On Clubhouse, a conversation about ‘the future of S.F.’ sparks familiar debate

The conversation about the “Future of SF” was supposed to be a small affair, just a few dozen people chatting on Clubhouse, the latest must-have, invite-only Silicon Valley app. That was according to the discussion’s host, Michelle Tandler, who tweeted about the event to her 13,000 followers a day before.

Her co-host, Mike Solana, a vice president of venture capital firm Founders Fund, who is widely known for skewering San Francisco government and dunking on anti-tech sentiment, retweeted the notice to his nearly 40,000 followers.

“We’ll be having beers, talking future of SF, and seeing if anybody joins us. *Prayer-hands emoji*,” Tandler wrote. “Re invites – reply here if you need one. I bet there are some people with extras.”

This, naturally, is not at all what happened.

Instead, the discussion quickly turned to crime and public safety, attracted the attention (and then the participation) of San Francisco District Attorney Chesa Boudin, grew to nearly 3,000 listeners and drew accusations of racism after Black and Latino participants determined they had not been invited to or represented in a conversation that was, ostensibly, about the future of a city where many have lived for generations.

It was a moment that encapsulated two of the city’s familiar conflicts: the friction between moderate, affluent San Franciscans and progressive city leadership, perfectly embodied by Boudin, a former public defender who is arguably the most progressive elected prosecutor in the country; and the tension over a lack of people of color in conversations about crime and criminal justice, when they’re often disproportionately affected by both.

It was, in other words, a classic internet-fueled meltdown that seemed to revolve around a few all-too-common questions: Whose city is this? Whose concerns matter the most? And who gets to determine its future?

Briefly, for the uninitiated (and uninvited), Clubhouse is a San Francisco-based “drop-in” audio platform where people can visit digital “rooms” and listen to live conversations. If so moved, a listener can “raise their hand” to indicate they’d like to be allowed onto the virtual “stage” to speak. Moderators — in this case, Tandler and Solana — are in charge of fielding those requests.

Clubhouse rooms can range from guided meditations and workshops on how to grow your social media following to discussions about Caribbean herbs and sex talks for singles. All conversations are contemporaneous; they aren’t saved or archived. That gives the app a certain immediacy — if you don’t catch the dialogue in real time, you’ll miss it (unless someone has covertly recorded the discussion, a no-no). But it also presents significant challenges for moderation, something for which the app has come under fire more than once.

For the past year, Tandler, a lifelong San Franciscan who is working on launching a life-skills education app, has dedicated a significant percentage of her time — 10%, she guesses — to learning about the city with a self-described focus on “crime, the drug epidemic and homelessness.” This includes many tweets about the city’s homeless population, the increase in certain crimes, anecdotes about friends leaving and other perceived failures of local government. “My main goal is to engage people in a dialogue and get more people talking about San Francisco local politics,” she said.

Her tweets sometimes include the sort of language that would make many progressives wary — comments about the “broken windows theory” or the how the city needs to be “tough on crime.” At the same time, she made it clear multiple times in an interview Friday that she likes the progressive Boudin and is increasingly understanding of the constraints his office is under. (Solana, who has called for Boudin’s resignation, is decidedly less so.)

Tandler says she’s been wanting to host a public conversation with Boudin for a while now, but Thursday’s virtual gathering was not supposed to be that. Rather, she describes it as a test run to check out Clubhouse’s tech. She’s been a member of the app for a while but had previously only dropped into conversations; this was her first go at moderating.

Testing out @joinClubhouse tomorrow evening at 6pm PT/ 9pm ET with @micsolana.

We’ll be having beers, talking future of SF, and seeing if anybody joins us.

Re invites – reply here if you need one. I bet there are some people with extras.

— Michelle Tandler (@michelletandler) January 14, 2021

In tweets and in an interview after the Clubhouse event, Tandler said she had expected it to amount to a few dozen people talking about the much-discussed tech exodus and maybe real estate prices.

Instead the conversation attracted an audience of hundreds early on and, according to multiple interviews and recaps of the conversation, Solana and Delian Asparouhov, a principal at Founders Fund, swiftly focused their comments on an increase in local crime and placed the blame, at least in part, at the feet of Boudin. Homicides and burglaries were both up considerably year over year in 2020, while car break-ins, sexual assaults and other assaults were down. As a result, Boudin is facing a recall campaign just a year into his tenure, and there’s an ongoing effort to fund an independent journalist dedicated solely to investigating the district attorney and his office.

Tipped off to the conversation by a constituent, Boudin was soon in the room, raising his hand to speak.

“He logged on and heard a tremendous amount of misinformation and disinformation,” Rachel Marshall, Boudin’s communication director wrote in an email to The Chronicle. “He was invited to join the conversation, and did so, intending to spend just a few minutes correcting misconceptions.”

Tandler says Boudin’s appearance was a surprise and a welcome one. (She had invited Boudin to the Clubhouse app a couple days prior, she said, but not to the “Future of SF” discussion specifically.) What followed initially, Tandler later tweeted, was a “heated conversation that took on an overly aggressive tone.”

With Boudin participating, the event went viral, attracting around 3,000 listeners. Tandler, by this point, was “feeling nervous and surprised.”

Eventually, tempers settled enough that the conversation turned into a QA with Boudin. He spoke about how the pandemic had led to a logjam in jury trials, his office’s decision to enter into a plea agreement with Troy McAlister, the man accused of killing two women while driving intoxicated on New Year’s Eve, and the ongoing push to reduce the state’s prison population. Tandler described this part of the event as “pretty powerful.” It’s not often that one of the city’s most high-profile politicians faces a panel of critics, on the fly, before an audience of thousands.

Boudin wound up leaving the room after about an hour, just as one of the speakers asked Nancy Tung, Boudin’s onetime political rival and persistent critic to weigh in on how she’d charge a hypothetical crime. “I’m going to gracefully exit because we’re in a land of speculation,” Boudin said on his way out.

As all of this was happening, frustration was growing elsewhere. Even before Boudin had joined the discussion, other Clubhouse users had caught wind of the “Future of SF” conversation and noted that many of the speakers were white people advocating tough-on-crime policies that have historically hurt marginalized communities and people of color the most. (Boudin’s office was quick to highlight this dynamic in its statement sent to The Chronicle that said that Boudin was “disappointed to see a lack of diversity in the conversation and the exclusion of important voices of those who have personal experiences with the criminal justice system.”)

Had to create the spin-off room in #TheBayIsInTheArea https://t.co/SNVSSFPtrU pic.twitter.com/Nrkyt5PPaV

— This Is Us Stan Page (@DNas) January 15, 2021

Bivette Brackett, a community organizer and co-founder of the advocacy group SF Black Wallstreet, joined the Clubhouse conversation early and says she was immediately struck by the tone. She described it as “Nextdoor on Clubhouse,” referencing another online platform that often draws criticism for giving space to covert racism from white and wealthy participants. Speakers in the “Future of SF” room, she said, were talking about how “they had to take our San Francisco back” and calling for increased law enforcement, all of which struck her as dog-whistle politics.

When Brackett and others raised their hands to speak, she says, they were ignored. Tandler says she was overwhelmed by the number of requests, but Brackett doesn’t buy that (at least one other speaker, angel investor Balaji Srinivasan, was allowed up to the stage during the fray). Nor does she buy that it was a complete surprise that Boudin showed up. It’s not uncommon, she says, for celebrities and politicians to join rooms on Clubhouse after being alerted that they’re a topic of conversation.

“We’re supposed to be in community,” Brackett said. “The purpose of Clubhouse is to have a balanced conversation. It was the weirdest. This is the most destructive asinine group I’ve seen on Clubhouse ever.”

“The conversation was completely tone deaf and privileged,” said Tinisch Hollins, another co-founder of SF Black Wallstreet. “This really hits home for me because this has been a long-standing issue.”

Eventually, a spin-off room, started by Leon “DNas” Sykes, popped up, this one called “‘Future of SF’ really means ‘Make SF more white.’” Sykes lives in Oakland, but when a friend told him about the conversation, it reminded him of others he’d seen on Clubhouse. “A lot of these rooms are mostly white people who are in tech having these conversations about the Bay Area or San Francisco,” he said. So he made one for the people he thought were being left out. Screenshots from that room show the audience included many people of color.

Brackett eventually stepped in to help moderate that room’s discussion, which drew around 800 people (including former city Supervisor Jane Kim) and became a freewheeling conversation among longtime San Franciscans and those who said they’d been pushed out. Other speakers, including Krea Gomez-Jones, countered what they saw as the bad-faith arguments being made in the original room.

“The point of contention comes around this audacity to be concerned about the future of S.F. when so much of the conversation is around whether I should leave or not,” Gomez-Jones said later in an interview. “I’m really grateful that we were able to hold space for Black and brown San Franciscans. We’re not invited to these conversations unless we make them ourselves.”

By the next morning, nobody seemed particularly happy.

On Twitter, progressives and people of color were still calling out the lack of diversity — in skin color, in class, in point of view — of the original conversation. On Twitter, Solana said he regretted (eventually) politely interviewing Boudin. “It was chaotic, it was nebulous, it was manipulative,” he tweeted. And Tandler, who received messages of both support and derision in the days that followed, wondered what she could have done differently and whether she would ever host a discussion on the platform again. “I don’t know if I have thick enough skin.”

Boudin’s office was succinct in its sign-off: The district attorney, a statement read, was “hopeful that future conversations around criminal justice in San Francisco center people from communities most impacted by, and with more knowledge of, the legal system.”

In the end, of course, there was no consensus about the future of San Francisco — not after one night of conversation on an invite-only app with no public record — rather just a tense reminder of the city’s persistent divisions and the voices often left out.

San Francisco Chronicle assistant audience editor Jenna Fowler contributed to this story.

Ryan Kost is a San Francisco Chronicle staff writer. Email: rkost@sfchronicle.com Twitter: @RyanKost