IPOst-mortem?

Perhaps it was the hubris of appropriating the acronym LGBT and literally turning it into a monetary symbol.

Perhaps it was the massive overspending.
Perhaps it was the megalomaniacal higher-ups who flew around the world on the company wallet.
Perhaps it was sheer karma for selling gay media down the river like a dressed up whore.

Whatever, Bill Gates' $25 million hasn't helped Planet Out/Gay.com from tanking.

Yeah, I worked for them - each - briefly.
Here's a few 2000-era articles that I wrote for them, dredged up and linkified a while back.

I actually got some good work done, when I wasn't being backstabbed by a catty talentless copy editor, sabotaged by sociopathic co-producers and other assorted freaks.

Schadenfreude? Mebbe. The people I had to work with aren't there any more. I don't even think they have humans working there anymore; just bots.

Inevitable? Didn't have to be.
Predictable? Oh, yeah.

(other sources:)
Bay Area Reporter
CNBC
Joe.My.God
Queerty has a hilariously snide history of following this.
Chris Crain's is a bit more measured.