Chris Sacca - from seeking angel support became a donor of such.

Chris Sacca breaks into the Midas top ten--and the billionaire ranks--thanks to his early bets on Twitter and Uber as well as a host of other startups such as Stripe, Twilio, Docker, Lookout and Automattic. His Lowercase Capital was also one of the first investors in Instagram (acquired by Facebook in 2012 for about $736 million). The former Google executive is known for his garish cowboy shirts and brash opinions.

Sacca decamped from San Francisco a couple of years ago to split his time between Truckee, Calif., Los Angeles and Montana.

While still at Google, he wrote an angel check for $25,000 to Twitter and ultimately bought more than $1 billion of shares before Twitter's IPO. Sacca made his investors more than $4 billion and amassed a position for himself worth about $500 million today. His early $300,000 check to Uber, plus later additions, have helped his first fund, Lowercase I, become worth about $1.3 billion at Uber's last valuation. All for a Buffalo native who got fired from his attorney job and then spent months trying to catch the eye of Midas Listers to no avail. They notice Sacca now.

"I ask founders two things," Sacca says of his investing approach. "Can I affect your outcome, and will I be proud to say I backed you?"