GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162

Today's show: Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about. First up, Jason thinks it's time for Tim Apple to exit the stage in lieu of a product obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair? PLUS we're talking Ripple's acquisition of Rail, Donald Trump's new AI chatbot, Bumble's new direction, Airbnb's potential paths forward and MUCH MUCH MORE. Timestamps: (0:00) Why Jason thinks Apple lacks innovation (plus a look back at his 2019 thoughts) (08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST (09:54) Show continues… (20:10) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today! (21:18) Is GPT-5 coming for Lovable and Bolt? (29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.com/Twist. (30:55) Show continues… (35:05) Ripple buying Rail, and why sometimes regulations are GOOD for companies (43:28) Is Ripple about to become the MicroStrategy of XRP? (47:48) Truth Social AI is perplexing, powered by Perplexity (53:27) Should people be using ChatGPT for therapy? What do you think? How does that make you feel? (01:04:42) Anthropic's Dario Amodei recalls his greatest haters (01:11:04) Bumble but… for friendship? (01:12:20) DoorDash's crazy growth, and the guys discuss who should buy Airbnb Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST (20:10) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today! (29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.com/Twist. Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jason Calacanis?

  That's what Steve Jobs actually wanted to do. He wanted to make these products here. And you and I were having a private discussion about just how disgraziad this company is.

• 0:10Speaker 01

  It's disappointing. That's how I feel. I feel disappointed. I, I, when we got the iPad, when we got the iPhone, you were looking forward to a lifetime of exciting Apple products. You were gonna, every five years, there was gonna be some new amazing innovation. And it has not been realized, that vision.

• 0:28Jason Calacanis?

  Once we got through the pipeline of whatever Steve Jobs had thought of, there was no, nothing bold left. And I said on CNBC, I think there's a case for, for Tim Cook, you know, leaving.

• 0:49Speaker 02

  This Week in Startups is brought to you by Sentry. Your team should be focused on shipping features, not chasing down bugs. New users get three months free of the business plan, which covers 150,000 errors. Go to sentry.io/twist and use the code TWIST. Northwest Registered Agent. Starting your business should be simple. With Northwest Registered Agent, you can form your entire business identity in just 10 clicks and 10 minutes. From LLCs to trademarks, domains to custom websites, they've got you covered. Get more privacy, more options, and more done.

• 1:27Speaker 02

  Visit northwestregisteredagent.com/twist today. And AlphaSense. Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at alphasense.com/twist.

• 1:43Jason Calacanis?

  Hey, everybody. Welcome back to This Week in Startups. Alex is taking a little break, and we're doing our show. With my guy Lon Harris, the original, one of the original co-hosts of This Week in Startups, 14 years ago.

• 1:56Speaker 01

  The original, episode one.

• 1:58Jason Calacanis?

  You were the original.

• 1:59Speaker 01

  Yeah, well, Tyler was sort of behind the scenes producing, Tyler Crowley, our old friend.

• 2:03Jason Calacanis?

  Yes.

• 2:04Speaker 01

  And then, but I was the newsreader like right off the bat, yeah.

• 2:07Jason Calacanis?

  And he's still on the lam?

• 2:09Speaker 01

  You see, he's somewhere in Thailand, I believe, somewhere on a beach in Thailand. People don't believe me. When I said, people ask, like, hey, whatever happened to Tyler from This Week in Stars? Why isn't he around? I say, he's on a beach in Thailand. They're like, no, really?

• 2:22Jason Calacanis?

  Not only was he on a beach in Thailand, shout out to Tyler, come on the show anytime. He took the model of like doing events and stuff like that. Then he learned working with me, which I gave him my blessing on him, took it to Stockholm, Sweden.

• 2:36Speaker 01

  Right.

• 2:37Jason Calacanis?

  Made like a million dollars a year for five years, bought a beach resort and then hung it up.

• 2:43Speaker 01

  Right, he's retired. Every time I see a poster of him, he's on a hammock.

• 2:48Jason Calacanis?

  Yeah, I'm an idiot, I'm still here 10 years later.

• 2:50Speaker 01

  Yeah, he taught him everything you know.

• 2:51Jason Calacanis?

  I made a fortune. Today Uber went up $3.45. And I'm sitting here, still doing four episodes a week.

• 3:01Speaker 01

  You and I are here Thursday afternoon, you're giving up for podcasting, that's what you're doing with your life.

• 3:06Jason Calacanis?

  Unbelievable, unbelievable. Well, you know, I love it, I love it. Okay, we have a big docket today. I want to get right to work here.

• 3:12Speaker 01

  So much.

• 3:14Jason Calacanis?

  Yeah, where do we start here? I mean, do we have a funny story you want to start with to warm the audience up? Or do we want to just get into the big chat GPT-5, which launched today? Do we want to get into Apple genuflecting and bringing a gold bar to the press? And I mean, there's so much going on in the world.

• 3:33Speaker 01

  Yeah, I did love that, there's that shot, you know, the reporters are asking Trump about Epstein and all these other stuff, and it's back and forth, and then JD Vance is jumping in with his thoughts on all of it. And Tim Cook is there in the middle, just kind of standing there. Did you see that shot of him just looking around like, what do I do now?

• 3:52Jason Calacanis?

  Yeah, they should just put the, they should put the Larry David music to it.

• 3:57Speaker 01

  Yeah.

• 4:01Jason Calacanis?

  But, I mean, in all fairness, you got to play the game on the field. And Tim Apple is doing a spectacular job. He showed up for the inauguration. And then he's the guy who. Has the most at stake when it comes to tariffs. And what did he do? He came to the White House and said, how much do you want me to invest in America?

• 4:25Speaker 01

  How big is the check? How much is the check for?

• 4:28Jason Calacanis?

  And listen, I mean, say what you will. If we're sitting here a year from now and actually, Apple's making products here. That's what Steve Jobs actually wanted to do. He wanted to make these products here. And you and I were having a private discussion about Apple. I think we'll start here. Just how disgrazia'd this company is.

• 4:48Speaker 01

  It's disappointing. That's how I feel. I feel disappointed. I, when we got the iPad, when we got the iPhone, you were looking forward to a lifetime of exciting Apple products. You were gonna, every five years, there was gonna be some new amazing innovation. And it has not been realized, that vision.

• 5:06Jason Calacanis?

  And you and I were in Santa Monica doing mahalo. And we would go to the Apple store, which had just recently opened. We were there for the iPhone launches.

• 5:14Speaker 01

  We waited in line overnight, yeah.

• 5:17Jason Calacanis?

  Yeah, and it was like some of the greatest moments in technology history was that showmanship and that commitment to releasing new groundbreaking technology. And I think once we got through the pipeline of whatever Steve Jobs had thought of, there was no, nothing bold left. And I said on CNBC, I think there's a case for Tim Cook, you know, leaving. I didn't say get fired, I don't think. I might have said that. And it was like six or seven years ago. We had the clip. I don't know if we still have it handy here. Be a great one to play because we're gonna talk a little bit about Apple today and OpenAI and innovation.

• 6:02Jason Calacanis?

  And Apple had, when you think about a run, the MacBook Air, the iPad and the iPhone. The MacBook Air was a revolution in how light it could be to have a A laptop. In fact, when he showed it, he put it in a Manila folder or like an inter-office memo. Remember, we used to send inter-office memos in those brown bags, the brown reusable folders, like envelopes.

• 6:30Speaker 01

  Those big brown envelopes, yeah, with the with the string on it.

• 6:33Jason Calacanis?

  With the string on it. I mean, it wasn't like you're tying it up to lock it. You weren't like licking it like you didn't want it to have to rip it open, but you reuse them. And he pulls it out of that. It was like, wow, my mind is blown. And then, of course, you have, you know, like the Apple Watch was kind of underwhelming. It's not essential.

• 6:51Speaker 01

  The Vision Pro is the one I couldn't get. I literally, we were talking about this the other day. Somebody mentioned, oh, there was also the Vision Pro. I'd forgotten that product existed. You hear about it so seldomly.

• 7:04Jason Calacanis?

  I think they forgot because they haven't released a new one, haven't talked about it, which if you're going to commit to AR and VR, at least take three swings at the bat.

• 7:13Speaker 01

  Well, that was supposed to be the developer one. And then that was going to come out. People were going to start making amazing apps for it. And then you'd sort of think by now I would have one, right? Isn't that the idea? Like, where's my AR game?

• 7:26Jason Calacanis?

  Or at least the developers would have a second one that was a little lighter, faster, better.

• 7:31Speaker 01

  Right. We should be on our way to consumer facing AR apps. And I know in my Founder You pod, most recently, we had an amazing company that is designing 3D AR experiences. They look awesome. They're working with Snapchat. They're not working with Apple.

• 7:48Jason Calacanis?

  And I think, you know, leadership, this is the important lesson for people. Who you put in charge of something and what their skill set is, people generally do what they're good at, right? So for me, I'm a media guy. When I, as a communicator, when I got into the venture business, I was like, well, I guess I should do this podcast this week in startups because then I could talk about the startups I'm investing. We'll just do it one a week. It'll be like 50 episodes a year. I'll have Travis on, I'll have Cal on, and maybe I'll meet some founders and maybe I'll learn something. So, you know, Media Guy does that. Other people are developers, or maybe, and so they, you know, put up a bunch of servers. Like, there was one group that put up a bunch of AI servers, a bunch of H100s, and offered them to their portfolio companies. It's all different

• 8:30Jason Calacanis?

  things. Some venture firms have recruiting. Some venture firms have PR and marketing. They all have different things they can help you with. Some of them even do corporate development, where they bring in 10 big companies and they have them meet 10 of their founders.

• 8:43Speaker 01

  Yeah, yeah.

• 8:44Jason Calacanis?

  See if they get some deal-making going, right? Your first customer. But I said that Tim Cook should step down on CNBC.

• 8:56Jason Calacanis?

  When your website or your app goes down, you don't want to hear a bunch of excuses, and you don't want to waste your time. You just want the problem fixed, fast. And that's where Sentry comes in. They're handling all the real-time error monitoring and tracing, so the moment something breaks, you know exactly what happened and why. They've also got Sear, S-E-E-R, an AI-powered debugging agent that can sniff out the root causes of your problems 94% of the time, and growing. And like all great startups, Sentry is constantly shipping new features, bells and whistles and updates. They just added AI agent monitoring to the platform. When your LLM agent starts hallucinating, Sentry traces the entire timeline to find out what went wrong and take the guesswork out of it. Plus, it's built into

• 9:39Jason Calacanis?

  the same system that your team is already using and relying on. So try it out for yourself. Go to sentry.io/twist and actually start making sense of what your agents are doing. That's sentry.io/twist.

• 9:54Speaker 01

  I've got, I've got it here. It was, it was in September 9th, 2019. Angel investor Jason Calacanis says, "Tim Cook needs to step down." You want to take a look?

• 10:04Jason Calacanis?

  Sure. I mean, it's a bit cringe-worthy. I'm also 10 pounds. No, 30 pounds.

• 10:09Speaker 01

  It's a little while ago. Here, let's think. We could, we could give it a little watch.

• 10:12Speaker 03

  What Jason, does Apple need to do in your estimation to get an investor like Dan Niles more excited about the story?

• 10:18Jason Calacanis?

  Yeah, you gotta fire Tim Cook. It's a disaster. I mean, I think they haven't done anything innovative since this device, which is magical. The iPods are amazing.

• 10:26Speaker 03

  See, I thought you were joking. You're being...

• 10:27Jason Calacanis?

  No, I'm being dead serious. I think it's time for him to pass the baton because the... Steve Jobs passed away. The phone has been in decline since. There's no reason to upgrade your phone. So, peak phone was what, 2015? And it prints money, sure, but the major problem is, they believe that any company that innovates out there is not as good as theirs. They need to watch what Zuckerberg did with Instagram and WhatsApp, and what Google did with Android and with Instagram. Dan's gonna buy back into the stock if they buy Tesla, if they buy Peloton, if they buy Spotify, and they start putting that 200 billion to work. Yes or no? Yes or no?

• 11:05Speaker 03

  Well, I mean...

• 11:06Jason Calacanis?

  If they had that... I mean, if they put Peloton in every store, would you buy?

• 11:09Speaker 03

  I'm not a... Well, I like my...

• 11:11Jason Calacanis?

  It's an incredible product.

• 11:12Speaker 03

  I like my stairmaster.

• 11:13Speaker 04

  The point that Jason's making though.

• 11:14Speaker 03

  But the point he's making actually has a lot of validity to it, in the sense that if you think... The one thing I will say Tim Cook has done better than any CEO is deal with the current administration. And so, he's put his personal feelings aside.

• 11:27Jason Calacanis?

  Yep.

• 11:28Speaker 03

  Obviously, openly gay man.

• 11:30Jason Calacanis?

  Interesting.

• 11:31Speaker 03

  High-profile CEO on Wall Street, and he's done a great job dealing with the Trump administration. So, more than any other CEO, you have to give him a lot of credit for that. Now, on the innovation front, I completely agree with them. It's something I've said before, Apple, since the passing of Steve Jobs... But to be fair, he's a once-in-a-generation, maybe somebody like an Elon Musk that you're gonna see. So, that's a really tough...

• 11:52Speaker 04

  What's the stock up... Is the stock up 250%? Or, I forgot what the number is. That number may be wrong. My point is, though, the stock is up a lot under Tim Cook.

• 11:58Jason Calacanis?

  That's because they're extracting so much money from their loyal fans. The margin on this is 150 dollars, right?

• 12:03Speaker 03

  Well, and don't forget, they have a huge buyback. They have a massive dividend. And so, that's great that the stock does really well right now. You guys were ahead of the curve here. But if you're looking out for this company over the next 2, 3, 5 years, once that buyback starts to peter out and that balance sheet starts to wind down, they're not innovating that much. They're 1 year behind Samsung on 5G. When you're trying to have somebody cough up a thousand bucks for a new phone, I think that's a big deal. So, you know, I think the stock's gonna actually do relatively well between now and when they have to report the fourth quarter. If you think of last year, right, stock did great for the first nine months.

• 12:38Speaker 01

  Should we keep going?

• 12:39Speaker 03

  They had to sell 50% more phones in the fourth quarter. And I was on your show in August, saying, I think Apple's gonna have a huge problem because people are worried about China, yet they're somehow not worried about Apple that's got high teens percentage of revenue.

• 12:50Speaker 01

  Stock's only 20 bucks off the high.

• 12:51Speaker 03

  Yeah, but that has nothing to do with what Jason's talking about in terms of innovation, etc.

• 12:56Jason Calacanis?

  What got you here will not get you there. And that's their core problem. They are resting on the laurels of Steve Jobs's legacy. They need to put Tim Cook in another position, get Elon Musk in there, let him run the company. Find somebody like that, somebody who is maniacal about product. I mean, let's just sit here and realize that iPods are the greatest headphones ever made, and that's the greatest thing they've done over there in 10 years? It's a disaster. And if they take that store footprint and they put a Model 3 in every one, if they put a Peloton thread in there, and I've been using the thread.

• 13:28Speaker 01

  No, I think you're right there. I mean, that was always Peloton's thing, is you had to just take the, go buy a Peloton. It wasn't on sale in a place you already were.

• 13:36Jason Calacanis?

  It would go from 500,000 Peloton subscribers to at least 10 million. That's the type of acquisition you need to make if you're gonna compete. And they just have way too much pride. They think that they make the best products in the world and nobody else can.

• 13:50Speaker 03

  There we go.

• 13:51Jason Calacanis?

  Okay, so, you know, when I look back on that, and the Peloton, obviously, they had big problems because they spent money like drunken sailors, and it was a mismanaged company. But that category, if Apple went full bore into health, not just the watch, but actually bought Peloton and Tonal, and they had a whole health thing, and it was in, it was connected to the watch, it was connected to the health app, they would be what Whoop is. The Whoop is a better product. Whoop is more innovative than the Apple Watch. It's not easy to be more, it's not difficult to be more innovative than... It's just not difficult today to be more innovative than Apple.

• 14:33Speaker 01

  Yeah. The other, the other one that shocks me is that OpenAI Johnny Ive puck they're working on like,

• 14:40Jason Calacanis?

  if it's a puck, yeah.

• 14:41Speaker 01

  Yeah, well, whatever it is like, why that should be at Apple. That feels so naturally like what Apple would be working on. We're going to change the AI conversation with this new device that takes the tech and reinvents it in a way you hadn't thought of before. Like, that's what the iPhone was.

• 14:58Jason Calacanis?

  So the lesson here is you put a maniacal supply chain person in charge of an innovation technology company, what you will get is a, the most amazing, efficient supply chain in the world. What you will lack is somebody who fires the leaders of Siri, somebody who invests in, you know, AI five years ago, and somebody who had the hoot spa to launch a car. They did a project, project Triton.

• 15:31Speaker 01

  Yeah, I think that's right.

• 15:32Jason Calacanis?

  Project Triton. Was it Triton or?

• 15:35Speaker 01

  Triton project. You're correct. Oh, wait, no, maybe not. Hang on, hang on. I'll, I'll look at it.

• 15:39Jason Calacanis?

  Something like Triton or then internal term for it might have been a metal. As opposed to that, but they had hired a thousand people to work on that. They had like a.

• 15:50Speaker 01

  Titan. It was Project Titan.

• 15:54Jason Calacanis?

  Titan.

• 15:54Speaker 01

  Like the Greek, like the Greek god, the Titans.

• 15:57Jason Calacanis?

  I mean, if Apple had launched their own car, self-driving, AI, it would have been, we'd have a completely different discussion about it right now, but Apple went for printing money and, and gooseing the stock price. But at some point, even Warren Buffett, who cares about those issues, sold the stock. Cause he realized in his infinite wisdom, well, if you don't have more product, then what's going to get sold next? I was just listening to the incredible. Incredible. I'm almost done with it. The biography of Barry Diller. And he talks about taking over Paramount and how they had this like really bad funnel of pictures. They had to like ride them out, but then they created a whole series of like one win after the other,

• 16:42Jason Calacanis?

  including Raiders of the Lost Ark and, you know, Friday the 13th. Everything from genre pictures to blockbusters and they just crushed it. And then he went on to do Fox, the fourth network.

• 16:51Speaker 01

  Right.

• 16:52Jason Calacanis?

  That is a product innovation guy who makes mistakes and iterates. Steve Jobs, a perfectionist who iterates and is got that vision and that has taste. And this is, we're sitting here wondering what's going to happen with Apple. I mean, they've got lock-in, but the iPhone might go away at some point. If, if the future interface is a blank screen where you just ask an AI to do something.

• 17:19Speaker 01

  Right, yeah.

• 17:20Jason Calacanis?

  Continues to be my experience is instead of being, you know, on a, on an app, I'm just in a chat window, you know? And so that is kind of mind breaking. The whole app ecosystem could change, you know? You want to order Uber Eats or DoorDash, you might just open the Uber app and just say something to it. You might open ChatGPT Claude and everything.

• 17:45Speaker 01

  I was gonna say.

• 17:46Jason Calacanis?

  And it's hooked into your Uber Eats account and it just does it for you.

• 17:49Speaker 01

  I think we're on the verge of you don't open an app at all. You just tell your phone, I want to order Uber Eats and your phone knows, oh, that's the Uber Eats app.

• 17:57Jason Calacanis?

  Which Siri was supposed to do, but because there's nobody with taste there using the products. I wonder sometimes if Tim Cook uses the products because all of us are sitting there saying, by the way, the last four times I updated my phone, it broke or it was sloppy or the, the interface isn't good. Steve Jobs would have read them the riot act and I guess better late than never, but I heard that.

• 18:22Jason Calacanis?

  Two things have occurred. They fired somebody in charge of AI over the weekend and then they've been having their whole AI team get poached.

• 18:30Speaker 01

  Yes, they're losing a lot of people to Meta. And the interesting, like, we have, I think we have this at a later story, we're not seeing that necessarily with every other company. Like some, like Anthropic is much better at holding on to its people even when they get extreme, you know, offers from Mark Zuckerberg, whereas Apple's sort of bleeding out.

• 18:50Jason Calacanis?

  Yeah, they just moved, oh god, the responsibility for Siri was moved from John Giandrea, Giandrea, who was from Google, to Mike Rockwell, the exec behind Vision Pro.

• 19:06Speaker 01

  Yeah, John Giandrea.

• 19:07Jason Calacanis?

  What could go wrong?

• 19:08Speaker 01

  That's it.

• 19:08Jason Calacanis?

  Yeah, Giandrea. What could go wrong?

• 19:12Jason Calacanis?

  I mean, the fact that Siri cannot set a timer, or like pull up a song, or give me proper directions without a spinning wheel of death for 45 seconds. I mean, have you had that experience? Do you even try to use Siri, Lon?

• 19:26Speaker 01

  I gave up. But there was a time where I was really trying to use Siri. And Maps, I think, is the most frustrating. Because I have work, home, like, I've done the legwork of programming that in. So I should be able to take Siri directions home, and the phone should just know it. And it never works. I've tried it like three or four times, and then I gave up. It never works. The other thing, like, there's a million just like little frustrating annoyances now with iPhones. I constantly, you know, you have to like, you flick up to close the app, like, I'm done in Safari. But that also opens Siri. So half the time I'm trying to close an app now, it opens Siri, and I don't want Siri. And there's no, I haven't figured out how to turn that off. It's a nightmare.

• 20:13Jason Calacanis?

  Founders, if you've got a product, maybe you've got some customers or even just a little bit of traction, guess what? You've got yourself a startup and it's time to make things legit. You want to be official, tighten it up. Investors don't want to wire money to a Gmail account with a P O box. No, they want to know you're a serious person and that your company is incorporated. In 10 clicks in 10 minutes, you can follow your LLC, get an actual domain name, launch your official website, claim your business email, and even start fast-tracking your trademark application. That's right, you need Northwest Registered Agent, the service that's going to do all of that for you. With NWRA's Privacy by Default option,

• 20:56Jason Calacanis?

  they're going to use their address for all your public documents, not yours. So you're not going to get a ton of spam or junk mail. And you can also get a legit address and working phone number with their virtual office setup. So get more than just an LLC, get your entire business identity. Go to northwestregisteredagent.com/twist and show the world you're in business. All right, let's get into ChatGPT. Yeah, we got to talk about ChatGPT. This is, it's a good backdrop because Sam Altman wooed away like somebody with taste. You know, Steve Jobs' partner, John Ives, he made an acquisition. And here's the problem, the

• 21:37Jason Calacanis?

  the people who are staying at Apple right now are probably not being put under the pressure, Steve Jobs, nor being given the inspiration. So inspiration plus perspiration is like, that's the leading, that's the height of management in a competitive environment. You sat in my senior meeting on Monday and you see how I operate, which is, hey, you don't have to be at this company, this venture firm, but if you do, here's what it requires if you want to win at venture. And Tim Cook has not given that speech to everybody, that we need to beat ChatGPT, we need to beat Grok, we need to beat Tesla, we need to be OpenAI. He hasn't given him the pressure to do that. And then you have companies running amok.

• 22:22Jason Calacanis?

  How is Perplexity able to create two great products? How is Elon able to catch up with Grok to everything in like under a year with XAI? To build a data center with more GPUs than anybody in under a year? Inspiration, perspiration. It's the pressure that creates the diamond. Tim Cook should announce a successor and he should just buy five companies. This is what I would do. I would tell, I would have the board, if I was on board of Apple, I'd buy five companies. I'd have five lunatic founders in a little group, a SWAT team, like a Seven Samurai situation. I'd buy seven. I'd have

• 23:06Jason Calacanis?

  my seven Samurai and I'd say, battle it out. Just like the head of Gulf Western did when he had Katzenberg, Eisner, Barry Diller, and the kid stays in the picture.

• 23:20Speaker 01

  Oh, Bob Evans.

• 23:22Jason Calacanis?

  Evans. He, I mean, the amount of talent in Paramount Pictures at that time.

• 23:28Speaker 01

  Yeah, it's crazy.

• 23:29Jason Calacanis?

  I just had four people who went on to run, oh, and I think they had Geffen too, maybe, at one point. So they just stacked the place with seven great leaders and see what happens. And I told them, they could have bought Tesla at $50 billion when I was saying, you should just buy Tesla for 50 or 75 billion. And then you would have had Elon in the building, or you know, who knows who. So anyway, let's, what did we learn today about ChatGPT-5? It came out, I watched it, I didn't, I wasn't impressed by anything. I'll be totally honest. So am I alone in this? Underwhelmed?

• 24:04Speaker 01

  I think that's fair. I will say, I tried it out today. Chat, you can, if you are an OpenAI subscriber, you can just go right now and it's live and go to chatgpt.com. It didn't, it was only like an hour.

• 24:18Jason Calacanis?

  It's there for me now.

• 24:18Speaker 01

  Yeah, an hour before we went live, it popped up. And I will say, here's one thing I tested it on. So for Honest Trailers a while ago, we had this question. We were writing jokes about Buffy the Vampire Slayer. We were like, you know, there's a lot of shows that were inspired by Buffy the Vampire Slayer. And I went to ChatGPT and I was like, give me a list of every show other than Buffy that also has like, high school kids, monster hunting, fantasy, but it's also realistic. And the answers I got from GPT-4O, they were okay. I tried it again. Today with five, they're much better. It's it's not it's it's you get more thorough answers, but you get more correct ones. You know, there's always like it's 50 50 like these are good answers.

• 24:59Speaker 01

  These answers were not exactly what I was looking for. Five, I do think is closer to like 80, 90% of the answers are what I'm looking for. Fewer false positives. So I do think on a personal level, it does seem to have a little bit of an upgrade. Having said that, watching the presentation, it seemed a little inside baseball, a lot of it for me. Like, it wasn't like stuff that was there to wow you. It was like, well, okay, that that is cool. That's a cool thing.

• 25:26Jason Calacanis?

  I just did a search. Tell me, please tell me what was discussed in the last five episodes of the All In Podcast in bullet points with the related links to news stories. Didn't do it. Claude would have crushed this.

• 25:35Speaker 01

  Claude actually would have probably crushed that, I will say, based on my experience.

• 25:40Jason Calacanis?

  I mean, okay, it's supposed to be faster, better, cheaper.

• 25:45Speaker 01

  Yeah.

• 25:45Jason Calacanis?

  But you also need to have the wow. And the thing they showed, the first thing I noticed, which I'm sure is in the docket here, was a lovable.

• 25:54Speaker 01

  Sure.

• 25:55Jason Calacanis?

  Coding. App building coding, but more vibe coding than a co-pilot like Cursor.

• 26:01Speaker 01

  Yes.

• 26:02Jason Calacanis?

  So tell me about that.

• 26:04Speaker 01

  Yeah, so the GPT-5's ability to write applications and write and edit code got a lot of attention from the stage. We actually have a little clip of Michael Truell from Cursor demoing that GPT-5 is already live in Cursor, so you can do your vibe coding with ChatGPT-5 right now. And it did, it's like, a lot of people online were saying this, that lovable, Bolt new, Rosebud AI, all of the Replit, all of these kinds of interfaces. Well, if people could just go right to GPT-5 and do that, you know, are they going to be using all of these sort of third-party services? It was one of a few categories that it seemed like that might happen.

• 26:44Jason Calacanis?

  I'm gonna go with yes, because I think these models are never going to do all the nooks and crannies and be able to keep up.

• 26:51Speaker 01

  Right.

• 26:52Jason Calacanis?

  And so, you know, if you've got, again, back to inspiration and perspiration, you can be sure the lovable team and the Bolt new team, which do vibe coding, which is different than Cursor, which is more, I think, co-piloting for a developer. And the vibe coding is for non-developers. My guess right now is it's going to be much more.

• 27:15Jason Calacanis?

  I think it's gonna, excuse me, I think we're gonna see those services actually do better. And they can also change their underlying model or use multiple models. So I think what I learned from the chat GPT five launched today is the biggest announcement is maybe that the pricing is better.

• 27:33Speaker 01

  Right.

• 27:33Jason Calacanis?

  Is that, maybe that's the biggest thing. I have to use it a bit. You know, this all came out, you know, just in the last couple of hours.

• 27:41Speaker 01

  Yeah, there was a tweet that you sent that that I thought was interesting that also was sort of taking a, you know, sort of like the more cynical view of whether it's gonna sort of just replace everything. I'll bring it up here. I'll share it. So you know that this guy Klaas Tropper, Klaas Foppen, who's an SEO guy, he had tweeted, goodbye lovable, goodbye Bolt. You know, chat GPT five is just gonna take it from here. And then Logan Colpatrick, who is actually a product lead for Google AI, said, that's not how it works. They get to use the models by default and take on a more advanced, robust set of user problems, likely to be very positive some for them, which is the point of building a product that benefits from model progress. Their product is X percent better today.

• 28:25Speaker 01

  So it's kind of what we've been, you know, saying, like, I feel like this is always the back and forth in AI arguments is, is AI going to replace the person? Is AI going to replace this old way of doing things? Or is it gonna like level it up? And so that that seems to be the debate these two guys are having as well.

• 28:44Jason Calacanis?

  I wonder if this is like, we're in now, and I had said this in my Nostratana's presentation I did two weeks. Thanks for helping on that. There is like a commodification of LLMs happening. This is what I thought of. Yeah, somebody showed the circle of all of them.

• 29:04Speaker 01

  Yes.

• 29:04Jason Calacanis?

  And then just move the you are here to OpenAI. But even that, other people started saying, well, wait a second. Here's the objective results on that. There's a human test. I forgot the name of it.

• 29:15Speaker 01

  The last, uh, the humanities last exam.

• 29:18Jason Calacanis?

  Okay, humanities last exam. I love that name.

• 29:21Speaker 01

  Yeah.

• 29:21Jason Calacanis?

  That sounds like a Twilight Zone episode, right?

• 29:23Speaker 01

  Really? It sounds like we're facing a test as a species that could wipe us out.

• 29:26Jason Calacanis?

  Let's write a Twilight Zone episode and we should, and then we'll make it with, um, we'll make a trailer for it with VO3 or something.

• 29:33Speaker 01

  2,500 questions and the idea is it's from every, a broad range of disciplines. So it's like all, all sorts of human knowledge.

• 29:45Jason Calacanis?

  The key to running a successful startup company, or even having a profitable portfolio, it's data. If you don't understand the numbers and you're not watching them closely like a hawk, you're literally flying blind. But how can you be sure you're getting the best and most accurate information? Or that you're even looking in the right place? The answer is AlphaSense. This is the world's most trusted AI platform for market intelligence. It's currently used by over 6,000 leading companies, including 88% of the S&P 100. Their expert, domain-specific AI, has been trained on over 500 million business documents, like earnings reports, equity research, expert interviews, filings, and more. And it's designed specifically to help your team uncover the latest financial trends.

• 30:28Jason Calacanis?

  The faster and more efficient your team gets at the research, the more founders you meet, the smarter and more informed bets you can make, the greater your chances of catching a unicorn. So it's time to accelerate your entire process with deep research from AlphaSense. Start your AI search and market intelligence journey today and get deeper insights to power your business. We're even going to start you out with a free trial. Go to alphasense.com/twist to get started. And people are like, it's the same. You know, Grok had done better. Grok 5 had done better. So I think we're in this like dogfight where these things are hitting some level of parity as people move from startup to startup because of the competition for talent.

• 31:11Jason Calacanis?

  Another ramification of that is they bring all the best practices from the last place, or all the techniques and strategies and tactics. So now what Zuckerberg really did by poaching all those OpenAI people is all of their innovations or their strategies, their management techniques, their philosophies, you know, that's all going to go into Meta's open source. So we might be... It's possible we might hit a trial of despair in the startup curve. There's this sort of initial enthusiasm, right? And then you kind of reality sets in like, oh, this isn't getting things done that I need to get done, or the product like Siri is not that great, or my iPhone's battery keeps

• 31:52Jason Calacanis?

  crashing, or, oh, my Tesla FSD doesn't work when there's traffic cones. You know, you kind of get into the, this messy middle.

• 32:00Speaker 01

  Yeah.

• 32:01Jason Calacanis?

  Or trial of despair is the two ways to refer to it. And then you start to get real product market fit in specific verticals and then you start scaling it. I, I thought we were going into the scale phase, but maybe we're actually still in the messy middle here.

• 32:14Speaker 01

  Yeah, I mean, I don't know. To me, I feel like there are things that AI does so amazingly well, but we're trying to use it for everything. And, and, and I feel like that, that creates a lot of those experiences. There are magical experiences with AI. Like, I talk about Notebook LM all the time. I praise gummy search on here many times, but like, uh, you, you do still have those, like you just had, where you were like, oh, maybe it can pull up all this great information about the last five all-ins. Oh, no, it can't. Like, and we are, we're, I feel like we're all in a constant push and pull where we're having those experiences every day.

• 32:46Jason Calacanis?

  Yeah. So we'll have more on it Monday. We'll get into some more details. Everybody's going to bang on this thing all weekend.

• 32:53Speaker 01

  Sure.

• 32:54Jason Calacanis?

  Back to Apple. I, I do think the greatest innovation Apple had under Tim Cook is going to be like these M4 processors, M5 processors. All that silicon they made.

• 33:06Speaker 01

  Silicon team, yeah.

• 33:08Jason Calacanis?

  I mean, shout out to them because every time I buy a new machine, it lasts longer and longer, it's better and better and cheaper and cheaper for the compute power. So the, you know, the Mac Mini, I've, M4, I've praised to the cows come home and just an incredible, incredible device. I think Apple should have done their TV. There was a rumor 15 years ago that I talked about, I think on This Week in Tech, even before I had This Week in Startups.

• 33:36Jason Calacanis?

  Because Apple, I had heard from some people, I was at an event or something, and people were drinking and having a little talk, and somebody let out that, yeah, we might put a TV out there.

• 33:45Speaker 01

  Yeah.

• 33:46Jason Calacanis?

  And then they came out with Apple TV, but supposedly when they were doing the biography, what's his name? Walter Isaacson, he was doing his biography. He said he had figured out television. And I think what he figured out with television was how to give one interface to all the different networks.

• 34:04Jason Calacanis?

  And you could easily find anything and have the video jukebox in the sky, which was Steve Jobs' really prescient innovation for music.

• 34:14Speaker 01

  It just, Amazon did it, not, not Apple. Like, Amazon is this exact thing. You could buy a Fire TV, it comes preloaded with Prime, all the other streaming services are available through Prime Channels.

• 34:27Jason Calacanis?

  In the television.

• 34:28Speaker 01

  In the, in your Fire TV.

• 34:29Jason Calacanis?

  You don't put an Apple TV, and they decided they had to have that box. And now I see some boxes have like some amount of Apple TV in it, or AirPlay.

• 34:37Speaker 01

  Yeah.

• 34:38Jason Calacanis?

  The scotziad. People would have loved to have an Apple TV.

• 34:42Speaker 01

  Yeah.

• 34:42Jason Calacanis?

  Like, physical one on their wall.

• 34:44Speaker 01

  I stream my Apple TV Plus shows into my Amazon Fire TV. It, it, literally, they figured they flipped them. Now it's, Apple's making the content, and it's the Amazon TV that you watch it on. They screwed up so bad.

• 34:58Jason Calacanis?

  Hmm. Alright, so we'll, we'll do more on that.

• 35:03Speaker 01

  Sure.

• 35:03Jason Calacanis?

  What else do we have?

• 35:05Speaker 01

  Oh, we got, we got so much. We got Ripple, we got Trump.

• 35:08Jason Calacanis?

  What's going on at Ripple?

• 35:09Speaker 01

  Oh, Ripple is buying a stablecoin service. They're buying Rail, a stablecoin startup for $200 million. This comes, of course, just a few weeks after the passage of the Genius Act, which codified the rules and regulations around stablecoin. So now it is full speed ahead for these stablecoin companies. So Ripple has picked up Rail. It's a payments business. They use stablecoins and banking partners to help people move their stablecoins across international borders quickly and efficiently. It's the initial promise of crypto. It's what we were always told crypto was going to be. Rail raised a 10.4 million Series A last July with Galaxy Ventures leading the round. They were previously called Layer 2 Financial, if that means anything to you. And they reported earlier

• 35:52Speaker 01

  this year that they now control 10% of the world's B2B stablecoin payments, a value of about 3.6 billion.

• 36:02Jason Calacanis?

  Yeah, this just shows you, there was so much potential lost in the last decade of crypto being this underground technology. And why was it underground? Well, you know, regulations, we're not prepared for this. And so we talk about regulations. Regulations can be good for technologists. And this stablecoin regulation is a perfect example. So now, we talk all the time, "Oh, we have to get rid of regulations. We have to get rid of regulations."

• 36:34Speaker 01

  Right, yeah.

• 36:35Jason Calacanis?

  And now, we're sitting here saying, "Well, wait a second. The entire industry has been enabled by a new set of regulations." What you need is a balance, Lon. You need to be able to say, "These regulations are old, antiquated, and do not apply to this new technology. Therefore, we're going to come up with a new series of them." What people do with regulations is they do regulatory capture. They use them to keep their market share as opposed to enable new markets to exist. Say what you will about different administrations, you know, 45, 46, I just like to refer to them by numbers. You take the names out, it kind of frees peoples. You know, people are, you said it really well the other day in our group chat, that people were in a psychosis or something?

• 37:15Speaker 01

  Oh, Facebook psychosis, social media psychosis? I do think-

• 37:19Jason Calacanis?

  Yeah, explain your thesis, because this stuck with me so perfectly.

• 37:22Speaker 01

  Sometimes you hear people speak, and just by the way they're talking, I feel like you could tell, not only, my real personal pet theory is, not only you could tell they spend too much time on social media, I think sometimes you could tell what social media platform they spend too much time on. Like, based on the way people, some people speak and the way they present arguments and their understanding, you're like, "This person reads tweets all day. All their information is coming from these bite-sized soundbite. Like, they heard a slogan or a phrase that sounds good. They really don't know exactly what it means, but they saw that on Twitter." And then Facebook, it's, we saw, we were watching a video. It was from Representative Mike Flood, who is a Nebraska congressman, Republican congressman from Lincoln, Nebraska.

• 38:05Speaker 01

  And he had a town hall this week that was, he was getting yelled at by his constituents. It was very lively, and we were- Watching a video of a woman yelling at him. But she was upset about so many different things at once. She was yelling at him about like eight different trending stories. Like, why did you, why did Trump fire the Bureau of Labor Statistics guy? Why is this tariff happening? Why, what about that? What about that? And it's like, this is not her own mo- these are not things that she's upset about. She was reading about this on Facebook and she's getting-

• 38:39Jason Calacanis?

  She might have been on Drudge Report or whatever her for you feed is.

• 38:43Speaker 01

  And she's getting these different Facebook articles that she read mixed up. And she's not quite clear on exactly how it all fits together, the overall narrative. And you saw this, you see this all the time where people will use these catchphrases or they'll refer to something like "the laptop from hell." And you're like, unpack that. Do you really know what we're talking about? Or have you just seen this go by a whole bunch of times? And now you're upset about it because you read about it? And I don't, I, for the, I'm using some of these examples. I think this is true of people on the left or the right. This is not partisan to me. Like, I think this affects millions of Americans from every political strike.

• 39:17Jason Calacanis?

  And then the second you try to unpack it and ask those same people the question, "Okay, what should the regulations be for crypto?" They don't have anything. I spent years on this podcast saying, "Here's a way to allow, to have a framework for crypto." I said, "Have a sandbox. You can raise up to $10 million from up to 10,000 people. And you can build a project. They sign a waiver. You have to know who they are. And then if it grows to 100 million in value, you have to register with one of these agencies. And then you have to have insurance. And in order to even be in the $10 million sandbox, you apply with the SEC for a sandbox-like license. And then those people who want to be in it have to take a basic test,

• 40:00Jason Calacanis?

  like a basic accreditation test that allows them to play in the sandbox. And then on the SEC website, you have, "Here are the sandbox projects, you know, board apes, this, that, the other thing." And you can go play in the sandbox. If you answer these 10 questions about diversification, if you have a proper bank account and social security number, so it's not money laundering. And if you lose your money, you knew you were gonna lose it, right?

• 40:22Speaker 01

  Yeah.

• 40:22Jason Calacanis?

  And I just had all these like very simple ideas. And people would be like, "So you hate crypto?" Or, "Oh, you want to destabilize it all?" And it was the same thing where they had been programmed to have a framework without just saying, "From first principles..."

• 40:39Jason Calacanis?

  Would it be great to pay 0% fee when we sent each other money?

• 40:42Speaker 01

  Right.

• 40:43Jason Calacanis?

  With a stablecoin and not have any intermediary? If I, just like I can hand you a hundy and be like, hey, here's the hundred I owe you. And not pay anybody.

• 40:52Speaker 01

  Yeah, we don't have to go through a payment process. Yeah, exactly.

• 40:55Jason Calacanis?

  Why shouldn't that exist? And if the technologists can build it, special interest, et cetera. So when we think about regulations, that's just something for people, I think, to keep in mind. For Ripple, pretty amazing that this company got out of their SEC investigation. They were like the number one in the crosshairs. And I think it would have been pretty severe. I don't know if it would have been FTX like, because that was just outright fraud. But I think they had broken so many rules collectively, they just, you know, you have to. It's not just, you know, allegedly, according to this indictment. Is that what it is, the case?

• 41:30Speaker 01

  I believe so.

• 41:31Jason Calacanis?

  Yeah, yeah, an indictment, the case the SEC had against them, which after they donated, I don't know, three, four, or five million dollars to the crypto inauguration fund.

• 41:40Speaker 01

  Yeah, they were, they were merely under investigation. So it wasn't even, it didn't even raise.

• 41:44Jason Calacanis?

  No, no, no, they had a case. There was an SEC case that was filed for sure. Yeah. And then they, they won the first case, actually, because they wanted to see if Ripple was responsible for selling securities. But the security sales were happening on other platforms and Ripple wasn't even aware of them.

• 42:01Speaker 01

  I got it, yeah.

• 42:02Jason Calacanis?

  And so they couldn't prove that.

• 42:05Speaker 01

  Yeah.

• 42:06Jason Calacanis?

  Yeah, yeah. So anyway, that's, all that's over. Stablecoins is the first viable business. When interest rates come down, which it seems like when we get a new head of the Fed, and based on the unemployment numbers, we just saw the revisions to them, there's definitely going to be two cuts later this year. And we'll probably have inflation go above 3% again. And it'll be funny to see like, the group of people who were complaining about inflation be like, oh, no, inflation is totally manageable at 3 or 4%.

• 42:32Speaker 01

  That's, this is the social media psychosis I'm talking about. That's exactly it. You'll, you'll, you'll start to hear all of those arguments again, and you'll know like, well, people are seeing it on their Facebook wall and their.

• 42:43Jason Calacanis?

  Without people ever recognizing that these are complex systems, and when you turn one knob, it can make other metrics change, so. You know, hey, you know, in this case, if you lower the interest rate, people invest more money, more money gets flooded into the system, people make less money from their savings account and they'll make less money on the float of all this money in a stablecoin, which means people will be like, oh, that's not a good option. I should put my money back into the stock market to get a return because people, to stay in cash was considered dumb for the last 15, 20 years because interest rates were 1 or 2% and you would be losing money every year if the stock market was growing 7. The number between 1 and 7 would be the percentage you were losing but not keeping up or missing that opportunity. So

• 43:28Jason Calacanis?

  it's probably a smart move for them because they have sold, I think, hundreds of millions to billions of dollars in Ripple, put that into their coffers. The XRP token, I don't know that anybody uses that, but they have built some other banking tools. I don't know the status of them. I've never heard of any startup ever using XRP for anything, ever. So like as a platform, I hear people all the time talking about using Solana all the time, using Bitcoin or Ethereum. I never heard anybody using XRP. Put it all aside. This is a great way for them to get into, albeit a competitive, but a known business. So there's two known businesses in crypto that seem to be working, three known businesses in crypto that work really well. Stablecoins because you make the interest, have an exchange

• 44:12Jason Calacanis?

  because you make the fees on the exchange like Coinbase or FTX previously or Kraken today. And then, what was the third? I had a third. The float for stablecoins. Oh, and then having a treasury like

• 44:29Speaker 01

  Right.

• 44:29Jason Calacanis?

  MSTR and just having a vehicle where people can buy a stock that has a bunch of Bitcoin in it and putting that. Those seem to be the only three models really working today.

• 44:39Speaker 01

  Yeah. Actually, I just pulled up a blog post on Binance where somebody is arguing Ripple is about to become the micro-strategy of XRP. They're going to stop selling it is the theory and just hold on to it. They have $122 billion worth of XRP, 41% of the total supply.

• 44:57Jason Calacanis?

  Yeah. So what they did when they built that, it was really clever. I knew the co-founder, Jed.

• 45:03Jason Calacanis?

  Imagine if you created Bitcoin, but you kept half of it.

• 45:06Speaker 01

  Yeah.

• 45:07Jason Calacanis?

  And then you sold 1% a year for whatever number of years. It's kind of what they did. So they originated all their coins. They didn't have like a mining concept. So, smart move for them.

• 45:20Speaker 01

  Did Binance say?

• 45:21Jason Calacanis?

  They need to find a business in there.

• 45:22Speaker 01

  Bitwise CEO Hunter Horsley said in a recent interview that this is the plan. Ripple is going to undergo an identity transformation and become the world's largest crypto asset treasury. So there you go.

• 45:33Jason Calacanis?

  There you go. Okay. That's fine. But that is based on people wanting to own XRP.

• 45:38Speaker 01

  Right.

• 45:38Jason Calacanis?

  I think this is all going to end in tears. There was some legislation or an executive order today. I don't know if you saw that. There was an executive order to a lot of people in their 401Ks.

• 45:47Speaker 01

  Oh, yes, I did see this. Yes.

• 45:48Jason Calacanis?

  To buy crypto assets.

• 45:50Speaker 01

  Private equity in crypto. Yes.

• 45:52Jason Calacanis?

  Yeah. So the private equity and crypto, I mean, I agree with both of those. Your money, you should be able to do what you want with it. But this is...

• 45:59Speaker 01

  And real estate as well.

• 46:01Jason Calacanis?

  Yeah. Basically, private market assets. So, you know, you could buy a REIT. So let's say you have a million dollars in your retirement account and you, hey, I got plenty of time. I'll put 100K into Bitcoin. I'll put 100K into a bunch of apartments that are being built in, you know, Austin and I got a 20-year window for this. So I want to just be hedged against the other balanced portfolio in my 401K. Kind of makes sense. It will result in more crying in the casino.

• 46:30Speaker 01

  For sure. Yeah.

• 46:31Jason Calacanis?

  There will be more crying in the casino because I do this for a living. I do private assets for a living. They're not regulated. In some cases, they're fugazi, fugazis, or whatever else.

• 46:43Speaker 01

  Yeah. Well, your, but your philosophy, you know, the way that you operate, you're making so many bets. It's like, well, we don't need all these bets to come through. Like, that's how you could do it in an organized way. But if you're a random individual putting your 401K into a company, you don't want to just make a random bet.

• 46:59Jason Calacanis?

  Well, you see how much work it takes to make 100 bets a year.

• 47:02Speaker 01

  Right. Exactly.

• 47:03Jason Calacanis?

  You basically, I think, to hit diversification in my book, Angel, I asked a bunch of people, how many seed-stage bets do you need to make in order to have, like, angel bets before they get Series A and they're anointed? And I got numbers 20, 30, 40, and 50 were the most common numbers. So I'll just say 30 to 40 is probably the mean. And the median that people said is what you need for diversification. What grandma in Florida or retiree in Arizona is going to have the ability to pick 40 different companies?

• 47:35Speaker 01

  Exactly. That's out of the reach of most 401K holders.

• 47:39Jason Calacanis?

  Yeah. You'd have to meet with 4,000 to do it the way we do it, which is to invest in less than 1% of the companies that you meet or less than 1% of the companies that apply. Okay. I saw also Trump added perplexity. Oh, sorry. Truth Social. I shouldn't say Trump. Truth Social.

• 47:55Speaker 01

  I really like. I feel like this is a glimpse into our, like, the most dystopian version of our AI future. The president's media company, Truth Social, he owns a chunk. It's not his exclusive company. He owns a big chunk of it along with his family. So the company, Truth Social, announced their own AI chatbot, Truth Social AI. It is powered by perplexity. You could try it out right now. I signed up. I've been on it all day. It is available only through the web version of Truth Social, but it's coming to the iOS and the Android apps very soon. Now, they're saying this is, it's going to give you more accurate answers. The chatbot's going to give, and I quote, "direct, contextually accurate answers with transparent citations

• 48:37Speaker 01

  in an effort to exponentially increase the amount of information available to Truth Social users." But here's the rub. They're using perplexity's sonar API. But as with anybody running their own custom version of perplexity, they decide what sources get fed into it. It has nothing to do with perplexity. The AI is just going to search whatever sources Truth Social tells it to pull up information. So Axios got access and started asking questions like, what happened on January 6, 2021? Why was Donald Trump impeached? Did Donald Trump lose the 2020 election? And they noticed that all the responses had citations from Fox News.

• 49:19Speaker 01

  Many had citations from Fox Business, The Washington Times, Epoch Times, Trump-friendly publications. And they noticed that if you go to general public perplexity, it'll give you responses from Reddit, from YouTube, from Esquire, from Politico, from NPR, all over. You don't get those responses from Truth Social. You really only get these like Trump-friendly. Resources. So you could search whatever you want. It's powered by perplexity, but Truth Social is really controlling what information gets pulled into the AI. I think that's, I think that's dangerous because people trust AI. They think this is a computer. It's not going to be biased.

• 49:56Jason Calacanis?

  This is just an extension of the echo chamber. If you're on Twitter, you get one view of the world. If you're on Instagram, if you're on Blue Sky is Falling, if you're on, what was the Instagram Twitter knockoff? I forgot it. I forgot the name of it now.

• 50:09Speaker 01

  Instagram Twitter.

• 50:11Jason Calacanis?

  Threads.

• 50:12Speaker 01

  Threads. It's still there. It exists. You can go to Threads.

• 50:14Jason Calacanis?

  I, I know, because when I'm on Instagram, it puts the spiciest, most viral thread images in my Instagram feed to try to hijack me.

• 50:26Speaker 01

  Lure you over there, yeah.

• 50:27Jason Calacanis?

  Lure me over there. I think it's just more of the echo chamber. I, I think people are going to just, as it learns about you, one of the big things in the ChatGPT 5 is memory. You can ask ChatGPT 5, what do you know about me? Or give me a summary of all my searches and what I'm like. And it was like, oh, you really like dire straits.

• 50:45Speaker 01

  I tried this with both ChatGPT and Claude. Claude is scare. Claude's getting scary. Claude knows a lot about me.

• 50:52Jason Calacanis?

  Yeah. Well, I don't need to, don't put that on the screen.

• 50:55Speaker 01

  It's nothing bad.

• 50:56Jason Calacanis?

  I don't know if we all need to know about your Japanese manga.

• 51:00Speaker 01

  I'm on a business account on Claude. I'm not asking him anything untoward. No way.

• 51:05Jason Calacanis?

  So I think it's interesting. I think memory is going to do that as well. If you say, I am a Christian. I don't believe in gay marriage. I don't believe, you know, in abortion. I don't believe in contraception. It'll just like, you know, over time, it's not going to tell you those things. And you could tell it, I believe, you know, this side of this war is correct, that side isn't, and just show me results that I like. These things are built to please. And that's a big thing that people have to understand is we're building these things not for truth. We're building them to please people. So it is what it is, folks. If you're looking for truth, do not look for it in LLM, because LLM is garbage

• 51:49Jason Calacanis?

  in, garbage out. If you ask it for health advice. The health advice is they scraped WebMD or other known sources, just like PageRank does, you know, Google's original innovation, and they just take all that and they regurgitate it to you. So if something changes, like statins, there's a big debate over statins right now, right? Are they healthy? Are they not? Should you take them? Baby aspirin? Should you take them? Should you not take? You know, all these kind of things. If you ask an LLM, it's not thinking, oh, you know, for lawn at this age and this BMI and this diet, they should do this, this, and this. It's just thinking, what did I read? What did I learn? What did I train on? And let me just rephrase it so I don't get a copyright infringement when I rephrase it and give it to them.

• 52:34Speaker 01

  I just worry we're not teaching people that. Like, people don't understand that. They think the computer is brilliant and it knows things and it's intuitive and it's like putting all this together and calculating things. And I worry, like, and I, yeah, I say this not as an AI hater, but I do worry about that.

• 52:49Jason Calacanis?

  I mean, Eliza, E-L-I-Z-A, I think we talked about it here before, in 1964 and 1967, this computer program that was designed to like, basically communicate with you in a chat interface. It wasn't AI. It was just keying on keywords. Oh, you talked about your mom? Tell me more about your mom. Kind of like a therapist might do in an open-ended way. You know, that confused people. But this leads to our next story, which is this ID, which is Governor Pritzker. We were just talking about this, you and I, the other day, about how, and producer Nick, formerly of This Week in Startups, now the producer of All In.

• 53:25Speaker 01

  The All In Podcast.

• 53:27Jason Calacanis?

  The All In Podcast. That is causing, people are doing therapy with ChatGPT and other LLMs, and they're building friendships, and young kids are doing it. And it's so placating and pleasing.

• 53:45Jason Calacanis?

  That now people are getting worried because there was this therapist who wrote a story in the New York Times, abusively praising, like, "This is as good as me," or "This did things that I didn't think of doing as a therapist," which leads you to believe one of two things: either that person got one-shotted, is a new term people are using, or, there it is, "I'm a therapist, Chachi Piti is eerily effective," or, "Therapy is like a playbook that could be replicated in a, to some extent,"

• 54:20Speaker 01

  Yeah.

• 54:21Jason Calacanis?

  Not well, maybe, but, I mean, if you think about what it does, it paces you, you ask open-ended questions, and a lot of therapy, based on my psychology degree from 30 years ago, was, just the idea of sharing with another human being as your witness was cathartic and helped you get through things. So, to that extent, if you believe this is sentient in some way, or a genius in some way, which is how it was presented today, Sam Altman said this is like a graduate student and will soon be the smartest human being on the planet.

• 54:51Speaker 01

  Yeah, it's like talking to a PhD, yeah.

• 54:53Jason Calacanis?

  So, if it's being pitched as a PhD, then consumers, if Sam says this is a PhD, well, you know who else has a PhD? Clinical psychologists.

• 55:01Speaker 01

  Right.

• 55:02Jason Calacanis?

  Therapists. So, Governor Pritzker signed legislation on Monday prohibiting AI therapy in Illinois. Now, I don't know if people were actually using it, but I think he's kind of getting ahead of the curve, which I'm curious what you think about that.

• 55:19Speaker 01

  Yeah, I mean, I am troubled by the idea of AI therapy, mostly because, yeah, it's not, they didn't actually design an AI and like, teach it to be a therapist. They just fed it a lot of text, and now it's a good predictive engine, it knows how to respond to you. But, it's not a therapist, it's not licensed, it doesn't know that what it's saying is going to help cure you. It's just trying to come up with the best possible response it can to what you said. And, you're right, that, I think, I've been in therapy, and 80% of the time, that is all a therapist is doing. They're just like, hearing what you said, throwing it back at you in a slightly different way, or, "What if you thought about it like this?" Or, "Maybe this relaxation technique might work," and AI, an LLM could

• 56:03Speaker 01

  do all of that. But, it's those, it's those 10% edge cases where... Where there's something that you could say that would be the wrong thing or that would be a dangerous thing that you might not even realize is the wrong.

• 56:15Jason Calacanis?

  Just like self-driving, you know, like there's gonna be a time when a garbage bag goes flying across the front of your car and it thinks it's a truck and slams on the brake and then somebody hits you from behind and it's like, okay, well, that's like a random thing. A giant tarp flew across the highway. I've never seen that in my life of 50 years on the road, but I'm sure at some point a tarp will fly across the road and a Waymo will think that's a truck, slam on the brakes.

• 56:41Speaker 01

  Yeah.

• 56:42Jason Calacanis?

  And, yeah.

• 56:42Speaker 01

  And like, like I said, like, yeah, most of the time, if you're simulating like a person going to their therapist to be like, I feel anxious. And then the therapist is gonna be like, well, here's a breathing exercise. Like, there's, there's not a ton, that couldn't go too wrong. And the person ends up seriously injured. Like, maybe they learned a breathing exercise or two. That's fine. But there are gonna be those times where somebody's like, I'm having suicidal thoughts. And like, you, you, you don't want the AI then. You want a real...

• 57:09Jason Calacanis?

  To encourage you?

• 57:10Speaker 01

  Well, what, I mean, I don't think an AI necessarily knows. I don't know what to say in that situation. Why would an AI like...

• 57:16Jason Calacanis?

  I mean, no, there was literally a case with this character AI software. I wouldn't say it told the person when I saw the chat transcript. I don't have it committed to memory.

• 57:26Speaker 01

  It was a 15-year-old and they were, they were having this discussion with character AI.

• 57:30Jason Calacanis?

  They were doing a role play.

• 57:31Speaker 01

  Right.

• 57:31Jason Calacanis?

  I think would be a best way to say it. So if you tell, hey, do a role play where we're both mobsters and we have to go solve this problem. We gotta go whack somebody. It's like The Sopranos or it's like Code Fellers. Like, yeah, it might tell you to kill somebody because it thinks it's writing a script. And so the line is getting blurred here. I heard these same arguments about Dungeons and Dragons, about certain television shows where these new things, you know, so there is a personal responsibility here. The one thing I will point out here is remember we had this concept at the AI summit a couple of weeks ago about federal versus local regulation of AI.

• 58:08Speaker 01

  Sure, yeah.

• 58:09Jason Calacanis?

  So I wonder if Pritzker is specifically doing local AI regulation and we'll see Texas or, you know, whatever, New York follow suit, which is, hey, we know what's best for the citizens of our state. We don't need the federal government telling us. You know, which is run by one party right now telling our local constituents who didn't vote for the president, you know, if it was specifically California, or I don't know if Chicago went for Trump.

• 58:41Speaker 01

  Oh, I believe Illinois went for Biden.

• 58:45Jason Calacanis?

  That's a good question, because that's, I think they're like, kind of purple, right?

• 58:49Speaker 01

  All the swing states went for Trump, right?

• 58:52Jason Calacanis?

  So, yeah, yeah, yeah, they did. It was crazy.

• 58:54Speaker 01

  So, here you have it, folks. They, Kamala won Illinois 54% to Trump's 43%.

• 59:01Jason Calacanis?

  Okay, so, yeah, that was a big win. So, should the Trump administration tell the sovereign state of Illinois their AI regulation? Should, I don't know, if Pete Buttigieg wins 2028 and AOC wins, does Texas, I can tell you, Texas don't want AOC telling us what to do in regards to AI here.

• 59:27Speaker 01

  Certainly not.

• 59:28Jason Calacanis?

  In the great state of Texas. So, I have been thinking a lot about this, and I think states have some rights in the operating system of America and I don't know, federal regulation.

• 59:43Speaker 01

  I am, and, boy, far be it for me to say this too often, but I am a little bit partial to the, the sort of the David Sacks AI czar argument, that that is putting a huge onus burden on these companies, that if I'm Anthropic, if I'm Perplexity, even if I'm Google, and now it's like, I've got 50 different states and they all might have different approaches. It's what we're seeing right now with Australia and Great Britain and age verification. I don't know if you've been following this, but if you want to...

• 1:00:13Jason Calacanis?

  I have, explain it to the audience.

• 1:00:14Speaker 01

  If you want to be on social media now, in Australia and Britain, they have laws against minors under 16 being on social media. So if you want to be on, you know, YouTube or Twitter, those kinds of services, Instagram, you've got to age verify and prove that you are over 16. And they're coming up with all kinds of, there's AI tools that'll look at your face and evaluate, there's all kinds of, credit cards, whatever. But, you know, like YouTube's very upset about it, because they're like, well, we're not even a social media site, we're on TVs, like, you shouldn't have to prove that you're of age to watch YouTube. But... They're making them. As far as I know, that they're still making them do it.

• 1:00:55Speaker 01

  So that's an example of putting a huge onus on companies that want to operate in your country, because now they have to figure out this age verification login problem.

• 1:01:04Jason Calacanis?

  But you also, if you went to a drugstore or, you know, a 7-Eleven, you can't buy nudie magazines as a minor or cigarettes, right? There's age verification for those things.

• 1:01:15Speaker 01

  You gotta show ID if you want smokes, yeah.

• 1:01:18Jason Calacanis?

  Yeah, and so if you were a parent, you know, unlimited unrestricted porn, Instagram, predators on these platforms, like, I kind of understand the, I understand why these societies are deciding social media is not a net benefit for kids and kids should be required to log in. I actually am in favor of it. I think it should come from the industry, not from legislation. I think the industry, if it had good leadership, would do this. But Zuckerberg controls social media, and I don't think he's a great actor particularly.

• 1:01:52Speaker 01

  Yeah.

• 1:01:53Jason Calacanis?

  And if he just said, "Yeah, you gotta age verify under 16 for Instagram and Facebook, and you get a Facebook Kids account and your parents set it up for you." By the way, if you want to set up an Uber Teen account, you can set up an Uber Teen account now.

• 1:02:05Speaker 01

  I didn't realize they had that.

• 1:02:07Jason Calacanis?

  Yeah, so you set up an account for your teens, it goes, you get, and then that becomes a benefit, because you get to watch your teen in an Uber. You get selected with the most reputable drivers, with the cleanest records, yada, yada. And, you know, the billing is all consolidated, but you see them, and you know when they're getting dropped off, and you know where they are on the map. And I think they record those.

• 1:02:28Speaker 01

  Oh, yeah, that makes sense.

• 1:02:30Jason Calacanis?

  So amazing if there was like some creepy Uber driver, or if your child was being abusive towards the driver, you had a bad kid. Like, pretty, pretty great solution, right? I think that should be the solution. And I think the two phone comp, the two phone operating systems should have gotten together and said, "We're requiring age verification for social media sites." I think that's how it would have worked.

• 1:02:54Speaker 01

  Yeah.

• 1:02:55Jason Calacanis?

  You could have had a consortium that just said to parents, when you see this good housekeeping seal of approval, it means your kids, if they have their iPhone set up properly, because you can set up kids' accounts on iPhones, the parents, the kid can ask to install Instagram. The parents have it. The parents see the instant messages. They see who's following them. It lets them know if a keyword came up in a direct message, et cetera. Like, I can see my kids' devices and where they are. Like, there's like a whole family location thing. It's a great feature. When we go out to a park or a, you know, like, we went to the parade or something like, you know, local July 4th parade in Hill Country or a fair. We went to a fair and, hey, you let the 15 and 16-year-olds

• 1:03:39Jason Calacanis?

  go do whatever they want and you know where they are on the map. You just go find them if you need them.

• 1:03:43Speaker 01

  I'm 47. My mom would use this all day.

• 1:03:46Jason Calacanis?

  Yeah, she would.

• 1:03:47Speaker 01

  She'd still be using it.

• 1:03:48Jason Calacanis?

  They have this in Korea. If you, according to producer Claude, I just asked producer Claude, if you want to do this in Korea, to register for social media in Korea, you usually need a Korean phone number. And for many platforms, a form of Korean identification, such as a resident registration number, basically your social security, or alien registration card, your green card.

• 1:04:07Speaker 01

  Yeah.

• 1:04:08Jason Calacanis?

  This makes it difficult for short-term visitors or tourists to sign up for local services, but foreign residents with valid IDs and phone numbers can register just like Korean citizens.

• 1:04:16Speaker 01

  Wow.

• 1:04:17Jason Calacanis?

  Kakao, Talk, Naver, all those local apps.

• 1:04:20Speaker 01

  Yeah. Thing to bear in mind, if you're visiting Korea, you're not going to be able to access the local internet. What a shame.

• 1:04:26Jason Calacanis?

  No. You can get the local internet. You just can't get the local services.

• 1:04:28Speaker 01

  Right. You can't sign up for the Korean services.

• 1:04:31Jason Calacanis?

  Uh, any good startup questions for me this week? Or any kind of breaking news? Oh, okay. Where do we want to go next?

• 1:04:37Speaker 01

  If we got some other news. We got Anthropic News. They put together-

• 1:04:40Jason Calacanis?

  What's the Anthropic News?

• 1:04:41Speaker 01

  Uh, okay. So during a recent podcast with John Collison, Stripe co-founder, friend of the AllinPod, Anthropic CEO Dario Amodei discussed his company, investors and more. We got some good quotes. So here's how- How the market reacted to Amade's early revenue expectations for Anthropic. So he told, he told John Collison, AI is strange in a number of ways. I think one of the ways it's strange is that because it's an exponential, we have a hard time calibrating exactly how big the business will be. So we had the following experience in 2023. I'd never raised money from institutional investors anymore. And so our revenue was zero at the beginning of 2023 because we hadn't released a product. I was putting together something and I'm like, oh, I think we could probably get to 100 million in revenue in the first year.

• 1:05:26Speaker 01

  And this caused investors to say-

• 1:05:27Jason Calacanis?

  That's a big number, by the way.

• 1:05:29Speaker 01

  That's a big number. And this caused investors to say, this is crazy. This has never happened before in the history of capitalism. You've lost all credibility with me. Goodbye. But then, but then they actually did it. And in the next year, he was saying, oh, well, I think we can go from 100 million to a billion. And having done it the first time, he wasn't dismissed as crazy, but was still often dismissed as crazy. And then he did it again. And so this year, we're halfway through the year. As you mentioned, they're well past 4 billion in revenue in the logarithmic space. So they're going to add another order of magnitude. So this, this was notable also because it confirms the $4 billion number, though reporting, of course, now pegs it already at over 5 billion.

• 1:06:09Jason Calacanis?

  I think the total TAM for, and I said this on an earlier episode, the total addressable market is going to be like $10 trillion for the language models and associated tool sets. You could put Lovable in there, just all the, the revenue from this. I base it on a billion people in the modern world, what we used to call the first world, spending, call it 50 bucks a month. That's 50 billion a month. Now, they might spend it, you know, $25 on this, $10 on that. Some people might spend 200 on, you know, Claude Pro and other people might just use the free version and that's enough for them. Or run a local version of an LLM eventually. But if you put all that together-

• 1:06:53Jason Calacanis?

  You know, 50 billion a month, 600 billion a year across just that billion users. And that's not like other businesses that will be built with AI. You times it by, you know, 20, now you got a $10 trillion.

• 1:07:06Speaker 01

  It is, it's when you find an AI, an AI app that's sticky, that works for you, that you need it and build it into your workflow, that's it. You're not, you're never gonna not sign up for that. It, it, it's very like, once you're in, you're in. And, and so I feel like there's not gonna be a ton of churn with a lot of these AI apps.

• 1:07:25Jason Calacanis?

  I just upgraded, yeah.

• 1:07:27Speaker 01

  I never want to get rid of Notebook LM. I, that would ruin my life if I had to get rid of Notebook LM. I use it every day.

• 1:07:35Jason Calacanis?

  It's, um, and you use it for putting up transcripts of shows or podcasts and then asking questions against them?

• 1:07:43Speaker 01

  Here's the thing that if you produce podcasts for a living is a constant headache, that you know somewhere in this hour long video is a quote that I need, is a little bit that I need. Somebody said something in an episode, I think it was this one, maybe it was this one. You're just constantly hunting for a thing you filmed a week ago, a month ago, a piece of footage that you want to show on your show. And I used to have to just scrub half my day, scrub, looking, is this it? Is this it? Maybe it was five minutes before this, maybe it was five minutes after this. Notebook LM, you just drop the link into Notebook LM or you put the video in there and you ask it in regular language. Does Jason say something about Apple's earnings in this video? And it, it pulls it right up. And it can even tell you, it can't tell you time codes yet.

• 1:08:28Speaker 01

  I'm sure that's coming. Google, if you're listening to this, time codes in Notebook LM, amazing. But it can tell you where it'll be like, it's towards the beginning or about halfway through. Like it can even get there.

• 1:08:39Jason Calacanis?

  Wow, that's wild.

• 1:08:40Speaker 01

  And you could even look at the transcript and find exactly where it is. It could be like, it is, it, it changes the entire game. It changes the whole game.

• 1:08:49Jason Calacanis?

  Yeah. And imagine you have it automatically doing that with a larger corpus of like the 2,000 episodes we've done.

• 1:08:56Speaker 01

  Yeah, if you could put, right.

• 1:08:57Jason Calacanis?

  200 from All In.

• 1:08:59Speaker 01

  And that's coming. I, I know that one day I'll be able to do that and just put in our entire archive and be like, what's every time John Colson from Stripe was on and find every quote he ever gave about traction? And it'll just be like bloop, bloop, bloop. And that would have been months of work.

• 1:09:15Jason Calacanis?

  You know, it's, I go back and forth between trying to figure out

• 1:09:22Jason Calacanis?

  if all this money being invested, because we're deep in a J curve right now, we're spending hundreds of billions of dollars on this infrastructure. And you know, Anthropic's got five and you know, whatever, I don't know, Grok's got a billion or two and you know, ChatGPT, OpenAI has 10 billion, going to 20.

• 1:09:40Speaker 01

  And, and every single day, there's another story about this company's getting another billion. This company's looking for an extra billion. They're spending a two billion on chips. It's a $10 billion data center. I mean, it's just constant. It's constant.

• 1:09:51Jason Calacanis?

  So, you know, and you know, what they're, what the depreciation of all those are and can we ever get above water is the question, you know?

• 1:10:00Speaker 01

  Yeah.

• 1:10:00Jason Calacanis?

  I think, yeah.

• 1:10:01Speaker 01

  I mean, this way we're pot committed. That's what I keep saying, like, there are so many skeptics. If you go on Blue Sky, everybody's like, it's, AI is gonna be, go the way of the bored apes. It's gonna, it's not gonna last.

• 1:10:10Jason Calacanis?

  Really?

• 1:10:11Speaker 01

  Oh, yeah. There's a lot of that still. And, and it's like, I think we're just, we're too invested in it at this point. Like, we can't afford to not have AI work. Yeah, it's too big to fail now.

• 1:10:19Jason Calacanis?

  I mean, also, the results are just too good, you know, like I, this story we just did on AI in, in Chicago or in Illinois.

• 1:10:26Speaker 01

  Yeah.

• 1:10:26Jason Calacanis?

  I was able to, even though we didn't have it on the docket, put it into producer Claude, get the bullet points and then read it to you. Now, that was something a producer would have spent 20 minutes on.

• 1:10:33Speaker 01

  Yeah.

• 1:10:35Jason Calacanis?

  So there you have it, you know, it's like, it's brilliant at certain things. Other things, we got, we, we, uh,

• 1:10:40Speaker 01

  Oh, yeah. When it comes to

• 1:10:41Jason Calacanis?

  Some work needs to be done.

• 1:10:42Speaker 01

  Organizing and sorting through big collections of data, it's revolutionary. I mean, it is, if, that's ever a part of your job, you love AI, because it does save a tremendous, like, there's nothing that compares to it in, in those terms.

• 1:10:58Speaker 01

  We got some earnings, we got Bumble and DoorDash earnings, we got some reddits, we got a, a

• 1:11:02Jason Calacanis?

  Tell me what's going on with DoorDash and Airbnb. You know, Bumble, I see they lost users and they're struggling. All these dating apps are gonna have a problem because young people don't date anymore.

• 1:11:11Speaker 01

  Right. Well, actually, that's an interesting, Bumble, they're into, one of their plans for getting back on top, they're introducing a new BFF app for Gen Z'ers. It's not a dating app, it's a friendship app. They're just gonna try to help you build IRL friendships, host community events, specifically because the young people don't, they're not interested in dating, so.

• 1:11:31Jason Calacanis?

  This COVID generation got dealt a really bad hand and I think they didn't learn in a lot of cases, you know, how to make friendships, how to be a friend.

• 1:11:40Speaker 01

  Yeah.

• 1:11:41Jason Calacanis?

  They lost like, you know, four or five years now of

• 1:11:45Speaker 01

  And those

• 1:11:46Jason Calacanis?

  socialization.

• 1:11:46Speaker 01

  Right.

• 1:11:47Jason Calacanis?

  And they also learned how Yeah, and they also learned how delightful it can be to not be social and have me time. Right? Like, you know, like sometimes people get out of prison and they were in solitary or whatever, and they just want to be left alone. Like, you'd think they would come out and be like, "Yeah, I want to go party seven nights a week." And it's like, now they kind of want to just get into their rhythm again and just

• 1:12:12Speaker 01

  Yeah.

• 1:12:13Jason Calacanis?

  you know, lead a quiet life.

• 1:12:14Speaker 01

  You could definitely fall into that loop, yeah.

• 1:12:16Jason Calacanis?

  You can just stay home and just order DoorDash. Speaking of which.

• 1:12:20Speaker 01

  Oh, right. Let's jump into DoorDash next.

• 1:12:22Jason Calacanis?

  I just gave you the perfect segue.

• 1:12:23Speaker 01

  You did it. They beat revenue and profit projections. Orders are up 19% year over year, hitting 761 million. People love those taxi rides for their burritos. Revenue's up 24% over last year to 3.3 billion. Total platform spend grew by 20%. The company anticipates significant ongoing investment in both new categories and international markets. And of course, you'll recall, just back in May, DoorDash acquired two companies, UK delivery startup Deliveroo for 3.9 billion, and Seven Rooms, a restaurant tech company, for 1.12 billion.

• 1:12:58Jason Calacanis?

  Yeah, they've also experimented with like food halls. They had a food hall experiment. They're doing drone delivery reportedly. They've got like their own little laboratory doing that. So it's a pretty innovative company. They have a singular mission. The founders are still there. Tony, you know, is still running it. So I think they're going to do great. And then Airbnb, I think they're growing, but maybe not as much as people thought they would. People thought Airbnb was going to run away with it. And Airbnb's stock has been one of these stocks that maybe came out very high. And if you were to look at

• 1:13:40Jason Calacanis?

  the five-year chart for Airbnb, which you can do in the comment browser or Claude, they all have like really nice things. Check out the five-year chart for Airbnb.

• 1:13:52Jason Calacanis?

  It's an incredible company. It's been growing, but I guess this means it has to, you know, if you put, I don't know, if you put a dollar, if you bought a share for $200, you lost 40% as of today. And they've been growing. So it's pretty strange. I think that maybe has to do with they just had such a strong IPO and they're doing catch up, which could be what we see from Figma, Circle.

• 1:14:19Speaker 01

  Sure.

• 1:14:20Jason Calacanis?

  And CoreWeave, that these incredibly strong IPOs take a decade to catch up.

• 1:14:26Speaker 01

  The initial frothy excitement when they first landed. So growth based on nights/seats, that's their primary metric, grew about 7.4%. That's about the same growth rate as they saw in Q2. Q3 revenue was 3.1 billion, net income 642 million. They did warn the rest of this year, they're concerned about tough year-over-year comparisons due to demand trends. Lots of recent forecasts warning travel demand is about to drop due to worsening economic activity uncertainty, and they're showing slower gains than the rest of the world in North America, which is about 30% of their total. They're just

• 1:15:09Speaker 01

  saying slower gains in North America impacted global results. If you leave domestic American travel out, total nights and seats booked would have grown by double digits. So it's it's North America that's holding them.

• 1:15:22Jason Calacanis?

  Yeah, I think they have some markets they're not allowed in or they're restricted in now. I know in Tahoe.

• 1:15:28Speaker 01

  Right.

• 1:15:28Jason Calacanis?

  Tahoe had a big crackdown on it. They've limited the number of licenses. A lot of communities, you know, got taken over by speculators, buying homes, turning them into Airbnbs, annoying neighbors, removing the sense of community.

• 1:15:43Jason Calacanis?

  You know, which is really a more of an issue of we don't have enough housing supplied. And so people are getting a little tweaked about there not being enough housing for people who live in Hawaii or New York City. And New York City, I think, every time I try to go everywhere else, when I travel with the family, we do like, you know, getting a house and LA is amazing for it.

• 1:16:05Speaker 01

  Oh, yeah.

• 1:16:05Jason Calacanis?

  Not possible. I have to stay in a hotel.

• 1:16:07Speaker 01

  Airbnb capital of the world, LA.

• 1:16:09Jason Calacanis?

  Palm Springs, San Francisco, a lot of places that do a really great job on it. So, but, you know, they, the founder there is incredibly dialed in. They keep doing incredible new product releases. So I am long-term a fan of their business. I do think it maybe would be good to be part of another business. I wonder sometimes if Expedia plus Airbnb.

• 1:16:35Speaker 01

  Wow.

• 1:16:35Jason Calacanis?

  Expedia is public and they've got, you know, they own a collection of Expedia stock.

• 1:16:42Speaker 01

  Well, and Expedia is also great because you, it's already kind of the all-in-one travel. Like you could do the rental car, you could do the hotel, you could do all the little bits and pieces.

• 1:16:52Jason Calacanis?

  Expedia is only worth 16 billion. There was talk about potentially Uber buying it because Dara worked for, speaking of Barry Diller, he worked and ran Expedia for a while. So if you have an everything app, I do think we're going to see consolidation in the coming five years.

• 1:17:10Speaker 01

  Even like TripAdvisor or something.

• 1:17:13Jason Calacanis?

  All of these travel, buying tickets for things. There's Vader or something for experiences, Vader or something.

• 1:17:20Speaker 01

  Oh, right. Vader, yeah, yeah. V A E T O R or something like that.

• 1:17:24Jason Calacanis?

  Very popular in Europe where people, you know, people travel.

• 1:17:26Speaker 01

  Vieter.

• 1:17:27Jason Calacanis?

  Vieter, which I think might be part of Expedia or part of another conglomerate.

• 1:17:32Speaker 01

  TripAdvisor, it's a TripAdvisor company.

• 1:17:33Jason Calacanis?

  It's a TripAdvisor property.

• 1:17:34Speaker 01

  Yeah.

• 1:17:35Jason Calacanis?

  So you have all these properties and a lot of these properties were based upon advertising.

• 1:17:43Jason Calacanis?

  And then, you know, becoming marketplaces and then they have to buy their customers from search engines to get them there. So that does make it difficult, too. I was planning a trip recently and I was using Claude and some other services to do it and it was just giving me direct links to the hotels. And then I have my assistants call and check, you know, and then sometimes they'll ask, you know, hey, we're considering different things here. What's the best deal you can give us? And when you call a hotel direct and you say, hey, I'm coming for five days. We're looking, we have four or five different options. I'm on a corporate account. What's the best deal you could give me for a corporate coming for five days for this type of room? Is there anything you can do for us? And you'd be surprised when you call a hotel direct, especially smaller hotels where they're

• 1:18:27Jason Calacanis?

  not just like, oh, just go to the website and order it there. It's the same price. They'll do all kinds of deals for you.

• 1:18:32Speaker 01

  Fabulous.

• 1:18:33Jason Calacanis?

  We'll see you all on Monday. Bye bye.