Lost in Startuplandia: Wayfinding for the Weary Entrepreneur

By E. Keller Fitzsimmons

Entrepreneurship seems like a thrilling, lucrative adventure—until things go horribly wrong. As crisis after crisis hits, even the most seasoned founder can get disoriented. Whether you're in the throes of business woes or just getting into the game, E. Keller Fitzsimmons has written a field guide outlining the terrain to help you avoid getting Lost in Startuplandia.

Keller has been there, done that, starting six businesses over twenty years. In this honest, personal guide, she draws on her trials and triumphs, as well as those of fellow entrepreneurs, to share their most valuable lessons for surviving startup failure. From staying self-aware to redefining success to prioritizing relationships, Keller illuminates the pitfalls that can make or break even the most resilient entrepreneur.

Startuplandia can be as exhilarating and rewarding as you dreamed—as long as you're ready to navigate the inevitable crevasses and quicksand along the way.

• Language: English
• Publisher: BookBaby
• Release date: Apr 5, 2019
• ISBN: 9781544502861

Book preview

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Advance Praise

Whether you’re the CEO of a multibillion-dollar company or a startup founder, this book will make you stop, reflect, and then act more purposefully. Lost in Startuplandia is the go-to resource we all wished we had at the start of this tumultuous journey.

—Jeff Joerres, retired chairman and CEO, ManpowerGroup

Kelly knows the pain of entrepreneurship all too well. Her willingness to share about the shadow side of startups offers much-needed clarity, assurance, and companionship.

—Julie Wainwright, founder and CEO, The RealReal

Failure is something every entrepreneur faces. It can either decimate you or be the key to your long-term success. In this insightful book, Kelly shares personal stories on how she and other founders—myself included—have traversed this difficult terrain.

—Chip Conley, New York Times best-selling author and hospitality entrepreneur

Keller Fitzsimmons has navigated some of the toughest startup terrain, sharing her wins and painful failures. In this deeply personal resource, you’ll find a trustworthy and refreshingly witty guide.

—Don Layden, operating partner, Baird Venture Capital

In entrepreneurship, failure is our constant companion, whether we wish to admit it or not. Too few of us talk about this harsh reality and the toll that it takes. Here, you will find a new way to look at failure as experience and come to appreciate it as your faithful, honest guide to true success.

—Kay Koplovitz, founder and former CEO, USA Network, and cofounder, Springboard Enterprises

When failure happens, we have the power to choose how we will hold it in our life. It can be our greatest teacher if we can let go of ego and see it as such. In this personal book, Kelly offers practical insights on how to navigate the hard times and choose our next steps more purposefully.

—Nan Gardetto, president, Every Day Good Foundation, and former CEO, Baptista’s Bakery

Everybody loves to talk about their brilliant wins—but most of us won’t talk about what happens when things go sideways. Quite frankly, if you’re an entrepreneur, it’s inevitable you’ll deal with some really spectacular blowups. That’s when you really need guidance and support. I’ll take Kelly by my side any day of the week. Not only has she been ultra-successful, but she’s also gone through all the pain that comes from spectacular failure. You’ll get the real unvarnished truth mixed with her irreverent humor that always makes me laugh. No matter how dire my situation, she’s got a story to top it.

—Yanik Silver, author, Evolved Enterprise

It’s like a trail of blood-soaked breadcrumbs for entrepreneurs.

—Marcus Ranum, security technology entrepreneur, innovator, and consultant

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Copyright © 2019 E. Keller Fitzsimmons

All rights reserved.

ISBN: 978-1-5445-0286-1

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For Mom & Dad

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Contents

Prologue

Introduction

1. Self-Awareness

2. The Shadowlands

3. Sighting Your Summit

4. Self-Belief

5. Self-Care

6. Social Connectedness

7. Decision Making

8. Resource Mapping

9. Focus

10. Entrenchment

11. Reorientation

Conclusion

Epilogue

Acknowledgments

About the Author

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Prologue

It was a clear, warm August morning as my dad and I hiked down from his log cabin in Edwards, Colorado. For years, I had been asking him a simple question. Again and again, he waved me off. And yet, I couldn’t drop it. In fairness, I wasn’t the only one asking. That summer, my father was the focus of international media attention for doing something rather incredible and almost unprecedented.

A few months prior, my dad had walked away from something north of $100 million. Instead of selling the company he had built over sixty-two years to a competitor or private equity firm, he turned it over to his very surprised employees.

My father was living true to his values. At eighty-five, he was giving back to the people who he credited for his success. I wanted to know more.

Dad, I asked, what is the secret to your success?

He got quiet.

You know, he said, I’ve been thinking about that lately.

More silence.

If I am really honest with myself, the secret to my success is that I’m lucky. I would have never admitted this at your age. In fact, I would have denied it. But looking back on it now, it’s clear.

Lucky? That wasn’t the answer I was expecting.

And annoyingly, he was right. I wasn’t ready to credit my success to luck. It felt off. That’s not the narrative we know. Entrepreneurship is about the hero who defies the odds, takes bold risks, and through their unparalleled brilliance, prevails.

Luck is for casinos, not entrepreneurship, right?

And yet, something deep inside me nodded. I knew he was onto something.

Over my twenty-five-year career, I’ve been lauded as a visionary, luminary, and powerbroker. I’ve got the awards (somewhere?) to prove it. I started businesses in three different industries before they had properly coalesced as industries: information security (1996), voice interface (2006), and virtual reality (2012). Of my six startups, I merged one (Sun Tzu Security into Neohapsis), exited one (Neohapsis), blew one up (PRISM), sold one to my partner (Five Hawk), transitioned twice as CEO (Neohapsis and HarQen), and am still active in one (Custom Reality Services). Five out of six of my original startups are still in business.

So am I a visionary or lucky?

There is an entire literary genre dedicated to works by successful entrepreneurs who believe that it’s all them and, better yet, they have replicable mojo. This literary category can be best summed up by the catchphrase Here’s how I made my millions, and you can too! These books tout the qualities of that particular entrepreneur and advise the reader to follow their roadmap to success. If you follow in my footsteps, you will succeed! GUARANTEED!

While that sounds nice, it is utter horseshit. Too often, the real success of these entrepreneurs comes from you buying their books and paying for the ongoing mega-millions training. But even when the entrepreneur is being sincere, it is still not helpful. We are different people with different talents, skills, backgrounds, and experiences. Even if the Venn diagram of our strengths and the author’s perfectly overlaps, their insights invariably discount the role of luck in their success.

Sadly, there is no roadmap to success. We cannot replicate someone else’s achievements. The market conditions that gave rise to their success are now in the rearview mirror.

That said, we can learn a lot from an entrepreneur’s failures. While there may not be any guaranteed path to success, there are some surefire ways to fail. And thanks to my good fortune, I have tripped into these predictable, well-trodden terrains—again and again—and come out the other side. I am not alone here. The secret is that all entrepreneurs visit these dreaded wastelands. The problem is that few of us want to revisit those painful memories and let our trials there become a part of our larger public image.

While my father set the bar high with a remarkable legacy, I hope to stake out a decidedly different claim. I want to be known as the entrepreneur who told it straight and shared the hard-won lessons from my failures—not my successes. At twenty-nine, I found myself on the wrong side of an industry meltdown and a $5 million personally guaranteed debt. How I learned to navigate that provides only one of the many stories I tell here. I have the good fortune of knowing many well-known entrepreneurs who have achieved extraordinary public success and are willing to share their harrowing tales and their lessons learned too.

Failure is not a friendly guide but a steadfast one. It is always there. We can choose to hide from it or learn from it. Are we brave enough to look failure in the eye and ask, what could I have done differently? Our ability to internalize the lessons and act upon them determines our fate.

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Introduction

If we believe every success story out of Silicon Valley, Startuplandia is a magical place where entrepreneurs’ dreams come true. The roads are paved with the gold of venture capitalists, who line the streets writing enormous checks based on napkin sketches. All the companies in Startuplandia will change the world, making it a better place. All the entrepreneurs are heroes, slaying the dragons of obsolescence. Innovation is the wellspring from which the headwaters flow. Disruption is the godhead worshipped at the altars.

But beware. There be dragons here.

Startuplandia is more like Middle-earth than Shangri-La. While wonders abound, the land is also perilous. The threats are real and relentless. We will be forced to navigate hostile landscapes, which will test our steadfastness and sanity.

The story of Startuplandia’s shadows is not well told—or rather, it is incomplete. A compelling story has three parts: Act One, the introduction of characters and the story; Act Two, the conflict; and Act Three, the resolution. We hear about Act Three, the culmination of success, a lot in Startuplandia. And if Act Three is spectacular enough, we hear about Act One: the garage where the founders used duct tape, chewing gum, and a discarded Speak & Spell to fashion the original prototype. But what about Act Two?

The vast majority of our entrepreneurial journey occurs in Act Two, where we meet conflict head-on. And yet this part of the story is largely untold. Why? Things get very messy in Act Two.

Entrepreneurship, at its core, is a struggle against reality. In the beginning, the thing we believe in doesn’t exist yet. We set off into uncharted lands to discover or create something new. Our path is dark and unformed. Soon enough, we find ourselves in the thick of it.

The only guarantee is that we will face adversity. It will test us. We will discover who we are when things fall apart. Do we rise to the challenge or fall prey to our inner demons? Because entrepreneurship is so damn hard, our struggles lay bare our rough edges and shadow qualities. If our startup is game-changing enough, our personal failings will be on public display. There is no ivory tower to hide in. The world will see us, warts and all.

We don’t get to choose the source of our adversity, but we do get to choose how we handle it.

While there is no guaranteed path to becoming the next billion-dollar startup unicorn, there are some predictable paths to failure. Attaining untold financial riches doesn’t mean you will succeeded as a person. Too many entrepreneurs entrench into thinking that they are the MAGIC and become the worst versions of themselves. Others take their misfortune personally and become embittered. Are we really a success if no one wants to be with us?

As an entrepreneur, I have been through the wringer numerous times. My first massive failure hit at the age of twenty-nine. My second startup, PRISM, was an information security company. As the dotcom bubble burst, the loans I’d taken out for PRISM were called, and there was nothing I could do about it. I was on the hook for a $5 million personal guarantee. I had a condo with maybe $50,000 in equity, but there were no other assets that could line up with that kind of debt. To say it was soul-crushing is an understatement. It fractured and exploded my self-belief into a million tiny pieces.

I felt fragile and weak. I internalized the idea that maybe I wasn’t meant to be an entrepreneur. Maybe the universe was trying to tell me something. Maybe I should just quit…

Failure made me dig deep. It forced me to redefine my journey from a quest for untold riches to an adventure in self-discovery. If I hadn’t learned to reframe failure, I don’t think I would have made it. The shame would have overwhelmed me.

Every time we fail, it creates yet another opportunity for us to reflect and choose to do it differently in the future. Until we die, we have the opportunity to become better versions of ourselves. If all we did was win, we would have no incentive to learn.

Throughout this book, I will share my hard-won lessons and those of several other successful entrepreneurs. Our businesses—and our own personal growth—were defined by how we navigated our versions of Act Two.

The lessons learned here come down to one word: resilience. Each of us had to tap into great stores of energy that, frankly, we didn’t know we even had. We had to find increasingly novel ways to keep ourselves going through the unrelenting storms and dark nights of the soul. We learned that resilience isn’t a given or a personality trait. It’s a precious resource that must be continuously and consciously managed.

Can the worst bring out our best? Absolutely. When we let failure be our guide, we discover the depths of our unique talents and capacity to grow. We learn who we truly are. This level of self-knowledge is as empowering as it is frightening. On one level, we gain tremendous self-belief. We know that we can handle the worst and be better for the experience. Conversely, we realize how profoundly vulnerable we are. With vulnerability comes the realization that we must take care of ourselves first and foremost. Without us, there is no success. Sacrificing our health and closest relationships on the altar of success is no longer an option. We see it for the folly it is.

Written as a field guide, I have designed this book to be approached in two ways. It can be read cover to cover, but more likely—given how busy we all are—it can be read as needed. Each chapter covers an aspect of Startuplandia’s terrain and offers specific recommendations on how to navigate it. Beyond my insights, I have collected the stories of other intrepid entrepreneurs who have traveled these harsh lands and lived to tell their tales.

No one gets through Startuplandia without adversity. In the end, our destiny is neither fully determined nor completely random. By getting clear about what is in our control and then working from there, we prepare ourselves to take advantage of our good luck…whenever it comes around.

For our story to be a complete story, we must find our way through Act Two. This is easier said than done. The vast majority of startups fall prey to a myriad of avoidable pitfalls. This book points out the dangers. How you navigate them is up to you. My intention is to give you a fighting chance.

May you find your way and live on to celebrate your own glorious Act Three.

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Chapter One

1. Self-Awareness

Start Where You Are

The ancient Greeks laid out their temple complexes around a single point. Within the temple gate, in the middle of the first step, there was a point set at approximately five feet, six inches off the ground. It was from this point—the average level of the human eye—that all the structures were positioned and angled. The human perspective was the most important point in classical Greek architecture. It determined everything.

From the moment we decide to become an entrepreneur and step through that gate, our vantage point determines the way we will experience our trials and triumphs. Everything starts and ends with how we see the world. It is our perspective—negative or positive, warped or clear-eyed—that will shape the challenges, threats, and opportunities we will encounter.

Thanks to this quality, Startuplandia has a way of manifesting our greatest fears. For many of us, it’s social embarrassment. We loathe the idea of being cut down and humiliated, exposed as the small, fragile creatures we actually are. And yet, Startuplandia loves to serve up heaping helpings of humble pie. At some point, we will be required to confront our fears and dig in. Yummy!

It took me six startups to see Startuplandia for what it is and, more happily, what it can be. Startuplandia has taught me far more than the practicalities of running a business. After twenty-five years, I realized that startups are a vehicle for self-discovery and personal transformation. Startups will change us. It is up to us to determine whether that change will be for the better.

After PRISM folded, my marriage dissolved. The world felt hostile and lonely.

One day, two friends took me to lunch and told me about Jan Smith and her executive coaching program at the Center for Authentic Leadership. The overarching promise of the program was to learn how to step into our authenticity and lead from there.

I had tried the alternative. I had faked it until I made it and then failed spectacularly. My persona of the bright, successful entrepreneur had been shattered beyond all recognition. There was no putting Humpty-Dumpty back together. Beyond that, I was exhausted by my ego and what I called The Kelly Show! I was ready for a change. I needed a change.

I enrolled immediately.

Early on in the program, Jan asked me a question that cut through all the haze: How can you lead others when you don’t know what’s driving you?

I was completely stumped. I’d never thought about it like that. What was driving me to be an entrepreneur?

If you asked me why I was an entrepreneur during the boom years, I may have said something predictable, such as, to build a billion-dollar company. However, that was not why I was really there.

I was there because being an entrepreneur made me look awesome.

Before the dotcom bust, I received so many awards and so much press that it became a running joke in my family. I spoke authoritatively on topics way outside my experience and expertise. At the height of the crazy, I walked into a PR workshop run by the area Business Journal just in time for the publisher to point at me and say, If you want to figure out how to get more press, ask Kelly. She’s in our paper so much we call ourselves the Hansen* Journal. (*My married name at the time.)

After PRISM failed, I didn’t look or feel very awesome. My superficial rationale for being an entrepreneur evaporated. Why in the hell was I doing this? What did I hope to achieve? My brain spun in endless, fruitless circles.

Social validation had proven itself to be an unreliable and, unfortunately, double-sided reward. As easily as we love to laud people for their accomplishments, we cannot wait to tear them down. My fear of being publicly exposed gripped me. I kept waiting for the other shoe to drop.

If I had been more mindful