Over the years I’ve seen the post going around in various forms of how Bessemer Venture Partners keeps a *robust* anti-portfolio on their website. It’s fun, self-aware, humbling, and differentiating. If you haven’t already, go have a look. (As an aside, I’ve been to their offices in Cambridge multiple times back in the day while visiting Kent Bennett, the venerable Felda Hardymon, my dear friend Steve Papa (if Steve was capable of “friendship”), and the young(er) founders of a company called Toast - Bessemer wallpapered their bathrooms with the rejection IRMs of said anti-portfolio).
Anyone who has been in the game long enough probably has their own version. Companies they could have invested in, but passed on, only to be made a fool when said company later becomes a decacorn. My personal opinion - and I tend to think one that Bessemer shares - is 1) we all make mistakes, 2) we’re human and at times quite dumb, and 3) hell, at least we had access in the first place. Venture investing is about seeing as many amazing opportunities as you can, even if sometimes that means missing a few…dozen. Either that or I’m totally full of shit and we’re just plain idiots. What do I know. I’ve only been doing this for three years. ¯\_(ツ)_/¯
In any case, in the spirit of giving myself a Father’s Day gift of crow, which I plan to eat, here are some of mine:
Toast: not sure if Steve P would have let me into his $4M or whatever it was round never mind the Seed or the A, but I feel like I could have convinced them. Steve F and Aman said they were going to fully rebuild a POS after running into integration nightmares with Micros, Aloha, et al, and I thought they were crazy. Old industry incumbents. Entrenched. Insert foot in mouth, and then pull it out and use it to kick my own ass.
Klaviyo: TJ Mahoney was a pre-seed investor and he told me about it. Said AB was a stud. I passed without even talking to them. $8M valuation or around there I think. Shopify ecosystem play? Ew. Sigh. I’m a dumbass.
Pillpack: mentored TJ a bit early when he was having some team stuff going on at Techstars. The hippie. $4M post or something. Said no. Whoops.
Drizly: Nick Rellas kept stonewalling me, the little twerp, but pretty sure I had a small spot. Pat Kinsel would have got me in. Slept on it. Round closed. I’m an idiot.
Draftkings: met Jason at a dinner and Ryan Moore told me to hop in at pre-seed - I already had a small play with a competitor. Jason and I became great friends (which we are to this day). Really knocked that one out of the park. Way to go, Phil! Good eye!
Anyway, PLENTY more where that came from and I’m sure I’m currently in the process of creating one of the world’s most epic anti-portfolios at Impellent Ventures. But, again, c’est la vie. Better than sitting on the sidelines and wondering what could have been. At least I know what could have been - a gazillion more dollars than I have right now. Ah well. Batter up!
*p.s. I’ve had some winners, too ;)
