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 […]

Power Laws in Venture Portfolio Construction

Every article that has ever given advice on investing in venture capital has said that you need to invest in a portfolio of companies, because each investment on its own is probably going to be worth nothing and if you invest in just a few you will almost certainly lose all your money. This is […]

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, 6/20/17: Kelly justified betting a larger amount of your bankroll when you have a larger informational advantage. But the Kelly Criterion itself imagines a specific scenario: sequential parlay betting when you have an edge. Since venture investing is never really sequential (the ‘bet’ is not immediately resolved) and only angel investors really parlay, it […]

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 […]