. A lot of people, especially young people, complain and claim
that they are just not hard workers. The truth is, with practice, anyone can develop this trait. How? Here are my four keys to becoming
a hard worker.
1. Work smart through prioritization. A lot of people say,
“Work smart, not hard.” I agree with half of that. There’s no
reason you can’t work smart and hard, and the first step in
that is cutting the distractions and only focusing on things that
matter. You know what the time-sucks are: unnecessary email,
unnecessary meetings, and activities that are not tied to the
results required to accomplish your goals. Busywork on small,
nonimpactful activities is the number-one obstacle to success.
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Don’t fall into the trap of working hard on nothingness. Make
every moment of your hard work count.
2. Keep your top goals and priorities in front of you at all
times. Create small, attainable goals and link them to specific
deadlines so you can feel your progress. Accomplishing goals is
addictive, and it turns hard work into a habit.
3. Find the habits that help you be the most effective you can
be. Some people I know work best when they set a timer and
pledge to be laser-focused for an hour, then give themselves a
10-minute break, then another hour of focus. I find that I do my
best work early in the morning, so I make sure to wake up, do
my workout, and get into the office before dawn. Figure out the
pattern that works best for you.
4. And finally, celebrate your hard work. Take the time to
acknowledge what you accomplish. At the end of the day, write
down a list of everything that you got done so you can hold
yourself accountable and see how disciplined and productive
you’re being. After a successful bout of hard work, treat yourself
with your own rewards, whatever makes you happy. Recognize
and celebrate others who worked alongside you.
Of course, there is an entirely different set of challenges, both for
workers and managers, associated with working remotely, which is
very common in the start-up world. The remote-team environment
magnifies leadership challenges, so managers need a mix of guidelines, accountability, and trust that the remote team members are
working as hard as those on-site. The best leaders build personal
relationships and get to know their remote workers as best they
can. They don’t rely on email to communicate, but use tech tools
for virtual meetings, instant messages, and file repositories to create
smooth processes for everyone.
If you’re considering working remotely, first have an honest conversation with yourself. Do you have the discipline to treat your
home office in the exact same way you’d treat a traditional office?
To get up on schedule and eliminate distractions? Some people do;
some people don’t. If you don’t, and you try to work from home,
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you’ll hamstring your career by limiting your effectiveness in the
short term.
Regardless of whether you work at home or at the office, one of
the benefits of working for a start-up is that it’s not a nine-to-five job.
It’s way more rewarding and exciting than dragging yourself into the
office and then fleeing right at five. But, at the same time, it does
mean that you won’t just work from nine to five. You’ll have long
hours, especially if you want to get ahead and become a leader at the
company. The incredible thing about working for the right start-up
is that it won’t even feel like long hours. I just went to a PentaSafe
reunion, celebrating the 15th anniversary of when the company was
sold. This was the company where I pushed my team to work so hard
they made the “I Survived a Quarter with Kahan” shirts. And yet,
when we got together, thinking back on those years, all we could
talk about was how our hard work back then didn’t feel like work,
not even for one day.
Show You Know Your Customers
During company meetings at Amazon, CEO Jeff Bezos leaves an
empty chair at the conference table and announces to attendees that
it’s occupied by “the most important person in the room”—the customer. Then, he backs up his talk with an array of metrics, 80% of
which are focused on what customers care about.1 You don’t have to
be founder and CEO to take a page from Bezos’s playbook. Understanding customers will help your company better invest time and
money, get to the heart of problems fast, improve your products or
services, and test ideas.
This is especially important to remember as you move up in a
company. Generally, the higher up you are on the corporate ladder,
the less you interface with customers. This means that, often, the
people making the biggest decisions are those who have the haziest
idea of what the customer wants. When I was at PentaSafe, Doug
1
Bob Thompson, “Take a Tip from Bezos: Customers Always Need a Seat at the Table,” Entrepreneur (May 28, 2016), https://www.entrepreneur.com/article/234254.
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Erwin combated this by creating a program that required managers
to contact five to seven customers, twice a year, within a two-week
time range and ask them five key questions. The questions were:
1. On a scale of 1 to 10, with 10 being extremely satisfied, please
tell us how satisfied you are.
2. Based on the answer above, please provide the reasons why.
3. Do our products help you achieve your goals?
4. How can we improve?
5. Would you recommend our products to a colleague?
After we’d all collected our data, the managers would present
the results to each other in a half-day session. Every single time,
we’d uncover essential insights into what thrilled our customers and
what frustrated them. Of course, all of the most valuable insight
in the world wouldn’t have mattered if we didn’t take any action.
Customers hate lip service, and all too often a company will sink
massive amounts of resources into data collection only to let that
data collect dust. We documented the feedback and chose the most
important items, what steps we would take, and who would be held
accountable.
We didn’t stop there, but instead, completed the feedback loop.
After the meeting, we made sure to follow up with the customers
and update them about whether we chose to adjust our product or
process as a result, and why or why not. This showed our customers
that we were paying attention to them.
So, if you’re looking for a great way to stand out right when you
arrive at a start-up, seek a better understanding of your customers’
needs. As you plan to gather their feedback, know what goals you’re
trying to achieve; prepare questions that will solicit honest, valuable
input; identify the right customers; add a feedback loop; and be prepared to take action. Here are ideas for gathering customer feedback:
•
•
•
•
Proactively interview them.
Send customer surveys.
Attend your company’s seminars so you can meet customers.
Create focus groups or customer advisory boards.
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• Seek input on social media.
• Go where customers hang out and get to know them.
All of these activities are easier at start-ups, where there aren’t
as many layers of policies or rules to work around. Once you have
your data, use it to develop new ideas and share them with your
managers and supervisors. This will show that you’re a motivated
self-starter, a proactive and creative thinker, who is primed for
promotion.
While the above initiative is a great start, don’t limit your analysis to the customers you already have. Expand your definition to
include prospective customers as well as internal customers. Internal customers are often the first downstream users of whatever you
work on. For example, when my marketing team creates a plan, our
first downstream users are our internal sales reps. Usually, these
people are your most valuable sources of feedback about your work.
Spend time experiencing your product or service from their perspective. Ask them what they need and what they expect. This opens up a
two-way conversation where you can also let them know what you
expect and need from them. Stronger internal bonds always yield
better outcomes.
When I closed a mammoth deal working in Europe, it only
happened because I had taken the time to get to know a prospective
customer. We had been working with a large prospect, ABN AMRO
Bank, headquartered in Amsterdam, for nearly two years. For
nearly the entire time, it felt like the deal was on the verge of
closing, but it hadn’t come together yet. In London, I started attending the meetings between Luke Brown, our sales rep, and John
Vincent, the decision-maker at ABN AMRO, to get to know the
prospect. We did these meetings for months and they enabled me to
do two things: (1) develop a clear understanding of ABN AMRO’s
business needs, and (2) develop a strong personal relationship with
John Vincent. Since the meetings had barely pushed the needle,
I decided it was time to leverage these two advantages.
Luke and I knew that John walked between two buildings in
London at a certain time. I essentially staked out in a café in front
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of those buildings, and waited. The thinking was that I could speak
with him outside of an official setting and have a candid, personal
conversation about the deal. And that’s exactly what happened.
I caught up with him on the crowded sidewalk and essentially said,
“John, look. You and I both know this deal is going to be a huge
win-win for both of us. We’ve been kicking the can down the road
for too long. Can you promise me, personally, that you will get it
done?” And he promised, and, sure enough, shortly after that the
deal went through. This wouldn’t have happened if I didn’t have
both an exhaustive understanding of the business benefits of the
deal, and a strong personal relationship with John. If you focus on
developing the same understanding of your prospective customers’
needs, it will set you apart in the start-up world.
Be Part of the Solution
If you’re not part of the solution, you’re part of the problem. You’ve
probably heard this before, but nowhere is this proverb truer than
in a start-up environment. A start-up’s quick-change nature means
more problems and surprises will pop up at a start-up than at an
established company. In fact, as Entrepreneur magazine points out,
by their very nature, start-ups are “companies in search of a problem
to solve.”2 To be a successful member of a start-up, you need to be
the type of person who seeks problems to solve. The key to this rests
in your mind-set—if you’re a negative person, problems can seem
discouraging, but if you keep a positive attitude and focus on finding
solutions, they’ll become exciting.
For example, a colleague of mine, responsible for competitive
intelligence, called to complain that the sales team was ignoring
his reports because his info was frequently out of date. He was so
despondent that he avoided the sales team altogether. Rather than
commiserate, I told him to shift his outlook to search for solutions
instead of just bitching about his problem. I suggested he put
2
Ali Beheshti, “Don’t Go Looking for Problems: Curing Your Own Pain Points Is a Good Way to
Develop a New Product,” Entrepreneur (March 19, 2018).
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together a core group to collect current intelligence, and involve
the sales team in the data-collection process. I told him to present
it as a competition to see who can provide the most relevant, timely
news flashes. He liked the solution and implemented it. It paid
huge dividends, and he was able to provide accurate, timely, usable
competitive intelligence. A week later, everyone, including the
sales team, was singing his praises.
Each one of us is faced with problems of various sizes every day,
inside and outside of work. Some will walk right past a “fire,” blame
others, moan about it, make excuses, or ignore the situation in hopes
that someone else takes it on. Obviously, not a good leadership style.
On the other hand, if you approach problems as one intriguing challenge after another, you’ll go far in business and in life.
That’s also not to say that you need to solve every problem that
pops up in your path like you do in a video game. Like with your
goals, it’s best to prioritize your problems. Ask yourself three questions about each problem: (1) How painful is the problem? (2) how
frequently does it occur? and (3) What are the benefits of resolving
it? Then spend time creating solutions for the problems that rise to
the top, based on these criteria.
This mind-set shift is the first step toward becoming a better
problem-solver, but not the last. You can’t solve most problems
by yourself, so seek input from people you respect. Estimate what
resources are required and how long it will take to resolve. Realize
that issues often take time to resolve. It’s too easy to slip into passivity when change doesn’t happen in a flash. It takes grit to hang
in there and keep making progress. Of course, the best way to solve
a problem is to prevent it. Use your intuition to predict where problems might arise, and take proactive steps to make sure they don’t.
Finally, I’ll leave you with this parable. A man was fishing
in the river when he noticed someone was drowning. He pulled
them out and attempted to resuscitate them. Shortly afterward, he
noticed another person in the river and saved them too. He then
noticed another, and another, and another. Soon he was exhausted
and realized he would not be able to save all of the drowning
people. He went further upstream to find out why all these people
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were falling into the river. He saw that a broken bridge was causing
the problem. He decided he would just go ahead and fix the bridge.3
Pay Attention to Details
(without Being a Control Freak)
A co-worker of mine once spent hours preparing an amazing presentation. He did all of his research, built a gorgeous PowerPoint,
and practiced for hours. On the day of the meeting, he showed up
and pulled out his laptop, but when he opened it, nothing happened.
The battery had died. He searched through his bag, but it was all for
naught: he’d left his charging cord at home. All of that work, and we
just ended up staring at a blank screen.
This sort of thing happens to all of us, including me. It’s easy to
look at the surface level and think that everything is on track, and it’s
easy to put so much focus on the big ideas that you forget to charge
your laptop.
The best way to prevent problems is to never lose sight of
the details. Every project depends on the success of its smaller
components.
In the larger corporate world, the highest-level employees have
swarms of assistants who handle all the details for them. At a
start-up, no one is too high up the food chain to ignore the details
crucial to their own work. Each person needs to build their own
presentations, practice them, and remember their own power cord,
at every level. You’ll never reach the highest levels if you don’t have
a reputation for minding the details.
Often, paying attention to details will allow you to find creative
or even upstream solutions to problems. For example, at one of
my past start-ups, thousands of calls were coming into our call
center. As the call volume increased, the wait time increased, and
customer satisfaction went down. We spent loads of time focusing
3
“Why Upstream?” Public Health for the People. Accessed April 23, 2019, https://upstream
thinking.wordpress.com/upstream-story/.
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on getting the call time down to handle the increased volume.
However, it wasn’t until we examined all of the details that we saw
the problem. We asked why there were so many calls in the first
place. What were they about? Did we have issues with quality or
usability? We discovered that we had a major product problem, so
we had to involve developers and the quality assurance team to
fix the issues, and then provide self-service access to training for
customers. If we had continued to focus only at the surface level,
we would never have understood the true reason for the call spike.
Running this level of analysis can be complicated. Getting into
the details takes time and extra effort. But paying more attention
to them will improve efficiency, minimize the risk of errors, and
turn a good result into a great result. Beyond that, getting the small
things right matters, because even little mistakes can have a big
impact on your reputation, your results, and your entire business.
A friend of mine worked for a large company that printed its
mission, vision, and values statements on slick, full-color cards.
They distributed them to hundreds of executive leaders at their
annual conference, and mailed them to thousands of employee
homes across the system. After they went out, several leaders
noticed that the cards included the line, “Excellence in everyting
we do.” Yes, “everyting.” Even though the cards had a beautiful
concept, purpose, and design—that small, overlooked detail was a
costly mistake that involved reprinting, remailing, and recovering
from the embarrassment.
To become a detail-oriented person, ask more questions, use
lists to keep track of details, audit projects, and get feedback
from others. Of course, there are people who are just not wired
to be detail-oriented. If you fall into that category, still try to do
everything in your power to become as detail-oriented as possible,
but if that fails, make sure you surround yourself with those
who are.
An important caveat: paying attention to the details is not the
same as being a micromanaging control freak. I’ve worked with
plenty of control freaks, and simply put, they don’t last long in a
start-up environment. You simply don’t have that much control.
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I knew one manager who would tell her team, “If the boss contacts you, I want to know about it.” This sent the message that she
didn’t trust her team to say the right things or handle situations
properly. When your team doesn’t feel like you trust them, it undermines everything you try to accomplish. They grow resentful, lose
confidence in you, themselves, and the team’s ability to deliver on
the goals.
Of course, starting out, you might not even have the chance
to become a control freak boss; you might end up underneath
someone’s microscope. If that happens, your goal should be to
create the type of relationship where you model good leadership
skills yourself. First, go out of your way to define the communication expectations in the relationship. Ask how often you should
share status updates, and at what level of detail. Listen to what
the boss wants, but don’t be afraid to clearly tell them what sort of
environment you work best in. For example, you might say, “No
problem, I can deliver weekly reports, but I operate best if I have
the freedom to succeed and some level of autonomy.” Once you
and your boss have reached an agreement, document it and send
it to your boss. That way, when the boss becomes domineering
and controlling, you can pull out the agreement and say, “This
is how we agreed to work together. Do you trust me to do the
right thing?”
Once you advance at a start-up and start leading your own
teams, it’s important to strike the right balance between being
attentive and available to your team without being overbearing.
Doug Erwin made a point to talk to employees at all levels to find
out what was going on in the trenches, but he didn’t believe in
surprise inspections—he made sure to talk loudly for a few steps
before showing up at an employee’s office. Then he’d sit down
with them and have a conversation with the goal of building a
relationship, not evaluating the performance. At the same time,
he learned valuable details that would inform his high-level
decisions. He was learning the details of business operations
in all areas, so he could use it for productive purposes, as good
leaders do.
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Add Value Through Simplicity
Simplicity is the ultimate sophistication.
—Leonardo Da Vinci, Italian Renaissance polymath
Ockham’s Razor states that, all things being equal, the simplest
and most direct solution with the fewest number of steps is usually
the correct answer to any problem. More than 700 years later,
Ockham’s maxim is truer today than ever before, especially in the
start-up world. The person who can take a complex situation and
simplify it will be the most valuable person in the room—especially
at tech start-ups, which deal in high-complexity concepts with
incredible speed. Time and time again, I’ve seen people get bogged
down creating complex, intricate plans that never come to fruition,
and stagnate their careers. While there’s a place for complexity and
details, more often than not, the best, most elegant solution will be
the simplest one, and those who can strip away the unnecessary
and focus on simplicity first—get to the why, the heart of the matter,
the essence—reveal themselves as clear leaders.
To be most effective, your commitment to simplicity cannot just
be the tip of the spear. It has to be encoded into your DNA at every
turn. When I worked for Quest Software (later acquired by Dell), we
used simplicity to differentiate ourselves. All of our products were
simple, user-friendly, and without a lot of additional features. This
is great—in the tech world, often bulky software packed with nifty
but useless bells and whistles go on to fail.
However, I noticed that, for some reason, we weren’t always
outselling our competitors with their bulkier, less elegant software.
I realized that while our products might be simpler, that was only
one aspect of the business partnership. In every other area of the
business, we had huge amounts of inefficient complexity. If we
wanted to be the simple solution, we needed to be simpler top
to bottom—with contracts, pricing, website, customer support,
installation—at every level.
I offered to start a cross-functional simplicity task force, and
my CEO not only agreed, but attended the meetings. We turned
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our tools and processes into smooth experiences just by simplifying
them. We made it easier for customers to try, buy, and experience
our products. We revamped our customer support portal so they
could quickly self-serve their product problems. The results were
immediate and improved the bottom line.
This process, it should be said, wasn’t easy. Almost everybody
in the tech world strives for simplicity, but it’s a next-to-impossible
goal because complex problems rarely have simple solutions. We
were only successful because we had a clear understanding of the
problem we were trying to solve—we didn’t overcomplicate the situation and we didn’t hide behind buzzwords. We made sure we knew
exactly what we were trying to fix, and then did it. That’s my advice
for an aspiring leader striving for simplicity: define the problem, and
then set up a framework and strategy that capitalizes on using simplicity as a competitive advantage.
Persist and Be Patient
Hold on one second longer than the other guy.
—Doug Erwin, chairman and principal, RedHouse Associates
Persistence is the magic of compounded hustle. Of all the strong
start-up leaders I’ve worked with, the one unifying trait is persistence. They all see failure as a temporary obstacle and a learning
opportunity. They don’t let it daunt them; instead, they persist and
find new solutions.
Developing this trait will benefit you at every phase of your
career. For example, as the marketing leader at one start-up, I saw
a prime opportunity for co-opetition. I realized that we could pair
my company’s technology with the tech from a different company
to provide a unique, improved solution to both customer pools.
I suspected this collaboration would lead to higher revenues,
though I didn’t just go on my gut. I validated my premise with
analysts and a few of our key customers, and I set out to propose
my idea to the other company’s executive leader.
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I hit a big, silent, concrete wall. I asked mutual contacts, called
his assistant, approached him at conferences, left messages, and
sent one email a month for six months.
I didn’t want to bug him, but I knew the only way he’d even
consider my idea was if I was able to connect with him directly.
I continued to hold on. My persistence and patience paid off.
I called him one day at 7 a.m. and, this time, he picked up. We both
had a laugh, although mine was more of a nervous laugh because
I thought he’d be upset. I asked for 60 seconds so I could concisely
describe my vision. Here’s where the hard work of preparation pays
off—I’d rehearsed the pitch for my idea countless times.
It worked. He was intrigued and invited me to an hour-long
meeting with him in his office the following week. At that meeting,
I drew on his window a picture of our combined solution and how it
would give us an “unfair advantage.” (His company used windows
instead of whiteboards.) I sketched it out for him like that, and
against the beauty of a blue sky, he saw the elegance of my idea,
and we put the plan into action.
Amazingly, this paid off in an even more impressive way than
I’d expected. One month later, his company bought our start-up for a
nice multiple. This successful exit would have never happened without my persistence.
In her article for Inc. magazine, Robin Camarote calls persistence one of the three characteristics that define high-impact leaders
(the other two are passion and kindness). Her reasoning, I think, is
revelatory. She writes, “Persistent leaders know that nothing works
all of the time or, if it does, they’re playing it too safe. Persistence
is setting goals—big goals—and pursuing them with an uncommon
drive and focus. Persistence is critical because everyone inevitably
gets knocked down, shut out, ignored or neglected at some point in
their professional lives. Persistence . . . enables high-impact leaders
to get up again and again.”4 In short, you need persistence, because
if you aren’t getting knocked down, you’re not trying to go high
enough.
4
Robin Camarote, “High-Impact Leaders Have These 3 Characteristics in Common.” . Inc.
(September 18, 2015). https://www.inc.com/robin-camarote/high-impact-leaders-have-these3-characteristics-in-common.html.
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Persistence almost always pays off. Either you’ll get what you set
out for, or, in the process of searching for it, you’ll learn a valuable
lesson or land on an even better solution. This is particularly true
in start-ups, where, at the onset, a company might go through four
or five different strategies as it searches out its niche. In this world,
you can have all of the talent in the world, but it won’t mean a single
thing if you quit when you hit the first little snag.
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Chapter 7
Choose Carefully the
Company You Keep
If you’re the smartest person in the room, you’re in the wrong room.
—Lorne Michaels, television producer
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A huge part of who we are and how we perform in business and in
life comes from the company that we keep. If you surround yourself
with smart, dedicated, hardworking, entrepreneurial people, then
their qualities will start to show up in you. They will inspire and
challenge you, and you’ll grow in turn. Even better, when other people see you around these high-performers, they’ll start to think of
you as a high-performer by association. The opposite holds true if
you surround yourself with underachievers. This chapter outlines
everything you need to know about how to pick the people to spend
your time with, and the best ways to build those relationships.
Surround Yourself with A-Plus Talent
Entrepreneur Jim Rohn said, “You are the average of the five people you spend the most time with.” If this is true (and I believe it
is), you’ve got to ask yourself how you will ever reach the C-suite
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if you spend the bulk of your time with the people glued to the
ground floor. Nobody starts their career knowing everything they
need to know to succeed—I didn’t, nobody I know did, not even Bill
Gates did. One of the fastest ways to learn these important lessons
is to surround yourself with A-plus people who have gotten results
comparable to what you want. Not only will you be able to learn by
mimicking—they will bring out your best work.
I’m not just talking about intelligent people; the world is
loaded with intelligent underachievers. I’m referring to people who
embody the total package—smart, capable, motivated people who
raise the bar for themselves and those around them every day. Or, as
an article in Entrepreneur defined it, you want to surround yourself
with relentless workers, those with positive attitudes, inquisitive
people, and dreamers.1
James Legg, president and CEO of Thycotic, pulled together a
core team of relentless, positive, inquisitive dreamers, and several of
those people have continued working together for 10 years or more.
“You’re only as good as the people you surround yourself with,”
Legg says. “I’ve been fortunate that many of the top leaders I work
with today have been with me from company to company. There’s
so much value in surrounding yourself with people who inspire you,
and the inspiration goes both ways.”
The last part of this quote is important—not only will A-plus
people help you grow, they will inspire you to reach for goals you
previously thought were out of reach, and also inspire you to produce your best work. Coming up with a clever solution to a problem
doesn’t happen in a vacuum, it depends as much on what we take in
as it does on how we think. Make it part of your career plan to surround yourself with people who challenge your thinking. Ideally,
surrounding yourself with top talent is part of your career plan.
The way to cultivate an elite inner circle starts before you get
hired. When you’re researching start-ups where you might want to
work, look carefully at the leadership team. Who are they and what
might you learn from them? Research them on LinkedIn and other
1 Gerard Adams, “The 4 Types of People to Surround Yourself with for Success,” Entrepreneur
(May 20, 2016), https://www.entrepreneur.com/article/276050.
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sites online where they’re quoted or profiled. Check to see which
leaders seem to be potential mentors.
Especially important is to see if the company you’re looking
at is led by people with an entrepreneurial mind-set. Sometimes
start-ups fill senior leadership positions with people who have been
successful in a larger corporation, but they soon find that they
aren’t equipped to handle the environment of a start-up. To figure
out during the interview process if you’ll be joining a place with
entrepreneurially minded leaders, ask about the company’s culture
and the types of talent they hire. It never hurts to ask to interview
with a broad base of people to get a better feel for the company’s
culture.
When you’re in an interview, ask questions like, “Hypothetically, it’s six months into my employment, and people are raving
about my results. What have I accomplished?” Not only will this
give you a good sense of their expectations and if you’re a good fit,
but it will also tell you if this is the kind of environment that will
push you to grow.
Once you’ve picked the right place, be sure you pick the right
people. Look for the relentlessness, the positive attitudes, the inquisitiveness, and the ones with big dreams who can bring out the best
in you and inspire you to grow. Here, it’s important to talk about
what exactly a high-achiever is. The best rule of thumb is to look for
somebody who, as a total package, is the type of person you want to
model yourself after. Consider who they are and their achievements
professionally, personally, and to a lesser extent, financially.
Observe what kind of a worker they are, how creatively they
think, how driven they are. How do they handle themselves under
stress? When they walk into a room, how do they carry themselves?
Don’t be overly focused on the career aspect. Make sure you surround yourself with people who have the same values as you. Are
they a good person? Are they kind and generous? Are they willing
to share what they know with those who are younger or less experienced? Do they have a family that they respect and love?
Don’t get blinded by an impressive title or a huge amount of
wealth. While these can be indicators of high achievement, they
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don’t necessarily mean that whoever has them performs at a high
level across the board or would be someone you’d want to emulate.
Once you identify a great role model, network with them, either
(or both) in-person or online.
Don’t be shy about approaching these top performers. When
I first started out, I got an assignment that required me to report
directly to the CEO. The CEO was a bit of a bully—he liked to
steamroll people and make them feel intimidated. At first, I was
excited, but also a little bit nervous. It didn’t take long before I got
through the CEO’s intimidating demeanor. Once I did, I realized
that communicating with him accelerated my learning.
This allowed me to discover two things: (1) that I should be
doing this sort of thing all the time, and (2) that nerves are a
good thing. I felt nervous because I wasn’t sure how to handle the
situation—that meant I was in a position to grow. Even now, if
I get too comfortable in a situation, I get worried. I try to always
put myself in a position that inspires a little fear. The key is to not
let that nervousness overcome you—I’ve learned how to channel
it into an ability to work harder, get up a little earlier, and be more
focused on my work.
I understand that approaching a high-achiever might make you
nervous. Good. Lean into it, and whenever you find yourself among
high-level people, use the opportunity to foster relationships with
them. I often see younger employees feel intimidated and hesitate
to seek counsel from senior leaders, those who are more successful,
or those who went to better schools. If that’s your mind-set, you will
stay stuck on the ground floor because it proves that you wouldn’t
be comfortable in the C-suite.
The hesitancy to foster relationships with high-achievers
broadcasts the message, “I think I’m inferior.” As we’ve covered,
the number-one key to success is believing in yourself. If you can’t
muster the courage to talk to your supervisor, how will you ever
run a company?
The other thing to keep in mind when approaching highachievers—and this should reduce the intimidation factor—is that
they’re just people. High-achievers like the same things that almost
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any other person likes, especially the chance to just sit back and
talk about themselves. You don’t need to go in and try to impress
them or try to have all of the answers to all of the world’s problems.
Just be authentic and polite, and you’ll be a hit. Once you like them
and they like you, that’s when the magic starts to happen.
In the start-up world, there’s no excuse not to make contact with
the top executives. If you work for Facebook, you’ll probably never
see Mark Zuckerberg. If you get anywhere near his door, one of his
security teams will bounce you right to the floor. But at a start-up,
the CEO probably has their office right next to yours, and their door
is probably open. Go, as soon as possible, and knock on the door.
Ask politely if you can schedule a time to grab some coffee and just
talk about their company and philosophy. Most CEOs will jump at
this chance—I did this with that bullying, intimidating CEO. He
was more than happy to talk, and the incredible thing is that I said
almost nothing in the meeting. Yet, when I walked away, I’m sure he
thought to himself, “That kid’s impressive.” You can, and should, do
the same.
It’s far better to seek out those who are at the top of their game,
ask them questions to better understand the company or one of its
projects, and soak up the learning. Invite your managers or top leaders to coffee or five-minute conversations; this shows the executive
team that you’re a potential leader who is serious about advancing
your career and helping the company grow.
Of course, you can’t always control who you spend time with.
Sometimes you get stuck working alongside poor performers or
people with negative mind-sets. In these situations, don’t drink
from their poison cup. Avoid spending one minute longer with
them than you have to, or they will drag you down and demotivate
you faster than you can let out a deep sigh. While poor performers
may be “nice” people and may deliver decent results, overall
they’re bad apples that can spoil the entire workplace. If you spend
too much time with the “negative-Nellies,” not only will your
results suffer, but your reputation will, too. Everyone will think
that you’re just like the other low-achievers, and you’ll be viewed
as expendable.
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Find the Right Mentors
Mentors are the secret weapons of successful start-ups.
—Rhett Morris, director of Endeavor Insight
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You never know too much to learn more. At every point in your
career, a mentor can help shorten your learning curve and accelerate your path to the C-suite. I’m no exception—at each point in
my career, a mentor helped me gain specific expertise or eliminate
a blind spot. As I grew, my needs changed and so did my mentors.
In all, I’ve benefited from 10 different mentors and guides.
While it is possible to succeed without a mentor, most don’t.
According to a survey by the American Society for Talent Development, 75% of executives say mentoring has been critical to their
career development.2 The reason for this is that nobody enters any
situation already as an expert. Nobody would expect you to ace
an organic chemistry final without a teacher. Therefore, it’s next
to impossible to achieve incredible results in business without a
guide.
For example, I’ll return to a story I mentioned earlier. I was at
KnowledgeWare and still incredibly green in the business world.
The company was trying to get a consulting branch up and underway, but the original manager could not get results. My boss asked
me to take over. I was eager for the challenge and the opportunity to
prove myself. At the same time, I sweat more than one bullet. Picture
this: me, in my twenties, going to an experienced group of consultants, all of whom were older than me, and telling them, “Hi, I’m
Steve. I’ve never done this before, and I’m your manager.” Sounds
like a recipe for disaster, right?
Luckily, I’d already met and developed a relationship with an
outside consultant who we brought on to help us manage our customer service organization. While he primarily worked with the VP,
I’d seen enough of his skills to be impressed with his knowledge and
2 Alyssa Rapp, “Be One, Get One: The Importance of Mentorship,” Forbes (October 2,
2018), https://www.forbes.com/sites/yec/2018/10/02/be-one-get-one-the-importance-of-mentor
ship/#1ec411b74343.
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ability to build plans and follow through. I made the decision to ask
for his advice on this new project. Thankfully, he said yes.
He helped me put together a three-day workshop to get everyone on the team aligned. At the time, I was just developing my
leadership skills. Such a step would never have occurred to me
without his suggestion, and the results would have suffered for
it. Ultimately, I was able to bring the team to the level of revenue
growth the company expected. To this day, I still put into practice
the things I learned from him as my first mentor.
Choose Your Mentors
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Don’t wait around for a mentor to select you. Be proactive about it.
Seek out advice when you realize that you’re in over your head. Or
even better, line up a good relationship with a mentor beforehand.
The key is to choose carefully and wisely. When you look for
a mentor, first define the areas you want to improve and which
skills and work habits that you need to be successful in your career.
Like any other goals, write these down and keep them in front
of you. Once you have that clarity, look for someone who can
help you enhance those skills. Also, be sure to find someone who
compliments your personality, skills, and needs.
A great place to start is to look at your goals and then identify
people who have achieved similar things. Then, pick one or
two A-plus-talent types who seem like they would be able and
willing mentors. This works best if you start with someone who
already knows your work ethic and with whom you already have a
relationship.
My first mentor told me that he only agreed to help me because
he could see that I was eager, enthusiastic, organized, and, most
importantly, open to new opinions and ideas. If you already impress
daily in the workplace, finding a mentor will be that much easier.
It’s possible to find mentors among those you do not yet know.
Mentors make themselves available at tech accelerators, business
MeetUp groups, and the like. But again, it’s ideal to start from an
existing baseline of a respectful relationship so you know you and
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your mentor share a connection, trust, and similar views on what
you want to get out of it.
Once you have your target, find the right time to engage that
person and open a dialogue so you can ask if he or she is willing to
mentor you. Don’t worry about whether the request will be seen as
rude or off-putting. Remember that almost everyone in a position
of power got there because they had mentors, and most are looking
to pay that generosity forward. Personally, I’ve mentored 15 people,
and I love seeing the people I take under my wing get results.
The right mentor relationship will seem like a natural extension
of the relationship you already have. You may want to start by getting together a couple of times to make sure it’s a good fit before you
both commit to a long-term mentorship. Like any other relationship, this one is a two-way street. The best mentors take their roles
seriously and give you the honest, tough-love low-down about yourself that others don’t want to tell you, and they will advise you on
the best ways for taking action. They can serve as sounding boards.
A great mentor will always look out for your best interests. All of
this can help you reduce mistakes and build confidence.
You have an equally important role as a mentee. For the relationship to be successful, take an active role in the partnership. It
can’t be treated as a casual thing—you must truly desire the insights,
wisdom, counseling, and coaching, and be ready to receive negative
and positive feedback. Take notes. Accept the guidance in a respectful way, ask direct questions, follow through on advice. And here’s
the top responsibility of a mentee: say thank you. Mentors only get
paid in gratitude, so make sure you offer plenty. They believe in the
value of sharing their knowledge with the next generation and they
want to know it’s being put to good use and appreciated.
Mentor/Mentee Relationship Guidelines
The best mentorships operate under a set of ground rules. For
example, the mentor will commit to a certain amount of time
and frequency, and you will act on the mentor’s suggestions and
circle back to let the mentor know how it’s working out or to seek
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additional guidance. After you’ve done that, a huge part of the joy
of mentorship comes from the new surprises and growth you experience. For example, another mentor of mine, and my favorite, has
been Doug Erwin who you know as my CEO at PentaSafe and The
Planet. I regularly sought out his opinions and guidance then, and
I still do at times today. He’s had a huge impact on my life and career,
and I respect his opinions and judgment. But our relationship has
evolved: now, I’d call Erwin my “friend-tor,” a combination of friend
and mentor. He’s not alone: nearly all of my mentors over time
have become friends for life, and I contact many of them at least
every quarter. If you don’t have a mentor, find one. If you have one
mentor, get another. Their insights and assistance will boost your
career in ways that you would never be able to accomplish alone.
Know When to Stay and When to Go
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High-performing start-up employees are like white rhinoceroses:
majestic, rare, and at high risk from poachers. If you follow the
advice in this book and start to shine at your chosen start-up, other
companies will notice and they will try to lure you away. Faced
with this plethora of opportunity, it’s not always easy to know when
to stay and when to go. This choice matters—a start-up with high
growth potential and strong leaders can be a great place to advance
your career, but a toxic environment can stall your career if you
stay too long.
There are other downsides to leaving a position too quickly. You
don’t want to earn a reputation as a job-hopper. Still, you need to
strike a balance. It’s not a great idea to spend your whole career
in one spot. Looking for the best work environment is a lot like
dating—sometimes you need to play the field enough to find out
what gets your juices going. Eventually, there will come a time when
you need to leave your first start-up, or a really excellent opportunity
will appear.
Still, it’s not always easy to tell when to stay and when to go.
This is one of the most difficult decisions you can make, and each
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time you face it, the situation will be unique and will require its own
approach. That being said, there are a few rules of thumb you can
follow.
When to Go
The first rule of thumb is to check your current environment to see
if it’s toxic. Sometimes, having the same experience every day can
make it seem “normal,” but some companies’ “normal” is unhealthy
and a career-killer. If any of the below statements applies to your
situation, it’s probably time for you to find a new start-up:
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• You’re miserable 24/7, and dread going to work.
• Your job is taking a toll on your health.
• Your workplace presents moral or ethical differences that you
can’t live with.
• The company has systemic problems, and it’s a sinking ship.
• It fosters illegal behavior such as sexual harassment.
• You’ve exhausted all opportunities to grow and advance.
During my long career, I’ve passed through many toxic situations that I needed to escape. For example, I once worked for a company where, at the end of a quarter, our numbers weren’t as good as
we had hoped. They weren’t bad, but they weren’t great, either.
The chairman blew his top. He was livid, and scheduled a daylong meeting on July 5, and told every senior leader that we had to
give a large presentation about where our division stood. My colleague and I spent hours of that holiday weekend locked away from
our families in a hotel room, working desperately to construct this
intricate presentation on our marketing department.
The meeting rolled around. It was a grueling affair, and most of
the other divisions presented before us. Then, when it was finally
our turn, the chairman just said, “Oh, you know, we don’t need
to hear from marketing.” And he adjourned the meeting. That was
it—all of that time that we could have spent with our families was
wasted. I felt disrespected and lied to. I no longer felt that I could
trust the chairman.
Ultimately, I left, mostly because of that instance.
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An important caveat: I didn’t leave right away. I gave myself
a few months to process what happened, and when I found that
I couldn’t move past it, I made the decision to leave. If you’re considering leaving a company, I suggest you do the same thing. Take
the time to think through the decision carefully and thoroughly.
Often, you will discover that the problem isn’t as dramatic as you
originally thought.
James Legg, president and CEO of Thycotic, says, “If you go
to work in a particular market or for a particular company, and it
doesn’t work out, go somewhere else. There are so many jobs in
technology. The world is changing and tech is growing. No matter
your religion, have faith that you will find the right fit for you.”3
When to Stay
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The following list includes reasons people decide to leave their jobs,
but they’re not necessarily the right reasons to jump ship. Usually,
these issues can be worked out if it’s to your advantage to stay and
continue to contribute where you are:
• You feel unhappy at work. Most people feel unhappy at work
from time to time. There’s a difference between the ups and
downs and being completely at the end of your rope. If you have
one particularly bad day, don’t make any rash decisions. Wait a
few months to see if a pattern develops.
• You think that the grass is greener somewhere else. This one
can be particularly deadly. If you constantly think about all of
the things that you don’t have, you might get impatient with
your current job and it might make working for a competitor
seem appealing. Before you decide, take an honest look at your
position where you are, and talk to people who already work for
the company that’s your other option. Then, evaluate how green
the grass over there really is.
• You get bored. This might mean that you’ve outgrown the company, but far more likely, it means that you haven’t sufficiently
explored other roles you can play, or a team you can lead, or
3
Author interview with James Legg, April 2019.
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something new you can learn at the company where you work.
If you haven’t exhausted your opportunities to grow where you
are, there’s no point in moving. To move prematurely means
your environment will change, but you will remain stagnant.
Focus on growth.
• You need to make more money. Money is an important factor,
but it doesn’t mean you have to leave the company where
you’re at to make more. Consider first if you are being paid
fairly for your position. Look up the going pay rate for your job
on salary.com to find out. Ask for a raise if it’s justified. And
look for opportunities to take on more responsibility or bigger
projects where you will provide greater value and thus be worth
a higher salary. Whatever you do, don’t decide solely based on
the money, as tempting as that may be. At the end of the day,
extra money is nice, but it’s not the most important thing. Also
consider the people, the challenges, and where you can make
the biggest impact.
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Leaving the Right Way
Whether you focus on putting down roots where you are, or growing shoots in someplace new, it won’t be possible to quickly assess
any of these aspects, and no matter how well you do your diligence,
any move will involve some risk. It’s up to you (with the help of a
wise mentor) to decide which risks have the biggest payout potential in knowledge, skills, location, experience, income, and benefits. Sometimes, the right decision is to leave a good situation for a
great one.
The hardest career decision I ever made came when I was working at The Planet in a job I loved, with a team that was like family,
and reporting to my mentor Doug Erwin. It was a beautiful workplace life. And then, Quest Software, a billion-dollar public company, offered me a higher-level position at more than double the
compensation. They valued my serial entrepreneurship and wanted
a marketing leader with a start-up mentality. I struggled mightily
with this decision.
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You may think the words “more than double the compensation”
would have been enough to sway me, but this decision rested on so
much more. I had to ask myself whether it would be worth it to leave
a workplace and team where I was thriving to head off into the wild
unknown for more pay and a new opportunity. Would I ever have
such a strong connection with a team again? I made a list of the
pros and cons, talked with my family, and consulted with Erwin.
His response was, “I can’t stand in your way.” He then wrote me a
heartfelt personal letter that helped me to make a balanced decision.
After a final gut check, I accepted the offer and left The Planet.
What ultimately swayed me wasn’t the money—I thought that
I would have an opportunity to grow, test myself, develop new
skills, and make a large impact with Quest. In the end, my gut
was right. I went on to build valuable new skills and relationships.
To really sweeten the deal, The Planet sold a year later, which
confirmed my decision and netted me some nice residuals. I didn’t
have to worry about breaking up with my workplace family forever,
as I’ve remained friends with many of them to this day.
A lot of times, moving on to work for a new company can be an
excellent choice, but as with everything else, you need to leave the
right way. If you decide to move on, define your ideal job and manager, create a plan, and set your goals. Never burn a bridge behind
you. No matter what, follow the golden rule to “do unto others as
you would have them do unto you,” which means giving adequate
notice, assisting with the transition, training your successor, helping
your soon-to-be-former teammates succeed, and keeping all communications professional and positive.
Trust Your Unique Path
If, after reading all of this, you still feel intimidated by the gravity
of this decision, that’s okay. There’s something that you can keep in
mind that hopefully takes a little of the pressure off: there is no singular, clear path to success. You will likely, especially in the start-up
world, especially when you’re young, bounce around from company
to company for a while. It might seem like you’re having false starts
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or having trouble getting going, but it all can be a part of the process.
The key is to learn at every stop, work hard, and follow the guidelines in this book.
Take, for example, Simon Azzopardi’s journey to where he sits
now as the senior vice president of international at Thycotic. As
a young man in Malta, he started out working in his dad’s travel
agency business until he took it over as the owner. At one point, the
company needed an updated and secure IT network, so Azzopardi
decided to learn how to do it and take care of it himself. As he did,
he realized he loved the business of IT more than the business of
travel. So he sold the business back to his family and set out on
a course to become a Microsoft certified engineer. Fast-forward
through Azzopardi’s early jobs at software companies. The important thing to know is that he learned when to jump ship and move
to another company so he could continue to expand his knowledge
and gain experience in different worldwide tech markets.
Eventually, he landed at GFI Software, where he created a successful model for accelerating the growth of software sales. His boss
noticed, and that’s when he hit his big break. The way he tells it: “It
was December 7, 2000, and my boss came up to me and said, ‘Hey
Simon, do you like the UK? I’m looking for someone to start up our
operations in the UK.’”
“I went home and spent the entire night setting up the proposal
and business plan for the UK, and I turned it in on December 8 with
no sleep. It took him by surprise. He hadn’t asked me to create a
plan, and he was shocked by how thorough it was. By 11 a.m. that
day, we shook on my new career title and location, and my journey
truly started. I moved to the UK in January 2001.”
Azzopardi says that if he could reread that plan now, he’d probably laugh at it. “In that case, I said ‘yes’ to an opportunity even
though I didn’t have all of the expertise at the time. It led me to so
many other opportunities in my life. Each of us must always offer the
best we can. If we say ‘no’ to an opportunity, we’ve missed it. I try to
say ‘yes’ and then figure out a way to do it.” Azzopardi has continued to take on progressively larger roles at start-ups throughout his
career at US companies, a Danish company, and now Thycotic.
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Looking back on those early years, Azzopardi’s advice is:
“When you’re young and recently graduated, you think you know
everything. The best way to learn how to move up is to realize
that you have two ears and only one mouth. Listen more than
you talk. Understand the culture of your company and where you
can add value. In my case, I’ve always wanted to utilize my skills
and knowledge in languages [he speaks five] and international
cultures, and I’ve been able to use those skills in selecting where I
want to move up. When you work with a start-up that’s growing
and exploding, it usually promotes from within. Joining a start-up
early and staying long enough to prove yourself and rise up, and
choosing who I surround myself with inside and outside of work,
have been the keys to my successful career in start-ups.”
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Chapter 8
Embrace the Power
of Kindness
Transparency, honesty, kindness, good stewardship, even humor,
work in businesses at all times.
—John Gerzema, author, social strategist, leadership consultant
Three things will determine how far you get in your career: your
talent, how hard you work, and how much people like and respect
you. The truth is that people always want to see the people they like
and respect to succeed the most. I’m not saying that every promotion
simply comes down to nepotism, and, indeed, in a start-up environment, talent and hard work are by far the most important. However,
all other factors being equal, and contrary to idiomatic belief, the
nice guys will finish ahead of the assholes. For that reason alone, you
should strive for kindness in the workplace. But beyond that, kindness can actually enhance productivity and make others perceive
you as a leader, all while improving the atmosphere of the whole
office. Here’s how.
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Walk in Others’ Shoes
Leadership relies, almost more than anything else, on empathy. If
you want to inspire people to work their hardest, come up with their
best ideas, and love working for you, you need to understand their
feelings and their perspective. Developing this one skill will give you
the ability to know what to say to motivate them and what environment they need in order to perform at their best. This soft skill is
an absolute necessity for succeeding in the C-suite, especially in the
start-up world. Start-ups tend to attract diverse workforces and also
employ remote workers who might come from places as far flung
as Norway or India. Effective cross-cultural communication completely depends upon strong empathetic skills.
That, and the fast-paced start-up environment, means that you
need to develop the ability to see something from someone else’s
perspective on the fly. This applies to understanding the boss’s reasoning behind a request or mandate, seeing the customer’s perspective, or understanding a co-worker’s thinking.
For example, if a co-worker says, “I propose we add lavender
paisleys to our product packaging,” and you think it’s the dumbest
idea of the month, you can train yourself to respond along the lines
of, “I can see that you’re excited about that idea. Tell me more about
why you think that fits with our brand.”
This gives them a chance to be heard and gives you a chance
to glean a greater understanding that might prove valuable in some
way. It also inspires them to keep sharing more (and hopefully better) ideas in the future.
In any culture, the lack of empathy will stop a leader in his or her
tracks. I once worked with a high-performer whose department suffered from high turnover among his direct reports. He was known
for being inflexible, demanding, and curt in his communications.
He never sought to understand the perspectives, needs, and feelings
of others. His most memorable trait was interrupting when someone
else was talking. Everyone knew it, and we all just resigned ourselves to the fact that he would bust-in midsentence when someone
else was talking. It was as though his priorities and ideas were the
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only ones that mattered. In short, he was the ultimate “I” person,
and you could see it in everything he did. All of his emails were littered with “I” statements, and whenever he spoke in meetings it was
always “I, I, I,” and never “we.”
Eventually, this kind of attitude wears people out, and they stop
wanting to work for you. For this reason, make sure to change the
“I” to a “we” whenever possible. It’s one small way to be seen as a
better leader and team player, and it will help you take your career
further. Being an “I” person, like the man mentioned earlier, can
tank your career. It happened to him; even though he was a high
performer, the CEO had to can him because the costs associated
with the high turnover rate he produced became insurmountable.
Some people mistake this type of attitude for good leadership.
They think that it shows strength and makes them bold, decisive
leaders. While you want to be all of these things, the only things
that an inability to empathize and listen displays is your own arrogance and insecurity. In the end, this will hold you back. I’m sure
you also know talented people who act this way, firmly keeping their
own shoes triple-tied and buckled, maybe duct-taped and zip-tied
to their feet so they don’t have to consider anything from another’s
perspective. Imagine you had the chance to promote one of these
people. Would you? Of course not, because nobody would want to
work with them, and like I said, we all want to see the people we
like succeed.
The data backs all of this up. In a 2018 study conducted by Businessolver, 87% of CEOs say they see a direct link between workplace empathy and business performance, productivity, retention,
and general business health. Additionally, the study found that 81%
of employees said they would be willing to work longer hours for
an empathetic employer.1 Authenticity and empathy are the new
business strengths. They build a greater level of trust and strengthen
relationships in ways that benefit everyone.
1
Karen Higginbottom, “Why Empathy Matters in the Workplace,” Forbes (May 31, 2018),
https://www.forbes.com/sites/karenhigginbottom/2018/05/31/why-empathy-matters-in-theworkplace/#7f2af6da1130.
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How to Develop Empathy
A lot of people believe that empathy is something you’re either born
with, or you’re not. While it’s true that some people are more naturally attuned to the feelings and moods of others, empathy is still a
skill you can develop and practice.
You can start by simply paying more attention to how you
contact your co-workers. One of the least-empathetic practices
that I see all the time is the email “reply to all” feature. Often,
sending a mass communication wastes everyone’s time in reading a
message that isn’t necessary for them to know. It’s even worse if the
message contains a course correction for a specific employee. These
sorts of messages are better handled privately—they spare your
employees embarrassment. Nobody benefits from a public flogging.
The greatest danger associated with the “reply all” practice is when
proprietary information leaks because someone hit reply all by
accident.
At one of the firms I worked for, some partners started discussing a potential acquisition while “replying all” to an email
thread, and a few employees who really shouldn’t have known
about it caught wind. The rumor mill started to spin, and soon the
entire office thought we were on the verge of being bought, which
wasn’t even true. Make sure you develop the habit of paying close,
careful attention to how you handle all of your correspondence.
Here are other simple ways you can practice empathy:
• Listen actively, don’t interrupt, and don’t formulate a response
while listening.
• Summarize your understanding of what someone said before
sharing your response.
• Find common ground.
• Ask empathetic questions such as, “What’s on your mind?” and
“How do you feel the new project is going?”
• Make eye contact to show you’re engaged.
• Practice 360-degree feedback sessions to get feedback from
those above, at your level, and below you in the hierarchy of
your organization.
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• Remember the 7% rule: communication is 7% verbal and 93%
nonverbal. Watch your body language, and learn how to read
your co-workers’ body language as well. It will allow you to
understand their emotional state and respond accordingly. For
this reason, it’s best to rarely use email and instant messaging
to communicate. These tools have their place, but they also
blur the intent, mask the accompanying body language, and
make miscommunications far more likely.
Get to Know Your Team
The most important part of empathy is simply getting to know
your team. This is because, as Prudy Gourguechon, a psychologist
who advises executives on critical decisions, explains in a Forbes
article, walking in someone else’s shoes means that you “Make
sure you are assessing how they would feel in their shoes, not how
you would feel in their shoes.”2 In other words, your goal is to find
out how they actually think and feel, not how you think they think
and feel.
To that end, any little bit helps. During lunch gatherings at
Thycotic, we play games where we each share about our weekends,
or we’ll reveal little-known facts about ourselves to the surprise
and delight of our co-workers. Some of the details I’ve shared:
I used to deejay, and I also once had a managerial role with the
Sugarland Skeeters minor league baseball team. Jon in accounting
told us about the three books of poetry he’d published, and Annette
in R&D told us about her antique sword collection. Sharing this
kind of information, while it might seem trivial, leads to a deeper
connection. It helps us to know who we are working with, and it
builds camaraderie and trust.
Taken a step further, it is also useful to gather information about
your team in a focused, targeted manner. When I offered to take over
2
Prudy Gourguechon, “Empathy Is an Essential Leadership Skill—And There’s Nothing Soft
About It,” Forbes (December 26, 2017), https://www.forbes.com/sites/prudygourguechon/
2017/12/26/empathy-is-an-essential-leadership-skill-and-theres-nothing-soft-about-it/#
351d147d2b9d.
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the lagging European branch of PentaSafe, I knew I needed to win
them over. My first course of action was to diagnose the problem.
What better way than by asking the people working there? Before
I arrived, I interviewed all of the employees in the European branch,
asking them for their diagnosis of the situation, what they needed,
and what I could do to help them. With each person I spoke to,
I made it a point to imagine what it would be like to know that your
previous manager had been fired, and that there was some new guy
coming in. I figured that they would be anxious about whether their
job would be in jeopardy.
I also had learned during the interviews that they wanted
the European offices to be run more like the Houston offices of
PentaSafe. In Houston, we had a lot of fun, as I’ve mentioned.
Big parties with kegs, armored cars with fat bags of cash, that
sort of thing. In Europe, they’d had a stodgy and stuffy work
environment.
The first thing I did was throw a party. I bought loads of good
European beer and brought little gifts and T-shirts over for all of
the employees. I used the party as an opportunity to get to know
my new team even better. I learned that they wanted to be great,
but that the skills and the management had not quite set them up
for their greatest success yet. I took this information (remember,
information is useless without action), and used it to inform
the changes.
My partner Steve McAleer and I organized daily sales trainings
to bolster their skills. But, since we didn’t want them cutting into
our sales day, we held them at 7:30 a.m. Anybody who’s spent time
in Europe will tell you that getting most Europeans into the office
early is no easy feat. But because I knew that they really wanted
to perform and because they trusted me, I was able to go to them
and say, “Look, you want to be great. I believe that you can be, but
we need to put in more work and grow our skills.” We came, we
learned, we sold. As you’ll recall, the European branch went from
underperforming the US to achieving comparable results and even,
during one quarter, outselling the US branch. The results spoke for
themselves.
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Say Thank You and Mean It
The way to develop the best that is in a person is by appreciation and
encouragement.
—Charles Schwab, American investor and philanthropist
If you were to take a straw poll of employees in just about any
company and ask how many of them felt underappreciated, you
might be surprised how many would say they were. Everybody
wants to be appreciated for their work, and when they are, it creates
an amazing, positive environment. I’ve worked with teams where
everyone seemed too busy to even mutter a thank you, and talented
people left because they didn’t feel appreciated.
Conversely, at PentaSafe, everyone was in the habit of saying
a genuine thank you whenever it was deserved, even when everyone was time-crunched by deadlines. When someone gave a presentation, everyone said thank you. When employees held drive-by
impromptu meetings at my office door, they said thank you. This
made everyone feel respected and appreciated.
The analytics about this reinforce the importance of gratitude.
A survey conducted by the John Templeton Foundation shows that
gratitude is enormously important in the workplace. “Ninety-three
percent of those polled agreed that grateful bosses were more likely
to be successful.” And, according to the survey, the benefits extend
beyond the workplace with more than 90% of those polled agreeing
that grateful people are more fulfilled, lead richer lives, and are more
likely to have friends.3
Conversely, when it’s lacking, people leave. A 2017 OfficeTeam
survey of workers and senior managers in the US and Canada
showed that two-thirds (66%) of workers said they would head for
the exit door if they didn’t feel appreciated. It seems that the influx
of millennials entering the workforce has driven the demand for
appreciation ever higher because as recently as 2012, only 51% said
3 Emiliana R. Simon-Thomas and Jeremy Adam Smith, “How Grateful Are Americans?” Greater
Good Magazine, published by UC Berkeley’s GGSC, (January 10, 2013), https://greatergood
.berkeley.edu/article/item/how_grateful_are_americans.
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they would leave if they didn’t feel appreciated. Among millennials
specifically, “the number of employees who’d leave if unappreciated
jumps to seventy-six percent.”4 Gratitude is the key to success today
and for the future, so it’s best to get into the habit now.
Gratitude Is Contagious
One of the best ways for a new employee to make an impact is by
practicing gratitude. You don’t have to rely on anybody else to do
it. You don’t have to wait for an opportunity. You don’t have to be
leading a team. You don’t have to be in the right place at the right
moment. You can create a habit of giving heartfelt thanks, and no
one can stop you.
This can also fast-track you into leadership because gratitude is
contagious. When you show up and start thanking your co-workers,
they will want to pay it forward. People will notice that you were
part of the shift, and likewise, appreciate it. And even if your gratitude doesn’t spread, then it will make you stand out as a positive
force with potential for leadership. This also works in the inverse. If
you have a habit of not showing gratitude to your co-workers, it will
breed resentment that leads to others not showing gratitude. This,
too, will be noticed.
How to Show Gratitude
Most managers and employees miss out on their best opportunities to show gratitude: an annual performance review. Often, these
mandatory reviews are dreaded on both sides. They tend to mostly
focus on areas to improve rather than on great work. I guarantee you
that most managers literally think, “Oh crap. I’m so busy, and I’ve
got to do someone’s review. Guess I’ll get it over with.”
Then during the review, they say, “Great job but you could do
these few things better . . .” and then everyone goes back to work.
4
“Thanks, But No Thanks,” OfficeTeam news release by Robert Half (April 12, 2017), http://
rh-us.mediaroom.com/2017-04-12-THANKS-BUT-NO-THANKS-Survey-Reveals-StrangestForms-of-Workplace-Recognition-Research-Also-Finds-Two-in-Three-Employees-WouldLeave-Their-Job-If-They-Didnt-Feel-Appreciated.
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That’s surface gratitude and not genuine or impactful. In my career,
I’ve had only a few meaningful reviews in which I felt truly appreciated for my hard work as well as gained feedback to address my
deficiencies.
At start-ups, reviews (if they exist) provide the opportunity to
become even more meaningful because of the smaller teams, fewer
direct reports per leader, and the lack of a formal HR structure for
the reviews themselves. If a review isn’t on the calendar at your
workplace, ask your manager for it. Request a serious, detailed
review of what you’re doing well and where you can improve. By
asking for this valuable feedback, your manager feels appreciated
and will see that you want to excel.
I didn’t do that in my earlier years at start-ups, and now I wonder
what golden gems of insights I missed because I didn’t ask. Reviews
also are an opportunity for you as an employee to express your gratitude toward your manager for anything they have done to help you
grow or push you to be a better version of yourself, or for any aspects
of their leadership style you appreciate.
Of course, there will be times when you need to offer someone a course correction. Whenever it’s necessary to give negative
feedback, lace it with a little gratitude. You’ll be amazed at how
it improves performance. Part of the beauty of gratitude is that it
softens the harsh reality of the inevitable negatives we all have to
deal with. There is a psychological aspect to why this is true, as
Dr. Camille Preston explains: “Gratitude, when it’s genuine, has the
power to help transform the emotional bankruptcy we feel when
confronted with negative feedback.”5
Appreciation is one of the easiest ways to make someone’s day,
energize them, and inspire them to do even more. Outside of performance reviews, here are other ways to show your appreciation:
• Say it face to face.
• Write a short note.
5
Dorcas Cheng-Tozun, “5 Competitive Advantages that Gratitude Gives Entrepreneurs,”
Inc. (November 19, 2018), https://www.inc.com/dorcas-cheng-tozun/5-competitive-advantagesthat-gratitude-gives-entrepreneurs.html.
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•
•
•
•
•
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Send an email with “thank you” in the subject line.
Publicly express gratitude in a meeting.
Send a quick text.
Shake someone’s hand in gratitude.
Send a thank-you card or gift.
Post a note or video on someone’s social media.
In public settings and when talking to third parties, thank anyone who helped you, by name.
A great rule of thumb is this: if you feel like you could do a little
more to show your gratitude, do even a little more than you think
you can do. There is literally no excuse not to—it costs nothing to
say thank you, or, at most, you might invest five dollars in a coffee
shop gift card.
If you think you don’t have time to say thank you, realize that
is a lame excuse. Even the former CEO of Campbell’s Soup, Doug
Conant, found time to write 30,000 thank-you notes to company
employees during a 10-year period. If the CEO of a large corporation
can find time to write personalized thank-you notes, so can you. The
results will be huge.6
Create Fun and Joy
People rarely succeed unless they have fun in what they are doing.
—Dale Carnegie, author, How to Win Friends
and Influence People
Any office that wants to be successful must first be fun. This
might seem counterintuitive—but the reality is that nobody will
ever work hard at an office if they don’t want to be there. For this
reason, a fun work environment can help attract and retain the
best talent. This is especially important in the start-up world, as
most potential employees are young and expect a certain level
6 Jill Griffin, “The Value of a Well-Written Thank-You Note,” Forbes (August 7, 2018), https://
www.forbes.com/sites/jillgriffin/2018/08/07/the-value-of-a-well-written-thank-you-note/#
2f106c936500.
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of stimulation from their surroundings. Beyond that, fun fuels
creativity and pushes people to innovate. There is even research
that suggests that fun and joy in the workplace improve overall
productivity. According to the University of Warwick’s Centre
for Competitive Advantage in the Global Economy, “Happier
employees are more productive by an average of twelve percent,
and in some cases, up to twenty percent.”
Fun-raising initiatives can take many forms. At one start-up
where I worked, we once hired a high school marching band to
help get the team psyched up and inspired. The band marched
right through our front door and down the hall toward our
meeting room, drums banging, trumpets blaring, walls shaking.
We were all sitting in our chairs as the huge sound came closer
and closer. Talk about loud; talk about awesome! It worked to
fire us up.
We’ve also held chili cook-offs, surprise ice-cream sundae stations, and company-paid coffees or cocktails. One time, when my
team heard it was my wife’s birthday, they invited her in for champagne and cupcakes. Employees at all levels from all departments
stopped in to partake, including customer support, marketing, and
the IT guys. Conversation took a brief reprieve from business. These
spur-of-the-moment, relatively inexpensive activities help to create
an engaging, memorable, and fun work environment.
If you enter a new work environment and you hear people
complaining about how they never have any fun, then step up. Offer
to put together and lead a little team that will find inexpensive ways
for the employees to have fun together. This will show initiative
and enhance your popularity around the office, two items that will
help you stand out. Finally, always remember that creating fun
and joy at your workplace starts with you. Enter each day with
the mind-set that you will enjoy your time at work. It works for
me. Each morning, often while I’m still in bed and about to jump
into my day, I ask myself, “How will I have fun at work today?”
I suggest you do the same. You’ll start to love your job, work harder,
and produce better results, all while having a great time along
the way.
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Exude Energy and Optimism
When something I can’t control happens, I ask myself: Where is the
hidden gift? Where is the positive in this?
—Sara Blakely, founder of Spanx
Negative and stressful events crop up almost daily at start-ups.
The most successful start-ups are the ones that can operate with an
air of high energy and optimism, because everyone feels like they
are part of something exciting. Instead of being beaten down by the
fight, they find it invigorating. The best teams never lose sight of
the fact that if the product goes big, it can change the world—and
their own lives. Unsurprisingly, in this environment, the most
valuable employees are those who are optimistic enough to put a
problem in perspective, create solutions, and energetically move
forward. This requires optimism balanced with a dose of realism.
Negative-Nellies don’t fit in, but Pollyannas can be annoying. We’re
aiming for a sweet spot near the middle.
If you’re too negative, you’ll never pull yourself out of the swamp
long enough to do anything well. On the other hand, if you have too
much optimism, you won’t be able to see areas of genuine weakness.
As super-angel investor Mike Walrath put it, “The entrepreneurs
that I see, that are the most successful, they have this tremendous
passion and belief that they are going to be successful, and then at
the same time, they can be incredibly honest with themselves about
how they’re actually doing.”7
If you can cultivate your optimism to rest at this magic point,
it will pay huge dividends for your career. It’s not just your level of
optimism that matters, but also the amount of passionate energy
with which you embody that optimism. Passion is one of the most
easily tangible attributes you can cultivate, and it can go a long way
in landing you lucrative jobs.
7
“Startups: Finding the Right Blend of Optimism and Realism,” FOXBusiness (May 19, 2014),
https://www.foxbusiness.com/features/startups-finding-the-right-blend-of-optimism-andrealism.
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Kevin Klausmeyer, a financial expert and noted recruiter of
top-flight talent, says that two qualities he looks for are passion and
tenacity. He goes on to say, “When I say passion, I mean they wake
up every day with a super positive frame of mind, willing and ready
to take on anything that gets in their way.”8
Klausmeyer asks interviewees to share about scenarios where
the dynamics changed and they had to pivot, or to tell him stories
around something they did in school or when working as a team.
He uses the vigor and enthusiasm with which interviewees tell their
stories to gauge their level of passion.9 In short, it’s not enough to
simply have a lot of passion—to be an effective leader and attractive
candidate for recruitment, you need to be able to communicate it.
Keep Your Surroundings Positive
I choose to surround myself with positive, optimistic (yet realistic),
people. They are more fun, more resilient, and they make better
decisions under stress. They don’t sweat the small stuff. And they
help to keep me optimistic, too.
On the flip side, I’ll go out of my way to avoid negative people—
they are a drain on energy. It seems as if some people carry
around a giant straw they use to suck the life out of everyone.
I strongly suggest that you do your best to avoid these types as well.
Give them a wide berth, and don’t let yourself get dragged down
into their negativity. One key to this is avoiding the rumor mill.
Never talk negatively behind the backs of any of your co-workers,
especially while you’re at work. These are simply distractions and
opportunities for insecure people to make themselves feel better
in the short term, but in the long run, it will undermine people’s
ability to trust you and hog-tie your career advancement. Don’t give
in to it.
8
9
Author interview with Kevin Klausmeyer, April 2019.
Ibid.
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How to Foster Optimism in Yourself and Your Environment
I’ve been fortunate to have worked in a number of amazingly
positive work environments, but I’ve experienced the negative
ones, too. I’ve often thought about what separates those positive
work environments from the stiff, gloomy ones. Is it the people,
the culture, the success trajectory, or the perception of the difference we make in the lives of customers? The answer: it’s all of
those things.
Like gratitude, optimism and energy are infectious. Just by practicing them within yourself, you can have a massive effect across the
entire company. For example, recently at Thycotic, we hired a new,
young employee. He asked me for guidance, and I agreed to meet
him at the end of a day after I’d had two four-hour meetings.
As I entered the room for my meeting with him, I felt completely
drained. But this kid came in with a giant smile and tons of enthusiasm and energy. After that meeting, I felt completely revived. He
came to me for help, but that day, just being around him helped me!
Being like that kid—positive, energetic—is a choice you can make,
and it’s one that will put you on the radar of higher-ups the next
time they’re looking for someone to promote.
This is not to say it’s easy. As Joe Robinson, a work–life balance
trainer and speaker points out, “The negative side is much more
powerful than the positive, so we have to be proactive about
bringing the positive forward.” He goes on to explain that research
from the University of California’s Barbara Fredrickson shows that
to keep a cheery disposition, we need three positive events to every
one negative event. Of course, that doesn’t mean you need three
more positive things than negative things to happen every day,
just that you need to focus on three more positives than negatives
a day.10
10
Posted by Joe Robinson, “Working Smarter: How Optimism Boosts Productivity and Work-Life
Balance,” https://www.worktolive.info/blog/bid/336460/how-optimism-boosts-productivity-andwork-life-balance.
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The key, then, is to train yourself to look for the positive. Here’s
how you can do that:
• Surround yourself with positive people.
• Regularly spend 30 minutes writing down all the positives in
your life and the things you’re thankful for.
• Expect highs and lows, and keep them in perspective. Things
that seem like the end of the world are rarely the end of the
world.
• Strive for good enough, not perfection.
• Focus on your strengths, your successes, and your goals, rather
than comparing yourself to others.
• When you hear negative self-talk in your head, deliberately
change it to positive self-talk, even if it seems forced at first.
• Gain a mentor’s perspective on ways to build energy and
optimism.
• When you feel pessimism setting in, interrupt it. Get out of the
office, go for a walk, head to the gym, watch a short comedy.
Then tackle the issues from a more positive, optimistic point
of view.
At the end of the day, you will never achieve great things unless
you believe you can. This is a huge part of why optimism is essential
to reach the C-suite: you must believe you will get there, and then
believe that once you’re there, you can steer the ship the right way,
and even when the skies darken, you will remember that the next
dawn is on its way.
Chapter 9
Take Care of
What Matters
I am not the product of my circumstances. I am the product of my
decisions.
—Stephen Covey, author and speaker
Young, eager professionals can be like high mass stars: they burn
fast, bright, hot, and out. At tech start-ups, the pace of the work
and the grueling hours can grind people down. That is why one of
the most important things you can do to guarantee your success in
the start-up world is to take care of yourself. You will never reach the
C-suite if you can’t handle working in the start-up world for years on
end, and you can’t do that if your mental and physical health aren’t
in top shape. In this chapter, I share how you can protect the calendar from needless time sucks and use that newfound time to put
yourself and your family first, manage your health, and live without
regrets.
Protect Your Calendar
Time is the only truly finite resource—once you lose it, you can’t
get it back. That means that you must exercise extreme care in
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how you manage your time. If you don’t protect your calendar,
people will abuse it. Consider the following calendars: one is
blocked out wall to wall with meetings and events, while the other
features vast swaths of blank space. Which calendar do you think
belongs to the more successful person? The one with all those
meetings, right?
Wrong. The calendar stuffed with meetings belongs to an eager,
excited young professional that I know. The nearly empty calendar
belongs to none other than Warren Buffett, arguably the most successful investor ever. If a man with thousands of people hunting for
a slice of his time can protect his calendar, so can you. According
to Bill Gates, this was one of the most important lessons he learned
from Buffett when the two first met back in 1991, just as Gates was
starting his career. Before meeting Buffett, Gates said, “I had every
minute packed, and I thought that was the only way you could do
things.” But Buffett taught him “the importance of giving yourself
time to think.”1 To make massive leaps in business, to really stand
out, you need to come up with excellent, fresh, innovative ideas.
You can’t have ideas like that if you’re constantly in meetings, on
calls, or answering emails. Sometimes, you just need to block out
time to reflect on the problem at hand and think through potential
solutions, and to set aside time to work on the major tasks that can
lead to large-scale impacts. On top of that, setting aside deliberate
thinking time enables you to get clear on your goals and consider
the paths to lead you to them.
For this and other reasons, it is vital that you aggressively guard
your time so that you can give the most focus to the things that truly
matter. While this may seem obvious, it can be difficult because
there are two major traps that I’ve seen countless professionals
succumb to. The reason they are traps is that they can masquerade
as effective uses of time, but they often are not: meetings, and
should-dos, instead of must-dos.
1
Catherine Clifford, “What Warren Buffett Taught Bill Gates About Managing Time by Sharing
His (Nearly) Blank Calendar,” CNBC (September 7, 2018), https://www.cnbc.com/2018/09/07/
warren-buffett-taught-bill-gates-about-time-management-by-sharing-his-blank-calendar.html.
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Meetings
According to the Harvard Business Review, “Meetings are the
scourge of modern business life, consuming sixty-two hours
per month of employees’ time, on average (a full half of which
is estimated to be wasted).”2 So the question then becomes: if
meetings are so reviled, why are they so ubiquitous? Sometimes
managers overload the schedule with meetings to cover up for
poor management strategies. For example, when a large company
acquired a start-up I worked for, the new head of marketing sent
out invites for daily stand-up status meetings. These were painful
and a waste of precious time. It gave the impression that she lacked
a more efficient way to receive process updates, and at times, it felt
as if she was subconsciously trying to slow progress.
If you end up stuck beneath a manager like this, you have the
opportunity to be proactive and stop the time-wasting. In this case,
our team got together and approached her with a more productive
way of getting her the information she needed. She listened and
changed her approach, and I recommend you do something similar.
Another cause of too many meetings is that some employees
and managers, particularly younger ones, make the mistake of associating more meetings with greater importance. I’ve seen the calendars of young employees who think if they accept every invite,
meeting, and optional event that comes their way, it will make them
appear more integral to the company’s operations. Unintentionally,
this allows other people’s wasted time to become their wasted time.
Then, when they get the chance to lead projects, they go ahead and
fling multiple meeting invites into the masses, and then wonder why
only a few co-workers attend. This kind of behavior only leads to one
thing: burnout—for the young employee and all those people who
come to the meetings they schedule.
The truth is that you can and should be picky about what meetings you attend. Let go of the mind-set that you have to accept all
meeting invites from higher-ups. Perhaps attend the first few on the
2
Dorie Clark, “How to Get Out of a Meeting You Know Will Waste Your Time,” Harvard Business
Review (January 3, 2018), https://hbr.org/2018/01/how-to-get-out-of-a-meeting-you-know-willwaste-your-time.
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schedule to measure the meeting’s value to you. You can then adjust
your schedule as needed.
Here are two strategies I recommend to reduce the number of
time-wasting, energy-depleting meetings you attend: (1) ask your
boss for help in establishing meeting priorities and which ones you
have the “air cover” to say no to. (2) When you’re invited to a meeting, ask, “Why specifically do you need me to be there?”
You may fear this will sound rude, but it’s just a question. There
may be a good reason for your presence, but many times you’ll find
that it’s not necessary for you to sit through the whole agenda. Often
it makes more sense for you to get a status update with the results,
or pop in for the part that is relevant to you. Learn to sort meeting
invites into two piles: a “must be there” pile, which you attend no
matter what, and the “nice to be there” pile, which you don’t.
You may think that declining meeting invitations will make you
less popular or make people in the office angry, but that won’t happen as long as you respectfully decline. Whenever you decide not
to attend a meeting, send a quick, polite note to explain why. Don’t
be curt—it will piss people off. Of course, this, like anything else in
business, is a skill. You may have a hard time saying no. I did, too,
at first, but it gets easier with practice.
Unnecessary meetings aren’t the only ones that can waste
your time—sometimes, important meetings suffer from poor
organization and result in meeting sprawl. For example, many
ad-hoc meetings start as 15-minute around-the-horns to quickly
share information and create actions, but they turn into 52-minute
drone-ons with each person trying to make their tasks sound beefy
and impressive, while everyone else is thinking about what they’re
going to say next, or wishing they were elsewhere. When this
occurs, the meetings become more about posturing than getting
anything done.
You can remedy this whether you’re the leader or a participant
by pressing for a purpose and an agenda. Start on time or request
that the leader gets started at the appointed time. Ensure meetings
end with a summary of what was covered and a set of action items
with accountability.
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Another piece of meeting advice: mix it up. Cookie-cutter
agendas and locations are boring. To add interest, you can choose
to deep-dive on topics, invite others to present, change the location,
and, whenever possible, keep them short. If you look around the
room during a meeting and people’s faces look like death has
descended upon the corner conference room, then you know the
meeting has gone on too long, become too boring, or gone too far
outside the range of value for participants—or all three.
The Should-Dos Trap
If you follow the advice in this book, you will probably start to set
weekly goals for yourself and make to-do lists of the things that you
need to accomplish. Then, when you accomplish them, you’ll cross
them off the list and you’ll feel a rush (if you haven’t already) of joy
and satisfaction to see that crossed-off item. You’ve accomplished
something, and here it is: proof in the form of a neat black line
through a bullet point.
This habit will serve you well in the start-up world, yet it’s easy
to get carried away with the rush of crossing things off. I’ve seen
this happen to many motivated young professionals—they get so
addicted to the feeling of knocking a to-do off their list that they
keep adding more and more tasks to it—mostly menial ones.
They do all of this stuff and feel like they’ve accomplished so
much because they’re crossing things off the list. What they don’t
realize is that success comes from deliberate, concentrated action,
not just any action. When you add a large number of superfluous
tasks to your calendar because they are easy to check off, it takes
away time that you could be spending on your most important
goals.
To avoid this trap, strive to be sure that your calendar and your
top priorities are in complete alignment. If you take on too many
minor things, you’ll end up busy as hell without going anywhere.
In order to achieve this ideal, do two things: (1) proactively put
the high-priority items on your to-do list first and (2) have an honest
conversation with yourself about how each task you give yourself
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moves you toward your overall goals. If a task doesn’t contribute to
your overall goals, you ought to question why it is on there.
Maybe one of your top objectives is really difficult and you
put a couple of lower-priority things first on the daily schedule
as a warm-up to give you the momentum you feel like you need
to tackle the top-priority thing. That’s fine. We all have our own
ways of working. And besides, it is functionally impossible to get
your activities to match up 100% with your top objectives every day.
Things pop up in life that you’ll need to take care of. The key is to
make sure that the top priority items still get done—if the way your
calendar is structured prevents you from doing that, go and excise
some superfluous items.
When you’re a young professional or when you’re working in a
start-up environment, it can be difficult to figure out what to prioritize, as the role you fill might be less defined. Early in your career,
it’s best to ask your boss to fill you in on the company’s top priorities as well as the important objectives within your specific department. Then you can seek advice on how you can take specific action
toward these objectives.
Here’s a great approach. Ask them, “If in six months, you and
I are having a cocktail to celebrate something I have just accomplished, what did I do?” Your boss’s answer will provide a better
sense of which tasks to prioritize, and help you stand out.
To leverage this into a way to be seen as C-suite material, make
sure to follow up. If your boss gave metrics for you to hit in a couple
of different areas, once you’ve gone out and done the work, come
back and say, “Hey, we hit the metrics here, but we didn’t quite reach
it in this area. I’ve thought about this, and here’s how I’m going to
fix it.”
Every executive I have ever met would treasure a young professional who did that, yet it almost never happens. If you do it,
it can help you stand out and move up and propel you into the
C-suite.
On the flip side, once you reach a management position,
it becomes your job to make sure that your team focuses on
the most important tasks. For example, in my work as CMO at
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Thycotic, I keep my team focused on our overall goal of growing
revenue. There are lots of other, smaller tasks or things that we
as a marketing department can do, many of which are easier or
a lot more fun than doing the things that contribute to revenue
growth. If you don’t pay attention, your workers will naturally drift
toward those tasks. This doesn’t mean that these tasks shouldn’t
be done, but that they must take a backseat to the company’s top
priorities.
Be Your Own Top Priority
The most important item on your calendar is you. You are priority
number one. Does your calendar reflect this? Go ahead and open
your calendar right now, and check to see how many appointments
you have with yourself this week. I’ll bet you have too few.
Think about the most valuable uses of your time, create estimates for how long your top business and personal priorities will
take you, and block out that time on your calendar—as early as
possible. First, block off the time you need to care for yourself and
your family. Personally, I look at my calendar at least two weeks in
advance and I block out time for myself, such as workouts, family
time, learning time, and strategy time. I then block out regular meetings that I know I need to attend.
Notice that I don’t just leave my personal time as white space
on my calendar—if you do that, people will think that time is free
and try to schedule you in another soul-sucking meeting. Blocking
off the time lets everyone know that I have priorities, and that the
blocks of time I listed earlier are untouchable, except in the most
extreme circumstances.
Regardless of what your calendar says, the person you have to
protect your calendar from the most is yourself. Good time management not only means you make sure to set aside the most time you
can, but also that you use your time efficiently.
Often, people try to enhance efficiency by multitasking. Don’t. It
doesn’t work. Focus on one priority task at a time. Finish it and move
on to the next. The American Psychological Association reported
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that “Multitasking takes as much as forty percent more time than
focusing on one task at a time.”3
In addition to setting aside time to handle your top-priority
work, make sure to add essential meetings to your calendar.
These should include regular touch-base meetings with your boss.
Such one-on-ones help you sync up, set priorities, and combine
brainpower to deal with issues. If you have a crappy boss who
doesn’t schedule time to meet with you, be proactive and request it.
You can even set this expectation in an interview before accepting
a new job.
Put Your Family First
Here’s a secret to my success: I’m a workaholic and I put my family
and myself first. Even at start-ups where long hours are the norm,
you don’t need to sacrifice your family to excel or make it to the
C-suite. Unfortunately, many make that choice and they pay a terrible price. Time is your most precious resource, in business and in
your personal life. Kids and grandkids grow up, marriages need nurturing, and elderly relatives may need attention, too. All too often
I’ve seen someone climb as high as they can in their career, and
then they look at their weathered face in the mirror and realize they
missed spending time with the people they valued the most. Success
loses much of its sweetness when you have no one to share it with.
We all face the conflicting priorities of work and family. Each
one of us has our own unique situations and priorities—there is no
one-size-fits-all solution to the problem, and, indeed, over the years
the amount of time you need to dedicate to work and family will
fluctuate.
It’s a constant tug-of-war. Part of the problem stems from living in an age of universal technology accessibility. Company leaders often hope and expect employees to stay connected and to be
available at a moment’s notice at all hours: early in the morning,
3
Matthew Toren, “Why Multitasking Is a Myth That’s Breaking Your Brain and Wasting Your
Time,” Entrepreneur (September 28, 2017), https://www.entrepreneur.com/article/299029.
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lunchtime, all afternoon, dinnertime, evenings, weekends, and even
on vacations. If you let them have it all, they will take it. Instead of
enjoying the ocean with your friends or family, you will be sitting
under a cabana trying not to get sand in the keys of your laptop.
To find the right work/life balance, you’ve got to ask the tough
question: how can you be the most effective provider for your
family? The typical answer to this question is that work and income
have to come first. But that puts you on a slippery slope. The right
answer to this question is that work and family time are equally
important because they are interdependent. I know that if I’m
unhappy in my personal life, it will negatively affect my work life,
so I don’t let that happen. Likewise, I know that if I’m unsuccessful
in my professional life, it will negatively impact my family, so
I do what I need to do to succeed at work. The key is finding a
happy medium.
This medium can seem impossible to find, but you will experience significant benefits by seeking it. A study by Family Living
Today and NowSourcing reported that 66% of full-time employees
don’t strongly believe they have achieved a work–life balance.4
The study went on to say that this lack of balance includes both
short-term and long-term consequences. In the short term, at
home, 51% of respondents said they’ve missed out on important
life events, and 40% said they’ve had time spent with the family
ruined by work. In the workplace, 68% experienced poor morale,
36% reported poor productivity, and 41% reported a high turnover
rate due to burnout and fatigue.
The long-term effects are downright scary, as those who lack
work/life balance carry a higher risk of heart disease and stroke, as
well as depression and anxiety. Striking a healthy work/life balance
could literally prolong your life.
And it is attainable. I’ve been an executive leader the better part
of 30 years while keeping my family as my top priority. I’ve always
worked hard to set aside time for my wife, my kids, their games
and performances (when they were young), and my friends. It
4 Cynthia Lopez, “Work/Life Balance in the Modern Era (Infographic),” Family Living Today (January 9, 2019), https://familylivingtoday.com/work-life-balance-modern-era/.
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wasn’t always easy, but co-workers have respected and understood
my commitment to being there for my family. Many have told me
that they appreciate the example I’d set, as it helped them feel
comfortable doing the same.
The key is to establish a boundary between work and home life
and stick to it. If you’re going on vacation, don’t work during the
day, and only answer emails within a specific time window. I also
unplug from work while at home and eat dinner with the family at
least four times a week. Literally, unplugging means no electronics
at the table or during family time, because if they are on or around,
the temptation to just tap out a quick email is too strong.
Of course, there have been times when I’ve been out of town or
attending an evening board meeting and had to miss a family event.
It’s okay as long as it doesn’t happen too often. Families understand.
As long as this kind of thing is the exception and not the norm, then
you’ll be well on your way to striking a healthy balance.
As early in your career as possible, be proactive about putting
your family first. Be present for important family events and
moments. Surprise your family by occasionally coming home
early or leaving for work later. Schedule work outings that include
your family. Plan special family activities, but also be there for the
day-to-day interactions. Work on becoming a good listener to each
person in your family or close friend group, so you know which
types of interactions are most important to each one. Co-workers
will come and go, but your family is with you for the long run and
should be paramount.
Make Health and Fitness a Priority
Start-ups move fast, and this requires you to be able to keep up.
You must have energy and stamina, focus, and be able to handle
stress. If you want to excel, create time to support your own health
and fitness. Taking care of your body will pay huge dividends in
stress reduction, as well as improve your efficiency and overall
mood. All of these benefits add up to a higher performance in
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the workplace. While it might seem like taking care of yourself
takes a lot of time, the opposite is actually true. You don’t have time
not to exercise, eat well, and sleep enough. None of us do.
Work Out
Just about any successful executive will tell you that working out
is a vital component of their success. Dick Costolo, former CEO at
Twitter, says that exercise “is probably the best investment in yourself that you can make. You’ll get a much bigger return from 20
minutes of exercise than you will from another 20 minutes wading
through emails or being in meetings.”5
The proof isn’t merely anecdotal. An article by the BBC cited
a study showing “that regardless of age, people experience ‘immediate benefits’ for cognition following ‘a single bout of moderate
exercise,’ such as fifteen minutes of moderately intense cycling on a
stationary bike. These findings suggest that working out during the
day could be even better than bookending gym time before or after
the office.”6
It works for me. I personally work out twice a day—once right
when I wake up, and again during my lunch break. Before I blocked
my calendar during lunch, it was difficult to say no to invites during this popular time for casual meetings. I would succumb to these
working lunches, and as a result, I felt less productive and less energetic in the afternoon. Finally, I got my priorities straight. While
there have been exceptions, I block out the lunch hour on my calendar and politely say no to invites. Working out has produced far
greater results in my work output and my health than using that
time for work or socializing ever did. I recommend that you do the
same—block off that time and protect it.
Over and over again, I’ve seen new employees at start-ups
quickly gain weight as they became so caught up in the long work
5 Pete Liebman, Work Stronger: Habits for More Energy, Less Stress, and Higher Performance at
Work (New York: Skyhorse Publishing, 2018).
6 Bryan Lufkin, “How to Exercise During the Workday (and Why It’s Important),” BBC (January 17, 2019), http://www.bbc.com/capital/story/20190116-why-you-should-exercise-duringthe-workday---and-how.
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hours and job demands that they stopped exercising and started to
neglect their own nutrition. Don’t let it happen to you!
One of the most common excuses people give for not exercising
is that they “Don’t have time to exercise.” Whenever I hear this one,
I always ask, “Do you watch TV in the evening? Do you sit in needless meetings? Do you make time to work on your B priorities? Can
you block off your lunch hour every day?” If they answer yes to even
one of those questions, then they have time to exercise.
Even Richard Branson, who founded the Virgin Group and has
started more than 400 companies, makes the time for working out.7
He described his “systematic fitness programme” to keep his weight
down and build his bone mass and muscles. He says that every day
he does an hour of weights and band stretches, changing workouts
and muscle groups every other day. He also plays tennis and enjoys
ocean kitesurfing. If Branson can find the time to work out while
planning a space trip and running the Virgin conglomerate, then
you can, too.
Of course, setting aside workout time can be more difficult
in a start-up setting. While larger companies may have employee
wellness teams, on-site gyms, or a complex wellness program
complete with incentives, start-ups often don’t have the bandwidth
or budget for such initiatives. Employees are often left to maintain
their health on their own accord, so you have to be proactive
about managing your fitness. If you don’t want to get sweaty in the
midday, at least take a refreshing mental break to get away, take a
walk, or find a park bench and read a nonwork book—anything
that gives your mind a chance to disconnect and reboot. After work
hours, go to a gym or go to YouTube where you can find everything
you need to exercise outside or at home with free online guidance.
Any exercise is better than none, so take the walk, take the stairs,
get out of the rideshare car a few blocks early so you can walk the
rest of the way, stretch at your desk, go dancing after work, or hire
a trainer. Bottom line: do whatever physical activity makes you
feel good.
7
Richard Branson, “New Year New Goals,” Virgin.com (January 2019), https://www.virgin.com/
richard-branson/new-year-new-goals.
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Eat Right
Good nutrition benefits your body and boosts your brain’s performance capacity at the same time. Marcel Daane, acclaimed
executive and fitness coach, wrote in Headstrong Performance, “In
today’s highly competitive and volatile business world, executives
are expected to be able to accomplish more with less resources,
thus resulting in a demand for a capacity to inspire, perform, and
innovate that is much greater than we have ever seen before. . . .
To maintain performance capacity, those resources need to be
replenished periodically by high quality fuel.”8 In short, eating well
will not only extend your life, but it will also help you reach the
C-suite.
With so many experts promoting wildly different nutrition programs and advice, I’m not going to suggest any “fuel” plan in particular, but you already know that none of them includes a side of fries.
When eating to maximize capacity, avoid fried foods as well as foods
that are heavy in bread or sugar, as they tend to cause an energy
crash after you consume them. I like to eat as many different types of
vegetables as possible and stick to leaner proteins. Some co-workers
I know find that avoiding large morning and midday meals and just
snacking on protein foods, like nuts, helps keep them sharp. Find
whatever diet makes your body and brain feel the best, and stick
to that.
Sleep More
Finally, any discussion about health should include the topic of
sleep. We spend about one-third of our lives sleeping, and we
know that how much we sleep impacts every area of our lives. If
you’re not getting enough sleep, use this as a wake-up call to make
changes.
As an article in Inc. points out, sleep is undervalued. “For
entrepreneurs, sleep is often one of the first casualties of growing
8
Marcel Daane, “Brain Capacity and Leadership Behavior,” Headstrong Performance, https://
headstrongperformance.net/brain-capacity-leadership-behavior/.
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a company. In our culture where being busy and working beyond
capacity is celebrated, sleep is undervalued—but that is changing
as we learn more about the importance of adequate rest. Instead
of being wasted time, there’s mighty ROI in a good night’s sleep,
especially considering that a lack of sleep contributes to a host of
health problems from heart disease to obesity to reduced cognitive
function. Yet, approximately a hundred million Americans don’t
get enough sleep.”9
To make sure that you reach the C-suite, and are alive long
enough to enjoy it, see that you get enough rest.
Personally, I live by the following rule: sleep when and as much
as you need to. I think any study that says “you must get X hours of
sleep” is B.S. When you’re getting too little sleep, you’ll know. You’ll
be walking around almost like a zombie, unable to focus on your
work, irritable, and in want of good ideas.
Pay attention to how much sleep you get and notice your relative
performance. That will help you zero in on how many hours you
need. I know some people who need a full eight hours to be their
best, and some who get by just fine on five and a half. Find what
works for you.
Duration is only part of maximizing the efficiency of your
sleeping habits. The other part comes from understanding whether
you’re a night owl or an early bird, and then, as much as possible,
planning your sleep and work schedules accordingly. For me,
I know that my most effective hours come in the morning, so I get
up at an hour that most people would think is ungodly, go work out,
and get into the office usually before most others arrive. Because
I know this about myself, I try to schedule as many important
meetings and presentations in the morning as possible. I can still
perform in the afternoon, of course, but it takes extra effort, so as
the day goes on, I try to schedule less and less.
Now, you may know that you’re a night owl, that it’s impossible
for you to get up super early and drag yourself to work, but at night,
when everyone else is asleep, you can sit down, focus, and knock
9
Entrepreneurs’ Organization, “Wake-up Call: Eight Ways Entrepreneurs Can Get More Sleep,”
Inc. (November 6, 2018).
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out a ton of top-notch work. This can be a challenge if, for example,
you’re a night owl and your boss is a morning person. They might
see you come in a bit later in the day and say something like, “Why is
it that I never see you in here at 7 a.m.?” To which you can say, “Well,
since I leave so late, between you and me, I think we’ve got the clock
covered.” You can defuse a potentially tense situation by turning
it into a joke, and reminding your boss that you still get the hours
in. If you’re polite, any competent manager will respect the work
schedule that maximizes your personal results.
Live Life to the Fullest
I vividly remember conversations with my grandfather when he
described how, someday, he would open a deli in Chicago. His
eyes would sparkle and he’d smile as he described his plans with
passion and detail. He had the entire business plan in his mind.
You could tell he had put years of time into thinking through every
detail. But eventually, all of these conversations ended with his
spark of passion fading, and him falling back into his well-practiced
excuses. I would tell him it wasn’t too late, but he passed away six
months to the day after the last time he shared his restaurant dream
with me. My grandfather was an amazing man who accomplished
much, but he never acted on the true burning desire of his heart to
open his restaurant, and he died with regrets.
We all want to live life to the fullest and say yes to the people,
experiences, and careers we’re passionate about. Yet so many people, like my grandfather, sit on their dreams, and end up in old age
pondering the things they woulda, coulda, shoulda done if only the
time or situation had been exactly right. Here’s the thing: the situation will never be exactly right, and neither will the time. You
will never reach a point where you’re completely ready to follow a
dream. You just have to start.
So, how do you start? Figure out what you want. Close your eyes.
Ask yourself these questions and answer them honestly. What are
you super passionate about? What do you keep putting off? What
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type of workplace would invigorate you and your dreams? Do you
already regret some area where you haven’t yet taken a leap of faith?
Are you willing to take that leap now? How will you feel when you
start taking action on your passion?
If you answer these questions honestly, you’ll have an idea of
what your dreams and passions are. Once you have an idea, start to
take the first baby steps toward those goals, make time for them on
your calendar, do your due diligence, and take the leap.
Watching my grandfather die with so many regrets broke my
heart. Yet I learned from his suffering. I have taken many leaps of
faith—in fact, my entire career has been a series of leaps of faith.
Often, I did not know how I would achieve a result, but I trusted that
I would figure it out. I did not know how it would work out for me to
change companies, or if the new company would be successful. But
I’ve learned that if we make time for our dreams and priorities, we
will achieve the landing on our leaps of faith more often than not.
I’ve gained career and life success beyond my wildest dreams,
and it all started with the biggest, wisest leap of faith I ever could
have made: joining a tech start-up.
Acknowledgements
O
ver the past 30-plus years of my career, I’m fortunate to
have collected so many meaningful and memorable experiences. Now I feel especially fortunate to write a book that
draws from those experiences and shares them in valuable ways.
This process has led me to reflect on the meaningful people and
relationships that have made it all possible.
My list begins with my loves.
My wife, Terry, my love always and in all ways, who has been by
my side through every step of this incredible life journey. For more
than 30 years of marriage, she has made our house a loving home
and sacrificed in many ways for me, our family, and my career. She
is truly the CEO of our home, and I am forever thankful for her love
and for her passion for motherhood as we raised our two wonderful
children.
My children, Christopher and Jennifer, who have become such
successful, accomplished young adults who I am immensely proud
of. My third child is my son-in-law, Ryder. We couldn’t have chosen
a more perfect son-in-law if we had tried, and I’m blessed to say I
have three children.
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ACKNOWLEDGEMENTS
My first grandchild, Hunter, who is my number-one play
partner. I love watching his smiles and laughter light up a room.
He puts life and work in perspective. I look forward to meeting
Savannah, my second grandchild who will be born soon.
My mother, Laurie Stone, who is an inspiration to everyone. She
is the only person I know who could have ever been elected chairperson of the board of a junior college without having graduated
college, and her honorary degree is well-deserved. She has taught
me so much about what true accomplishment really means.
My father, Harvey Kahan, who inspired us to outwork everyone;
that value has served me well.
My siblings, Dave Kahan, Larry Kahan, and Andrea Biwer, and
their children Lexi, Rachael, Beth, Brandon, Sarah, Chase, and Lea,
who collectively create our large, loving, close-knit, and supportive
family.
My list continues on the professional front, and I am grateful to
each of the following people.
My book team, who helped me turn my ideas, even the ones
I thought were gibberish, into this cohesive work that I am proud
of, that feels good to share, and that I hope will inspire readers to
discover their own greatness that exists inside. These professionals
include Robin Colucci, Dylan Hoffman, Jennifer Jas, and my literary
agent, Linda Konner.
My colleagues who provided great inspiration and guidance to
help me succeed at levels I never could have imagined. I’m forever
grateful to these stellar individuals that include Kim Addington,
Simon Azzopardi, Doug Erwin, Kevin Klausmeyer, Jim Legg, John
Ortbal, Chris Smith, and Josiah Sternfeld.
All the start-up leaders, marketing team members, co-workers,
mentors, competitors, investors, vendors, and consultants who have
helped to shape my career and whose examples have inspired me to
refine and create the seven keys to the C-suite.
The scores of men and women who have called me “friend” at
the many stops along my journey, and who have honored me with
their easy laughter and hard truths.
My life is richer for knowing each of these individuals who
remind me on a daily basis how truly wealthy I am.
About the Author
Steven Mark Kahan has successfully helped to grow seven start-up
companies from early-stage development to going public or being
sold, resulting in more than $3 billion in shareholder value. He is
currently CMO at Thycotic, which will become the eighth.
Bringing passion and positive energy, Steve inspires teams and
their organizations to take on the impossible and succeed. He is best
known for his ability to plan marketing strategy and execute it so
that companies can accelerate revenue, grow market share, and consistently deliver superior returns for shareholders.
In his current position as Thycotic’s chief marketing officer,
he has helped take the company from $10 million to nearly $100
million in four years. It’s been a similar story with the other
companies where he’s brought his talents over the past three
decades, including KnowledgeWare, e-Security, PentaSafe, Postini,
Bindview, Quest Software, and The Planet.
Connect with Steve at www.stevenmarkkahan.com.
151
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7 percent rule, usage, 121
360-degree feedback sessions,
practice, 120
A
ABN AMRO Bank, 90
accelerators, 21
accountability, usage, 47–8
achievement, indicators, 103–4
active listening, usage, 120
adaptability, 47
advisory boards, creation, 89
American Society for Talent Development
mentor survey, 106
annual performance review, usage,
124–5
anxiety, feeling, 73–4
A-plus talent, 28, 101–5
application-only programs, 21
APPTIO, 56
authenticity, 119
Azzopardi, Simon, 76–7, 86, 114–15
B
Ballmer, Steve, 9
“Big Company or Bust” graduates,
success, 4
Bindview, 9
Blakely, Sara, 128
blog posts, examination, 27–8
BMC Software, 17
Book of Beautiful Questions, The, 58
Brandenburger, Adam, 41
Branson, Richard, 53, 144
breakthrough revenue growth, operation,
34
Brown, Luke, 90
Buffett, Warren, 44, 134
Burning Glass Technologies, labor
survey, 4
buzzwords, avoidance, 97
C
calendar, 133–40
Camarote, Robin, 98
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career, 12, 60
focus, 103
growth, 64
path, trust, 113–15
Carnegie, Dale, 126
CEOs, questions (usage), 56–9
chaos, 51, 77–9
clarity, absence (impact), 83
C-level positions, 8
Colbert, Stephen, 28
common ground, discovery, 120
communication, 118
7 percent rule, 121
professionalism, 79
skills, 44–7, 55
technology knowledge, combination, 46
communicators, speaking habits, 45–6
company, 54–5, 82
failure, 26
leaders, interviews/blog posts
(examination), 27–8
selection, care, 101
seminars, attendance, 89
success, commitment, 64–5
compensation, examination, 113
competition, 29, 40–1
competitive attention, 71
competitive energy, channeling, 41
competitive impulse, 40
Computer Associates, 17
Conant, Doug, 126
confidence, 37, 52
control freak, avoidance, 93–5
co-opetition, usage, 40–1
corporate environment, work, 13
corporate job, instability, 8–9
corporate red tape, 10
Costolo, Dick, 143
Covey, Stephen, 133
co-worker, 118, 120
negative talk, avoidance, 129
success, celebration, 40–1
creative thinking, jumpstarting, 67
creativity, 67, 127
credit, taking, 49
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cross-cultural communication, 118
cross-functional simplicity task force,
starting, 96–7
cross-selling, problems, 61
C-suite, 16–17, 32, 35, 106
attainment, 131
material, 138
presence, 101–2
culture (tech start-ups), 14–16
customers, 88–91
success, support, 59
support, change, 96
surveys, supply, 89
cybersecurity, 21–2, 25
cloud-based solutions, 80
D
Daane, Marcel, 145
Da Vinci, Leonardo, 96
decision-maker, becoming, 81
decision making, 63–5
facts, impact, 80–2
Dell, 96
destination, focus, 79
details, attention, 93–5
distributed denial of service (DDoS),
impact, 78–9
Durant, Will
dynamics, change, 129
E
efficiency, improvement, 94
elevator pitch, 33–4, 53, 61
elite inner circle, cultivation, 102–3
email, avoidance, 87
empathy, 118–26
employees, 109–15
happiness, 127
hiring rate, 7
State of the American Workplace report,
15–16
understanding, summary, 120
weight gain, 143–4
work-life balance study, 154
employment, 9–18, 110
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energy, 128–31
entrepreneurs, 11, 112
errors, risk (minimization), 94
Erwin, Doug, 27, 33, 72–3, 88–9, 95,
109, 112
excellence, importance, 94
exercise, priority, 143–4
expectations, management, 79
expert, becoming, 41–4
eye contact, making, 120
k
F
face-to-face tactics, 64, 125
fact-informed gut decisions, 80
facts, impact, 80–2
family, importance, 140–2
fear, feeling, 73–4
Feder, Zachary, 49
feedback, 54, 89–90, 94
360-degree feedback sessions,
practice, 120
value, 125
financial expertise, development, 44
financial rewards, 13–14
first-wave hiring, second-wave hiring
(contrast), 20–1
fitness, priority, 142–7
focus groups, creation, 89
Fredrickson, Barbara, 130
friend-tor, friend/mentor combination, 109
fun, creation, 126–7
G
Gates, Bill, 9, 102, 134
General Electric, 80
genius, zone (finding), 11
Gerzema, John, 1167
GFI Software, 114
goals, 70–5, 87
focus, 79, 131, 138
Golden Rule, 113
Gourguechon, Prudy, 121
gratitude, 123–6, 130
gut check, execution, 68
gut decisions, facts (impact), 80–2
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H
habits, focus, 87
hand, shaking (gratitude), 126
hard work, 85–8
health, 110, 142–7
high-achiever, approach, 104
higher-ups, rapport, 12
hiring, 20–4, 33–4
Houston, Drew, 19
Human Firewall Council, 56
humility, 40, 49–50
I
Ibarra, Herminia, 69
idea person, identity, 66–8
ideas, testing, 68
illegal behavior, fostering, 110
in-demand soft skill, importance, 45
initiative, 54, 65–6
in-person entrepreneur events, 21–3
inquisitiveness, 103
internships, 24–5
interviews, 27–8, 34, 103
intimidation factor, reduction,
104–5
intuition, improvement, 81
I person, interaction, 119
issues, tackling, 131
J
jobs, 111–12
application, preparation, 27
websites, checking, 21
Jobs, Steve, 8, 43, 80
John Templeton Foundation gratitude
study, 123
joy, creation, 126–7
K
Kane, Chris, 3
kickoff meeting, 83
kindness, 98, 117
Klausmeyer, Kevin, 30, 43, 129
knowledge, 47, 56–7
KnowledgeWare, 12, 106
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L
labor, providing, 24
Last Lecture, The (Pausch), 66
leaders, 11–13, 23, 39, 62, 69
characteristics, 98
interviews/blog posts, examination, 27–8
Navalent study, 63
persistence, 98
leadership, 40–52
empathy, 118–26
executive leadership opportunities, 16
fast-track, 124
model, 79, 95
qualities, demonstration, 10
questions, usage, 56–9
reliance, 118
skills, development, 37
style, problems, 92
learner, continuation, 41–4
learning, acceleration, 104
learning plan, creation, 44
Legg, James, 17, 102, 111
life, living (fullness), 147–8
LinkedIn, 21, 23, 102–3
lip service, 89
listening, importance, 58
love, display, 55
M
Management by Objectives (MBO), 76
management team, VC investment, 27
marketing, 42, 62, 75–6
McAleer, Steve, 122
meetings, 72, 83, 135–7
gratitude, public expression, 126
MeetUp, 30, 107
mentees, 25, 108–9
mentors, 25–6, 106–9, 131
millennials, workforce entry, 123–4
mind-set, 75, 105
mistakes, responsibility (taking), 48
mobility (tech start-ups), 5, 16–18
money, making (increase), 112
Morris, Rhett, 106
multitasking, problem, 140
Kahan660408 bindex.tex
must-dos, 134
must-haves, focus, 79
N
Nalebuff, Barry, 41
narrative, writing, 38
Navalent leader study, 63
need-to-haves, expenditure, 28
negative thoughts, cessation, 52
nepotism, 116
nice-to-have technology, 28
notebook, usage, 57
notes, writing, 125
Nussbaum, Barbara, 38
nutrition, priority, 145
O
Ockham’s Razor, 96
online jobs, research, 21
opportunities, 5–9, 16–17, 31, 59–62
acceptance, 114
exhausting, 110
optimism, 128–31
order, creation, 77–9
outside consultant, relationship
(development), 106–7
overanalysis, avoidance, 79
overwork, avoidance, 85–8
P
parties, usage/advantages, 122, 127
passion, 98
patience, 97–9
Pausch, Randy, 66
PentaSafe, 23–4, 41, 78, 88, 109, 122–3
perfection, striving (avoidance), 131
performance, 95, 125, 145
persistence, 97–9
personal achievement, 42
personal goals, focus, 72
personal plan, 42
personal time, protection, 139
personnel decisions, 54
pessimism, interruption, 131
Picasso, Pablo, 43–4
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Pick, Chris, 56
positive attitudes, 103, 130
positive people, presence, 131
positives, recording, 131
presentation, preparation, 93
Preston, Camille, 125
priorities, 74–9, 87, 139–40
prioritization, 75, 86–7
problems, 47, 65–6, 91–3
products, usage/creation, 30, 54, 62
promotion, 47–8, 82–4
public speaking, development, 45
Q
quality people, values (sharing), 27–8
questions, 48, 56–9, 65–6
Quest Software, 61, 96, 112–13
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R
relationships, 54, 57, 95, 104, 119
relentlessness, 103
relevance, 70–1
remote work, challenges, 87
reply to all process, danger, 120
reputation, importance, 57
response, sharing, 120
responsibility, taking, 47
results, quality, 94
revenues, increase, 97, 139
risks, payout potential, 112
risks, taking, 59–62
Rohn, Jim, 101
roles, 11, 31
S
Sahibzada, Khatera, 49
salary, increase, 112
sales team, 19, 34, 91–2
Schroeder, Christopher, 48
Schwab, Charles, 123
second-wave hiring, first-wave hiring
(contrast), 20–1
seed accelerators, 21
self-belief, 50–2
self-care, 133
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self-confidence, development, 37
Self-differentiation, 53–6
self-doubt, impact, 50
self-esteem, 51–2
self-funding, 32
serial entrepreneurship, value, 112
services, creation, 54
sexual harassment, impact, 110
should-dos, trap, 134, 137–9
should-haves, ignoring, 79
simplicity, 96–7
skills, building, 55
sleep, priority, 145–7
Small Business Administration (SBA),
start-up definition, 5
social media, usage, 90, 126
solution, search/impact, 91–3
Southwest Airlines, 343
speaking engagements/habits, 23, 45–6
specificity, 70
start-ups, 5–6
ambitiousness, 29
entrepreneurs, creator role, 11
executive leadership opportunities, 16
ideas, 8
State of the American Workplace employee
report, 15–16
status quo, challenge, 59–62
Sternfeld, Josiah, 3
stock options, 13–14, 32
strengths, focus, 131
stress, 128
success, 38–41, 130–1
surroundings, positive atmosphere, 129
T
talent, 6–7, 126–7
teams, 121–2, 139
tech businesses, operation (Cyberstates
report), 6
technology, impact, 21, 46
tech start-ups, 9–19, 23–34
employment, 88
growth potential, 109
initiative, display, 54
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tech start-ups (continued)
online jobs, research, 21
opportunities, 5–9, 20–6, 31
quick-change nature, 91
relationships, building, 54
text, sending, 126
thank yous, usage, 123–6
The Planet, 24, 50, 112–3
time, management/waste, 133–4, 136,
139–40
time-sucks, 86–7
Transparency, importance, 51
True North sessions, holding, 76–7
trust, increase, 119
Tucker, Todd, 56
Tumbler, success, 30
Type A personality, 40
U
understanding, summary, 120
unfair advantage, 98
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value, display, 77
Value (addition), simplicity (usage), 96–7
values, sharing, 27–8
venture-backed start-ups, failure, 26
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venture capitalists, involvement, 32
Vessyl, 28
Vincent, John, 90–1
Virgin Group, 144
vision board, creation, 38
vision, description, 98
visual goal, creation, 73
visualization, 38–9
W
Walrath, Mike, 128
weight gain, problem, 143–4
Welch, Jack, 80
winning, remorse (absence), 40
work, 85–8
attendance, dread, 110
complaints, 127
environment, enjoyment, 127
family, priorities (conflict), 140
home life, boundary (establishment), 142
unhappiness, 222
work/life balance, 141
workload, inertia (impact), 70
workout time, creation (difficulty), 144
workplace, goals/differences, 72, 110
worth, display, 82–4
Wozniak, Steve, 8
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