Prior to his life as an angel investor, Chris Sacca was an attorney in Silicon Valley, where he dealt with venture capital. He later joined Google and became the lead of special initiatives, and started a new business development group within the company. Showing his wide range of skills, Sacca was also a volunteer and advisor for Barack Obama’s 2008 presidential campaign. Yet, it was Sacca’s investment skills that ballooned his net worth and made him one of the hottest names for hopeful companies looking for early investments. “What I’m looking for are founders — individual entrepreneurs — from whom I can sense the inevitability of their success. They just know in their bones that this thing is going to work out,” Sacca told USA Today about the traits he saw in the founders of companies he invested in, like Kickstarter.

Even with his clearly gifted intuition in investing, in addition to the lucrative rewards, Sacca still tries to stay humble among all his triumphs. “What’s success anyway? Is success about making the most money? No, money — for the most part — turns people into jerks,” he explained during his 2011 commencement speech at the University of Minnesota, which NPR ranked as one of the best ever. He also doesn’t take himself seriously when dressing, usually sporting a Western shirt, even on “Shark Tank.” According to Sacca, he first bought a cowboy shirt at the Reno, Nevada, airport, and it became part of his uniform ever since.

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