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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

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

There is a large random factor in the success of any company. So the guys you end up reading about in the papers are the ones who are very smart, totally dedicated, and win the lottery.

What are the most common reasons for failure in this type of business that you've observed again and again?

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

sometimes as an entrepreneur, you have to over-index to courage. You have to think about the world that you wish to exist, not the one that does exist. As investor, I'm constantly looking at distribution of probabilities, that those outcomes will in fact be achieved.

“I will fail many times, and I will be really right once” is the entrepreneurs’ way. You have to give yourself a lot of chances to get lucky.