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Microsoft millionaires unleashed: 12 Microsoft alums who spent their money in the most magnificent ways

Microsoft millionaires unleashed: 12 Microsoft alums who spent their money in the most magnificent ways

For those lucky enough to hitch their wagons to Microsoft early on in its meteoric rise to the top of the computing market, the payoff was huge.
Some analysts estimate that thanks to the stock options the company gave to early employees, Microsoft has created three billionaires and as many as 12,000 millionaires. And even for those who didn’t quite get to those heights, the rewards were huge.

Here’s a look at what some of Microsoft’s most successful alumni have done with their post-Redmond lives, from fine art to spaceflight.


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.”

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 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 cofounder Paul Allen owns two pro 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-1980s.

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 he 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, and 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.

RealNetworks founder and Microsoft millionaire Rob Glaser.

Brad Silverberg used his Microsoft millions to go into venture capital at 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.

Seattle’s Richard Hugo House.

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 third album, 2013’s Q.E.D., garnering critical acclaim.



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