Michael Saylor's Brief Embrace of a Dating Guru

MicroStrategy CEO Saylor and new author/old girlfriend Jess McCann at the launch party for her book, "You Lost Him at Hello."
MicroStrategy CEO Saylor and new author/old girlfriend Jess McCann at the launch party for her book, "You Lost Him at Hello." (Roxanne Roberts - The Washington Post)
By Amy Argetsinger and Roxanne Roberts
Thursday, August 21, 2008

Millionaire bachelor Michael Saylor keeps a tight lid on his personal life, so imagine our surprise when his name appeared -- as a "past flame," no less -- on an invite to celebrate a new dating book.

Turns out MicroStrategy's CEO briefly went out with Washington's Jess McCann, saleswoman-turned-author of "You Lost Him at Hello." Saylor (trim, tan, looking like a chipper, younger Dennis Quaid) dropped by the City Tavern Club on Tuesday for the book party. "I think the world of Jess," Saylor, 43, told us. So, she was your girlfriend? "I never kiss and tell, but we were associated."

We waded through the crowd (all sipping cocktails, none eating the cupcakes) to the newly minted dating guru, who's 31, blond, svelte and relentlessly confident. Her definition of dating: "Getting to know someone until the guy decides he's in love with you."

McCann's bio boasts a background in sales, a stint on the Fox reality show "The Rebel Billionaire" and relationships with pro athletes, TV stars and one of the Forbes "40 Richest Men Under 40" -- who sounds a lot like the never-married Saylor. (She's says their romance lasted a "couple months" back in 2004.) She told us she's had several serious boyfriends, lots of proposals, but hasn't found anybody she wants to marry. Her book treats love like a marketing plan: promote the product, identify clients, close the deal. "Everyone uses sales," McCann said. "There's no reason why it can't work in dating."

Saylor's advice on attracting a $300 million man? "Be yourself. That's my best dating tip. . . . I have to go."

Conventional Wisdom

· Is this Poorer Half Siblings Week on the campaign trail? Days after an older half sister stepped forward to contradict Cindy McCain 's references to herself as an "only child," the Italian edition of Vanity Fair reports it tracked down George Hussein Onyango Obama, 26 -- the youngest of Barack Obama 's many half siblings -- living in a ramshackle hut on the outskirts of Nairobi. According to a translation in the U.K.'s Telegraph, the younger Obama said he does not like to admit his relation to the candidate because he is ashamed of his poverty. The brothers have met only twice; in his autobiography, the candidate described George as a "beautiful boy with a rounded head."

· Toby Keith is a Democrat? The jingoistic country star -- who has aimed lyrics such as "We lit up your world like the Fourth of July" at the Taliban -- says he is and that he's liking Obama. While promoting a new movie, Keith said he was impressed by the candidate's trips to Iraq and Afghanistan.

Love, Etc.

· Born: Twin sons to Ricky Martin, 36, who welcomed them into the world a couple of weeks ago with the help of a surrogate mom. Who knew? His rep told reporters that the never-married superstar singer will spend the rest of the year out of the public eye while adjusting to family life.

This Just In . . .

· Stranded : British '70s glam rocker Gary Glitter, 64, a man without a country after being sprung from a Vietnamese prison. Glitter, known for sports anthem "Rock and Roll (Part 2)," served nearly three years for molesting children; after his release Tuesday, officials tried to ship him back to the United Kingdom, but he refused to board a connecting flight in Bangkok, where Thai officials denied him entry. He then flew to Hong Kong but was turned away by Chinese officials. Unclear what happens next.

Hey, Isn't That . . . ?

· Benji Madden getting his hair cut at Georgetown's Okyo Salon on Tuesday before the La Plata native's sold-out Good Charlotte show at the 9:30 club. Also there at the same time: Brian Baker, a founder of D.C. hardcore pioneers Minor Threat (and currently with Bad Religion), who -- despite having slagged Good Charlotte's pop-punk stylings in a couple of interviews some years ago -- walked over to chat amiably with the younger, richer guitarist. Madden was later heard telling his stylist what a legend Baker is.

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