This is the kind of possibility that the pointy-haired boss doesn’t even want to think about. And so most of them don’t. Because, you know, when it comes down to it, the pointy-haired boss doesn’t mind if his company gets their ass kicked, so long as no one can prove it’s his fault. The safest plan for him personally is to stick close to the center of the herd.
Within large organizations, the phrase used to describe this approach is “industry best practice.” Its purpose is to shield the pointy-haired boss from responsibility: if he chooses something that is “industry best practice,” and the company loses, he can’t be blamed. He didn’t choose, the industry did.

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Some of the most successful founders start out tentative and lukewarm. Especially the young ones, who are often far from certain they want to run a startup. As they should be, because it's not for everyone, and they don't know yet what they like.

Don't fear competitors who've raised a lot, unless you can say precisely how all that extra money is going to make them beat you. E.g. if ads are the only way to acquire users, and they can buy all the ads, you're in trouble. But money per se is not dangerous.

It's a mistake for startups to treat fundraises as a series of milestones. There's something even more impressive than raising a series whatever: to be making so much that you don't need to. Eventually all companies have to reach this point. The sooner you do, the better.

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The most dangerous way to lose time is not to spend it having fun, but to spend it doing fake work. When you spend time having fun, you know you're being self-indulgent. Alarms start to go off fairly quickly. If I woke up one morning and sat down on the sofa and watched TV all day, I'd feel like something was terribly wrong. ... But the same alarms don't go off on the days when I get nothing done, because I'm doing stuff that seems, superficially, like real work.

I suspect one of the rarest skills is to have any sense whatsoever of how different things were in the past. I believe it's as rare as being able to solve hairy integrals, but we don't realize that because there are so few explicit tests of it.