Taking Kid Gloves to All-In: My Reflections on Silicon Valley's Iconic Podcast

After catching up with co-host Jason Calacanis, a discussion of tech's party line.

Back in 2016, Jason Calacanis invited Katie Benner and me onto his show This Week in Startups to talk about Peter Thiel bringing down Gawker, the fall of Theranos, and the fight over Facebook’s lax moderation policies.

The conversation presaged many of the same debates that we’re having today. Benner and I were criticizing Facebook’s facile arguments about algorithmic neutrality — just as today I roll my eyes at hollow invocations of freedom of speech for social network platforms like Twitter. (Both frames are shameless attempts from tech leaders to oversimplify arguments they know to be more complex.)

Re-watching the episode, it’s easy to see signs foreshadowing Calacanis’s success with All-In. Two of his high-profile friends came up during that 2016 recording session. We teasingly pried into whether Chamath Palihapitiya (now a co-host with Calacanis on All-In) had trounced Calacanis in a game of poker at the Code Conference. And Calacanis took stock of the odds of landing an interview with Elon Musk. (Possible, he judged.)

Back then, just as we are today, we were interested in the relationship between tech and the media.

Calacanis, famous for his angel investment in Uber, was unflinching in describing powerful tech elites’ interest in finding safe spaces to communicate with the public back in 2016. “When people get escape velocity, they’re only going to speak with people who they’re certain are going to use kid gloves,” Calacanis told us in 2016.

These days, Calacanis is among the most successful practitioners in what we now call “going direct” — aiding those tech elites with escape velocity from facing direct questions from the media. Calacanis’s second ranked technology podcast — with Palihapitiya, David Sacks, and David Friedberg — gives the tech industry a powerful connection with the public, cutting out any pushy media middleman. (I’m a regular listener and generally enjoy the show — except when Sacks is allowed to filibuster on right-wing talking points without any credible pushback.)

At Kara Swisher’s final Code Conference this fall, I pitched Calacanis on coming on Dead Cat, the podcast I co-host with Insider reporter Tom Dotan and regular special guest Benner. Calacanis discussed the request on All-In and bragged about the numerous interview requests that the besties were fielding (and declining) from reporters. Then, interest in Calacanis grew when he started advising his friend Musk about what to do with Twitter. (Calacanis messaged Musk during Twitter acquisition talks: “Board member, advisor, whatever… you have my sword,” adding, “Put me in the game coach! Twitter CEO is my dream job.”)

Before Thanksgiving, Calacanis finally agreed to sit down and record an episode with Dead Cat — though he warned us that he wouldn’t talk about Twitter, try as we may.

We had a lively conversation with Calacanis, digging into the success of All-In and the changes in tech media since that 2016 conversation.

Going All-In on the Tech/Media War (w/Jason Calacanis)

If anything, I think All-In has been underestimated by the media. In August, the New York Times asked if Pivot podcast co-host Scott Galloway was the “Howard Stern of the Business World?” That show, co-hosted with Swisher, has largely ranked just outside of the 100 most popular podcasts in the world on Apple. Meanwhile, All-In has regularly cracked the top 50 most popular podcasts in the world and has recently made appearances among the top 20 most popular podcasts on Apple. The four co-hosts on All-In have built their following without churning through big name guests to attract podcast listeners.

It’s not just mass appeal. The podcast is popular among some of the most powerful people in Silicon Valley. And for the tech onlookers — I’m sure you’d get better business advice listening to All-In than Galloway.

Both shows represent the splintering media ecosystem. Media talking heads and business leaders live amidst their own self-contained AirPod vibrations. Just like Pod Save America gave Barack Obama’s diehards and MSNBC-types something to listen to while they prepared their arugula and Chapo Trap House gave the dirtbag left an outlet to grieve their persistent electoral disappointments, everyone gets to live in their own information ecosystem.

Many venture capitalists would love to create the magic-in-the-bottle of All-In. Logan Bartlett with his Cartoon Avatars is listened to by venture capitalists and startup founders, especially when he features Zach Weinberg’s contentious exchanges with crypto zealots. (Though I don’t think the show has cracked the mainstream.) Andreessen Horowitz, infamously, went big in podcasting and self-publishing with the launch of Future. While the firm’s eponymous podcast ranks 15th on the tech lists, it falls below the New York Times’ Hard Fork (6) and Calacanis’s This Week in Startups (8). I have to imagine there’s a pretty steep decline from the top few podcasts to the also-rans. All-In, ranked (2) behind Lex Friedman’s podcast, is in another stratosphere.

Calacanis, who was once firmly a tech reporter but now sees himself as a “commentator” and a prolific angel investor, reminisced in our discussion about a time when the tech media relied on access from powerful tech CEOs to stay relevant. Tech media publications would be careful about being too hard on someone like Steve Jobs for fear that he wouldn’t let them cover Apple’s next big product release.

Calacanis said, “[Jobs] pulled our access. That was a major financial hit when he pulled our access to going to the Steve Jobs keynotes for Engadget. That could have been a death blow. And I had to negotiate directly with Steve Jobs to get Engadget back inside the Apple keynotes.”¹

But Calacanis insisted that Jobs’ leverage over reporters didn’t unfairly bias the coverage. “I don’t think that people had to compromise their coverage back then,” Calacanis said. “But it certainly had to be on the minds of the publishers and the CEOs.”

To me, that sounds like the definition of compromised coverage.

While I agree with Calacanis’s gloss of the evolution of tech media from one that was generally positive and concerned with access to one that is deeply skeptical and produces feisty, independent reporting, I don’t share Calacanis’s longing for the world we left behind. Yes, tech media has become marginally too negative but that’s because its source base has largely shifted from tech CEOs to tech employees and the public impacted by tech. Tech elites just want to plug their ears and blame the messenger.

Fundamentally, I just don’t think there has been a technology advancement akin to Google search or the iPhone since I’ve covered tech. (I’m cheering for the next generation of artificial intelligence.) So the coverage has reflected concerns that more incremental technologies like Uber were being sold as world-changing. Forget flying cars or self-driving ones, where are the ubiquitous environmentally friendly, traffic-reducing carpool rides? Oh right, Uber couldn’t make them work profitably.

“What incentive does somebody have to actually face hard questions besides you just being sort of a masochist to engage with people?” I asked Calacanis. “Most people — they have no incentive, they have their own audiences — so they have no reason to face hard questioning. What’s the solution to that? Do you think that’s a problem?”

Calacanis replied, “Has anybody here asked a hard question to the CEO of TikTok recently? Has anybody been able to ask a hard question to Mark Zuckerberg.”

It seemed to me like an effort to brush past my implicit critique of Musk and some of Calacanis’s All-In besties. But I let it slide and replied, “Shouldn’t people be more upset about that?”

“I honestly think it’s a mess right now,” Calacanis said. “Sometimes things have to collapse in order for something new to be built. I think that’s part of the process that we’re going through. I think this is like the messy middle. And there’s something new coming out the other side. The three of you — the four of us here — talking is part of that process. I think it’s the messy eye of the storm right now.”

I appreciate that.

But I think we’re living in a perverse world where 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.

Palihapitiya was the frontman-in-chief for SPAC mania and took many retail investors for a ride! But All-In touches that reality with only a toddler’s winter mittens.

Of course, Palihapitiya isn’t afraid of the media. He spoke to me early in the SPAC craze and generally seems happy to go on CNBC — but much of that time was spent hyping his SPAC investments, not taking accountability for the crash.

During our Dead Cat interview, Calacanis was happy to criticize the crumbling crypto industry. But I asked him, “Don’t you think the same thing could be being said about SPACs? Have you guys been hard enough on Chamath about the SPAC craze?”

“We want to have more public companies and we want to democratize access to them,” Calacanis explained. “But it was probably the bad timing of when this happened, when retail was kind of losing their minds, buying everything that was a new issuance, and, you know, Chamath can defend himself if he wants to—”

Benner replied, “It would be so fun to talk to him.”

I appreciate that Calacanis is at least willing to engage with skeptics.

I think All-In will remain a popular and compelling show as long as their friendship doesn’t unwind amidst clashing egos. At the same time, I’m feeling optimistic that this tech downturn is reorienting some of the bizarro world thinking that suggested that the people asking the hard questions on behalf of the public were the spoilsports and the tech elites bragging about their prowess were the unvarnished truth tellers.

All-In’s appeal to many of its fans is the sense of honesty — the co-hosts rib each other and brag about their lavish lifestyles. But I think that performed, informal honesty can often serve as a cloak for the questions not asked and premises that go unchallenged. As some of the excesses of this tech cycle come further into focus, I think those disjunctions will be harder to cover up with chest thumping male ego.

To Musk’s chagrin, the workers he’s exiling from Twitter are calling reporters. Widespread layoffs should further help reveal startups that sold the impossible. While I hope some of the unvarnished culture war hostility to tech bosses will recede, I don’t think the deep skepticism that’s been driven by employees, the public, and, yes, the media will go away.

Now that interest rates are rising, crypto scams are imploding, and tech emperors are looking a little more naked, it portends to be a cold winter for the tech industry. In these conditions, the tech set can wear their kid gloves all the want. But from my vantage point they’re starting to look a little worn.

1. Almost immediately after I published this newsletter, Peter Rojas, the co-founder of Engadget, emailed me. Rojas wrote, “Hey, saw the bit about Jason claiming that Engadget was banned from Apple events.”

Rojas denied that happened. “We certainly angered Apple plenty of times, but we were never cut off from keynotes.”

Rojas wrote that Calacanis was wrong to say that Jobs had pulled Engadget’s access. “That never happened and if anyone would have dealt with that it would have been me, not Jason,” Rojas wrote.