Zipcar Fundraising Breakdown

Thank you to Tom Eisenmann of HBS, who gave valuable feedback on a couple of iterations of this. I teach entrepreneurship at Columbia University. We devote the second-to-last class to a Harvard Business School case study about the early years of Zipcar. It’s a good case and we can review most of what we learned through […]

20 Minute VC with Harry Stebbings

My friend Harry Stebbings interviewed me for his podcast The 20 Minute VC a little while ago. He published it today. I love his podcast, he asks great questions and tailors them to his guest. You get a distilled view of what they’re thinking about. He and I talk about some of the things I’ve […]

Ruling out rather than ruling in

One of the dangers of working alone is that when you start doing things oddly there’s noone to call you on it. It’s almost nine and a half years since I started angel investing as a full-time thing, plenty of time to develop strongly held beliefs that happen to be completely wrong. The only thing […]

Betting your Beliefs

Here is the second-best thing any entrepreneur has ever said of me, to another entrepreneur: “you should talk to Jerry. He’s one of us.” I was an entrepreneur once, I have a different job now. But the implication that I was like them, that I understood them, that I would have empathy for what they […]

Venture Follow-on and the Kelly Criterion

EDIT, 10/31/19: I’m withdrawing this piece. I’ve become convinced that since the Kelly Criterion is not directly applicable to venture, using the spirit of it to justify follow-ons is cheating. I still think I’m right, but if I want to make the argument I think I have to do the math. EDIT, 6/20/17: Kelly justified […]

On being special in the venture business

Chris Douvos, one of the smartest fund-of-funds guys, once asked me the three questions he asks people who are raising a VC fund for the first time. The third was: “what makes you so special?” I was stumped. I couldn’t think of an answer. I figured I’d come back to the process once I did. That […]

AR will be startup dominated, VR will not

[I really meant to write this in a longer post because it’s arguable and I like to argue. But while this is timely because of the excitement around Pokemon Go, I’m working on something else and only had a few minutes to put it down. Not sure why I’m apologizing for not giving you another 25-page, […]

Disruption is not a strategy

I was at a research lab to talk about commercialization. The presenter put up a slide of some exciting new technologies. The slide’s tagline said these technologies would “disrupt the biomedical industry.” My first thought was that disrupting the biomedical industry–“to interrupt by causing a disturbance” or “to drastically alter or destroy the structure of something”–is probably the exact […]

VCdelta now part of Mattermark

I built the @VCdelta twitterbot five years ago to solve a problem. I needed to keep on top of the companies the firms I respected most were investing in. The obvious way to do that was to keep track of the firms’ portfolio pages. I found it really useful. Other people found it useful too, and […]

Strategies Against Systems

There is one other circumstance, peculiar to human conduct, which stands in the way of successful social prediction and planning. Public predictions of future social developments are frequently not sustained precisely because the prediction has become a new element in the concrete situation, thus tending to change the initial course of developments. This is not true […]