The Pentagon Wants Equity in AI Startups | E2336

Lon (0:00)

Apple has launched the $1,999 iPhone Duo. Cheaper models are reportedly being pushed to spring 2027

Jason Calacanis (0:09)

Apple took an existing product category that was very popular for a very long time, and they reinvented it. If Siri becomes an open source LLM, and everything on my phone that's powered by AI is using a local model, that could be very interesting to me.

SPEAKER_3 (0:25)

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Jason Calacanis (0:54)

All right, everybody. Welcome back to This Week in Startups. It is Friday, September 11th, 2026 Can't believe it's 25 years from September 11th when I was living in New York and was wondering where my brother was, who was a firefighter at the time for half the day. Really intense memories I have from those days. Yeah, I can't even imagine. Been thinking about it. Don't have too much to say other than my heart goes out to the families and for those people who don't have a memory of this. Get a bit educated on it and exactly how intense it was for this country and then how aligned the country was. Being a New Yorker, one of the most amazing moments I experienced in my life was the unity that I felt walking the streets of Manhattan. And I was in Manhattan for it. I watched it happen with my own eyes and I stayed in Manhattan. The island of Manhattan was locked down. You weren't allowed to leave and you weren't allowed to get on the island. I didn't leave. I wasn't allowed to leave after that. So I was there the whole time on 26th Street, at my loft on 26th and 11th. Memory I remember was coming out of my building after the second terror got hit. And in my building on 26th Street, there was a secret garage which housed the FBI and a bunch of other agencies in my loft building.

There was an FBI agent with a machine gun. So imagine a guy in a suit like Sicario, like wearing a perfect suit but having a massive automatic rifle. And I came out and I said, what's the latest? He goes, we're under attack. They bombed the Pentagon.

And I have never seen an individual law enforcement officer look so rattled. And I was like, oh my God, I went to the West Side Highway and I looked down.

And you took out your, had a cell phone at the time in 2001 They weren't super common. No service. Everybody was trying to call, find their loved ones. It was the most disturbing thing I've ever seen in my life when those towers fell. It was visceral.

Lon (2:58)

We were not prepared. Like Americans didn't think that anything like that could happen on American soil. It was shocking on a level. I don't know if people who weren't around can really appreciate it.

Jason Calacanis (3:07)

But to the camaraderie, for those next 30 days, you'd be walking around Manhattan and everybody would just say, how are you doing? How are you holding up? And Manhattan is one cacophony of never-ending symphony of people yelling at each other and blasting their horns.

I saw somebody like three to four days after 9-11 honk somebody.

And the person got out of their car and like kind of did one of these. The other person got out of the car and did one of these. I'm throwing my hands up like, what are you doing? The other person put their hands up. They walked up to each other. They hugged each other. Said, I'm sorry. I just thought you didn't see the light. It was like the act of just honking somebody, which is what New York drivers live for. You're doing that 20 times every mile as you're honking somebody because I'm trying to get somewhere. New Yorkers were embracing each other and just holding each other. It was unbelievable, my experience from that. And I basically, my entire life is bookmarked pre-9-11, post-9-11. I think about my life as like two chapters because that was the end of the innocence, I think, for a lot of us.

Lon (4:20)

Well, yeah, in the 90s, there was this idea and then we'll move on, we got to show you. But in the 90s, I think there was this idea that we were at the end of history. You know, we sort of figured out, we figured everything out. We got the Cold War was over. We kind of figured out racism and prejudice. And there was this idea like this, everything was just going to be sort of easier from now on. And then 9-11 happened and it was just like, oh no, we were wrong. We don't have anything figured out. We don't know what we're doing.