If terriers had long enough legs to reach more things, the breed would not have survived. - Paul Graham

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.

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.

If you'd asked me as a kid how rich people became poor, I'd have said by spending all their money. That's how it happens in books and movies, because that's the colorful way to do it. But in fact the way most fortunes are lost is not through excessive expenditure, but through bad investments.