Hughes had the good fortune of being Mark Zuckerberg's roommate at Harvard, and he helped Zuckerberg build what became Facebook. Zuckerberg considered Hughes the most socially adept of the founding team, and he helped with the site's user experience and worked with writers to get Facebook's first press coverage.
Hughes decided that the site wasn't going to be his life, and stepped away after three years. But those three years got him a 2% ownership in the company, and that stake ultimately brought him $500 million (R5.9 billion) after Facebook went public in 2012.
"I made a lot of money at a young age, but I didn't feel a connection to the work that I put in," Hughes told us in a recent episode of Business Insider's podcast "Success! How I Did It."
"So success, I feel like, for me, is having an opportunity to work on what I want to work on, and hopefully having an impact on the world as part of the process," he said.
Hughes first began to feel this in college, when he knew he wasn't willing, as Zuckerberg was, to drop out and move to California to turn their dorm room project into a real company.
"I loved working at Facebook, but it wasn't a religion for me in the same way it was for Mark," he said. "And I think to be able to be in the trenches and have the resilience and the dedication — with any startup, really — you have to believe in the mission of it. Almost with a kind of religious zeal."
In 2007, he joined a group that he could have that zeal for: the initially long-shot presidential campaign of freshman US senator Barack Obama. He was praised in the media for his successful work on building Obama's online presence.
When he found himself several years later with what he called the "boatload" of Facebook money, he decided he'd try to turn around the struggling New Republic magazine and turn it from a niche liberal journal into a mainstream hit with millions of readers. After spending $25 million (R297.9 million) over four years and dealing with an outpouring of talent in response to changes he was making, he decided to sell it.
The experience taught him, he said, that he could no longer set "really unrealistic goals." He needed to be driven by purpose, but it needed to be grounded in reality.
It's why with his newest project, he feels he has a clear definition of success that can guide him. As outlined in his new book "Fair Shot," he's working through his nonprofit the Economic Security Project to advocate for a guaranteed basic income of $500 (R5950) for working Americans making under $50,000 (R59,560). He's already overseeing an experiment with it in Stockton, California.
"I have to stay focused on what I care about most," Hughes told us. "That's the work that I do on a day-to-day basis, and, of course, my family. And as long as I'm focused on the impact that I want to have through work, through my family, then I'll be fine."
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