12 Highlights

Nobody wants to talk about their self-doubts and the insecurities that fuel them. Every business is “going great” until it fails.

Nothing is more humbling than everyone passing by your three-foot cube that represents your future without even taking a second look.

The two greatest addictions in life are heroin and a weekly salary.

Fred Wilson

While many people paint an incredible long-term vision for their teams, the prospect of long-term rewards is insufficient for long-term motivation.

In hindsight, seeking positive feedback was toxic, because it was giving us the impression we were on the right track.

Another example of a dangerous fake win is raising capital. Funding shouldn’t be celebrated. If anything, raising money should make you nervous: It means you have more to lose and more people you are responsible to.

The impediment to action advances action. What stands in the way becomes the way.

Marcus Aurelius

During great moments, we are liable to have an inflated sense of self. We believe we are right more often than we actually are.

With any achievement, we’re liable to overestimate the role we played in it and underestimate the role of others—and of luck.

If you’re building a new business, you’ll be tempted to describe what you’re making in the context of what already exists as a shortcut to relatability, like the “Uber for massage” or the “Apple of razors.” The pressure to conform stems from the natural desire to be understood. But what you gain in relatability by latching onto an existing model, you lose in free-range innovation.

Whenever I meet with a team that lacks clarity or feels stuck, their breakthrough often comes from a new question or problem to solve rather than a better answer to the original question.

Invention requires a long-term willingness to be misunderstood, ...When you do something that you genuinely believe in, that you have conviction about, for a long period of time, well-meaning people may criticize that effort.

Jeff Bezos