The myth of the impervious leader

A fateful dinner

I opened the door to the dimly lit restaurant. A mix of anxiety and excitement washed over me. The dinner was being hosted by First Round Capital who had recently invested in my startup, the startup that only a few short months before had no customers, no clear idea, and was on the verge of insolvency.

Looking around the room, I recognized many famous founders. These were people I had only read about before and who, in my mind, made up Internet royalty. The hostess showed my co-founder and me to our seats at the long table.

The blond woman seated next to me turned to me with a big smile.

“Hi!” she said. “My name is Leah.”

“I know!” I replied awkwardly. “It’s really nice to meet you!” I tried to recover. I recognized Leah Busque instantly, the quite-famous-even-then founder of TaskRabbit.

The couple across from us also offered their hands by way of introduction. Their names were Susan and Eric, the wife and husband co-founders of a little online clothing retailer called ModCloth (which would soon grow to become an internet giant in its own right.)

Sitting at that table, meeting these founders I had idolized for years, I could feel the blood rush to my face. I could also feel the emotions that had characterized my elementary school years come rushing forward. I felt awkward, self-conscious, out of place.

I felt like an imposter.

Until sitting down at that table, all I knew about these founders I had read on TechCrunch. And, based on what I had read, these founders were like gods.

In my mind, they were brilliant (true!), educated at the world’s premier universities (some), with heads full of big ideas of how the future might be (most). They brought those ideas to bear easily and flawlessly (none) starting businesses that grew quickly and attracted eager money from top venture capitalists.

These people knew what they were doing. I, on the other hand, did not.

They were on the inside. I was on the outside.

They were impervious to fear, failure, or self-doubt. I was wracked by fear and self-doubt and had tasted failure repeatedly in recent years.

They belonged at that dinner. I did not.

Or at least that was what I believed walking in.

Looking back, that dinner was such a gift in my life.

Walking into that restaurant, if you asked me why I was attending and interested in meeting the other founders present, I may have told you I was interested in learning from them so that I could improve as a leader and help my own business succeed.

Looking back, what a waste that would have been. So much more was possible. What I actually received from that dinner, and the conversations we shared, was much more.

Leah, Susan, Eric, and many of the founders present offered me something much more valuable than advice. They offered me an invitation. Not an invitation into some secret club or inner sanctum of Internet foundryship, as I held it before that evening, but rather they invited me into a realization that they were no different from me.

That night marked the beginning of a multi-year journey into real friendship with dozens of founders and leaders. It also marked the beginning of the end of my belief that there exists a subset of founders or leaders who are impervious to struggle, self-doubt, and the other challenging parts of being human and creating something from nothing.

I came to see I was not alone. Neither, my friend, are you.