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How not to regret your career, from the head of Silicon Valley's greatest startup factory

Sam Altman
President of Y Combinator, Sam Altman speaks at TechCrunch Disrupt NY 2014 - Day 1 on May 5, 2014 in New York City. Brian Ach/Getty Images for TechCrunch

Y Combinator President Sam Altman looked onto the room of 3,000 interns at Internapalooza in San Francisco on Thursday night, and delivered good news — to only one person.

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"Someone in this room I am very confident is going to found a multi-billion dollar company that will change the world in a very big way," Altman said.

"And 90 percent of the people in this room will end up with a career they somehow regret," Altman continued.

He said many of the high-achieving students in the audience repeat the same steps: go to Stanford, get a fancy internship from Uber, graduate and work at Facebook, then become a venture capitalist at Andreessen Horowitz.

"Here's the mistake: It looks like it's the same thing and you're just on this train stopping at these prestigious stations," Altman said. "And you've done that and it's worked for you so far, so you keep doing it."

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The 90 percent of attendees will end up regretting their careers because they don't take the few years it takes to figure out what they like. Instead, people are stuck chasing names of companies or job titles rather than realizing what they want to do or or the problems they want to solve.

"Try a lot of different things. You only have to be right once, but you have to be really right that once," Altman said. "I don't think people spend nearly enough time thinking about what they like and what they're good at."

As Y Combinator's president, Altman does have a bias towards people starting their own companies. 95 percent of Internapalooza attendees said they wanted to start their own companies, but Altman cautioned them against setting themselves up for failure by rushing into it.

"Startups are really hard and you should wait until you get yourself a reasonable chance," Altman said. "You want a really good idea, and really good co-founders that you know really well and you should hold yourself to those."

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He's told plenty of people to go work at Uber and Facebook instead, he said. It's about not hitching yourself to the prestigious train because you haven't found a way off of it, but setting yourself on a trajectory that leads to no regrets.

"If you have the opportunity to go be an early employee at a company that's just going crazy and you believe it's the next Facebook or Google, you should go join that company," Altman said. "If you have a startup that's keeping it up at night because you think it's so great, then you should do that."

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