Featured on Jan 10, 2011
"A whole person is one who both has walked with God and wrestled with the devil. - Carl Jung"
An old guy who was there at the beginning. Over my career I've been a tech reporter; a co-founder of one of the earliest ad-supporter web-based media businesses; co-founder of the first Internet-specific venture firm (CMG@Ventures); a co-founder (with Fred Wilson) of Flatiron Partners; a teacher; a writer; and now a Life/Executive Coach focused primarily on entrepreneurs.
- Title: Life Coach
- Age: 47
- Location: Union Square
- Contact: The Monster In Your Head
As founder of a company and VC firm, I’m sure you are asked for leadership and advice on a daily basis, but what made you go specifically into coaching?
I remember the moment when I realized that I wanted to do this. A young man had come to see me about advice and networking connections in order to get a job at a start-up. He was a lawyer, an associate and he was clearly miserable. I asked why he became a lawyer in the first place and he started to cry. This happened after I'd left Flatiron and JP Morgan when I was in the midst of my own existential wanderings. I realized that what I loved about work--what I loved about every job I've ever had whether it was being a VC or being a reporter--was the "conversation"--the dialogue about meaningful things. (Like this conversation, ;-).)
I realized, too, that I had a unique opportunity to help talk with people about the overlap between what we typically refer to as life and work (I don't necessarily see those as separate as the conventional wisdom purports). I could speak cogently about both the anxieties AND the pragmatic process of funding your business.
In a sense, by becoming a coach, I've taken the best of what I loved about being a VC and distilled it into full-time work.
What are some of the uniquely rewarding aspects of being a life/executive coach to technology entrepreneurs?
There's something infectiously fun about hanging around with, supporting people who believe in their hearts they can change the world. There are very few pessimistic entrepreneurs. More seriously, though, it's deeply fulfilling and emotionally rewarding to experience that moment when it clicks, when things click for my client and then tell me, as one client said just last week, that while the last four months of our working together have been difficult (because we're often looking at hard issues), she's happier than she's ever been as an entrepreneur--more focused and more clear about what she needs to do.
And think of it...I get paid to witness that.
You currently live in Long Island. We’re curious, what are some of your favorite things about living there?
I split my time. We have an apartment on the Upper West Side as well as a house in Port Washington. We moved out here for the schools when our kids were young and stayed. Port's a great little town (although my kids think it's boring). It's very pretty though and I like being surrounded by trees and being close to the water.
I also like the fact that I can be in mid-town Manhattan in under 45 minutes.
In a previous interview you mention that you discovered that Fred Wilson was the right partner for you when he canceled your initial meeting because of his daughter’s kindergarten graduation. At that moment it became clear to you that his values were in the same place as yours. How do you think that Fred Wilson came to the conclusion that you were the right partner for him?
:) I know the exact moment 'cause I've heard him say it. He met me one day in an office I was using at 200 Park Avenue South. I was using an office at the headquarters of Point Communications. My old firm, CMG@Ventures, had helped start Lycos and Lycos had a acquired Point and so I moved into that office to help. Fred walked into my office and I was sitting behind my ratty desk wearing torn jeans and an old t-shirt and a Yankees cap on. He says, he looked at me and, thought, now THIS is a VC.
Some believe that New York’s lack of an elite technical school like Stanford or MIT hinders the ability for startups to find talented engineers. As a teacher and alumni of Queens College in Flushing, are there any initiatives that New York’s public universities can take to encourage the growth of local technical entrepreneurs?
Well first I'd challenge your initial proposition. NYU-Polytech and Columbia University are pretty damn good schools. Moreover, the CUNY system is outstanding. Moreover, as things like We Are Tech NY and Techstars (which I just joined as a mentor) show, there are plenty of talented entrepreneurs who are here and plenty more willing to move here.
Moreover, things like NYCSeed (catalyzed by Owen Davis and the activities by the Bloomberg administration to support tech companies have been helpful. In my view, it's the self-organizing things like We Are Tech NY, Tech Meetup, and NextNY that are really the key to sustaining what is already vibrant and growing community.
You’re one of the mentors for the new TechStars NYC program that is being run by David Tisch, who we just recently had the honor of having on this site. If the roles were reversed and you were a new startup just accepted to TechStars NYC, which mentors would you like to work with during your time with the program and why?
What a great question...I've got a lot of friends and other people who are also mentors...so it's a hard question to answer 'cause I feel like all of them will make great mentors. But that said, I'd choose Joel Spolsky. He's had tremendous experience, he's level-headed and thought-ful and leads with his values--all qualities I admire.