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Two Drinks With the Writer Kevin Sessums: From Celebrity Profiles to Eavesdropping on Techies

The celebrity profiler is turning his talents toward startup land.

Nellie Bowles

two drinks withI sat down for two drinks with new San Franciscan Kevin Sessums, the latest in our Re/code series called “Two Drinks With” (you can order kombucha, but I will judge you). Sessums talked about celebrity profiles, terrors of techies and Jack Dorsey as a sex symbol.

Although we entered the party with Solange Knowles, encountered a live camel and shirtless men in pharaoh hats before taking an elevator with Senator Mark Leno, Kevin Sessums was not particularly fazed by the Mark Hopkins last night.

“I know what a reporter needs,” he said, sipping ginger ale as the evening wrapped up.

He does. A celebrity profiler during the heyday of magazine decadence, Sessums wrote 27 cover profiles for Vanity Fair in the ’90s — famously diving into celebrities’ lives, bathing with Courtney Love, smoking a joint with Heath Ledger — before falling out of favor with editors and falling into substance abuse (crystal meth).

Now, sober and chastened, the 58-year-old Sessums has turned his eye to San Francisco. He has taken over the queer lifestyle magazine FourTwoNine and started a new Web series, “In the Land of Startups,” about people building new lives in San Francisco.

We met first at the Fairmont, but I’d accidentally gone directly to the Mark Hopkins where I’d found the camel. I told Sessums, in the Fairmont lobby looking dapper in his uniform of jeans and tie, that I’d never seen a camel before tonight.

“What about some camel toe?” he said, looking around for one.

He ordered a double espresso and a lemon tart. I got water.

So, I asked, how are you adjusting to San Francisco and tech-land?

“When I first moved here, my glib analogy was it’s like having a really sexy boring boyfriend,” he said. “And when you get bored, and you’re on the sofa you look over and think, at least he’s pretty.”

When he uses the word “startup” — as in his “In the Land of Startups” series — he says it’s a metaphor about people coming to San Francisco to rebuild their lives. He’s been studying the technologists.

“I’m an old loner. I eavesdrop on … what do you call a group of them? Like a murder of crows but, maybe, ‘a terror of techies,'” he said. “So I see a terror of techies, and I sidle up and I listen, and they are creative in a way.”

They use certain aggressive words that jar him.

“They have a word in their vocabulary I don’t, which is — killing,” he said, making a very hard k. “They make a k-illing. They k-ill something and then they move on.”

He continued: “Killing and disrupting. It doesn’t sound like we’re talking about tech — it sounds like we’re talking about ‘Breaking Bad’ and ‘The Sopranos.'”

That said, they’re not all bad. He once ran into Jack Dorsey on Grant Street, “looking a little lost.”

“I will admit a lot of tech guys are my type. I love Jack Dorsey even though he’s straight, supposedly. But Jack Dorsey could pass. Nerdy but dirty,” he surmised.

The next cover of FourTwoNine will be James Franco with a story from the actor: Straight James Franco talking to gay James Franco.

The magazine’s office is in mid-Market, right around the corner from Twitter and Uber.

“Did you hear that, Jack?” he said, speaking to my notebook. “I’m close to Twitter.”

Researching the technologists has been a challenge. Sessums understands just about every kind of character — women, “the black chauffeur,” “the kid,” “the Cambodian girls” — but techies are hard.

“It’s the straight boy with the ponytail, the techie that I can’t get in,” he said.

Again, he leaned into my notebook: “If there are any straight men with ponytails who like Asian women, contact me.”

He lives in an apartment on the top of Telegraph Hill and has a tiered private garden in back with camellia trees. The magazine’s owners gave him a car as part of his hiring, but he returned it. Instead, he rides bikes and wears a velvet riding helmet. He writes many of the stories himself, coming up with a variety of pen names to make it look like he has a larger staff.

His memoir, “I Left It on the Mountain,” comes out in February.

Nellie Bowles

We walked over to the Mark Hopkins, where designer Ken Fulk was having a party in honor of his winning the job to redesign the whole thing. Sessums ordered a ginger ale and I got a Manhattan. We ran into all the usual San Francisco dames (old Society here can feel like it’s about 15 people). I assumed Sessums was having fun, but he’s a quiet man. He hung back and watched everyone.

As I headed out to leave, Senator Mark Leno was posing with a drag queen, kissing her on the cheek before he joined us in the elevator.

“She’s doing a profile of me,” Sessums said, pointing to me.

“Do we need it to get more interesting?” Leno suggested. (What would this entail?!)

“You’re in it now,” Sessums replied.

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