What's REALLY going on with those "ads" in ChatGPT | E2220

This Week In Startups is made possible by: Superhuman - https://superhuman.com/podcast Squarespace - https://squarespace.com/twist Enterpret - https://www.enterpret.com/dlp/this-week-in-startups Today's show: A screenshot showing a "Target Ad" in ChatGPT results went viral… over the weekend, but the OpenAI chatbot has NOT actually opened the advertising floodgates just yet. As ChatGPT staffers were quick to explain on social media, this was actually an invitation for a user to integrate their Target account into ChatGPT, for an easier agentic browsing and shopping experience. But it does prompt Jason and Alex to ask some intriguing questions… Is OpenAI just waiting for Google or someone else to launch AI ads first, and face the inevitable flood of backlash they'll presumably receive? Is there someone at OpenAI already thinking DEEPLY about how these in-feed ads should work? And what does this mean for their wager on when ChatGPT is going to actually get ads? Is that already decided? These answers and more are coming your way on today's action-packed TWiST… PLUS the latest on the Warner Bros Discovery-Netflix deal, PR guru Lulu Cheng Meservey's new venture fund, and why Jason and Lon are obsessing about Apple TV's "Pluribius." Timestamps: (01:59) They put Target ads in ChatGPT? Or was it just an integration? Is there a difference? (5:24) Is someone at OpenAI really thinking deeply about how in-feed ads should work? (07:36) Is OpenAI just waiting for Google to start running ads to post their own? Jason has suspicions… (10:01) Why Jason thinks startup people have so much trouble communicating with normies (10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at http://superhuman.com/podcast (13:22) The insane competition now facing down OpenAI and Sam Altman (18:40) Why Jason will no longer use data from SaaS companies looking for a marketing win (19:52) Does this mean ChatGPT TECHNICALLY has ads? Does Alex win the bet?! What does Polymarket think? (20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist (25:17) Why Jason is already tired of the Netflix-Paramount-WBD story (30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action. (34:03) President Jason's new proposal: A 60-day "pre-approval" antitrust window (47:29) Why Jason's not interested in news commentary… just the facts. (51:40) Jason and Lon take a few moments to praise "Pluribus" (54:45) PR guru Lulu Cheng Meservey is starting a venture firm… here's why she wants to start a "movement" (58:05) Why PR people hate but also respect Jason Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/ Check out the TWIST500: https://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: (10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at http://superhuman.com/podcast (20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist (30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action.

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

• 0:00Jason Calacanis?

  Oh, let me guess. Let me guess.

• 0:02Speaker 01

  Hit me.

• 0:02Jason Calacanis?

  I have some concepts here because that ad is for Target. It's a generic ad. The copy up there was for some sort of technical memory. It went by pretty quick, but some memory technology hardware looked like discussion it was having with ChatGPT. So it's not a targeted ad. It's an ad for Target.

• 0:20Speaker 01

  Kind of. Keep going.

• 0:21Jason Calacanis?

  Okay, it says shop at Target. So here's what I think happened. I think this person downloaded a Chrome extension or some other third-party app that was inserting ads covertly or sneakily. And that they wound up conflating that with OpenAI doing it. And that's why it looks so weird. Now, that wouldn't look weird if you were looking at a, I don't know, the Drudge Report and you saw a Target ad. You'd be like, fine, it doesn't make any sense. If it was an ad from OpenAI, their idea is to look at the memory and what you've searched for over and over and over again. And it would be hyper-targeted.

• 1:01Speaker 02

  This Week in Startups is brought to you by Interpret. Interpret turns feedback noise into customer intelligence so your team knows exactly what to fix and build next. Head to interpret.com/twist to book a demo and see it in action. Squarespace, turn your idea into a beautiful website. Go to www.squarespace.com/twist for a free trial. When you're ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. And Superhuman, get AI that works where you work. Unlock your superhuman potential at superhuman.com/podcast.

• 1:36Jason Calacanis?

  All right, everybody. Welcome back to This Week in Startups. Welcome back to Twist. I'm Jason Calacanis, he's Alex Wilhelm, and there is a, um, I guess some big news out of OpenAI. They called a code red. And now there's been some discussion of advertising. Listen, Alex.

• 1:53Speaker 01

  All right. So there was a viral screenshot of someone's ChatGPT conversation. And Jason, I'm going to pull it up here on the screen. Take a look at this. Now, if you were just looking at this without any context, you would just see a normal chat conversation with an AI. And then at the bottom, there is a shop for home and groceries target module. Everyone thought, hey, this is an advertisement. We're talking about OpenAI adding ads for some time now. And so this was criticized pretty heavily. It turns out, however, that that ad-looking module.

• 2:23Jason Calacanis?

  Oh, let me guess. Let me guess.

• 2:25Speaker 01

  Hit me.

• 2:26Jason Calacanis?

  I have some concepts here because that ad is for Target. It's a generic ad. The copy up there was for some sort of technical memory. It went by pretty quick, but some memory technology hardware looked like discussion it was having with ChatGPT. So it's not a targeted ad. It's an ad for Target.

• 2:43Speaker 01

  Kind of. Keep going.

• 2:45Jason Calacanis?

  Okay, it says shop at Target. So here's what I think happened. I think this person downloaded a Chrome extension or some other third party app that was inserting ads covertly or sneakily and that they wound up conflating that with OpenAI doing it. And that's why it looks so weird. Now that wouldn't look weird if you were looking at a, I don't know, the Drudge Report and your sort of Target ad. You'd be like, fine, but it sticks out like a sore thumb. So I think that it doesn't make any sense. If it was an ad from OpenAI, their idea is to look at the memory and what you've searched for over and over and over again. Then tell the AI, given the history of Alex and everything he's talking about, you know, 20 different advertisements, would you serve to him?

• 3:30Jason Calacanis?

  And how would you make the message to him that would resonate? And it would be hyper targeted. Okay, so tell me what happened.

• 3:39Speaker 01

  I love the hypothesis, not entirely wrong. I can't give you full points. I'm going to show you a headline here, Jason, that helps explain what we're seeing here.

• 3:45Jason Calacanis?

  Okay.

• 3:45Speaker 01

  This is from November 19th, 2025, and it reads, OpenAI and Target partnered to bring new AI powered experiences across retail. This is partially OpenAI doing work for Target and also a Target application that you can connect into inside of ChatGPT. So as far as we can tell, this little module that you and I both think is an ad, turns out is actually an invitation to connect to Target inside of ChatGPT. You can now argue that that's an advertisement, but OpenAI is taking the position that it's not.

• 4:16Jason Calacanis?

  It's an ad. It's not a targeted ad. It's in-house promotion. It's an in-house ad. So when you are working at the New York Times and they have some extra ad inventory, they might say, hey, check out our new podcast. Hey, you know, come to this Times discussion at the whatever. And so those are in-house ads. So this is like an in-house ad. Yeah, it's somewhere in between the two. It wasn't a hacked ad.

• 4:41Speaker 01

  No. Now, let's talk about what the company said really briefly. Nick Turley, he runs ChatGPT, says, quote, "I'm seeing a lot of confusion about ads, rumors in ChatGPT. There are no live tests for ads." And then also, one of the company's execs said, you know, "I agree that anything that feels like an ad needs to be handled with care, and we fell short." Looping back, Jason, to your point about code red. He said, "We've turned off this kind of suggestion while we improved the model's precision." The code red that OpenAI called was to improve ChatGPT, and it pushed back things like advertising. So right now, we are not seeing ads in OpenAI as we expected them to. And I think that what they tried to do here was a partnership and a connection tool, and it ended up just being sloppy and kind of gross,

• 5:23Speaker 01

  which doesn't give me a ton of confidence, Jason, in their product decisions, to be honest.

• 5:27Jason Calacanis?

  This sounds to me like they don't have a person deputized to think about how advertising or in-house ads, cross-promotion, should exist inside of the product. So sometimes when you're running a company, there'll be like two outfielders, you know? And, you know, one person's in left field, one person's in center field, and there's a shortstop and whatever. The ball kind of is in between those three players, and it just drops in between all three, and they all look at each other. And that's what happened here. And what they really need to do is say, "Hey, call it when it's in the air." So when somebody said, "Hey, we're going to do this. We have to get this target promotion up for Christmas. We have an obligation to them. We sold it." Sam Altman said it.

• 6:11Jason Calacanis?

  Somebody, you know, if left field was the tech team, and center field was the UX team, and the shortstop was the business team, somebody should have said, "I got it," and they should have just shepherded it home, full stop. Now, what they're going to need to have is a partnerships coordinator, who is just responsible for how this stuff looks in the end product. They're overreacting to all this. Every time you insert ads into a product on a site like X, or Twitter, or Reddit, or Hacker News, our industry is going to overrespond and get all their, you know, hand-wringing, et cetera. It's coming, folks, and it's going to be awesome. And if you want free ChatGPT, and you want to burn, you know, an H100 to make your funny memes,

• 6:56Jason Calacanis?

  somebody's got to pay for it, and it's going to come from advertising. My belief is... The 75% of the revenue at OpenAI that's coming from consumers is going to go down to, you know, at least 50% in the next two years. People are going to stop paying for these things. When ChatGPT was one of one, people paid for it, of course. Now that you have Gemini, Grok, you know, and everything in between, they're going to stop paying. Consumers are not going to pay for this. It doesn't provide so much value that an average consumer will pay for it. So then, how will it be distributed? It will be distributed by advertising because of the code red they called, because the LLM is falling behind Gemini and other Grok and Claude are making better products and leapfrogging OpenAI. They're in a panic mode because they realize they don't have a better mousetrap.

• 7:40Jason Calacanis?

  They have the same mousetrap as everybody else and everybody's mousetrap is getting 5% better every three months. And in a situation like that, they're going to need to actually get ads on faster. If I was OpenAI, I would be working to get ads on there faster and have it ready to go. When they said they were pausing it or not focusing on it, I call BS, I call. I think they're tripling down on it and having it ready so that the second somebody else puts ads in, i.e. Google, they'll have it ready to go. Because if they don't, man, it's going to be Netscape all over again. I brought up that analogy for the last couple of months.

• 8:15Speaker 01

  Can I ask a question about code reds and startups, Jason? Because we often think about startups as an idea, you build a product, you find product-market fit, you grow like hell, eventually billions of dollars appear. How often do startups need to call a code red like this? And is that a weakness or is that something that you should use tactically inside of a startup to ensure that you don't kind of like get too lazy?

• 8:34Jason Calacanis?

  All right. You want the candid version or you want the real version? The candid, the real, or the sugar-coated?

• 8:40Speaker 01

  I want you to give me the one you would tell a founder on a phone call at 3 a.m.

• 8:44Jason Calacanis?

  Sure. So the way founders use this is to shock the system, figure out who on the team is committed and who's not, and as a way to get results quickly. So if you call a code red and people are like, oh, you know, I got a wedding this weekend. Oh, you know, I'm taking my kid to Little League. Oh, you know, I'm going to my aunt's funeral. And they consider all the things in their life, like a funeral, their children, their spouse, whatever it is. All of a sudden, you're like, okay, here's the people who are hardcore and here's the people who are going to their, you know, second cousin's funeral or whatever. So that is, and most people will consider this dark, there is like sort of a hardcore test implied in it.

• 9:27Jason Calacanis?

  Code red. Figure out who's hardcore, figure out who's not. And you don't have to say it. It's not like you have to be like, yeah, these three people, they're not bringing it. It's like, they're not here this weekend. Okay. Everybody knows who didn't show up this weekend during the code red. There's that piece to it. There's also the piece to it. Hey, you got competitors, you could get displaced, and you want to prove to the team that through deliberate hard work, everybody rowing in the right direction, we can fix a problem. And that builds confidence. So there's the confidence building aspect of this. There's the reality of competition aspect to this. And then there's the, are you actually hardcore? And are you in this like a Jedi? Or pick your analogy that no worldly

• 10:10Jason Calacanis?

  possessions, relationships are more important than the mission of this company. Now, that is going to ring to a normal, well-adjusted person as insane. You know, like if AOC is hearing this, and she's like, what? Like, why would the union allow this? Like, this is like hardcore stuff. And that's what Sam's doing. He's trying to figure out who's hardcore, and if this squad is actually going to get them there. We test out a ton of AI tools behind the scenes at my venture firm launch, and a lot of them make big claims, and they can't back it up. That's why I'm so enthusiastic about one of my favorite companies, Superhuman. Their productivity suite combines three of the best tools on the market today. Grammarly, which is your personal editor, makes your

• 10:52Jason Calacanis?

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• 11:35Speaker 01

  I didn't think, Jason, on this show, you were going to point out that AOC is a is a normal and well-adjusted person, but I appreciate you pointing that out for everybody.

• 11:41Jason Calacanis?

  No, no, I'm not saying she is. I'm just saying for people who like would represent, you know, normalcy, it's it's so hard to talk to like two groups of people, people who do startups or are in SEAL Team Six.

• 11:55Speaker 01

  Extreme athletes, like people that have a singular singular focus people versus general focus people.

• 12:00Jason Calacanis?

  Exactly. So I'm just saying AOC or like the union might be like, wait, we're coming in on a we're staying late on Saturday night to clean the Starbucks and make it spick and span. And we're going to have like a bond raising or in my case, every Wednesday night I have a management team dinner and it starts at 5:30 PM Texas time. So at the end of our day, I bring in dinner, I bring in a nice sushi, whatever the team wants. We talk for two hours. It goes from 5:30 to 7:30. So, hey, yeah, you're missing dinner with your family, your loved ones, you might give up yoga if you go to yoga after work, whatever. It's like, don't work at a startup for or a venture firm for a maniac who says, hey, yeah, every Wednesday, you got to give up that day. You got to be late. If you have something, you got to tell me why you're missing the management team meeting.

• 12:42Jason Calacanis?

  It's like, oh, should be a little intimidating for a person to like tell their boss, I'm going to go to yoga and miss the management team meeting. Like there's yoga classes all the time.

• 12:50Speaker 01

  I think also if you opt into being an executive at a startup by, you know, applying for the job and getting it, you are essentially seeding some of your personal life to that role. The only thing that I would throw in here as a caveat is I do always create an exception for people with kids who are sick or whatever, but apart from that, I think that makes perfect sense.

• 13:07Jason Calacanis?

  Sick kids make sense. Yeah. Yeah. And if it's a life event for a kid, like they're in the play, you got to go to opening night of the play.

• 13:16Speaker 01

  Oh, for sure. But like, I would put the the taking care of your children's life events and then yoga entirely on different ends of the barbell. Jason, I have the tweet here from Michael Burry about OpenAI being the next Netscape. I think it's worth reading just so everyone has to quote. Everyone that knows anything knows this. OpenAI is the next Netscape doomed and hemorrhaging cash. Microsoft is trying to keep it afloat while keeping it off balance sheet and sucking out the IP. Not wrong. So why do they keep getting funded? The whole industry needs a 500 billion Million dollar IPO ASAP, essentially arguing, Jason, that there's been so much private capital put into this firm that if it goes down, then everyone's hosed, I think is his point.

• 13:54Jason Calacanis?

  You know, I gotta think about that. If OpenAI had their valuation stumble and was forced to do a down round at 250 billion, what would happen? I think it would be a shock to the system for sure, for three or four days. Stock market would go down 10%, 20%. And then I think what would happen is people would take out a chart. I made a chart. I had to be here on my team, make a chart of OpenAI versus the world. OpenAI versus the world in terms of market share. What people will realize is the first person up the hill takes the arrows. And they will process in the, I would put this at a less than 10% chance. So, and I'm not rooting for it.

• 14:35Jason Calacanis?

  Less people think what I'm being critical of OpenAI is like, I got some axe to grind or whatever. I'm friendly with Sam. I would consider him a friend. I mean, we don't go to like dinner socially, but we've known each other for 20 years. So I would consider us more than just acquaintances. I think we have like somewhere between an acquaintance and a friendship. What I would say is there's a 10% chance that could happen. They could stumble. And there's a 90% chance they'll just keep soaring and it could be flat or up. But the reality is first person up the hill takes the arrows. When you have 100% of the market, the only way to grow. And when you have these competitors, the only place you can go is down. Let's go through the competitive set that they're facing. Elon Musk is not a competitor you want to have. That's like having a competitor like Terminator 2, Arnold Schwarzenegger, P competitor.

• 15:17Jason Calacanis?

  You don't want that competitor. Trust me. Ask anybody who's had that competitor. It is the nightmare competitor. Then by the way, you have Microsoft and Google as, and Zuckerberg as competitors. So those three are the four horsemen of the apocalypse. Like if you are Sam Altman. Elon, Satya, Sundar, Zuckerberg. This is like.

• 15:40Speaker 01

  Dario.

• 15:41Jason Calacanis?

  Well, yeah. And then let's add some others. You got Dario from Anthropic, but I wouldn't say Dario has the reputation, the chip stack of those individuals, right? He's strong, but he would be peers with.

• 15:54Speaker 01

  Oh, I see your point. Yeah. Okay. Okay.

• 15:56Jason Calacanis?

  So I'm saying those four are like truly scary because they've built trillion dollar companies. Those are the trillion dollar competitors.

• 16:05Jason Calacanis?

  That's a very scary thing. Now, in what world do those four, and let's throw in Anthropic. Let's put those five up as your, those are your five competitors. In what world do those five get less than 10% of the market? No, no world that I've ever heard of or conceived of. Thank you. Now let's pull up this chart we made. Everybody's seen the like trending version of this chart, which showed, you know, three years ago. It was a stack bar chart and it showed all the different ribbons of, and I think it went to present. So you see the one, two, three, four, five, six, seven, eight, eighth bar over is present day, right? With 32% of the market being other than ChatGPT and 68% of the market being ChatGPT.

• 16:46Jason Calacanis?

  Now, if you go just to three years ago and two years ago, and even 18 months ago, that was a market that was either 100% or 95% OpenAI ChatGPT. Today, they have two thirds of the market. Pretty impressive, right? Having two thirds of the market. So you have to ask yourself. Incredibly impressive. Credibly impressive. However, you yourself said those five competitors, there's no world in which they don't get 10% each. So if 10% each would be 50% of the market. So what I just did was said, okay, let's agree on that and go to 2026, 2027, 2028 and 2029. I'm going to estimate in somewhere between 27 and 28, you will see ChatGPT go to 45 to 55%, in other words, less than 50% of the market.

• 17:31Jason Calacanis?

  This is percentages and market share. What this doesn't take into account is that the pie is growing rapidly. So even though they only have less than 50% of the market, they will still have a much larger business. These two things will be true at the same time. But what it means is the market, when ChatGPT were to have a stumble or, you know, have headwinds where they were growing slowly, it's going to be a shock to the system until people go, oh, this is bigger than anything we've ever seen before. Okay, we're gonna, we're gonna keep investing in this. So I would say Michael Burry pointing out. The Netscape analogy.

• 18:09Speaker 01

  Yeah.

• 18:09Jason Calacanis?

  Like I did, super valid, but it doesn't mean that Amazon, Google, Yahoo and Facebook and LinkedIn don't grow as well during that time period and the number of users online.

• 18:20Speaker 01

  All right, Jason, here's the charge you wanted. It shows generative AI traffic share over time, starting 12 months ago, working forward to today. As you kind of intimated, we do see a decline in OpenAI's market share and the biggest growth here is from Gemini, which has done fantastically well. And we can also see a decline in DeepSeek's market share, but consistent erosion of OpenAI's market leadership through a different lens.

• 18:40Jason Calacanis?

  All right, very good. From some data provider online who I will re- um, this is, this is, with pace and love to all SaaS companies trying to slip in data to get customers. Your content marketing skills have no power here.

• 19:01Speaker 01

  Well, I, hey, I, you saw, you saw us like that. I took that to heart. I'm at, I'm at her shooting stuff down left and right.

• 19:07Jason Calacanis?

  This is what happens when you have a podcast. These, the PR people, content marketing people are so good now. They're like, oh my God, we have an incredible data set. We want you to talk about us on your podcast and our SaaS product. I'm like, not going to fall for it, but we'll use your data.

• 19:20Speaker 01

  We have a bet here, just to wrap this up. We have a bet that we put in place on August 15th, 2025. OpenAI advertising, uh, launched in ChatGPT, 12 months less or more. I took the under, you took the over. Uh, what's interesting though is as we look at our bet with this.

• 19:35Jason Calacanis?

  Wait, wait, say it again. What was the, what was the date when OpenAI would have ads?

• 19:40Speaker 01

  August 15th was the start of the bet, one year time window. Do they have ads before or after that 12 month reset? And I said, it'll take less than a year for ads. You said it'll take more than a year for ads.

• 19:51Jason Calacanis?

  Okay.

• 19:51Speaker 01

  We had this new news about the code red and so forth. So I thought for today's poly market, we should look at what the market thinks about the chances of there being ads in ChatGPT.

• 19:59Jason Calacanis?

  You should be making an argument here. I mean, as your counsel, that was an ad. It was an in-house ad, but it wasn't ad. But it's not ads in chat GPT intellectually.

• 20:12Speaker 01

  You know, Jason, the day I pick a fight with you, it's gonna be over more than a hundred dollars. I'll tell you.

• 20:17Jason Calacanis?

  I mean, no, but I mean, it would be an angle shot for sure. But this is what people do in these prop bets. They're like, technically speaking, it is an ad.

• 20:24Speaker 01

  Did you see what happened to Alan Keating at the Hustler live game with Senor self?

• 20:29Jason Calacanis?

  Yeah, he got up and left because they were being little, because they tried to angle shoot him on not turning his cards over during a prop bet. And he did. Did you know Squarespace is our longest running sponsor in the history of This Week in Startups? You can find episodes from more than a decade ago with me singing the praises of this wonderful platform, Squarespace, and how they're gonna help you build an incredible website for your new business. That kind of longevity is no accident, folks. Squarespace has been in the game for some time because there's no better, easier way or faster way to make your first website. And they're constantly upgrading and making their product better. They now have an AI-powered blueprint feature which works right alongside you, helping you upgrade your design game. And it was just named one of Time Magazine's Best Innovations of 2025.

• 21:13Jason Calacanis?

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• 21:36Jason Calacanis?

  We're keeping the bets at thisweekinstartups.com/bets. You can always find our bets and hopefully we have this some deep mantra ones because those are all gonna be coming to. And those are for big, big money.

• 21:47Speaker 01

  All right, so here's the the latest from our friends over at Polly Market. And there's two ways to look at this data, Jason. There is, will there be ads in chat GPT by December 31st? The market has decided that that's not going to happen, currently at 4% and dropping over $400,000 in volume there. What is interesting, though, is the fact that they added this March 31st timeline. Now, there's not a lot of betting yet on the extended timeframe for will there be ads in chat GPT by then, the end of Q1. But still, not a lot of optimism here. People really don't think it's coming. So these folks think that it's gonna be at least Q2 before we see advertisements in chat GPT. And you always ask, what are the terms of resolution?

• 22:29Speaker 01

  And what matters is the market will resolve to yes, if OpenAI integrates ads into any of their major GPTs. And that is made available by the date. And critically, this is what I wanted to check in on. Limited advertisement releases restricted to a specific region will qualify. So this is actually pretty, I would say generous. Like if they launch ads in like, you know, Bangladesh, then that counts.

• 22:53Jason Calacanis?

  Yeah. So this is a really interesting market. I think the challenge is going to be, and this is like a game of chicken. Whoever launches ads first also will take a bunch of heat for putting ads in their product. So if you add ads, the first person to put it on a website got a bunch of heat. I think it was Wired putting the Zima ad up. You know, a lot of people claim different ads first time on the internet. Putting ads into RSS feeds, putting ads into podcasts. It was all very controversial. Putting, we put ads into blogs. We had the first ad in a podcast, on the Autoblog Podcast. People did do the hand wringing, as I've talked about earlier. But it does degrade the consumer experience marginally.

• 23:38Jason Calacanis?

  So you have to give to get. So what they should say is if you allow ads, you get deep research. You get unlimited searches. You get pro, you get pro if you turn on ads. And you just have to give something at that moment in time. So in this great game of chicken, we'll see what happens. I think if I am ChatGPT, Claude, or even Google, when you do a deep research, you know how it says using deep research for this? Come back in a minute, we'll send you a message. Like they'll even send you a notification on your phone. That's the perfect time to say, and your deep research is being brought to you by. And then just put a little thing, brought to you by your friends at LinkedIn Jobs, Chipotle. Click here to start an Uber Eats order, whatever it is, you know, DoorDash. And you can make that based upon previous searches.

• 24:22Jason Calacanis?

  So that is what I think will be the winning one. This is called an interstitial in the business. So a lot of times you'll see websites now, you click on a link. And before it lets you go to the link, it shows you a survey or like a box. And then you have to hit the X or skip. Those kind of interstitials force you to just consider the advertiser for a microsecond, or in I guess YouTube's case, it counts down from five seconds. That's what's coming, folks. And why not? If you can get deep research for free, that's a, and it takes a couple of minutes. Anyway, it's kind of a win, win, win. The advertiser is not putting you out because you're getting the deep research for free. The, you know, they're going to make a nickel or a penny from Claude for they're going to be able to charge for that, etc.

• 25:03Speaker 01

  So I also think that the consumers are willing to take such an insane ad load in general, like if you think about the, the ad mix on professional sports, on Amazon's e-commerce marketplace, on YouTube streaming service, people take a lot of ads and they still use the product. So a lot of money on the floor there. Next up on the docket, we're going to talk about Warner Brothers Discovery, covered it on Friday. Lot of breaking news. I asked our dear friend, Lon Harris, editorial director here at Launch to join us. Lon, where are you at?

• 25:28Speaker 03

  I'm right here.

• 25:29Jason Calacanis?

  This is great. The deal's closed as we, it looks like Netflix won and the deal's over. Everybody's very happy about it. The people who competed all said, hey, great competition. You won. I congratulate you on the win and Mousoltov, good luck.

• 25:46Speaker 03

  We've moved the Stranger Things kids into the water tower next to the Animaniacs. We're all done. Everything is, no, Alex didn't get that one. See, the Animaniacs on that old cartoon show, Alex, they lived in the WB water tower and the studio. So I'm joking.

• 26:01Speaker 01

  Just old enough to recall Animaniacs, but I wasn't allowed to watch a lot of TV growing up. It was more Jesus.

• 26:07Speaker 03

  I'm joking that now Netflix is going to jam the Stranger Things kids in there with the Animaniacs because they're owned by the same company.

• 26:14Speaker 01

  That might not work out because President Trump has weighed in.

• 26:18Speaker 03

  Yes, there's, there's a lot of resistance going on. I mean, obviously from the public, there was a lot of outcry. People are very worried. They're, you know, they're not going to be able to see their WB movies in theaters anymore. Their Netflix is going to cancel theatrical distribution for all time. But it seems that some of these concerns are being shared by our wonderful, terrific, amazing, praiseworthy American president. POTUS has jumped into the ring and said that he could share some of these antitrust concerns. Here's the quote, I have a lot of respect for him. I think he's talking about Ted Sarandos. I have a lot of respect for him. He's a great person. He's done one of the greatest jobs in the history of movies and other things, but it is a big market share. There's no question about it. It could be a problem. And then another quote, they have a very big market

• 27:02Speaker 03

  share. And when they have Warner Brothers, that share goes up a lot. I'll be involved in the decision. That's the key part of the takeaway. He said that? Trump said specifically, I'll be involved in the decision. So he's putting himself in the middle of this negotiation. A lot of people are reading that as very favorable to Paramount, because of course, the Ellison family sort of aligned themselves with Donald Trump. So people are saying if he's going to play favorites, he may just throw this to the Ellison's over at Paramount. However. However. As if things were complicated enough. There's also been some drama over the weekend between our president and the people of Paramount. He's not happy with them over a 60 Minutes

• 27:45Speaker 03

  segment that aired. He feels like the real problem with the show, however, wasn't the low IQ. They had Marjorie Taylor Greene on 60 Minutes. Trump did not like that. So he's saying, but he's saying even the real problem with the show, however, wasn't the low IQ traitor, Marjorie Taylor Greene. It was the new ownership of 60 Minutes. Paramount would allow a show like this to air. All caps. They are no better than the old ownership who just paid me millions of dollars for fake reporting about your favorite president, me. Since they bought it, 60 Minutes has actually gotten worse. Oh, well, far worse things could happen. So, so now chaos. I mean, is Trump going to side with Netflix, who he's praising is a great company?

• 28:26Speaker 01

  You forgot, you forgot the critical last thing for Jason to respond to. Paramount also today, Jason, launched a $30 per share, all cash offer for the whole company, not just the part that Netflix wants to buy. So we have a hostile bid.

• 28:37Speaker 03

  I was gonna get that. They're offering a lot more money.

• 28:41Jason Calacanis?

  Is it a lot more money? Explain to me like the difference in the deals, if you can.

• 28:45Speaker 03

  It is more money.

• 28:46Jason Calacanis?

  It is more money, and they're willing to buy. The cable assets.

• 28:51Speaker 03

  Correct. Here's the quote from Ellison. He told CNBC, "We are offering shareholders $17.6 billion more cash than the deal they currently have signed up with Netflix. And we believe when they see what is currently on our offer, then that's what they'll vote for." And then, of course, they're also suggesting Paramount still believes they will have an easier time getting through these regulatory hurdles than Netflix will, because their businesses are more aligned and less directly competitive. Paramount Plus isn't the chief rival for Netflix the way HBO Max is. So that's kind of the overall argument.

• 29:27Jason Calacanis?

  Got so much to unpack here.

• 29:28Speaker 03

  I know. To bring it all into the numbers, the Paramount offer, $108.4 billion for all of WBD. The Netflix offer, $82.7 billion just for the Warner Brothers Film and TV studio.

• 29:41Speaker 01

  And those are both enterprise valuations, not enterprise.

• 29:44Jason Calacanis?

  All right. So number one, I'm an idiot because I J-traded Warner Brothers, lost a little bit of money, then sold it to bank the loss last year so that I could offset it against some gains I had. And I missed the Hail Mary, and it would have been, I think, a double up for me at the current share price. Could have 2Xed in three years. But I don't invest in companies for Hail Mary outcomes. But here it is. There's a Hail Mary outcome. If you're not listening to your customers and iterating based on their feedback, your startup will fail. So if you're drowning in feedback from support, reviews, calls, it's time for Entertain. Entertain is the customer intelligence platform that helps you turn random comments and feedback into actionable insights that help grow your company.

• 30:27Jason Calacanis?

  Their AI system is already trained on your business and your product. It then reads all your support tickets. It reads all your reviews, call transcripts, and surveys. Then their agents actually update your team in Jira, Linear, Zendesk, and Slack. So this feedback doesn't just sit in some email or messaging thread, but it actually helps keep your team moving the ball forward. Find out why Panva, Notion, and Perplexity are already using Entertain to stay on top of what they need to fix or build next. So if you're ready to turn feedback chaos into customer intelligence, head to entertain.com/twist to book a demo and see it in action. That's E-N-T-E-R-P-R-E-T dot com slash twist.

• 31:10Jason Calacanis?

  Putting me aside, there is a concept here of an auction. And what should happen next is, there should be an auction. And the auction should go to, and stick with me here, fellas, because it's going to get complex, the highest bidder. By definition, that means the person who puts the biggest number up. So we've had a bunch of this back and forth. I'm tired of this story. And this is all meaningless. It's meaningful to people who work in Hollywood, who are directly impacted. I get it. But the truth is, you are all rearranging a bunch of deck chairs on the Titanic.

• 31:47Speaker 01

  Thank you.

• 31:48Jason Calacanis?

  Or, you know, insert another analogy here, because total minutes on YouTube, TikTok, Instagram dwarf all of this nonsense. This is a bunch of rich people trading magazines 20 years ago. This is a bunch of rich nepo babies, and I don't mean that in a derogatory way. I mean, when I say nepo babies, what I mean is, people I'm extremely jealous of, because I had to build this goddamn chip stack. If I could have started with $100 billion, if I started with a $100 million chip stack like Trump or this Ellison kid, man, I would, I would be a trillionaire.

• 32:25Speaker 03

  You weren't playing with Oracle's bankroll.

• 32:27Jason Calacanis?

  Anyway, I'm extremely jealous of the chip stacks of nepo babies. But what I will say for the nepo baby crowd is, like, sure, this is exactly what happened. The rich widows, the nepo babies, they all love to bid on the previous shiny objects. They love to own the Atlantic. They want to buy the Washington Post. Or actually, Bezos bought that. But you get my point. They love to buy the famous restaurant, the famous movie studio. They're always looking in the rearview mirror. Why? We're all status-seeking creatures. Some of us seek status by being blue-collar hard workers who make it, like myself. Other ones are like, I'm going to go buy.

• 33:10Jason Calacanis?

  My daddy's or my mommy's love by buying the thing they love. That's what's happening here, folks. I hate to get all Freudian on you.

• 33:16Speaker 03

  I do think there's one element we're overlooking, which is Netflix is a much healthier company in 2025. Paramount can make this deal, but they're basically just putting themselves in a very, very deep hole of debt, taking this money from, you know, sovereign wealth funds and Redpoint Capital, anywhere they could get it. Whereas Netflix, I mean, they are also taking on loans and they've got banks on board to help them, but they're a company that can afford to just sort of.

• 33:48Speaker 03

  Exactly. So I do think that might be part of it. If you were Warner Brothers and you were looking for who can support the long-term health of this TV and film studio. I do think there's an argument for Netflix over Paramount, which is just going to end up probably scrapping everything and selling it off for parts anyway.

• 34:05Jason Calacanis?

  Here's what I'm going to say. From now on, there should be a 60-day pre-vetting approval process for antitrust. This is when I'm president, Jason.

• 34:19Jason Calacanis?

  I run for president.

• 34:20Speaker 03

  I like it.

• 34:21Jason Calacanis?

  I'm going to lean a con this. And what I'm going to say is from now on, we're offering for the low, low price of $25 million, your ability to get your deals pre-vetted. So if you are Google and you want to buy YouTube, if you're Adobe and you want to buy Figma, if you're Adobe and you want to sell Photoshop, if you're Google and you want to sell YouTube, we will tell you who is going to trigger an antitrust deep review and who is not. And we are going to make it easier for these transactions to go through. So you don't need breakup fees. You just need to pay the government to put people on it.

• 35:05Jason Calacanis?

  And then what we'll do with the 25 million is we'll hire four independent, you know, assessors of this who will write four reports for $5 million each. We'll pull them from a pool of, you know, 50 possible intelligent people. We'll collate that. We'll share it with the public because it's got to be in the public's best interest. And Ernst & Young and McKinsey and Boston Consulting Group and whoever wants to write these reports can write really thorough reports of what they predict will be in the best interest of consumers. This is a great idea. This is like it's TSA Pre-Check, but for M&A deals. Yes, yes. I'm creating clear, clear your deal. TSA Pre-Check for your deal. Now, what this will do is reduce drama and then it will take out the favoritism.

• 35:47Jason Calacanis?

  Because the decision will be based upon a collection of reports by really intelligent people and based on a very simple test. What will be in the best interest of consumers and competition? That's it. That's it. And some smart person, McKinsey, might say, you know what? When comparing the viewership of this to YouTube, TikTok, and you do the full minutes consumed by generations, they'll say, listen, when these boomers are gone and these Gen Xers are gone, it's not going to look good for these companies. Like, this is not where the competition is. Here's where minutes are being spent. Okay, so that fixes the regulatory thing. Which, and we're going to have an auction. And the auction will have terms to it. It'll go from five bidders to best three bidders to best two.

• 36:32Jason Calacanis?

  And, you know, we're going to run an auction process. Winner wins. That's it.

• 36:36Speaker 01

  Who runs the auction in this model?

• 36:39Jason Calacanis?

  Well, in this model, you would hire Allen and Company or some bank to run the auction on behalf of-

• 36:43Speaker 01

  Catalyst or whatever. Okay. You were like, we're going to have intelligent people, these five, and then you started listing off Ernst & Young and McKinsey, and that's where you lost me. I mean, that's giving consultants way too much credit. I just wanted to make a me-

• 36:53Jason Calacanis?

  No, no, no. These consultants are actually very good at these kind of things. They, this is something where they do a great job, because they can look historically and they know inside these businesses really well. Like, they understand the nuances of these existing businesses. Where McKinsey or Boston Consulting Group might be, have a more challenging time is what we do in Founderland. Like, hey, we're going to create this disruptive thing called Robinhood and it's going to, you know, destroy all these, you know, trading companies. They'll be like, wait a second. We don't have the data on that because it doesn't exist, you know? And that's where venture capitalists have an advantage. They actually have an advantage on venture capitalists and- Folks like private equity people do because they understand existing assets so well because they probably have worked with them or in them.

• 37:38Jason Calacanis?

  So somebody like BCG has probably been inside of Disney doing 27 different projects in the last 10 years. They've spent, they've done 15 projects for Netflix. They understand those kind of mechanics. So that's where they would actually do a pretty good job. And then you could have futurists. You could say, hey, I'm going to hire Kevin Kelly, a futurist, and give him and his consulting group a million dollars to do their take on it. You can have a lot of fun with that and really do a thorough job that is, that takes away, it's Lena Kahn leaning people towards this, or Biden, or this, you know, combo of, you know, liberal lunatics, you know, who are biased, or it's Trump anointing people who,

• 38:19Jason Calacanis?

  or it's Obama who gave people a Netflix deal, or this person gave Obama a $10 million podcast deal, or a $20 million book deal, the Clintons got this deal, or, you know, everybody's getting these deals from the media companies. We need to make these groups more independent and we need to have them answer not to the executive branch, but to the people. I'm Jason Calacanis. I'm running to be your president in 2028. I hope I have your vote.

• 38:49Speaker 03

  And I approve this message.

• 38:54Jason Calacanis?

  There's only one thing left here. The final thing that's left here is President Trump's comments and trying to interpret them. He's going to comment on the failed news any chance he gets. Let's take this 60 minutes. That's just him grinding 60 minutes and, you know, working the refs, whatever, like anybody else does. But he does particularly well and he does it in a pretty comical way. Let's put aside that and let's go to just his very granular comments here because I do think people don't give him enough credit for the things he says. And you have to get past some of your biases here, or one's biasing towards him that he's just riffing. He's not riffing. There's a couple of things embedded here I noticed. I have a lot of respect for him, Ted Sarandos.

• 39:39Jason Calacanis?

  He's a great person. He's done the greatest job. He's done one of the greatest jobs in the history of movies or other things. Praise a very influential media channel that he actually knows is going to win this.

• 39:53Jason Calacanis?

  So he's giving him his praise, giving him his flowers. Why? Got to work with him. Hey, and Netflix is going to give him a documentary series when he gets out, just like they gave it to everybody else.

• 40:02Speaker 03

  Well, maybe, maybe Amazon. Melania's documentary is coming to Prime Video. So there's going to be some bitters. There's going to be some bitters.

• 40:08Jason Calacanis?

  I know, but what he's doing here is he's prepping Netflix to do a similar thing, right? He wants to keep them in the game.

• 40:14Speaker 03

  Absolutely.

• 40:14Jason Calacanis?

  Very smart. But it's big market share. There's no question about it. It could be a problem. That's actually accurate. If you're not considering TikTok and YouTube. It is a lot of market share of the old thing, which represents like half the number of minutes now, or a third of the number of minutes and some percentage of the revenue. Their share is going to go up a lot. I'll be involved in this decision. This is the key. He's not supposed to be involved in the decision. Like that creates a legal out for anybody. Like if he were to give it to Paramount and he were involved in it, then you've got the lawsuit of all lawsuits. Netflix can come in and say, listen, he said it right here. By the way, people aren't watching the lawfare going on,

• 40:55Jason Calacanis?

  but he did a similar thing where he scuttled his own case against Comey and Letitia by saying, we're going to go after them. I don't know what his exact quote was there, but he basically said, we're going to do this. Now, there is a concept here that we can't have a prejudicial justice system. By saying those things, he's created the ultimate easy way to have a case dismissed. The president of the United States, the most powerful man in the world, directed the prosecution of Letitia James and Comey?

• 41:28Speaker 03

  I mean, if you're thinking of that, that tweet that he sent, or that Truth Social message to Pam Bondi, there's, there's ambiguity. Some people think that he did that accidentally and it was meant to be a direct message.

• 41:41Jason Calacanis?

  There are no accidents.

• 41:42Speaker 01

  There was further reporting law in that it was actually a mistake. He mentioned that as a deal.

• 41:46Jason Calacanis?

  Okay, I don't think it is. I don't believe, I'm by the minute. But I'll say, there's no way he makes that mistake. Even if it was a mistake, he said plenty of other things about going after them. He said before the election, I'll be your retribution. We're going to put all these Democrats in jail. And that is why those cases recently got canceled. Like,

• 42:05Jason Calacanis?

  It's the easiest out in the world, or it's among the reasons these things got canceled, or got canceled because he put it in a lawyer without having them approve properly or whatever. Ah, Lindsey Halligan. Yeah, it's all prejudicial kind of situation. I think he's doing that on purpose here. I think he just wants this thing to be over. He's saying he's going to be involved in it. That makes it like, okay, we just got to give this to Netflix, get this thing done. Boom, it's done. It's going to Netflix. There is a family, the Ellison family, who bought from the other family, that private transaction. That family got to make that decision because they were the primary shareholders. In this case, the primary shareholders are not a family, it's the

• 42:50Jason Calacanis?

  public and pension funds, etc., which makes it super easy. Highest bidder, best offer, and that's what this is going to go to. Now, if the Ellison's have made the best offer, then this could get reconsidered, I guess. I don't know if this is locked up, but

• 43:05Speaker 03

  The board opted to go for Netflix, but now Ellison is trying to basically do a hostile takeover, go directly to the shareholders, you're getting screwed, you should go with my deal instead, and we will see what happens.

• 43:19Jason Calacanis?

  The other possibility is Netflix made this offer, they got that $5.8 billion fee for the breakup, and maybe they realize like, hey, okay, I guess we're not going to get through antitrust, or maybe the chance, we're not going to get through this antitrust, and so, yeah, let him outbid himself and overpay for the asset.

• 43:36Speaker 03

  There was a Puck News piece that suggested that this is all elaborate game theory by Netflix. They knew they were going to get rejected, they didn't think they were going to make the acquisition go through, but you tie up your main rival in the streaming marketplace for a year and a half, two years, while everything goes through. They can't get acquired by anyone else, they can't acquire anyone else.

• 43:59Jason Calacanis?

  Yes.

• 43:59Speaker 03

  You're sort of freezing them out for a year or two while you continue growing and expanding. There are people in Hollywood who think that's what's going on, and this is just Netflix throwing a... Wrenched in the work.

• 44:11Jason Calacanis?

  And if you happen to get it, great.

• 44:12Speaker 03

  Win, win. Yeah, you either pick up your chief rival or you tie them up for two years distracting everybody while you grow.

• 44:19Speaker 01

  Just a clarification, Netflix pays the $5.8 billion if the deal falls apart.

• 44:23Jason Calacanis?

  Yeah, that's what I'm saying. Like, so they may at some point want to like not have to deal with that. So they, in other words, in the game theory, they create chaos, they get their top competitor distracted.

• 44:36Speaker 03

  Exactly.

• 44:37Jason Calacanis?

  Were, and if the other party wins, they don't have to pay the breakup fee. And if they win.

• 44:42Speaker 03

  They, they assume they soak up HBO Max, their chief rival, so it's win, win.

• 44:46Jason Calacanis?

  That's all they want. They want HBO Max and they want the DC characters. That's, that's my theory. That's the only.

• 44:50Speaker 03

  Well, Harry Potter, there's a lot, there's a lot.

• 44:52Jason Calacanis?

  Yeah, I mean, Harry Potter's nice, I guess. Yeah.

• 44:55Speaker 03

  And they're making that new HBO show, The Lone Sopranos, you know, it's a lot of stuff.

• 44:59Jason Calacanis?

  There's, yeah, Ted Sarandos would like that. They did model, you could tell me if I'm wrong or not, Lon. Did they not model Netflix when they first went out as HBO prestige?

• 45:10Speaker 03

  Netflix would cite Casey Boy's stuff at HBO as like the North Star. And you could tell when you look at like House of Cards, that initial pack of shows, Ozark, they were obviously basing it on prestige TV from HBO, places like AMC. You know, that, that was what they were aiming for.

• 45:27Speaker 01

  How did it become, is that cake? Like, have you seen that show when they had to guess if the thing is cake or not? How did we go?

• 45:33Speaker 03

  They figured out, and this is they brought in Bella Bajaria, who now runs content for, for Netflix. And she was like the, the real sort of figurehead behind this realization. A lot of people are putting on Netflix in the background while they're on their phone, while they're cleaning, while they're doing other stuff. And that a lot of the stuff that does the best on Netflix is that kind of background viewing. It doesn't, not everything has to be Squid Game. Some things people just like to kind of leave on while they're doing other stuff. It's very low impact. And those are a lot of the biggest shows, Emily in Paris, Ginny in Georgia, even like Bridgerton. It's like pretty to look at. It's not hard to follow. You can check in and out. And I, I noticed too, a lot of Netflix original movies, and even Stranger Things started doing this.

• 46:16Speaker 03

  They signpost constantly in the, so every time they get somewhere new, they're like, well, here we are, the state fair where we said we had to go investigate that clue you found, because they know you're kind of checking in and out, you're on.

• 46:28Jason Calacanis?

  This is because of dual screen, because of two screen viewing, people playing chess, which I find myself doing. A chess alert comes.

• 46:35Speaker 03

  Scrolling Tik Tok.

• 46:37Jason Calacanis?

  I forget to pause and then I was doing this with Landman last night. I was taking a bath. My back was hurting. I'm watching Landman and I got a chess alert and I move over and I'm like, oh my God, what am I doing? Like this is like such a great performance happening in this latest episode of Landman with that old guy, um, Sam Elliott. And I'm like, I'm missing the Sam Elliott performance of the season. So I basically pulled it back 10 minutes, put my notifications off. I was like, I need to actually soak this in, so to speak.

• 47:03Speaker 03

  There's your explanation for like, that's why so much Netflix content is that kind of, is it cake stuff?

• 47:09Jason Calacanis?

  So annoying. Yeah. This is why I think they should have gotten CNN because you would keep, if you had CNN, they would have it running constantly. They just don't want to touch politics.

• 47:20Speaker 03

  News and politics. I think especially because of the international, so much of their viewing is overseas, all these different markets. I think they don't want to have to worry about customizing and individualizing that content for all these.

• 47:32Jason Calacanis?

  That's already been done. So what they should do is they should figure out who was running CNN back in the day when it was just straight reporting and they didn't have opinion stuff and roundtables. If they went to straight reportage, hey, we're here in Baghdad. Things are blowing up.

• 47:48Speaker 03

  BBC has changed a lot, but this used to be BBC too. And like the nineties, when you'd watch BBC news, it was very like, here's an anchor and here's the news and here's another news story. And it was very matter of fact. Yeah.

• 48:00Jason Calacanis?

  There was nobody with an opinion.

• 48:02Speaker 01

  It's expensive to have, you need to have Middle East girls and you need to have a bureau in Beirut and you need to have stringers and camera crews.

• 48:08Jason Calacanis?

  But you don't need to give Anderson Cooper 25 million.

• 48:12Speaker 03

  That's true. Or keep sending Stanley Tucci to Italy to wander around for a few months.

• 48:17Jason Calacanis?

  Well, no, but let's call it what it is. I think actually sometimes you got to zig where people, you got to zig and zag here. When I am running Disney, I'll buy CNN or I'll launch a news network.

• 48:29Speaker 01

  Presidency first, studio ahead first?

• 48:31Jason Calacanis?

  Yes, I'm going to do two jobs. Elon's got two jobs.

• 48:33Speaker 03

  You, you will own ABC News Studio when you have Disney.

• 48:36Jason Calacanis?

  Perfect. I will make ABC News. ABC News will be ABCN. ABCN will have just reportage. Anybody has a personality, GTFO.

• 48:48Speaker 03

  You could have a little personality. Yeah, we don't want to hear your opinions. We just want to hear the news.

• 48:52Jason Calacanis?

  The most personality allow would be Alex and you gotta be under Alex in personality. I don't want any.

• 48:59Speaker 01

  I'm the Mendoza line for commentary.

• 49:01Jason Calacanis?

  Yes, yes. I would like them to have less personality than Alex as a rogue.

• 49:07Speaker 03

  Oh, man. Van Jones, you're out the door, man. Sorry.

• 49:10Jason Calacanis?

  No, Van Jones, forget it.

• 49:12Speaker 03

  Van Jones is out the door.

• 49:12Jason Calacanis?

  First guy out the door. Enough. He's, he's got insights. He's reconsidered things. I don't want anybody. Your opinion is incredible for you to write down in your journal during your morning notes over coffee. And at night, you could namaste, have your chamomile tea and write it down in your journal as well. When you're on ABCN, your job is to report a fact.

• 49:35Speaker 01

  I'm sorry.

• 49:35Jason Calacanis?

  And if the fact changes, you report that fact.

• 49:38Speaker 01

  Yeah.

• 49:38Jason Calacanis?

  If anybody doesn't, and by the way, you're all getting paid the same goddamn salary. Here's the salary structure. It's a hundred fifty thousand dollars a year. Bust your ass. And every year you hear it, you get six percent more and that's it. If you don't like it, GTFO.

• 49:53Speaker 03

  MS Now is just down the street.

• 49:56Jason Calacanis?

  Go to MS Now. But can you imagine how amazing it would be to turn on news? And just have them tell you what's happening?

• 50:04Speaker 03

  And they, it's weird that every time a new person goes in to run a place like CNN or CBS News, they always say this is the plan. Like, we're gonna get away from all this commentary and talking heads arguing and we're gonna get back to more like practical, here's what's going on, current events, news you could use. And then it never quite seems to happen. It always just becomes a different person's opinionated perspective.

• 50:28Speaker 01

  In the same way, Lon, that I think Netflix ends up at, is this cake? I think CNN's obvious, you know, point of denouement is next up on our CNN panel, right? It's because it's easy, it's cheap, there's no prep required.

• 50:42Speaker 03

  Their new show is Tony Shalhoub traveling around the world tasting bread. This is true.

• 50:46Speaker 01

  Well, I mean, that's why we have HGTV.

• 50:49Jason Calacanis?

  No, but Alex is right. If you get four talking heads with different opinions, you have them scream at each other. It used to get ratings. It was a good ratings playbook and it was theoretically cheaper until Megyn Kelly, Tucker, Anderson Cooper, these people became expensive. These people came twenty five million dollars a year. I mean, Anderson Cooper, twenty million a year. Wolf Blitzer was fifteen. Jake Tapper, eight million. It just says producer Claude. No, I think they've all been run down.

• 51:19Speaker 03

  He's now worth it, man.

• 51:21Jason Calacanis?

  Aaron Burnett, six million. Aaron Burnett, six million?

• 51:25Speaker 03

  Yeah, I mean, she's famous. I got, I got.

• 51:27Jason Calacanis?

  How about, how about we get like, I don't know, the next Aaron Burnett, and if you're on air, you get paid $150,000 a year. And you're on for four minutes. You tell us the facts and then you hand it off to the next person to tell us the facts.

• 51:42Speaker 01

  Yeah, no, it sounds good.

• 51:43Jason Calacanis?

  Lon, what are you watching? What's your favorite streamer show right now?

• 51:45Speaker 03

  Ooh, wow. Tough, tough choice. Uh, you know, I was, I've been enjoying the It show on HBO Max. Welcome to Derry. But I don't know. I feel like they might have, they might have lost me this week. It went pretty far outside uh, the parameters, but I am loving Pluribus on Apple TV, uh, the new Vince Gilligan.

• 52:02Jason Calacanis?

  Well, yeah, in the new year, I asked Lon on the Friday show to come on and we're going to do a little thing at the end of the show where we go off duty. And we're going to give you our takes on great media things for your weekend. And Pluribus is my pick as well. This, have you watched this now yet, Alex, or you have?

• 52:17Speaker 01

  No, no, but I, no, I keep hearing about Pluribus. And so I'm actually, to hear Lon recommended as well, it's high praise.

• 52:24Speaker 03

  Jason, do you think that it is a metaphor for AI? Because that's what a lot of people online.

• 52:29Jason Calacanis?

  I think it is simultaneously. I know they said it isn't. It is a metaphor for AI, the singularity.

• 52:35Speaker 03

  Yeah.

• 52:35Jason Calacanis?

  Socialism.

• 52:37Speaker 03

  Mm hmm.

• 52:38Jason Calacanis?

  Democracy and the end of the American empire. All of these things.

• 52:41Speaker 03

  Wow. Yeah, there's a lot, there's a lot going on. It's a really interesting perspective, but once I started thinking about, is this an allegory for AI? A lot of stuff fits, like the kind of the way that the humans talk to one another now has a very chat GPT kind of sensibility to it.

• 52:58Jason Calacanis?

  Logical, sycophantic, everything.

• 53:00Speaker 03

  Right. They're always like, oh, Carol, we love you so much. That's such a great idea.

• 53:04Jason Calacanis?

  That's a great idea. Let's workshop it. Yeah. I mean, it's, it's always the same, you know, AI. It's AI slop.

• 53:10Speaker 03

  Right. The world has become a form of AI slop in a way. Yeah.

• 53:14Jason Calacanis?

  It is AI slop and like one of the characters is living in the ultimate AI slop, right? In Vegas is unbelievable, but I would say the protagonist to me. Represents America. I have a slightly different. I think it represents personal freedom, American exceptionalism, self-determinism.

• 53:31Speaker 03

  Sure.

• 53:32Jason Calacanis?

  How messy it is. And then the collective represents socialism.

• 53:37Speaker 03

  I think it's also, yeah, I think that makes a lot of sense. I think in a lot of ways, it's just about that feeling of feeling alone. The entire world is on board with something and you personally feel like you're not a part of it.

• 53:50Jason Calacanis?

  I love that too. The rugged individualism of like, hey, I still want to read a book. I want to make my own breakfast.

• 53:55Speaker 03

  Yeah, but even in a way, like the feeling of being depressed or that feeling of being isolated, where like the whole world is sort of feel, right? Like that, it's a very human thing. And I think you could almost apply it to any scenario. It's just about that emotional state of feeling alienated.

• 54:11Jason Calacanis?

  If they stick the landing in the next three weeks, I think this is going to be one of the top five shows of the new century.

• 54:16Speaker 03

  It's been, it's been spectacular and it's coming back. We already know it's coming back for season two.

• 54:20Jason Calacanis?

  Well, it has to come back. I mean, even if they fumbled it like Lost did in the end, but it's kind of like a better version of Lost in some ways. It's a more intellectually rigorous version of Lost where Lost, they were like, yeah, let's just do something weird. And they're like, what? It's a hit?

• 54:36Speaker 03

  We thought we were going to get canceled like everything else.

• 54:38Jason Calacanis?

  They know the ending of this. This is going to be a four series, five series max arc.

• 54:43Speaker 03

  Yeah, I feel like Gilligan has an idea of where he's going.

• 54:46Jason Calacanis?

  Oh, he does. He's not winging it. No, no. I think last thing I wanted to talk about here that I think is kind of interesting is that a PR guru who I don't think I've ever had the pleasure of meeting, but she wrote the Go Direct manifesto, which I think actually I get credit for, but okay. I think she probably rewrote my ideas. I don't know when her, let's see when this manifesto came out about going direct. Cause yeah, 24. Yeah. No, she gets no credit for that. Sorry. I created that going direct. Okay, whatever. But explain to us what's going on here. A PR person, this, I do find this fascinating. A PR person is starting a venture firm. That's really fascinating.

• 55:31Speaker 01

  Lulu worked at a large, a number of large technology companies in a comms role. She eventually left that, did a lot of talking in public, founded her own firm called Rostra, which is named after a part of Rome where they stood on old bits of ships and talked to the public. And her big pitch has been go direct, don't use intermediaries. Now, what she has done, as Jason just alluded to, is put together a firm, a $40 million vehicle to go along with that, essentially, as far as I can tell, investing in the companies that she works with. And she told Axios, the quote, "Storytelling is alpha, investing complements Rostra's work because narrative and capital both compound." And then she says this thing, which I've heard from a lot of other people, we'll talk about in just a second. "Right now, it's easier than ever to build new things and harder than ever to get people

• 56:16Speaker 01

  to care." So her argument is that building stuff, a little bit easier than it was, you can code faster, I don't know, vibe code, whatever you want.

• 56:22Jason Calacanis?

  No, you definitely build startups, but telling the story is like a big part of it, right?

• 56:27Speaker 01

  Yeah.

• 56:27Jason Calacanis?

  We all agree.

• 56:28Speaker 01

  So I was thinking about this story, and I know a couple of other examples that come right to mind. First one is Day1 Ventures. This is founded by Masha Bucher. Actually, I know her back from my San Francisco days. And she has put together a firm from her comms practice. So she runs her own venture firm and has raised not just one, but two, but three funds, Jason, each of increasing size. 20 million, grant 52, and then 150.

• 56:53Speaker 01

  Yeah, she was in True Bill at a $15 million valuation, sold to Rocket for 1.3. So some success there. There's another firm, VSC Ventures. This is part of the, an arm of VSC, another comms shop. And they also, again, stress the importance of getting attention for products. So not the first, not the second, but the third time, we've seen this trend of essentially service providers building venture capital funds. I like it.

• 57:16Jason Calacanis?

  It's somewhat interesting. I think it speaks to what we saw in journalism, when a bunch of journalists, and specifically a bunch of tech journalists or alma mater, were like, wait, journalism is dying. You know, there's no more competition for our services and like, this pays better. And it's essentially the same job, which. I think most people would agree I was the pioneer in that, but uh, cause I was the first to do it after Michael Moritz. So it was Michael Moritz, me, Omalik, MG Siegler. Yeah, it was like a, it was a good cohort and that job is also, you know, trying to figure out what the reality or the story is.

• 57:54Jason Calacanis?

  In the PR job, it's how to spin the story and to get attention or how to massage the story or how to scale telling the story, all that kind of stuff. If you were, I, I don't like PR, like PR people generally, cause it's just, you know, exhausting to deal with them. That being said, having one in the building who's really good, that makes sense to me.

• 58:14Speaker 01

  It makes a lot of sense to me. I have a lot of friends that work in and around the comms industry. And uh, if I was ever in trouble, I know that they're, they're my first call because they've been through it, man. They just know how to handle a crisis. They also, back to your point earlier on the show about being able to do a code red. You know who's really good at fire drills? Comms people.

• 58:32Jason Calacanis?

  The good ones, but this is the problem. As a former journalist, you became friends with PR people. This is always the trap, like the PR people know how to ingratiate themselves and spend time with journalists, et cetera. When I ran all of our pubs, we wouldn't talk to journalists. I banned the Engadget reporters, do not, I'm sorry, from talking to the PR people.

• 58:51Speaker 01

  Yeah.

• 58:52Jason Calacanis?

  Just do not talk to PR people. Just go to the subjects, talk to them directly. If PR people call you and want to talk to say, we don't talk to PR people. Same thing I do here at This Week in Startups, All In. PR people, email us. We have a little sentence. Thank you so much for your interest. We don't take pitches. Please remove us from your list. And PR people hate me, but they respect me because they know like, and then I would always have like clever people. Well, how do people do get on the show? I say, we pick them. How do you pick them? Well, I pick what I think's interesting. Oh, okay. Well, I'd love to tell you why this is interesting. I'm like, oh no, we don't take pitches.

• 59:19Speaker 01

  I don't want you to tell me what I think is interesting. My, my job is to be informed.

• 59:25Jason Calacanis?

  Yeah. And I made Molly, and I think I instructed you to do the same thing with This Week in Startups. I hope I did at some point, like just use the snippet. I want them to think there's no way to get on the show. And it's like a little uncomfortable at first to write that. I don't know if you found it uncomfortable.

• 59:41Speaker 01

  I've, I've had to say it on a lot of phone calls, like people like, hey, hey, hey, hey, hey, how you doing? I'm like, oh, good. They're like, hey, we got a guy. Well, when I first joined, everyone thought that I joined All In. And so they're like, can we get on the show? And I'm like, I, I'm not on that.

• 59:53Jason Calacanis?

  I don't even know.

• 59:54Speaker 01

  I'm sure maybe you can, but not, not through me. Uh, and eventually people figured it out and then they stopped trying because I kept saying things like, no, and we don't do that. Uh, and also you don't. We don't want to fake interest in somebody, you know, like I don't want to have someone come on the show and be like, I'm not compelled by this, Jason. Let's talk to them for 15 minutes.

• 1:00:13Jason Calacanis?

  The only thing that can happen is sometimes like somebody's like, I do Michael Dell's book. And I'm like, well, Michael Dell's a hero, whatever. And I'm like, yeah, just tell Michael to reach out. And they're like, okay, well, he doesn't do that. I'm like, and then I just said, okay. And they're like, okay, so he's going to be on the show. I'm like, no, I just told you, if Michael Dell wants to come on the program, tell him to ping me. He knows how to get me. And like, of course, like, what are we doing here? Like, if it's, if you're pitching me a friend of mine, or somebody who's been on the show, like, you didn't even know they've been on the show, or that we have a relationship? Like, what are you doing, PR people? PR people are just, 90% of them are just dumb. They're just low IQ. 90%. Alex is like, sure.

• 1:00:54Speaker 01

  Well, I mean, I don't know. What am I going to do? Interrogate that and argue that 75? I mean, no matter what, I look like an asshole. I want to point out, though, that everything you're saying underscores Lulu's philosophy. She thinks that you should go around intermediaries, be they PR people, or-

• 1:01:09Jason Calacanis?

  She cribbed my go direct strategy.

• 1:01:10Speaker 01

  Other notable venture capital firms started by non-traditional folks, Harry Stebbins and 20 VC has invested in Poolside, Emerge.Dev, couple of Twist 500 companies. And then there's a lot of other smaller ones that I found. So WPP, the big advertising conglomerate-

• 1:01:25Jason Calacanis?

  Yeah, that's a corporate, it's adjacent, but that's like a corporate VC arm.

• 1:01:29Speaker 01

  Yeah, yeah, but-

• 1:01:30Jason Calacanis?

  Corporate VC arm isn't like, I'm leaving PR, PR sucks, or I'm leaving this and going to that. But yeah, it's adjacent.

• 1:01:36Speaker 01

  It's adjacent. I found some like breadcrumbs about other PR firms, starting firms, starting funds that didn't really kind of make it, and the websites weren't up anymore. And then, if you want to go further afield to non-traditional venture capital firm founders, there's a number of celebrities, Serena Williams, Ashton Kutcher, Snoop Dogg, and Kevin Durant come to mind.

• 1:01:54Jason Calacanis?

  Yeah, that's another angle to get into VC is to use a chain smokers, to use your celebrity to get access to deals, and then use your platform to then go promote stuff. And it can work. It's worked out for Serena, obviously, and Ashton. All right, everybody, thanks for tuning in to This Week in Startups. We'll be back on Wednesday. Bye bye. All right, everybody. Tomorrow on the show, Alex will interview on Tuesday, a couple of Twist 500 companies coming at you. And Wednesday, I'll be back for the news roundtable. Bye bye.