SAN FRANCISCO — Sipping a cup of cold-pressed coffee. Digging into fresh burrata. Walking along the Presidio, laughing about the conference bicycles they saw at a meeting at Google headquarters the other day.

That’s where you’ll find what’s become the fastest-growing chapter of the Obama alumni association.


Barack Obama was a startup president elected by a tech-obsessed campaign, they say. Silicon Valley is the natural next step.

In part, it’s a reflection of America’s changing economy; New York, D.C., Los Angeles and a president’s hometown used to be the best places to cash out after a post-White House career. But for the people who helped get Obama elected and worked for him once he did, there’s something about San Francisco and its environs that just feels right: the emphasis on youth and trying things that might fail, chasing that feeling of working for the underdog, and even using that word “disrupting” to describe what they do.

“A lot of people who moved out here were present at the creation of the Obama ’08 campaign,” said Tommy Vietor, working the shears on a two-mushroom pizza at a restaurant in the Marina neighborhood, not far from his apartment. “There’s a piece of them that wants to replicate that.”

Vietor’s time with Obama goes back to driving a van before the first presidential campaign even started, and he rode the opportunity all the way up through being the spokesman for the National Security Council.

Vietor left the White House two years ago, and though he and his business partner, former Obama speechwriter Jon Favreau, briefly based the communications strategy firm they founded in Washington, they soon headed west. Favreau went to L.A. Vietor picked San Francisco. Now they have a focus on speechwriting for tech and other startups.

“If you’re writing for a CEO out here, they’re more likely to be your peer than your grandfather,” Vietor said. “They’re young, they’re cool, they get it.”

Even that kind of communications strategy firm is about as conventional as it gets for the Obama alumni who’ve descended.

It’s more than just David Plouffe, who moved out for a multimillion-dollar job at Uber. The not nearly exhaustive list includes: Obama speechwriter Kyle O’Connor, now at Nest; Michelle Obama’s former deputy communications director Semonti Stephens, now at Square; director of citizen participation Katie Jacobs Stanton, now at Twitter; ’08 regional and field director Mike Masserman, now at Lyft; Brandon Lepow, who did advance for the Obama campaign and communications for the White House, now at Facebook; legislative affairs special assistant Nicole Isaac, now at LinkedIn; director of research Liz Jarvis-Shean, first at Tesla and now and currently consulting for Civis; campaign staff director for technology Jim Green, now at Salesforce, along with Obama’s first chief information officer, Vivek Kundra; ’08 regional field director Alex McPhillips, at Google; ’08 regional Gillian Bergeron, at NextDoor; Organizing for America digital director Natalie Foster, at the Institute for the Future; Tech4Obama program manager Catherine Bracy, now at Code for America; ’08 deputy Wisconsin director Hallie Montoya Tansey, at an education-tech startup called Schoolzilla. Nick Papas, John Baldo, Courtney O’Donnell and Clark Stevens are all now at Airbnb. Jessica Santillo, the former White House assistant press secretary who handled much of the Healthcare.gov meltdown response, was the most recent to arrive, now to be a spokeswoman at Uber, along with White House director of strategic & message initiatives Jordan Burke, associate director of intergovernmental affairs Kellyn Blossom and assistant to the deputy White House chief of staff Sarah Fenn.

“There should be a welcome booth at the SFO airport,” said Jon Carson, the former Organizing for Action executive director, who commutes about twice a month from his home in Chicago as part of his job with the San Francisco-based rooftop solar-panel company SolarCity.

Ryan Gallentine, another Obama alum, recently moved out to San Francisco to work for Solar City himself.

Bobby Whithorne, a former Obama campaign aide and White House assistant press secretary who recently left Tom Steyer’s NextGen Climate Action to join public relations firm Porter Novelli, admits he’s become something of a San Francisco new economy poster boy: the Patagonia jacket he wears back and forth to his office in SoMA, getting to the airport by Uber, booking his hotels on Airbnb, getting his groceries delivered with InstaCart.

When he moved here last year, Whithorne had only ever spent a weekend in the city. But it quickly felt right to him, and not just because of the food and the weather or that he has more time to get home and cook dinner with his girlfriend (who also left an administration job to move here) or plan weekend hikes together.

There have been a few get-togethers, but Whithorne doesn’t spend a lot of time with other Obama alums. Knowing they’re in town, though, does help.

“It alleviates a lot of the anxiety about moving to a new place,” he said, “in the back of your mind knowing you can call someone you know and trust, even if you didn’t hang out a lot in D.C.”

Obama himself rarely misses an opportunity to come to San Francisco. He says he loves the energy there, loves the people. (The city’s ultraliberal leanings mean he was greeted as a rock star even during the dark days before last year’s midterms.) He’s even become friendly with Elon Musk.

And there’s no shortage of staffers at the White House who talk about a life in San Francisco once the next 18 months are done. It’s the opposite of everything they hate in Washington. It’s their city on the hill(s).

“Hard not to love this place,” White House political director David Simas tweeted on an official trip to the city back in February, along with a photo of Obama boarding Marine One, the Golden Gate Bridge in the background.

It hasn’t been just one-way traffic. Nearly three-dozen top tier techies have joined the Obama administration from all over Silicon Valley in the past few years to better integrate new technology, and they’re trying to recruit more.

Megan Smith, a former Google vice president who’s now the White House’s chief technology officer, recalled talking with then-chief technology officer Todd Park about persuading a promising engineer to pass on a job at a startup and say, “‘I’m going to join the VA digital service, because that’s the coolest thing.’ At the time, there was zero chance that anyone we knew would say that. But that was our goal.”

Very quickly, Smith says, that’s changing. “Government,” she said, “reminds me of the Internet in 1997 or 1998, before anyone realized what had happened.”

The sushi’s better in San Francisco, sure, but Smith said, “You can only eat so much.” The message she got from Obama was, “‘I don’t need you for your whole career. I need you to come and trade out.’”

Smith’s not sure what she’ll do after the administration’s over. Park has already moved out to Silicon Valley, working as a technology adviser.

People in the White House say that having all these San Francisco people around will probably only accelerate the migration to the Bay Area.

Some of that’s already started: In April, Defense Secretary Ash Carter announced a branch office in Silicon Valley, to build cooperation between the Pentagon and tech companies, and General Services Administration staff is already on the ground.

Like a lot of people who worked for Obama and have made their way out to San Francisco, Alex Lofton never considered himself a political junkie. Three years right out of college working for Obama’s 2008 campaign and at Organizing for America through the Obamacare rollout was enough.

But he said that his experience was crucial to what he’s doing now — with a fresh MBA from Stanford, he’s got a startup called Landed that’s using property management software and other technology to facilitate renting and home ownership. He’s hoping to develop some kind of shared-mortgage approach to combat income inequality.

“I think the campaign fast-tracked me into being really excited about working as an entrepreneur probably for the rest of my life,” Lofton said.

He’s got a lot of friends in San Francisco from his Obama days. And if any other Obama alums are looking to invest, Lofton would love to hear from them.

“The bank account,” he said, “is open.”

CORRECTION: Alex Lofton’s name was spelled wrong in an earlier version of this story.