Bill Gates, the world's richest man, is a huge collector of rare books and paintings. In 1998, he set a record for American art when he paid $36 million for Winslow Homer's "Lost on the Grand Banks."
Former CEO Steve Ballmer was reportedly interested in bringing an NBA team back to Seattle, but when those plans fell through he dropped $2.3 billion on the Los Angeles Clippers. Fortunately, the value of his Microsoft stock rose $3.2 billion in 2013 alone, so his pockets were definitely deep enough.
Microsoft co-founder Paul Allen owns two sports teams -- the Seattle Seahawks and the Portland Trailblazers, plus he's a part owner of Major League Soccer's Seattle Sounders. And he owns a massive yacht with a submarine on board. Take that, Ballmer.
Charles Simonyi oversaw the creation of Microsoft Office and was at the company until 2002. Now, he's a space-obsessed billionaire who took two trips to the International Space Station.
Bob Greenberg left Microsoft in 1981, well before its IPO, and would go on to help create the creepy-but-popular Cabbage Patch Kid dolls that were all the rage in the mid-1980's.
These days, he's working in software again, after his brief interlude in making hit toys.
Gabe Newell was a producer on the first three versions of Microsoft Windows, and was already a millionaire when he left the company in 1996. Now, Newell is the head of Valve Software, and a hero to gamers everywhere, who affectionately call him "Gaben."
Former Microsoft CTO Nathan Myhrvold has a reputation as a renaissance man -- he used his Microsoft millions to found a firm that specializes in intellectual property and patents, plus he's a renowned nature photographer and trained physicist who once worked with Stephen Hawking. But he's probably best known for his comprehensive and unusual 600-plus page cookbook, "Modernist Cuisine," which has sold at least $30 million worth of copies.
Richard "Quiet Lion" Brodie, was the original author of Microsoft Word and Bill Gates' former assistant. He left Microsoft in 1994 to pursue a career as a self-help book author and a professional poker player. He even went on Oprah once.
Ex-Microsoft employees Chris Peters, Mike Slade, and future RealNetworks founder Rob Glaser teamed up to buy the Professional Bowlers Association, for no other reason than they could. When they left in 1999, Microsoft stock was hitting some all-time highs ahead of a 2:1 stock split.
Brad Silverberg used his Microsoft millions to go into venture capital as Ignition Partners alongside a bunch of other Microsoft millionaires, funding hot enterprise startups like Wit.ai and Xamarin.
Andrea Lewis was a Microsoft technical writer, estimated to be worth $2 million. She used her millions to open the Richard Hugo House, a literary center in Seattle.
Jim Allchin was a key part of getting Windows 98, XP, and Vista out the door as a Microsoft executive. Nowadays, he's a renowned blues guitarist and singer, with his 2013 third album Q.E.D. garnering critical acclaim.
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