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 at the time, I would have asked better questions. Why did I care so much about what others thought of me? Why was I so desperate to impress?

The pursuit of answers to these questions turned out to be transformative.

What Makes Entrepreneurs Unique?

Is it our drive, confidence, willingness to be disagreeable? Is it that we are precious gems that will transform the world into a beautiful place? Countless research scientists have sought these answers. If only we could distill and bottle the qualities of Mark Zuckerberg, Jeff Bezos, and Steve Jobs, we could raise a next generation of ultra-entrepreneurs on the elixir.

Entrepreneurs are indeed unique (and not just because we are otherwise unemployable). We separate ourselves out from Main Street in several ways. However, these are not the traits we are likely to celebrate…or even acknowledge.

The University of California, Berkeley, released a study in 2015 reporting that entrepreneurs experience certain mental health disorders at three times the rate of mainstream Americans. In the study, 72 percent of the entrepreneurs self-reported a mental health diagnosis, including “depression (30%), ADHD (29%), substance use conditions (12%) and bipolar diagnosis (11%).”1 It’s pretty obvious why these stats don’t show up in the brochure.

Instead of having easily identifiable—and therefore replicable—superpowers, entrepreneurs tend to have massive monkeys on our backs. In my personal case, I have been clinically diagnosed with a generalized anxiety disorder and ADHD (commonly known as “Oooh, look over there. Aaagh!”). Over the years, I have self-medicated. So far, no bipolar diagnosis, although it runs in my family.

And what about depression, you ask?

By 2003, I looked like I had pulled myself back together. I merged Sun Tzu Security, my first startup that was still chugging along, into a larger security firm out of Chicago, Neohapsis, and I had become the CEO of the combined companies. I was attending the Center for Authentic Leadership’s Future Thinking program every quarter in Atlanta and bringing my insights back to the new company. A couple of years earlier, Jeff, my future husband, and I had met in Hawaii and were now living together in Milwaukee.

From the outside, my life looked pretty great…except one thing. I was still in debt. In spite of Neohapsis’s profitability and growth, and my equity stake, I couldn’t envision a realistic scenario where we could exit for enough to clear my debt.

What most people—including those closest to me—didn’t know at the time was that I was suicidal.

And it turns out, this is not uncommon.

“For at least two years after Pets shut down, I didn’t care if I lived or died,” shared my friend Julie Wainwright, former CEO of Pets.com, in her book ReBoot: My Five Life-Changing Mistakes and How I Have Moved On. “In retrospect, I wish I had been more proactive with my mental health. I did not recognize my state of mind as depression.”2

For renowned entrepreneur and best-selling author Chip Conley, the Great Recession of 2008 hit particularly hard. “I retreated to my home—once my sanctuary but now a place filled with beautiful things and ugly thoughts.”3 In August of that year, Chip had just finished delivering a keynote to a crowded room when his heart failed. “A wailing siren and a soft, reassuring hand” is all he remembers from the ambulance ride. Once he came into clearer consciousness, he had hard questions for himself. “What the heck was I doing on stage half a continent away from home in my condition?!” At the time, he was recovering from a serious infection and still on potent antibiotics. Why was he not giving himself time or permission to heal? Chip’s brush with death gave him a new lease on life at forty-seven. “I saw [it] as a kind of divine intervention,” Chip explains. “I started to explore why I felt so bewildered and full of angst.”4

Prior to PRISM’s collapse, I didn’t understand failure. I’d experienced only setbacks up until that point. I’d enjoyed a long string of successes that made me believe that simply working hard and putting my nose to the grindstone would lead to success. It had always worked in the past.

Now I faced something unprecedented: real failure. It became clear—slowly and then very quickly—that sheer grit and determination were not going to see me through this crisis safely. I couldn’t outrun this failure. I had to keep walking, step by painful step.

Illuminating the Path

One of the underrated upsides of failure is that it wakes us up. Failure lets us know—in explicit terms—how well we are performing in reality. When we are...