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Jerry Colonna – The Monster In Your Head

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We have an entire generation now that’s inspired and motivated by movies like The Social Network and shows like Shark Tank. They read these stories of billion-dollar exits, and yet they have little understanding of how hard it is to start a company, to build a product, solve a problem, get traction in highly competitive marketplace, etc.

What advice do you give first-time CEOs to help prepare them for the long journey that lies ahead?

Probably the most useful thing that I help people with in this regard is the understanding that most entrepreneurial ventures fail, or, to use your terminology, most efforts to innovatively disrupt an existing scene or situation will fail. And I don’t mean sort-of fail. I mean fail spectacularly. People really need to internalize that.

When I say they’re delusional, they actually do not believe failure will happen to them—just like you don’t believe you will die—when they start off. Now, that kind of radical, delusional belief in self is absolutely necessary to get the thing off the launching pad. But it’s also dangerous because it starts to set up a whole set of feelings that create massive psychological and existential suffering.

The second most useful thing is the notion that most people who are on this journey have a very difficult time. There is a tremendous amount of relief that comes into the eyes of a client the first time I sit down with them and we start talking about just how difficult it can be—especially if they’re a first time CEO of an entrepreneurial startup. A tremendous amount of relief comes when they start to realize that the incredibly difficult feelings they are having are actually the norm.

There is a tremendous amount of relief that comes into the eyes of a client the first time I sit down with them and we start talking about just how difficult it can be—especially if they’re a first time CEO of an entrepreneurial startup. A tremendous amount of relief comes when they start to realize that the incredibly difficult feelings they are having are actually the norm.

All of a sudden they no longer start to see that this is evidence of their failing as an individual or their incompetency. Their incompetency or competency may come into question, but the loneliness, high anxiety, constant sense of dread and inadequacy—which oftentimes is present in us anyway—gets exacerbated and played out for entrepreneurs. It’s tremendously relieving when they discover the fact that it is common. So, second is helping to understand what the journey is like in that regard.

The last useful thing is the challenge that occurs when you merge your own identity with the business itself. For example, I recently did an interview with Jason Calicanis. He was talking about this experience of, “I was Silicon Alley Reporter; Silicon Alley Reporter was me.” That sets up a whole dynamic for suffering, and the conundrum is that it’s necessary because the leader in a sense is the embodiment of the business.

Those three pieces are probably the most significant aspects that, in my view, the popular media misses. Because we want to celebrate Mark Zuckerberg and think of him as the next Bill Gates. We want to think of David Karp as the next Mark Zuckerberg. We want to think of Bill Gates as the next Henry Ford, or Cornelius Vanderbilt, or Alexander Hamilton. It never ends. We always have these archetypes of successful entrepreneurs who step out into the world and change things, and the myths that arise from them—what is The Social Network movie but one big myth?

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Jerry Colonna – former VC/Coach to Internet CEOs

It was 2005 and I was sharing office space with Fred Wilson when I met a young man who changed my life.

Fred and I had been friends since 1996 when we’d started Flatiron Partners. In 2001, we parted ways as partners but remained friends. I joined JP Morgan in 2002 and, within months, was miserable. The existential questions that had been haunting me for years were so loud, so relentless that I had no choice but to pay attention.

When I told my colleagues I was leaving, I said I wanted a business card with no company name, no title. I wanted to understand who I was stripped of any persona.

And so for the next few years, I sat on boards of directors, consulted here and there but mostly, I read, and sat, and learned to be still. I learned to listen.

Derek Walcott’s poem Love After Love comes to mind; I learned to love again the stranger who was my self who had loved me all my life, whom I ignored for another, who knows me by heart.

Then one day a young man came to see me. He wanted to leave his law practice and join a startup. Someone suggested that seeing the former VC would be a good first step. After asking him why he’d become a lawyer in the first place, especially considering he obviously hated his job, he began sobbing. I realized then that, through the act of listening, I had found my own way. Those years of sitting still began to pay off; I had to coach. And I’ve been coaching ever since.