The All-In podcast is a fascinating, infuriating safe space for Silicon Valley’s money men.

On Nov. 7, about a week after Elon Musk took over Twitter and laid off half the staff, a company vice president offered a group of concerned employees an odd form of reassurance: If you want to understand Musk’s intentions for this place, listen to the podcast All-In. “The most recent [episode] covers the current layoffs happening across tech and provides some insight into why this is happening/necessary,” the VP stated, according to Platformer.

All-In isn’t just any podcast, especially if you want to get a sense of Twitter in the Musk era, either from the outside or in. Hosted by four investors-slash-entrepreneurs-slash-online-gadflies, All-In is where Silicon Valley’s money says what it really thinks. Two of the hosts are of particular fascination right now because they’re advising Elon Musk at Twitter. One is David Sacks, a collaborator of Musk’s going back to the PayPal days, now a prominent tech investor (Airbnb, Bird, others) and increasingly prominent conservative voice in the technology industry. The other is Jason Calacanis, another well-known investor (Uber, Robinhood) with a long history in the tech press, and one of the most eager boosters of Musk’s Twitter bid. The two are part of the informal brain trust Musk has brought into the company; both have denied playing any “officialroles, despite getting company email addresses, according to the Washington Post. They’re also serving as its unofficial PR arm, railing against Musk’s “haters” on the show while celebrating the layoffs and looser content-moderation standards. They’ve hosted the Chief Twit on All-In twice: at a summer live show in Miami and during their final episode of 2022, for which Sacks called in from Twitter’s headquarters and invited Musk to sit right beside him. The videos for both segments are the most-watched hits on the All-In YouTube channel, which has nearly 300,000 subscribers.

If you hadn’t heard of All-In before this moment, you likely weren’t alone; although it often tops Apple’s and Spotify’s tech-podcast charts, coverage of the show is somewhat circumspect compared with other well-regarded tech pods (Sway, Marketplace Tech). Journalistic profiles of the hosts, all notable personalities on their own, may not mention All-In at all, or perhaps only in passing; quotes from the show are sometimes aggregated as their own news posts, with little explication beyond that. Tech journalist Eric Newcomer wrote in November that he thinks All-In “has been underestimated by the media.” Having taken a deep dive into the podcast and its tendrils of influence, I have to agree.

What is All-In? The pod kicked off in the early days of COVID lockdown, after Chamath Palihapitiya—a former Facebook executive and now venture capitalist who gained some fame in recent years as the “king of SPACs”—texted his friend Jason Calacanis about starting a podcast together. Calacanis already had a popular show of his own (This Week in Startups, on which Palihapitiya had previous appeared), but he agreed to the new venture. For an initial “test” episode they brought on poker buddy David Friedberg, a former Googler who went on to found and fund various agriculture and food startups, to speak as a scientific authority about the coronavirus. All-In kicked off in earnest when, as Calacanis claimed, that test episode drew in 100,000 listeners; the three then had mutual friend and business partner David Sacks join for the second episode, which Calacanis introduced with a firm new ethos: “If you’re not into speculation, if you don’t like to debate, if you don’t like to question authority, and you don’t like to get a shit-ton of inside information, then go turn this podcast off right now.”

With its poker-themed title, All-In promised something irresistible to tech-curious listeners dealing with the pandemic’s early doldrums: an arena in which to hang out with four “Besties,” a group of wealthy, intelligent, well-connected businessmen with plenty of unique general insights drawn from experience, as well as jokes. Guys being dudes, shootin’ the shit, dropping names and pop-culture references, but also teaching you things along the way and arguing about important topics—in ways you’d never get from the mainstream media, from your politicians (no matter what party), from any other authorities you trust. That’s the pitch, anyway.

The pod has garnered quite the following, boasting famous listeners like Gwyneth Paltrow, Steph Curry, and Trump administration apparatchik Richard Grenell, while finance figures like Anthony Scaramucci and Binance CEO Changpeng Zhao have responded to episodes that mention them. At a live summit the Besties held in Miami last May (which reached capacity at 700 attendees, Jason claimed), they talked to guests ranging from Mayor Francis Suarez to Oculus founder Palmer Luckey to Stanford professor and Zillow board member Claire Thielke. Participants celebrated the fact that the conference wasn’t a “boys club,” like so many other tech-world gatherings.

It’s easy to see how All-In caught on so quickly. The show has catchy intro music, and it’s free of ads across platforms. The hosts are longtime pals, and their interpersonal dynamics are funny and endearing: middle-aged fathers with large financial vocabularies and youthful energy, who are very into saying “love you” to one another (except for Sacks, who only responds with “back at you!”). Their subject matter ranges from markets to current events to general tech insights, and guests have included NBA players and crypto execs. What’s likely the most important factor in All-In’s listenership, however, is the hosts’ engagement with their hardcore fans. The Besties often shout out specific listeners and fan accounts on the show, or boost those followers’ projects (a stats tracker, devoted vloggers, clip creators, merch crafters), or meet with them IRL, like at the summit. They’re also sometimes refreshingly transparent when it comes to their thought processes on running the show, like in deciding whether to include audience input on discussion topics.

Jason “J-Cal” Calacanis, the self-professed World’s Greatest Moderator, usually takes charge of directing the conversations, and his manic interludes and animated facial expressions recall an old New Yorker profile’s characterization of him as a “buoyant carnival barker with big ideas about vaudeville.” Next up: Chamath (referred to on the show by first name, like Jason) is the finance expert and “Dictator,” Sacks is the politics buff and “Rainman” (because he’s not nearly as emotional as the others—yes, this podcast considers itself very non-PC), and Friedberg alternates as the “Sultan of Science” and “Queen of Quinoa” (referring to his several investments in the grain, including an entirely automated quinoa-bowl restaurant). At their best, the discussions can be thoughtful and unpredictable: Calacanis’ endorsement of Oprah as a 2020 running mate for Joe Biden, Friedberg’s thoughts on how government incentives interact with the private sector, Sacks’ missives against forever wars, Chamath’s analysis of intellectual property issues raised by artificial intelligence innovations. Plus, they employ fun gimmicks: hosting annual “awards” and predictions shows, asking ChatGPT3 to write a sample show script, reading mean tweets about themselves.

All-In also wallows in familiar tech-world grievances, falling back on shallow talking points when it comes to common bugbears—the media, “woke” and triggered libs, anti-capitalists, tech workers aka the “surplus elite,” criminal justice reformers. In their excoriations of the tech press (whose calls they never answer anymore, they say), the hosts often invoke Jason’s past media experience as an example of how to improve journalism, which is a bit rich. (A relevant Jason quote from those days: “People say I’m too in the industry to report on it. I guess that’s true.”) Some of the hosts can’t help but be wrapped up personally in many of the subjects they go over, whether it’s SPACs or holdings of cryptocurrencies like Solana or investments in energy markets; in a late 2020 episode, when the Besties congratulated Friedberg and Chamath on a SPAC going public, “the Sultan” asked, “This isn’t a self-promoting podcast, is it?” This extends beyond the tech and investment realm: Jason and Chamath and Friedberg condemn Fox News and Rupert Murdoch for their deleterious impact on political discourse, then give their blessings for Sacks’ appearances on Tucker Carlson’s show (“because it’d be good for [All-In] ratings,” Sacks said they told him). The group constantly laments how both Democrats and Republicans “politicize” everything from face masks to climate change, even as they dialed up vitriolic campaigns against Gov. Gavin Newsom (whom some of them formerly supported) as well as ousted San Francisco District Attorney Chesa Boudin, whose successful recall campaign in 2021 was in large part funded by Sacks (with some chipping in from Jason and Chamath).

The Besties are entitled to wet their beaks as they see fit. They’re not journalists, and they don’t pretend to be. They’re not beholden to advertisers, they’re plowing their own cash into the show, and they’ve made All-In a forum for them to talk about whatever they wish. Fair enough; Chamath does indeed reserve the right to change his mind on things. And the Besties don’t totally ignore outside views; it’s hard to when the basketball team you have a minority stake in doesn’t care for your podcast comments about human rights. Just leave it to the haters to mischaracterize things.

The growing profile of the show, coinciding with the Twitter acquisition and its frenzied aftermath, is indicative of one of the most fascinating media stories of the past few years: Tech elites’ attempt to do an end-run around the discourse via pseudo-populist, “free speech”–oriented communication. All-In represents the importance, to the many tech guys who listen and feel they’re being spoken for, of “going direct.” Meaning, the way personalities in the sector are utilizing the very tools they put out into cyberspace to direct the narrative back in their favor, taking advantage of a battered journalism sector and confounding political situation to craft their own safe spaces atop the chaos. It’s about, as a former tech journalist put it, an “industry-wide frustration with how the media changed from cheerleading [tech] to being a fierce critic”—and a desire from the other side to return the favor. But All-In presents a core example of Newcomer’s observation that “people like Musk and Sacks have somehow convinced a subsection of the population that by avoiding direct questions from independent media they are more aligned with the public.” It’s difficult to look at the podcast’s ties to Musk, his advocacy for it, and what’s happened with Twitter and not see All-In as a way for these business-executive hosts to bolster the real work they’re doing trying to refashion society in their image. To take one very concrete case, the show has mirrored the hosts’ political activities in California: At one point, they encouraged listeners to support the Newsom and Boudin recall efforts in exchange for personal recognition from the Besties. Another example: Friend-of-the-show Joe Lonsdale was also featured in the leaked Elon Musk texts, informing the tech titan that Florida Gov. Ron DeSantis wanted to support Musk’s Twitter bid; Sacks repeatedly boosts DeSantis on All-In and touts the “free state of Florida.” But don’t call it politicization.

Still, it would be unfair to dismiss All-In as some reactionary project. Jason grew up interacting with working-class cops and firefighters in Brooklyn, while Chamath was born to poor Sri Lankans who faced political persecution. Those backgrounds often inform their dialogues: Jason has spoken on the pernicious nature of racism in policing and the need for reform, and Chamath often insists on the need for social safety nets. Sacks may be the “token right-winger,” but, he’ll point out, he did previously donate to both Gavin Newsom and Hillary Clinton. Friedberg opposes onerous regulations but considers the “deep state” a necessity for democracy. It’s not left and right, but “insiders versus outsiders,” as Chamath characterizes it; they’re speaking on behalf of the “censored” GameStop trader or the struggling Californian priced out of the cities.

This can be a little hard to take seriously, though. The hosts are insiders of a $14 trillion, extremely unequal industry, as they themselves celebrate, and they have the ears of major players in Silicon Valley and politics (“this podcast is the exposed back channel”). They mock companies with large staffs and disregard laid-off tech workers; what to them is just a market necessity and a possible dip in net worth can be life and death for those at whom they scoff. Sacks makes free speech his rallying cry and claims to support gay Americans, then disparages Disney workers protesting Ron DeSantis’ education legislation as “Mau Maus.” (He also regurgitates misinformation, like claiming the New York Times “bought” Twitter followers, as fact.) They may agree that Donald Trump was a pox on American democracy, then mock liberals for getting “triggered” by his reign. The thoughtful deliberation always runs up against a hard limit.

Another interesting wrinkle is that All-In’s hosts are not at all on the same page. They often engage in some heated discourse of their own—regarding what the podcast is really for, regarding one another’s opinions, regarding the show’s responsibilities. It’s not new; in a summer 2021 after-show discussion hosted on Callin—an app launched by Sacks—the conservative co-host derided Jason’s moderation as “unbalanced.” But the willingness to disagree in a civil, studied manner is part of the appeal. To quote Jason: “I think what makes this podcast great is the diversity of opinion and the respect that we show for each other.”

Yet the anger has ramped up over the past few months, occurring alongside the Twitter takeover, to a noticeable enough extent that fans are getting concerned or exhausted. There’s Jason and Sacks squabbling over political campaigns and how much Jason interrupts others, Sacks vs. Chamath over inflation economics, Chamath and Jason going at it over venture capitalists’ culpability in the FTX debacle, Jason vs. Friedberg vs. Chamath on deficit spending figures, or Chamath vs. Friedberg on the future of nuclear fusion (the latter of which led Jason to wonder aloud whether their friendship was on the rocks). There are even more existential fights, like Friedberg’s desire for the show not to be reduced to sound bites, versus Sacks’ effort to promote clips of his monologues because he feels he doesn’t get enough say. For the most recent episode, involving a spate of 2023 predictions, the Besties didn’t clash so much, but they did turn off the YouTube comments, to the ire of free speech–loving followers. (Sacks stated that he and Friedberg were opposed to this; the general tenor of All-In’s YouTube comments definitely soured by the end of 2022.)

To judge from various comments and reviews, the fans don’t seem to love the right-leaning politicking, the shilling on behalf of Elon Musk and his Twitter regime (from which Friedberg sometimes dissents), or the loud verbal insults. They came to this podcast, they say, for reasoned debate over key issues and business stories, not for propaganda on behalf of another group of elites. Such notes reminded me of something Jason told Sacks in 2021—that he sometimes gives Sacks less airtime because he already knows what kinds of opinions he’ll offer. In their business, there are few worse sins than being boring and predictable.

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