“Black Swan Seed Rounds”, 2014-07-28 (; backlinks):
I started seed investing in 2010 (and much more actively in 2012) before becoming a full-time YC partner. In this period, I invested in about 40 companies.
So far, 5 of them [Stripe, Teespring, Zenefits, Optimizely, unknown] are in the “really good” category—a current value of ~100× or more, based on the valuation of the last round or last offer.
…Right before I invested in Zenefits, a prominent investor told me I didn’t understand the health insurance market at all and that the company was unlikely to survive another 3 months. When I made this investment, the company was worried about imminently running out of cash. I almost got talked out of investing by the other investor.
[Outcomes c. 2024: Stripe has gone on to huge success; Zenefits experienced serious problems beginning 2016 and probably returned much less; Teespring remains modestly successful; Optimizely did not do well and was acquired.]
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