James Altucher has founded 20 different companies (at last count), ranging from hedge funds to dating websites. He has sold a few for $10 million or more but admits that most of his ventures have failed.
This guy has risen from the ashes so many times he'd make a phoenix jealous.
But failure isn't as glorious as that analogy might paint it. It's a gritty, dirty, a bottomless pit.
"Failure really sucks," Altucher said. "When you fail it's not like you say, 'OK, I failed now. I'm here at the bottom.' There's no bottom. It feels infinite. It feels like it's never going to end. It's just going to get worse and worse."
But, Altucher, who has been called "the Oprah of the internet" for his sage advice, explains that you can't just get sucked into sitting at the bottom and wallowing in it.
"I know from experience that if I keep on living a healthy, honest good life that things will bounce back. I have to remember that every time I've been in these situations before, better things have happened as a result. So you instantly don't fail once you feel that way."
Despite being a successful entrepreneur, investor and author, Altucher now chooses to lead a minimalist lifestyle: He doesn't have a home. He lives in random places through Airbnb. He only owns 15 things, including a laptop, iPad and three sets of chinos.
The New York City loft he's living in right now has what can best be described as a go-go dancer cage. It's the first thing I saw when I stepped off the elevator. It's in the middle of the apartment.
"Do you want to get in?" James asked.
The cage felt like a familiar place that I put myself in after every time I fail. I was only in there for a minute – but it was a very long minute.