Jerry Colonna, CEO Coach, Real Leader 35

I’ve wanted to interview Jerry for a very long time. And, after many attempts, we finally found a time that worked. I hope you enjoy the conversation as much as I did.



About Jerry

As a certified professional coach, Colonna draws on his wide variety of experiences to help clients design a more conscious life and make needed changes to their career to improve their performance and satisfaction. He established his coaching practice in 2007. Prior to this work, Colonna was venture capitalist focused on investing in early stage technology-related startups.

In 2002, Colonna became a partner with J.P. Morgan Partners (JPMP), the private-equity arm of J.P. Morgan Chase where he led the firm’s investments in companies such as ProfitLogic Inc. Colonna served as a director at ProfitLogic until its purchase by Oracle Inc.

He joined JPMP from Flatiron Partners. With his partner, Fred Wilson, Colonna launched Flatiron in August 1996. Flatiron became one of the most successful, early stage investment programs. Before Flatiron, Colonna joined his first venture firm, CMG@Ventures L.P. in February 1995 as a founding partner. CMG@Ventures was the first “Internet-specific” venture firm. Prior to joining @Ventures, Colonna worked for ten years for CMP Media Inc.

Colonna also serves as a director, trustee, or advisor to a number of for-profit and non-profit organizations including Naropa University, the only accredited Buddhist-inspired university in North America. He is a recipient of numerous awards and a compelling speaker on topics ranging from leadership to starting businesses, Colonna has been named to Forbes ASAP’s list of the best VCs and Worth’s list of the 25 most generous young Americans. A graduate of Queens College, Colonna lives in Port Washington, New York.

I want to take a minute to tell you why we are doing this! I blog a lot about learnings which are essentially ideas. I think the stories of real leaders, put these ideas into context. At the end of the day, this is about understanding the Why, How, and What-to satisfy the curiosity.

So my first question, why are you doing what you are doing now? How did you get here? What’s the back story and maybe, the influences behind your career/life?

Jerry: Two things occur to me as a response. Firstly, looking back through the lens of hindsight, something is very clear to me across all the careers I have had (this is really the fourth career). I have also had a couple of side activities along the way-writing and teaching. The core about all the work I have ever done has been about what I refer to as having the conversation. One of the most important things for me in life is to connect in a real and authentic way with the other human beings. For me, that’s air and water-its absolutely essential. Every single job I have had from being a manager, to being a journalist, to being a VC, and to now being a coach has revolved around having that deep conversation. The way I look at it, the transitions have been more and more of a distillation of that process. That’s my first response.

The other response, is a story of how I decided to become a coach. In 2001 and 2002, I was entering a period of profound existential depression. I had agreed to take a job with JP Morgan. In the spring of 2001, I told Fred, I could not continue in our partnership. It was very painful because we were very close friends and had grown up together. I wasn’t sure what was happening for me. But I did know that I could not make a ten year commitment, in raising fund.

I went ahead and took a job with JP Morgan. I began working for them officially in January 2002. Within a very short period of time, I was seemingly depressed. I would come to the office, lock my door, close the blinds, and hide under my desk. I would cancel my meetings and I would just cry. Eventually I came to understand that I would have to leave that position as well.

In 2003, I went out on my own. Through 2003, 2004 and early 2005 – I was mostly doing internal work that I needed to do on myself. It was during this period that I did some teaching, a lot of writing, and served on a number of boards of directors-I was busy.

It was then I had met a young man who came to network with me for a job. He started to ask me a series of questions and he started to cry one day about how miserable life was. I gave him a book called Let Your Life Speak by a dear friend now, named Parker J Palmer-it is an extraordinary book. And the book had really moved me profoundly. When he left my office, I started thinking about that exchange and I realized that, this was something I wanted to do with my life. I called a friend who was a coach at that time and I said, “I think I want to be a coach”.

We began the process of talking through what that would account. For me, its very hard to separate the decision to become a coach and the path of the other positions I have held as an adult or for my own internal work. Its all been about deep conversations around existentially true issues.

Rohan: Do you think that the depression came about because you lost touch with these conversations for a while?

Jerry: I think the coping mechanisms I had developed in my 20s and 30s to deal with the existential questions broke down. It stopped working. I remember reading a very poignant quote in a book called Listening to Midlife by Mark Gerzon-he’s a fabulous writer. He tells a story of Buzz Aldrin, coming back, after orbiting the earth and suffering a major depression. And the quote that’s attributed to Buzz Aldrin is, “After seeing the earth from the vantage point of the moon, what else is there?” And I felt very thoroughly on hearing that. The coping mechanisms I had developed in my 20s and 30s were things, like the pursuit of money, the pursuit of external affirmations, and external validation. What I realized, in my late 30s, was that they don’t really work. They work for a while, but they don’t really stave off the demons. I had no choice, but to sit still, and listen.

I am a Buddhist. The way I like to tell a story is that when Buddha as a prince, came to realize the realities of birth, suffering, sickness, old age, death-became a wandering mendicant in the forest, became an ascetic holy man, he realized that wasn’t enough. The way I like to think of it is that, one day he just said “Fuck it!”. He had had it-it was enough and he sat down at the boddhi tree, saying to himself, “I am not moving until I figure it out”.

I like to think that, for me, that’s kind of what happened. I just said I am not going to move until I figure this out. I am not going to pretend anymore. And, what emerged was, Jerry the coach.

Rohan: I am trying to understand this. So it seems like the problem was not “what”, it was more of “why” you were doing something. Could you talk me through that? Did the purpose change?

Jerry: I think what happened was that I became more connected with my whole authentic truth. And I became more fiercely dedicated to moving to that fully integreted place. In reality, instead of having a conversation, within service of creating a story as I did as a journalist; or open a company as I did as a manager; or the investments as I did as a VC, I began having conversations that further the alleviations of suffering. And that changes everything.

Rohan: As a coach, I have seen you talk in other interviews about helping entrepreneurs with depression or helping people to ask these “why” questions and stay connected. How big a role does faith or spirituality play in this? In the past ten minutes, I have seen the role Buddhism has played in your life. Do you actively, encourage people to find that faith to help relieve them from their suffering?

Jerry: I don’t believe it matters what religion you believe in. I don’t believe it matters whether or not you consider yourself spiritual. I am not sure what faith means. But I do believe that a kind of radical self enquiry, a radical truth tell is absolutely essential to not only living a better existence, but also being a better leader. Being able to withstand the vicissitudes of everyday life as an entrepreneur. If you give in to the very human tendency, trick yourself, and lie to the world (and to yourself), you actually exasperate the highs and lows on the entrepreneurial world.

Rohan: But does the fact that you believe in something outside yourself, help? I guess that’s my question..

Jerry: Yes, one of the most important ways to break through the ineffaceable narcissicm as an entrepreneur – is a connection to something much larger than yourself. That could be community, that could be family, that could be the society in which you are trying to operate, it could even be a faith.

There is a balance between three things – the inner view, the outer view and the other. If it is only focused on the inner view, you end up falling potentially prey to a kind of self-indulgence-trapped in your mind. If you focus on just the outer view then, you run the risk of living a hollow life-what we call as “hungry ghost” in Buddhism. If you only live for the other, then life is going to be great but you are going to be disconnected from an authentic self. So you really need all three in balance with each other. The awareness of the other keeps you from trapped in your own bull shit.

Rohan: How do you put these great ideas that makes you put these ideas into context? How would you advice people to take practical steps to put this into their lives?

Jerry: Are there things that you can do on a practical everyday basis? Joseph Campbell, Writing in The Power of Myth says, “You must have a room or a certain hour a day when you don’t know whats happening in the newspapers. A place where you simply experience and bring forth what you are and what you might be.” I think that if we spend a little bit of time everyday (very pragmatic piece of advice) cut off from the noise-it could be walking, sitting in meditation, journaling, exercise, or just staring at the sky. Just a little bit of time reconnecting with you without your title, your obligations, your responsibilities, the things that plague you all day long. I think that enables you to build a foundation and then work your tail off. Who are the people coming to the website?

Rohan: I have a whole bunch of people who read the blog. A large group is people who are in my age in their mid 20s.

Jerry: All the people who you talk about can benefit from a little quiet time. One of the great traditions from religion, is that there is a prescribed general time of disconnection. Sabbath – a period of fasting, a period of self reflecting. Many people are so used to these rituals that they don’t use it for the kind of self reflection they were designed for. But what if you can reconnect to these practices?

When I speak to clients I say this, “How about having lunch by yourself and not in front of the screen?” What a radical concept. What if you took a walk around the building? What if you walked home instead of taking the subway? What if you went for a bike ride? And not listen to the iPod? What if you drove your car with the radio off? What if you did not turn the TV on? What if you didn’t check the email? What if you rode the elevator without checking your phone? What would happen?

Rohan: It almost seems like a push for introvercy right? In this world that is obsessed with being an extrovert?

Jerry: I think you make a good point. I am an introvert. Many of these things feel comfortable and natural to me. I am just as drawn to the distractions as anybody else. Maybe there is something that the quiet introvert can teach the rest of us. Maybe there is something beneficial about opening a book and reading poetry.

Rohan: How do you put these principles? What are your habits that make you effective?

Jerry: I am very boring at night because I tend to go to bed around 9 , 9.30. I wake up somewhere between 5 to 6 am. I journal usually with a cup of tea, meditate, check e-mail at that point, or go to the gym. It’s a lovely way to start the day. It takes time. I generally wake up 2 hours before I am supposed to leave. That shocks people. I try not to engage with the screen of any sort after 9, 9.30. I find that its just too loud. That’s a very typical day for me. And then the day proceeds, its very full, sometimes highly emotionally draining. If I had 7, even 10 sessions in a day, that’s a long day. I am working 10 hours. But for me to be fully present for my clients, for my own life, I need this ritual.

Rohan: Is there a message, quote or idea that you would like to share to the eclectic group of readers we have?

Jerry: ‘Don’t take it so seriously’, have fun, breathe, chill out. 90% of the time I spend my time ing people out of their crazy fears. So what would happen if you fail? So what? So whaat? Relax! Its no big deal, Its no big deal. That would be my message, ‘Its no big deal’.

Thank you, Jerry, for a very inspiring interview. I’ve started tweaking my daily morning schedule to emulate yours and have begun meditating every day, as well…

Real Leaders Team,

Dhanya, EB and yours truly..