A short excerpt from a YouTube interview in which Sam Altman advises entrepreneurs to 'ask for what you want'—be willing to make direct asks and be somewhat aggressive—and reflects that surviving repeated company crises becomes easier with experience because each crisis feels less scary over time.
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This was one of the other things I learned that I wish I had gotten advice on early in my career, is ask for what you want. You will get told no a lot, but sometimes it will work. And I think you see a lot of entrepreneurs shoot themselves in the foot because they don't ask that person to quit their job and come join them. They don't ask this big company to do a deal with them, and they're just not aggressive enough. And I think you being willing to ask what you want and be somewhat aggressive are really important characteristics of being an entrepreneur. People don't want to fail. They don't want to be told no. They don't want to end up in some crisis. Another thing that I learned, and I won't even say I wish someone told me this one, because I don't think it's a lesson anyone can teach you, you have to just live through it, is that each crisis gets less scary than the one before it. You're running a company now, I'm sure you've. I hope you've noticed this by now. You. There are a lot of things that really go wrong and they feel like company killing events and they feel like there's no way you're going to survive because the crises are really bad. And the thing you learn is that you generally do survive these and that the world doesn't usually end. And even if in the moment something happens, you have no idea how you're going to get around it. You eventually figure out a way. And because of that, on the 19th major crisis, you're like, well, I survived the first 18, I'll probably get through this one. And you kind of just do.