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

**Tim Miller** (0:00)
Hey, everybody, 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 Balzac, ended up going into the administration, and then another one is was Trump curious. Jason was the most middle of the road of the crew, and we did our first interview, God, a couple of years ago now, before the 2024 election, and have done a check-in every six, nine, 12 months. 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 JVL, as we do every Tuesday. So go give that a listen, download it if you're not subscribed to the Next Level feed. 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 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 eye rest 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 the whole series, the whole vibe of New York, the whole trajectory of society shifts, because Donald Trump decided he was a 12-year-old and wanted to do, 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 enjoying it. 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 hot in the second half, so hopefully I'll give you something to get your dander up. 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 cohost of the All-In Podcast. He's the best of the four, not really a competitive category. He just hosted the Liquidity Summit, a private investor summit for LPs, fund managers and elite entrepreneurs. That's fancy. It's Jason Calacanis. What's up, man?

**Jason Calacanis** (3:20)
How you doing, brother? Big fan of the show. Nice to be here for my second appearance. After five, you get the blazer.

**Tim Miller** (3:25)
Yeah, is it a third? I think it's third.

**Jason Calacanis** (3:27)
I don't know. I think you should make it five.

**Tim Miller** (3:29)
No, it's your third appearance.

**Jason Calacanis** (3:31)
Is it my third?

**Tim Miller** (3:32)
Okay, sure.

**Jason Calacanis** (3:33)
Well, I'm a big fan.

**Tim Miller** (3:35)
I'll go back and check the archive.
Your last appearance was at the six-month mark of Trump's term. We did a little check-in. Now we're at like a year and six months almost. It hasn't been quite a year. So we'll do an update. We'll get to that. But first, just for some people to know, we're taping this Monday afternoon. And so this will be a Tuesday show. So we don't know if the next of one game three tonight. I'm surprised to see you at your home studio because I've seen you not quite courtside like row two, row three, semi-courtside.

**Jason Calacanis** (4:04)
I had courtside for the wrap-up game in Atlanta, The Massacre. And I flew there with my brother. I went to Philly with Ben Stiller, my friend. We were courtside for the Philly game. They tried to block us.