E. Keller Fitzsimmons - Lost in Startuplandia: Wayfinding for the Weary Entrepreneur

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 couldnt drop it. In fairness, I wasnt 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, Ive been thinking about that lately.

More silence.

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

Lucky? That wasnt the answer I was expecting.

And annoyingly, he was right. I wasnt ready to credit my success to luck. It felt off. Thats 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, Ive been lauded as a visionary, luminary, and powerbroker. Ive 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 its all them and, better yet, they have replicable mojo. This literary category can be best summed up by the catchphrase Heres 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 authors perfectly overlaps, their insights invariably discount the role of luck in their success.

Sadly, there is no roadmap to success. We cannot replicate someone elses 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 entrepreneurs 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 terrainsagain and againand 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 failuresnot 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.