This Harvard M.B.A. has a sterling mainstream tech pedigree: CEO at Hightail (formerly YouSendIt), president of consumer applications at AOL and a senior vice president at Yahoo. As Ripple CEO, Garlinghouse, 47, has a 6.3% stake in Ripple the company — but that's not how he makes our list. Though Ripple controls 61.3 billion XRP, holdings that total $95 billion in value, Ripple's own venture capitalists value the company at only $410 million. Like so many operators on this list, it's his personal stash of XRP coins, confirmed "in the nine figures," that gets him here.