Inside Silicon Valley’s most lavish holiday party. Yes, there was unlimited caviar

When I arrived at the Palace of Fine Arts on Saturday evening, I crossed through a Waymo traffic jam and joined a line curving around the imposing faux Greco-Roman building. 

The crowd — better dressed than most in San Francisco — buzzed with excitement, ready to reap the rewards of hundreds of dollars spent on tickets. And no — this wasn’t a Sabrina Carpenter or Noah Kahan concert. 

It was a party thrown by Silicon Valley’s most powerful podcast. It was the “Holiday Spectacular” from “All-In,” and by “spectacular,” the organizers meant five open bars, heaping tins of caviar, and a private DJ set by Steve Aoki. 

“Who do you think the surprise guest is going to be?” one bro standing in line asked another. 

“Please be Elon!” 

The event was put on to celebrate a blockbuster year for the podcast and its hosts, self-proclaimed “besties” Jason Calacanis, David Friedberg, Chamath Palihapitiya, and David Sacks. 

Members of the media were not invited (I asked for a press pass but was politely declined.) So I decided to go anyway and bought a $650 general admission ticket, because my boss wouldn’t approve a VIP pass to have cocktails and dinner with the besties.

“All-In” launched in 2020 as a pandemic chat among poker friends. Five years later, it’s the top technology show on Apple Podcasts, with hundreds of thousands of listeners every week. This summer, the hosts landed an interview with Donald Trump in the wake of a glitzy Pacific Heights fundraiser hosted by Sacks and Palihapitiya. In September, they pulled off a three-day summit in Los Angeles featuring Peter Thiel, Elon Musk, and Marc Benioff. And that was all before Trump appointed Sacks as his artificial intelligence and crypto czar. 

How else to celebrate the foursome’s thriving media empire, immense cultural cachet, and rising political influence but by throwing a no-holds-barred bro-ligarchs victory lap bash that reportedly cost $1 million? 

Once I got through security and took a seat in my zone, I met Evelyn and Monica Brady. The sisters, who own an entertainment company and flew in for the day from Nashville, said they’ve been listeners for two years, and their favorite bestie is Sacks. 

“I think we’ve lost the ability to disagree in this country, and if we don’t talk, it’s dangerous,” said Evelyn. “But they talk, and they disagree, and they’re so, so funny.” Then she excused herself to run to the open bar for a glass of wine. 

Listening to the podcast is more than a pastime, Monica told me. It’s changed how the sisters socialize and do business. Influenced by the hosts’ discussions of poker, the sisters started a poker club and speaker series called “Distillicon Valley” to learn the game with friends.

“Man, it’s better than an MBA!” said Monica. “Teaches you so much about risk assessment, business decisions, reading people.” 

The two said other relatives have also caught the “All-In” bug, so much so that they’re planning to make next year’s podcast summit a family reunion. 

And then the lights dimmed, the band began playing the podcast’s catchy theme song, and the four besties walked onstage to whoops and hollers. 

Calacanis, in a Santa costume, opened the show with a special San Francisco greeting. 

“Santacanis is here to spread joy and stock options and bitcoin to all these fine San Francisco they, thems, its, whatevers,” Calacanis said. “Ho, ho, ho!” 

He then led a cheer for Sacks, who was leaning into his newfound White House appointment rather seriously by wearing a traditional Russian fur hat. 

Threaded through the conversation were several rounds of “Bestie Awards.” The biggest business winner? Sacks said Musk. The biggest business loser? Sacks said the legacy media. The biggest political winner? Calacanis said the PayPal Mafia. The biggest political surprise? J.D. Vance, whom Palihapitiya called “an incredible human being,” while Sacks noted that “even in deep-blue cities like San Francisco, the voters rejected the woke left in favor of the moderate alternative.” 

Some of the commendations took a more absurd tone: Palihapitiya, known for his love of expensive sweaters‚ gave the award for best new product to a Loro Piana cashmere collection and his moment of the year to “the greatest sexual encounter” of his life, with his wife. 

Sacks recounted how he and Palihapitiya came to host the Trump fundraiser at his Pacific Heights mansion, where tickets reportedly went for $500,000 per couple. When Trump’s team contacted Sacks, they said the fundraiser would have to raise a minimum of $5 million. 

“I thought, maybe that’s a hard number to raise, because there’s not many Republicans in San Francisco, so the first call I made was to this one, Chamath,” recalled Sacks. “I said, will you host this with me? Because I figured, OK, well, if nobody shows up, Chamath and I can just split it.” The fundraiser, which served as a coming-out party for a growing group of ultra-wealthy Silicon Valley conservatives, ended up raising a whopping $13 million, according to Sacks. 

Much to the disappointment of the bro I heard while standing in line, the world’s richest man did not show at the event. The big guest of the night wasn’t even another sexy figure from the MAGA-verse — quite the opposite. 

Aaron Levie, CEO of the cloud storage company Box, was honored onstage for “setting the most money on fire in pursuit of a failed campaign.” Levie, who supported Kamala Harris in the presidential election and is now urging Democrats to back Trump’s deregulation agenda, offered a roast of the besties and joined them for a few rounds of awards. 

The next guest promised to be huge — Calacanis checked in with security and told the audience that San Francisco International Airport had been closed for two hours — before inviting the 45th and 47th president of the United States onto the stage. The collective disappointment was palpable when a Trump lookalike in an orange wig walked up flanked by fake Secret Service agents. 

Ultimately, it was a holiday party, so the hosts thanked one another and their fans. Calacanis said he hopes they’re still making the podcast “40 years from now, in diapers at a nursing home somewhere in Italy.” 

I bid the Brady sisters farewell as they headed straight for the poker tables after the show and made my way to the “winter wonderland” party. Waiters served trays of gourmet hors d’oeuvres, guests grazed from tables full of exotic fruits and cheeses, and the aroma of freshly ground coffee drifted from the espresso martini station.

Attendees slammed back fresh oysters as rumors circulated that Google co-founder Sergey Brin was somewhere at the party doing magic tricks. 

It felt a bit like being trapped in James Bond’s Casino Royale — doors guarded by bouncers led to backroom chess games, a set of stairs next to an ice rink led to a mezzanine full of gambling games, and private security trawled the event, whispering into earpieces. 

But even as I tried to go “all-in” and have fun (who can really hate on caviar crostinis?), the overarching feeling was that of a Silicon Valley tech conference. The San Francisco spirit of shilling one’s company, regardless of the situation, was alive and well. 

Many attendees pitched me on their AI or crypto startups before sidling away when asked about their thoughts on “All-In.”

“This is like every other tech party,” one founder whispered to me. “People come, they talk, they eat.”