I met many aspiring artists in my early 20s. Observing their trajectories since then, I've learned that long-shot careers in the arts (famous singer, actor, songwriter, filmmaker, etc.) are long shots not because success relies on wild luck or rare genius or insane connections. Success stories pretty reliably happen for people who combine three not... See more

The secret is that taking risks provides optionality as well, via learning and differentiation. If you go to an ivy league school or elite consulting firm, however, you're merely one of many. Even something as prestigious as a Harvard degree makes you only one of 315,000. If you start a company, you can truly become one of a kind—you'll be one of a... See more

More often people who do great things have careers with the trajectory of a ping-pong ball. They go to school to study A, drop out and get a job doing B, and then become famous for C after taking it up on the side.

People want to start their own business or become financially independent. But you don’t end up a successful entrepreneur unless you find a way to appreciate the risk, the uncertainty, the repeated failures, and work insane hours on something you have no idea whether or not it will be successful

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.

However, true innovation and disruption comes from those outsiders courageous enough to believe they can enter a field and do it differently. The lesson here is that how you think is always more valuable than what you think.

there’s lots of successful people who don’t necessarily have high raw iq but they have high “fuck around and find out” attitude ppl who say fuck it and do the thing > ppl who overthink and get paralyzed by fear