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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

Sometimes the prize feels closer, other times farther away. Still other times it feels like we are drowning in aimlessness and exasperation. An identity crisis looms for any high achiever flirting with failure, and a calculation begins on the conflicting forces of sunk costs and lost time on the one hand, and reputational harm on the other. As entr... See more

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