The weird and wild ways Microsoft's first employees spent the millions they made

Bill Gates
Bill Gates. Gus Ruelas/Reuters

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.

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Some analysts estimate that thanks to the stock options the company gave to early employees, Microsoft had created three billionaires and as many as 12,000 millionaires by 2005. 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. 

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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 lost on the grand banks
Winslow Homer's "Lost on the Grand Banks." P. S. Burton / Wikimedia Commons

The record has since been surpassed — earlier this year, Jean-Michel Basquiat painting sold for $110 million at auction.

Source: The New York Times

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.

Steve Ballmer
Mark J. Terrill/AP

Ballmer has since said that he has no plans to bring the Clippers to Seattle.

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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.

paul allen
Steve Dykes / Getty Images

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. And in 2006, Simonyi told Forbes that he spent 6 months of the year on "Skat," his custom-built 233-foot yacht.

charles simonyi ex microsoft space tourist
Reuters

Source: Forbes

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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."

Gabe Newell fan art
Deviant Art/Darren Geers
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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.

Nathan Myhrvold microsoft modernist cuisine
Modernist Cuisine

But Myhrvold is probably best known for his comprehensive and unusual 600-plus page cookbook, "Modernist Cuisine," which has sold over $30 million worth of copies.

In 2017, Myhrvold outed himself as the anonymous author of "My First Gulfstream," an infamous essay breaking down the absurd costs of owning a private jet. 

Richard "Quiet Lion" Brodie, was the original creator 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.

getting past ok richard brodie
Amazon
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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.

rob glaser realnetworks
RealNetworks founder and Microsoft millionaire Rob Glaser. Randy Stewart/Flickr

Source: Sports Illustrated

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 Trifacta and Docker.

brad silverberg windows 95 launch
Microsoft
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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 richard hugo house
Seattle's Richard Hugo House. Wikimedia Commons

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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