Chris Sacca

Chris Sacca is the founder and chairman of Lowercase Capital, reported to be one of the most successful venture funds in history. A former Google executive, Sacca is now best known for being among the earliest and largest investors in companies such as Twitter, Uber, Instagram, Docker, Lookout, Twilio, and Kickstarter. His accomplishments have been recognized on a bunch of fancy lists but none brings him more pride than when GQ named him to its Worst Dressed list for his cowboy shirt obsession. These days, you an catch him as a Shark on Shark Tank doing everything he can to make Cuban and O'Leary miserable.