Jason Calacanis: The Silicon Valley Vibes Are Still Pro-Trump

Summary

Podcast Summary: The Bulwark – "Jason Calacanis: The Silicon Valley Vibes Are Still Pro-Trump"

Release Date: June 9, 2026
Host: Tim Miller
Guest: Jason Calacanis (Entrepreneur, Angel Investor, All-In Podcast Co-host)

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Episode Overview

In this special episode, Tim Miller welcomes back Jason Calacanis for their regular check-in to dissect the ever-evolving vibe in Silicon Valley—especially when it comes to technology, AI, investment trends, and the Valley’s shifting relationship with Donald Trump. With Calacanis’s signature mix of candor and insider perspective, the conversation ranges from banter about Knicks basketball (and the Trump curse) to deep dives on AI, automation, and political leanings within the tech elite.

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Key Discussion Points & Insights

1. Knicks, Trump, and the “Vibe Curse”

• Basketball Banter & the Trump Hex:
  • The episode opens with light ribbing over Jason’s Knicks fandom and the so-called “Trump curse.” Trump’s high-profile attendance at a Knicks game is joked to have derailed a winning streak and “salted the vibes” in New York.
  • Quote: “Trump showed up to the game, made it a massive hassle for everybody in midtown New York. Salted the vibes, fell asleep. Trump actually fell asleep for a little while… and then he left early. So as a result, the next 13 game winning streak is over.” (Tim Miller, 01:00)

2. Jason’s Courtside Hustle

• Jason’s Knicks Fandom & Networking:

  • Jason details his courtside experiences, using “micro celebrity” for premium seating, while also acknowledging he pays for most seats but isn’t above leveraging his social media following.
  • Quote: “What’s the point of having million followers on Twitter if you can’t just use it for customer support?” (Jason Calacanis, 04:53)

• Trump as a Knicks Fan?

  • Jason questions the sincerity of Trump’s Knicks fandom, putting him outside the “real fan” circle (Chalamet, Spike Lee, etc.).
    • Quote: “He’s not part of our group. And I put myself into that group just based on fandom, not celebrity, to be clear.” (Calacanis, 05:55)

3. The State of Silicon Valley: AI & Tech Trends

• AI’s Explosive Growth and Impact:

  • Jason paints AI as the most potent wave of technological change yet, far outpacing previous tech revolutions by an order of magnitude.

  • The conversation revisits a viral prediction Jason made: nearly complete automation in factories like Amazon’s in a few years, followed by executive memos and major layoffs at Amazon reinforcing that vision.

  • Quote: “AI is like every previous technology wave put together and then times 10 in terms of the impact, the opportunity and just the capabilities of what’s happening.” (Calacanis, 07:13)

  • Timestamp:

    • [07:13] – Deep dive into the state of AI, tokens as a currency for intelligence, and accelerating timelines.

• The Hype and Limitations:

  • While the “tokens” (units of AI capability) are “so compelling for people to use that people are spending too much money on them,” Jason recognizes the gap between hype and practical deployment.
  • AI Jargon: Jason explains AGI (Artificial General Intelligence—human-level smarts) and superintelligence (exceeding collective human intelligence), noting the industry’s (sometimes grandiose) race is for the latter.

• God Complex in Tech:

  • Valley leaders contend with a “God complex,” having already driven world-changing innovations and now holding almost religious debates over issues like universal basic income, automation, and the societal fallout.
  • Quote: “You do have this God complex amongst the Anthropic people, or, you know, Sam Altman, Elon, the whole group really has done some things that have changed the world dramatically. And then some of them are drama queens. And some are both.” (Calacanis, 09:49–10:14)

4. Politics in Silicon Valley: Pro-Trump Vibes?

• Note: Detailed discussion of Valley’s Trump leanings set up in the intro; actual deep political content follows after the provided transcript segment, so less detail here but context is rooted.

• Calacanis’s Political Context:

  • The Bulwark host clarifies the All-In Podcast’s dynamic: Jason is more centrist than his co-hosts, some of whom are outspokenly pro-Trump.
  • The segment hints at a prolonged “vibe shift” in the tech class that’s not moving away from Trump as rapidly as some pro-democracy listeners might hope.

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Memorable Quotes

• Knicks & Trump:

  • “I’m sorry that Trump hexed you, but hard not to enjoy it.” (Tim Miller, 02:30)

• Micro Celebrity Perks:

  • “If something’s not right… What’s the point of having million followers on Twitter if you can’t just use it for customer support?” (Jason Calacanis, 04:53)

• AI Wave:

  • “AI is like every previous technology wave put together and then times 10 in terms of the impact, the opportunity and just the capabilities of what’s happening.” (Calacanis, 07:13)

• Tech’s God Complex:

  • “You do have this God complex…Sam Altman, Elon, the whole group really has done some things that have changed the world dramatically. And then some of them are drama queens.” (Calacanis, 10:12)

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Timestamps for Important Segments

• [01:00] – Knicks/Trump “curse” and basketball banter.
• [04:50] – Jason’s approach to leveraging social media and fandom.
• [05:55] – Debating Trump’s legitimacy as a Knicks fan; social groupings among superfans.
• [07:13] – AI revolution: range, hype, looming job displacement, and big tech’s God complex.
• [10:12] – On identity and myth-making among Silicon Valley’s tech elite.

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Tone & Style

The tone throughout is conversational, witty, and at times irreverent, with Jason Calacanis offering unvarnished takes enriched by Valley insider knowledge and Tim Miller adopting a good-natured, skeptical, “outsider” lens. The exchange balances sarcasm and seriousness, pivoting quickly from sports snark to substantive tech commentary.

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For Listeners

If you’re seeking to understand how tech-industry heavyweights view AI, automation, and their own role in society—and why the Silicon Valley crowd remains oddly Trump-friendly—this episode offers sharp, engaging insight straight from the source. The highly quotable, wide-ranging dialogue makes the episode accessible even if you missed the basketball drama or the deeper political headlines.

Transcript

[A]

Foreign.

[B]

A few notes before the pod today. I taped yesterday afternoon with Jason Calacanis because I'm about to hit a plane to my father's retirement party, which we're excited about for the newbies. Jason is a little bit of a departure from our usual material here on the Bulwark Podcast. He has a podcast of his own called the All In Podcast. And his colleagues, two of them were very active Donald Trump supporters. One of them, David Ball Sacks, ended up going into the administration. And then another one is kind of a. Was Trump curious? Jason was the most middle of the road of the crew. And we did our first interview, God, a couple years ago now, before the 2024 election, and have done a check in every, you know, six, nine, 12 months. So we did one of those check ins today. We talked a bunch about the stuff that he really knows about, which is Silicon Valley and VC World, and then talked about what the vibe shift is looking like on Trump. It's not shifting as much as we would like. A little spoiler alert. So that's what's on this podcast. We also have the Next Level podcast. So if you're looking for just a politics fix, you can just pop on over to the Next Level. Feed me Sarah and jbl as we do every Tuesday. So go give that a listen. Download it if you're not subscribed to the Next Level feed. And I guess one more thing before we get to this show. Jason's a big Knicks fan, so we discussed the potential of a Trump curse and he was worried about a Trump curse. It turned out that he was right. Trump showed up to the game, made it a massive hassle for everybody in midtown New York. Salted the vibes, fell asleep. Trump actually fell asleep for a little while. He rested his eyes, lengthy rest about a 22 second irest during the third quarter, and then he left early. So as a result, the next 13 game winning streak is over. Don't know who else to point to on that except for Donald Trump would really be something if, if the whole, the whole series, the whole vibe of New York, the whole, you know, the whole trajectory of society shifts because Donald Trump decided He was a 12 year old and wanted to do what, what is J. Mark calling it? The Make a Wish Presidency. The Big presidency. You guys remember the movie Big, the Big Presidency where he gets to be a little boy that does fun stuff with all the grownups. So that's what happened last night. I'm a little, I'm enjoying it. I know I've got some Buddies who are listeners who are next fans. I'm sorry that Trump hexed you, but hard not to enjoy it. So anyway, stick around for me and J. Cal. It gets a little. It gets a little hot in the second half, so hopefully I'll give you something to get your dander up and if not, go check us out on the next level. And we'll be back tomorrow with our regularly scheduled programming. Appreciate you. Hello and welcome to the Bulwark Podcast. I'm your host, Tim Miller. Happy to welcome back to the show. A journalist and entrepreneur turned angel investor. He's the co host of the all in podcast. He's the best of the four. Not really a competitive category. He just hosted the Liquidity Summit, Private Investor Summit for LPs, fund managers and a leach. Entrepreneur. Entrepreneurs. That's fancy. It's Jason Calacanis. What's up, man?

[A]

How you doing, brother? Big fan of the show. Nice to be here for my second appearance. After five, you get the blazer.

[B]

Is it a third? I think it's third.

[A]

I don't know. I think you should make it five.

[B]

Notice. Your third appearance.

[A]

Is it my third? Okay, sure. I'm a big fan.

[B]

I went back and checked the archive. Good. Your last appearance was at the six month mark of Trump's term and we did a little check in now like a year and six months, almost has been quite a year. So we'll do a little update. We'll get to that. But first, just for some people know, we're taping this Monday afternoon and so this will. This is with Tuesday show, so we don't know if the Knicks have won game three tonight. I'm surprised to see you at your home studio because I've seen you not quite courtside, like, you know, row two, row three, semi courtside.

[A]

I had courtside for the wrap up game in Atlanta. The massacre.

[B]

Yep.

[A]

And I flew there with my brother. I went to Philly with Ben Stiller, my friend, fellow. We were courtside for the Philly game. They tried to block us. I was at two of the MSG games, but like you said, third row. Because even with my incredible micro celebrity, and you understand micro podcast celebrity, you

[B]

just leverage it a little better than me. Your shamelessness, I have to give you. You're out there on X just being like, give me a get. You know, who has courtside for me? I don't have the.

[A]

I mean, I pay for them, to

[B]

be honest, but even still.

[A]

But I do use the power. I mean, if you. What's the point of Having million followers on Twitter, if you can't just use it for customer support.

[B]

I agree with that.

[A]

If something's not right. And then Cleveland, they blocked us from getting courtside, so I had third row and I went to the spurs, both games. I am going to predict tonight the Knicks are going to win, and I think they're going to demolish them by 15 points. Well, no.

[B]

Tomorrow. Why are you not going? You're scared of Donald Trump. You don't want to deal with the hassle. You're worried he's hexing your squad.

[A]

There's some bad juju here with Trump going. It's bad juju. He should not have done this. You should not make the fans show up three hours early. And he got rid of the watch party, which has become this huge tradition. So, listen, he's the president. He can do what he wants. But I would have preferred him to do it. I was going to come in for it, but I've decided I'll just come in for game four and it's kind

[B]

of a different move. Yeah. I mean, and he's even a fan. Like, do you think he can name anyone for the 1999 team? I mean, I guess Ewing.

[A]

He used to go to games, but I don't know if. If he went to the games primarily because he was friends with JD or if he went because it was a celebrity thing to do. But he has not been going since. So I don't put him in the Timothy Chalamet, Spike Lee. He's not part of our group. And I put myself into that group just based on fandom, not celebrity, to be clear.

[B]

Well, based on your strong prediction on the Knicks, I'm going to fade you based on some of the predictions you've made that we're going to get into from the Trump.

[A]

Okay, here we go.

[B]

I'm betting on the. What's your team, by the way? Were you a pelican? I'm Nuggets. I'm Nuggets. I'm Nuggets.

[A]

Oh, Denver Nuggets. Yeah.

[B]

And, yeah, rough playoffs for us, but I'll bet on the spurs tonight. Modest wager on draftkings, and we'll see. The listeners will know who's right before we get to Trump, you know, because who knows how that'll go. I want to kind of get into your main area of expertise first. Want to talk kind of what's happened in Silicon Valley world? AI, I feel like. I don't know if you'll take this as a compliment or an insult, but I feel like you're a fair arbiter of conventional wisdom on, like, where the Valley investor class is on things like how things are going. And so rather than putting on your Jason hat, I just want to start there. Like, where is the Valley right now on both the economy broadly and also the AI stuff in particular.

[A]

Yeah. So let's start with AI. AI is like every previous technology wave put together and then times 10 in terms of the impact, the opportunity and just the capabilities of what's happening. Last time I was on the show, or maybe it was two times ago, we had a clip go viral where I said, listen, Amazon is going to be lights out in their factories. It's all going to be robotics and they have Zoox, so they're going to be delivering packages. And the idea that a human would touch a package between, like, you clicking order on Amazon and it's showing up at your doorstep will be insane or farcical in but, you know, three, four, five years. That went crazy. Shortly after that, Andy Jassy wrote a memo saying, hey, we're going to be going all in on AI. We're going to have a different staffing level. He laid off a bunch of people. And then the secret memo got leaked that they weren't going to hire 600,000 jobs. And the PR team is like, how do we deal with the fact that we're not going to be hiring humans anymore? Maybe we should give money to toys for Tots. I don't know if you saw this.

[B]

Not Cars for Kids, notably, some of their baggage there.

[A]

It could be, yeah. So essentially, and then if you watched, there was the figure robotic company also doing humanoid robots, had like a telethon where they had one of their robots sort packages. And so this timeline is increasing. So it is a huge opportunity. And the tokens which equal intelligence are so compelling for people to use that people are spending too much money on them. They're, like going crazy using them. And you've had to rein in employees for every story you hear that this technology is going to change everything. You'll have people who don't know how to apply it. But we use two terms in the industry, AGI, and then super intelligence, to keep it super simple. AGI means the artificial intelligence is as smart as the smartest human being. Super intelligence means it's smarter than all collective human intelligence for all time, and it will solve problems we can't even think about, like, we can't even conceive of. The race is really for super intelligence. AGI is, is like a little waypoint along the way. And that waypoint prints money. It prints money. And we have this grand debate on, all in all the time we have it publicly about job displacement, job destruction, universal basic income, and people in our industry have delusions of grandeur because we've done big things. Right. So you do have this God complex amongst the anthropic people, or, you know, Sam Altman, Elon, the whole group really has done some things that have changed the world dramatically. And then some of them are drama queens.

[B]

And both. And some are both.

[A]

Some are both, yes.