Meet Michael Saylor, Tech Playboy Who Still Lives Large (Corrected)

Michael Saylor lost a record $6 billion in the tech bubble nine years ago, so maybe that's why the MicroStrategy CEO isn't letting the current financial crisis crimp his style. (Update: Correction after the jump.) Is his conspicuous high-rolling meant to signal a comeback by the culty executive?

Page Six reports the software entrepreneur just threw a party on a 147-foot Dutch yacht before taking his G4 private jet to Cannes. (Update: Saylor says he doesn't own a G4 and was not in Cannes this year, see our correction.) The press-friendly tech exec — he once counted the media among his three key "constituencies," along with Wall Street and his own employees — didn't necessarily have anything to do with the tabloid item, or with his mention in a March Forbes article titled, "Ex-Billionaires Poised To Make a Comeback."

But back in 2000, even before he lost more in a single day than any human other than Microsoft founder Bill Gates (up to that point), Saylor's consumption was less flashy. He lived in "a dreary Northern Virginia townhouse," Slate reported. "Money holds little interest for him."

Saylor always had hubris, though. Here he is comparing himself to Thomas Edison and the ancient Romans in Fortune. So it's not a stretch to imagine he's now angling to be known as something other than a man done in by his own accounting error. If we're to be inundated with fresh news on Saylor, we might as well remind ourselves of who he is.

Meet Michael Saylor, Tech Playboy Who Still Lives Large (Corrected)

Claim to fame: He wishes it was McLean, Virginia-based MicroStrategy's data-mining software. Insted it's that $6 billion loss in personal wealth, incurred after the company retroactively slashed 1999 revenue by 25 percent due to erroneous accounting of two long-term contracts.

God complex: Saylor's employees have been known to say they are part of the "cult of MicroStrategy." The company is known for its six-week boot-camp for new recruits; for an annual winter cruise (no spouses allowed) and for an annual weeklong "university."

Saylor's sermons to staff have been known to run up to nine hours, the Washington Post has reported. His onetime chief of staff told the paper, "I've never seen someone who could transfix a room like Mike Saylor."

So he has issues?: Sure. WaPo also said he suffered from "volcanic impatience" and had been known to recite Bill Gates' well-known line, "That's the stupidest fucking thing I've ever heard." The newspaper cited his strict Southern Baptist upbringing by an Air Force Chief Master Sergeant for his "strong sense of insularity and control."

Doesn't sound like a playboy: No. In fact, Saylor used to hardly drink at all. That changed some time after he lost all that money, the Washington Post said, and now the New York Post has him jetting off to Cannes "with six friends."

Who does he date?: Interesting question! The Washington Post's gossips seemed pretty surprised when a woman there, Jess McCann, listed him as a "past flame" on an invitation to her book party. "Saylor keeps a tight lid on his personal life," the Reliable Souce column noted, and Saylor would say only of the woman, "we were associated" — not whether she was his girlfriend.

Slate thought it worth noting that Saylor "lets himself be advertised" as DC's most eligible bachelor.

WaPo once wrote that Saylor had once been known to invite women on dates, only to ask them to sit and read while he worked.