Mike Chalfen: How to Build Anti-Fragile Venture Portfolios Today | 20VC #904

(beeping) Three, two, one, zero. You have now arrived at your destination. Mike, this is such a joy to do. I've wanted to do this one for about seven or eight years. But thank you so much for joining me today, first.

Thank you so much for having me, and, you know, I'm sorry that, uh, I didn't join when you first, first asked me. But, um, you know, I'm a slow learner but I- I eventually made it.

Listen, it was only my mother that actually listened back then, so I think it was a strategic-

(laughs)

... and wise move for you to do. And for those the actually can't see, and would see on TikTok, Mike has the most brilliant bookshelf behind him, um, which just shows how wise he is. But we're gonna start (laughs) today with Mike's intro. And so, tell me Mike, how did you make your way into the world of venture? And then how did you come to found Chalfont Ventures; obviously, most recently?

I- I- I grew up sort of quite nomadically. We moved around a lot. And I was very interested in sort of fairness and in sort of how the world ought to be. Because wherever I went, I was a fish out of water and nothing seemed to be how it should be. Um, so I did the obvious path to get into venture, which is I started studying civil rights history. And, um, got a fellowship from the US to pursue more, more history. And, um, when I arrived, um, went to meet the guy I thought I'd study with who said, "You know, I hate this career. I can't recommend it. I read your submission, you could spend your whole life doing that and I cannot recommend it. Good luck. I'm going on sabbatical." So off I went, and started doing two things: uh, playing with the web, a little bit very early, but mainly sort of going and hanging around at the business school and ending up at BCG, which I didn't enjoy. Um, and I left, much to everyone's surprise, at BCG to join vent- a venture capital firm called Apex Partners, which was then a venture firm, in 1996. So, um, you know, I- I was sort of a believer in bottom-up change and that the- the web could enable it. And Apex was an unusual place, um, at the time. Partly because there were only three firms in London that did VC. Um, but it was a very sort of strong, analytical culture. Um, from the beginning, I had to sort of do all my own legals, do all my own numbers, um, write my own recommendations. And so it was very good training, in fact, for what I did later and do today. Um, sort of learned the craft very well. Um, and although the funds got very big, you sort of learned the value of- that every dollar counted. Like we didn't sort of walk away and just lose money casually, even though the funds were pretty big by the time I left after 10 years. But also, it peaked at, I think I was the 31st and youngest partner, but it peaked at 41 partners, so there was this sort of... I learned quite a lot about big partnerships. And, and lastly, um, you know, I- when I look back, I was managing my career rather than managing sort of the money I was investing. And everyone else in the building below sort of the very top level was similar. And, you know, that was something, again, I only realized much, much later. But it was, it was an unusual experience, and, um, really set me up well, both good and bad.