VC-turned-renowned executive coach Jerry Colonna on the unsorted baggage of CEOs

Jerry Colonna was a good venture capitalist. Still, when he became engulfed in a dangerous depression after the bubble’s burst — owing to the economic crash, to the terrorist attack in New York, to the approach of middle age — he saved himself by leaving VC, a kind of accidental if lucrative profession for him, and by learning how to coach others.

What he tells them from the outset — as he learned about himself firsthand — is that many executives hobble themselves unwittingly out of fear or some other driving force that they have no idea even exists, a driver that has be to identified to be conquered.

Colonna learned, for example, that he associated money with safety, having grown up in a chaotic environment with an alcoholic father, a mother with mental illness and six siblings who were at times separated and cared for by other family members. Among these were Colonna’s grandparents, who owned a building in New York and provided their grandchildren both love as well as that missing sense of security.

Of course, not everyone has access to Colonna, or his team of roughly 25 other coaches, or to one of his executive bootcamps. It’s for this reason that Colonna recently authored the book “Reboot,” in which he shares many of his own stories while also signaling to readers the importance of recognizing that they aren’t crazy, that much of modern life is a pretense and that with some introspection, it’s possible to understand the roots of one’s character structure and, perhaps, stop embracing them unconsciously.

We talked with Colonna about the book in a conference call attended by dozens of Extra Crunch readers. We’ll be releasing a transcript of that call shortly. In the meantime, we wanted to share part of our exchange that centered on the question: Are most executives ultimately trying to impress their parents — either living or dead? (Colonna had told us that the first person to come to him for real advice — when Colonna was still advising startups as a board member — was a young attorney who hated his profession but went to law school to please his father.)

In a nutshell, the answer, perhaps unsurprisingly, is yes — at least to some degree. “I think most of us are in an interesting dialogue with the belief systems we developed as children, and that most leaders are shaped, consciously or not, by those early belief systems,” he said. “If you believe the world is a dog-eat-dog world, where everybody is out to get their own, you’re going to unconsciously build an organization that’s filled with self-optimizers. Then you’re going to call a coach and ask, ‘Geez, why isn’t anyone trusting each other?’ ”

Indeed, Colonna’s view (and he has seen a lot of executives over the years) is that “one of the most important forces of any child’s life are their parents. They shape positively and negatively our whole world view because they give us the sense of love, safety and belonging; they give us our sense of worthiness as human beings.” It’s why when he’s doing his leadership coaching and development work, he works to “really understand the early structures of a person’s life — not so we can spend the entire time therapeutically going through it, but so we can have a context for what they might be struggling with right now.”

It was a wide-ranging chat, touching on whether people can become great leaders without facing some childhood adversity, the reason that coping skills sometimes become impediments, whether millennial leaders have it better or worse than their predecessors and why the 30s can be the trickiest decade of all for people who are leading organizations.

More on our chat soon, and if you don’t subscribe to Extra Crunch, you can learn more here.