Subscribe to read

By definition, you will likely succeed a vanishingly-small percentage of the time, but—as the saying goes—that’s a feature, not a bug. The point is to venture—fistfuls of money in hand—at the furthest extremes of capitalism, hoping to stumble upon that rare, proper intersection of technology and commerciality.By design, most investments will miss t... See more

I was at Amzn early '00s when we lost 95% of our market cap. Later at FB I negotiated a down-round in '09, and then in '12 our stock dropped 50% post-IPO. I was on the board of a public company that went bankrupt (Borders) and a start-up that went under (Hello). Some lessons:

C. Failing is OK: It usually takes overconfidence to stay the course through adversity, but a humble mind to evolve and iterate. While it became clear to me that I had overestimated my risk-tolerance for working in an early-stage start-up, I also began to realize from having personally invested in start-ups that I much preferred being the investor ... See more