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The world's second-richest man just spent $26.2 million on The Gays. PlanetOut, the struggling owners of Gay.com, got an investment from Cascade Investment LLC. As Seattlest notes, that firm is owned by Microsoft's Bill Gates. But it's not the first time Bill has been the backer behind PlanetOut.

PlanetOut's official history lists Microsoft's MSN as one of the networks that featured the company's content. But that doesn't begin to describe PlanetOut's relationship with Microsoft. PlanetOut also partnered in 1995 with Microsoft's V-Chat Communications (a "visual chat space" that ended up...well, you guess whether it worked out).

"In fact," Valleywag's bearish editor Owen Thomas says, "PlanetOut launched entirely as a channel on MSN, which used to be one of those goofy proprietary online networks before it was an Internet service provider and Web portal. The MSN service totally flopped, and PlanetOut had to do a panicked forced march onto the Web, running out of money all the while. So it's ironic that PlanetOut is getting rescued by Bill Gates - he didn't do that much for them last time around."

See also: Suck.com's 2000 review of PlanetOut, shortly after the site got a $16-million investment despite being, according to its CEO, "nowhere near profitability."

(Photo from Gay.com)