EVERY business fails. Every single one. Some businesses somehow manage to stay in business when they run out of money and keep going on until they succeed. However, that's what businesses are up against. I think going into that armed and aware is one thing that makes success more likely.
Another lesson to take from Steve's experience: the bigger the impact your startup is likely to make, the greater the chance it will fail. That might seem quite counterintuitive at first. Certainly, if there's a market and the demand is there, then success should be forthcoming, right?
Except if the problem is unsolved, it's probably unsolved for a reason. I'm reminded of something I read (I believe it was from "Germs, Guns, and Steel", but I don't have it to reference): invention is the mother of necessity! Safe startups give people something they already want. Great startups give people something they didn't even know they needed.
But humans are dumb animals. The first three times you show them something better, they'll turn their backs. So the more important your work is, the more likely you are to fail, and fail, and fail again. It's not you, it's just human nature.
That's why he's so inspiring. He's a protagonist you can identify with, who triumphed over setbacks and flaws.
When I was much younger and starting my first (fundably doomed) startup, one of my cofounders liked to say, "yeah, most businesses fail, but those statistics include companies trying to sell soft drinks to Eskimos and combination Chinese food/pizza restaurants". Then we'd all chuckle, knowing that the statistics most certainly didn't capture dynamic new technology firms like ours.
No. Most companies fail. Look at the list of dead YC companies. Those were screened by a team that has specialized in doing nothing but screening founding teams and then attempting to give them every advantage their considerable and growing infrastructure and connections can give them. And they still fail.
Because that is what startups do. They fail.
The best, most talented, most experienced founders in the world would presumably be among the first to tell you that you can't read anything about your self from the simple fact that your company failed. Learn what you can, but don't ever let it grind on you.
(Some people just shouldn't be in this game, for whatever it's worth, like Matt Damon said about the no-limit players in Rounders; not because they can't, but because it's not healthy for them.)