Jason Calacanis has been a harsh critic of San Francisco District Attorney Chesa Boudin. (Ozier Muhammad/New York Times)

Jason Calacanis has been a harsh critic of San Francisco District Attorney Chesa Boudin. (Ozier Muhammad/New York Times)

Chesa Boudin and Jason Calacanis almost sat down for a podcast. What happened?

Newly released emails between the DA and his outspoken critic tell the story

By Jeff Elder

Examiner staff writer

Tech investor Jason Calacanis (Uber, Robinhood, Calm and others) has been among the harshest critics of San Francisco’s embattled District Attorney Chesa Boudin, even starting a GoFundMe campaign to hire a journalist to investigate Boudin.

Somebody was looking into Calacanis and Boudin recently, it appears. A freedom of information request was filed anonymously seeking “all mentions of Jason Calacanis” or correspondence with him from the DA’s office.

The resulting emails, released to the public, reveal a surprisingly friendly correspondence between the two’s offices in February that almost brought the DA to guest on Calacanis’ podcast. A third-party had pitched the DA in an email about doing a spot on Calacanis’ “All In” show, saying, “I pinged Jason and he said he’d love to host you.”

The DA responded “Great idea. I’d be very happy to engage with them.” Calacanis’ team was also “happy to get something on the schedule.” The two sides then corresponded about a show with Calacanis and Boudin set for March 5. The agreement went sour a week later, according to the released messages, when Boudin’s director of communications emailed the Calacanis camp saying, “Unfortunately there has been a change of plans and the DA will not be joining you on the podcast.”

And that was that… until the next day, when Calacanis let Boudin have it with a little extra fervor on the podcast, saying The City has “turned into ‘Escape From New York,’ Gotham City-level chaos here” and criminals were taking “advantage of that weakness” he believes Boudin has exhibited. Co-host David Sacks blasted Boudin for “out of the blue, like a day or two ago, saying he’s not coming on the show” while another member of the crew clucked like a chicken.

When approached by The Examiner for comment, Boudin’s office said nothing on the matter. Calacanis emailed a simple, “Yep, they canceled,” later adding in another email referring to Boudin that, “for the good of San Francisco, I hope he gets recalled.” Who filed the documents request? Would the face-off have changed the discourse around the recall effort to oust Boudin? We may never know…

Chesa Boudin’s office had no comment about the district attorney dropping a plan to be on Jason Calacanis’ podcast. (Kevin N. Hume/Examiner file)

Chesa Boudin’s office had no comment about the district attorney dropping a plan to be on Jason Calacanis’ podcast. (Kevin N. Hume/Examiner file)

Sources close to DoorDash CEO Tony Xu say the gig workers’ protest at his house on Thursday was misplaced, literally. Xu doesn’t live at the Pac Heights address, but used to live nearby, they tell us. William Fitzgerald, who helped organize the event doing communications for The Worker Agency, an advocacy group representing labor campaigns, said the exact address was not the point. “We’re in the Pac Heights neighborhood where he lived. If he flew off to Hawaii, and his only response to this action is that he wasn’t there at the time, best of luck to him.”…

One tech center that isn’t empty these days is the Apple Store at Union Square, which is bustling, with dozens of patrons flowing in through the wide-open, oversized doors of the place. Are more people at the stores on weekdays than on Apple’s Cupertino HQ? Tough to say. Bay Area Apple employees said in a survey run by Blind for The Examiner that 41% of them have visited a corporate campus in the past month…

Speaking of hardware, one of our favorite pieces of new gadgetry to hit The City is the automatic pancake machine at the new Alaska Airlines lounge at SFO. OK, so Seattle has had one for a while, but a flapjack robot is still fun. BTW, love the current SFO Museum exhibit of East Bay glasswork artist Marvin Lipofsky (1938–2016)…

The Alaska Airlines lounge at SFO has installed a nifty automatic pancake machine. (Courtesy photo)

The Alaska Airlines lounge at SFO has installed a nifty automatic pancake machine. (Courtesy photo)

Everyone is so remote these days that new startups based in The City don’t always have any perceivable ties here. The AI company Pencil, which analyzes social media ads and advises companies on how to do marketing, sent out a press release this week datelined San Francisco. But the execs are in London, Utah, LA and mostly Singapore. What’s the SF connection? One cofounder, James Chadwick, used to work at Otter.ai in Palo Alto…

Tech types, like those at VentureBeat, are noticing that Levi’s, that most SF of companies, is building artificial intelligence into its processes. Rather than having engineers work with AI, as many companies do, the red-tagged OG jeans giant is putting all kinds of employees through AI bootcamps…

Yale researchers studied 13 million tweets and found that social media platforms like Twitter reward outrage, and that “moderate groups can become politically radicalized over time.” That really chafes my hide…

Cleopatra and Cash work at their San Francisco home with their owner, Wendi Garron, principal people business partner at Okta. (Courtesy photo)

Cleopatra and Cash work at their San Francisco home with their owner, Wendi Garron, principal people business partner at Okta. (Courtesy photo)

This week’s office dogs are Cleopatra and Cash working at their San Francisco home with their owner, Wendi Garron, principal people business partner at Okta…

Got an office dog pic or item for Screenshots? Send it to jelder@sfexaminer.com.

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