This Week in Startups
00:15:02 · Jason Calacanis, Lon Harris
[00:15:02] S0: was getting. Cost of living, that was number one. Clearly, affordability on people's minds. Sure. The war is dovetailing with that. Right. The state of the democracy, that's right up there. Peep... That's another way of saying corruption, or grifting that people are really concerned about. So, yeah. I mean, the the grifting, if that's what happened... And, I I hold out, I don't prejudge any of these situations. I basically say, okay. Let the investigation happen, and and we'll find out what the details are. If Trump put all his money in a trust and there's somebody trading his stocks, I'll give him the benefit of the doubt. If they're making a lot of trades and then it comes out that he was... His money manager sitting next to him in meetings Mhmm. And making the trades, you know, like, he's at Mar A Lago and, like, you know, Trump is, like, holding up, like, the iPhone and going, buy Apple. Like, it's totally different. Right? Like, he shouldn't be using his inside track, to make trades. So it's supposed to be arm's length. Let's keep going. [00:16:08] S2: Alright. We could do another one. This one is from, 05/14/2025. This was you talking about how the tariff situation seemed to be getting out of hand. And just generally, I think what we would consider, like, Trump chaos. Okay. So this was when it started to become clear, like, he's he's governing in a very chaotic way that the markets don't like and that Americans don't like. Let's take look. [00:16:31] S0: Gecko look. Yeah. Let's take a look. [00:16:33] S2: A little bit. Yeah. This wasn't the plan?
00:16:33 · Lon Harris, Jason Calacanis
[00:16:33] S2: A little bit. Yeah. This wasn't the plan? [00:16:35] S0: No. I think he was doing a ton of trial balloons and floating things. But wasn't well thought out. Because if it was well thought out, I think what you would have said is we have a 150 trading partners. We can put them into these three buckets. These ones are inconsequential because we don't do a lot of trade with them. These five are 90% of it. It's a Pareto principle. It's the power law. These five are the ones that matter, and then these are the ones in between. So I've told Bessent to do this group of people who are important, and then I'm putting Sachs and Elon or this person, that person, Lutnick on these ones, And here's the strategy we're gonna pursue. It's gonna be pretty aggressive. There's gonna be some pain. Here's what you can expect. Instead, it was like, oh, you put it at 50? I'm making it one fifty. And it was this Yeah. Attention seeking, crazy [00:17:22] S2: Yeah. Shake the globe thing.
00:17:24 · Jason Calacanis
[00:17:24] S0: Shake the globe thing. You know, I I had a nickname for Trump in the first presidency, which was captain chaos. Yeah. And he... You can be right about something, but you could execute in the wrong way. He was right about tariffs. We were getting screwed. Tariffs are an important part of, you know, not getting, abused in trade. You have a country like Japan, South Korea. You know, we're not allowed to bring our cars into South Korea. Why? You know, are we bringing Hyundai's into this country? Okay. There's some imbalance there. Let's talk about it. Let's figure out why this exists, and and there's a way to do it without Trump's chaotic insulting, bravado, and taking up all the news. I thought they should have all been done in closed rooms. They should have said, hey. We're in open negotiations. This is the tariff level, and then we expect negotiations to end here, the end, and stop talking about it. But, you know, Trump can't help himself. He loves to talk. He's a great communicator, and he knows how to fill the press cycle. He needed to have people around him who told him, hey, boss. And I I mentioned this on all in one time when I was like, hey, guys. You know, the the problem with Trump is he he has too many sycophants around him who are afraid to tell him the truth. And if you tell him the truth, he kicks you out of the circle. Right. And and then you don't get your goodies. You don't have access to power. And and, you know, that's true of anybody powerful. I have to be careful about that. I'm not, like, super powerful, but people will tell me what I wanna hear in my own company, my own venture company when we're doing deals, and I need a little bit of dissent. And I have to encourage it because it doesn't happen naturally. You have to be self aware of that. Somebody should have said him. Bessent,, hey, boss. We're making great progress here. We have the upper ground. This is gonna be great. We're gonna get you a billion dollars in tariff revenue. Let's get congress involved. Let's do it with them. And then you wouldn't have them all get overturned. So again... And the way I knew this was correct, Lon, was I was talking to our founders. I think I had Cuts Clothing CEO on I remember that, speak in Startups.
00:19:22 · Lon Harris, Jason Calacanis
[00:19:22] S2: Yeah. From Cuts And [00:19:23] S0: he explained to us in detail how this was affecting his business. So while people were telling me, my Republican friends were telling me, oh, you're anti Trump. You have TDS. You don't know what you're talking about. They mocked me. My... I was getting brigaded in the comments. Jason's low IQ. He's mid. No. I'm incredibly high IQ. I'm off the charts, in fact, according to the tests I've taken. Don't [00:19:49] S2: let [00:19:49] S0: the Brooklyn accent, you know, fool you. And I'm smart enough to know when I don't know about a topic to talk to people who are experiencing it and get firsthand experience. That was my journalism training. You can again criticize, oh, you're a journalist. That's a journalist in you. You know, when people criticize that, I grew up in an era when journalism was done in a very tight fashion and was a great vocation, a great education for how to assess the truth in the world. And the way you assess the truth in the world is when you hear those tariff claims, you don't listen to politicians or talking heads. Talk to the people who are impacted from it. I went directly to the source. And Ad[00:20:21] S2: and stupid. Ad[00:20:21] S0: That's why I was able to stand my ground, Lon, under mass pressure. Remember the pressure three on one on the podcast? Oh, you're a mid. Oh, you're stupid. Ad[00:20:29] S2: Yeah. No.
00:20:29 · Jason Calacanis
Ad[00:20:29] S0: They Oh, and the comments, Jason interrupts too much, everybody ganging up. And I I just said to myself, no. I'm right. I'm right. I'm right about the meme coin. I'm right about the tariffs, and let me go do my homework and make sure I understand what I'm talking about. And I go do a couple hours of research. I ask intelligent people, people far smarter than me. And that's how you learn in the world. Yeah. And it's an important lesson for everybody. Under pressure in a social group, you need to have, you know, the, your own conviction. You have to have the strength of your own convictions. You also have a... Have to have a process, for getting to the truth. I don't accept what the media tells me. I don't accept what the politicians tell me. I go right to the source. It's so easy to do. No matter how polished or well designed your app might be, every once in a while, something is gonna go wrong in production. Right? Even if you're a perfect UX designer and you know what you're doing. But that doesn't mean your team has to waste an entire day just to locate the source of the problem, the bug, the issue. We got Sentry now, everybody. And what I love about Sentry is that it gives you total visibility into your app in one place. This is not separate tools or endless context switching. No. Just your errors, traces, replays, and logs all linked together in one connected timeline. Right? You can actually play the timeline. So when there's an issue, you can see exactly where it started and what triggered it, and debugging these things is critically important because SEER, s e e r, is Sentry's AI debugging agent. It's got an agent. It's gonna take over this problem and unpack why the issue happened, point to the code that's responsible for the issue, draft a fix on its own, and even flag when your PR is about to cause a problem. In other words, it's gonna anticipate problems so you don't have them. This is what you need, folks. This is the perfect use of super intelligence. Go to sentry.io and check out their free dev plan. Plus, our listeners can use the code TWIST 26 for $240 in Sentry credits. That's sentry.io.
00:22:29 · Lon Harris
[00:22:29] S2: Yeah. I I think Steven is an interesting case too because he's a he's a diehard Trump fan. If you follow him on x, he's always praising Trump. So this is the guy to talk to. If he's coming to you and he's not... He doesn't have TDS. He's not like some crazed, you know, like, communist who's just trying to bring down the system. He's a guy who liked Trump who presumably voted for him, and now he's got this, you know, unique perspective on what's going wrong with the policy. Why wouldn't you listen to a guy like