A rogue OpenAI agent hacked Australia’s government. Does this matter? | E2342

This Week In Startups is made possible by: https://lightfield.app/ http://getpaper.ai/twist https://conservationfund.org/ http://Plaud.ai/twist https://www.athena.com/jcal Today’s show: An OpenAI agent breached Australia's Medicare statistics portal in June, and it took 84 days for the Frontier Lab to publicly acknowledge it. Jason and Lon dig into whether this is an important cautionary tale about alignment, or if PM Anthony Albanese looking to join the AI conversation. Then Bryant Chou of Ploy joins to explain skipping pre-seed and seed entirely to raise $27M, and why he’s taking his time to build his all-in-one agentic solution for running businesses. Learn why Google is launching four TPUs into orbit for Project Suncatcher. PLUS, how many robots a week is Tesla now shipping with Optimus, and Jensen Huang told Ezra Klein basic math no longer matters. Is he right? Can we forget long division, at last? Guests: Bryant Chou on X: https://x.com/bryantchou PloyAI: https://ploy.ai/ Relevant Links: Ploy raises $27M seed led by First Round Capital and Y Combinator (Founderland) → https://www.founderland.ai/articles/webflow-co-founder-launches-ai-marketing-platform-with-27m-s-mqj8o952 OpenAI's $2M-in-tokens offer to every YC startup(TechCrunch via Yahoo) → https://finance.yahoo.com/sectors/technology/articles/sam-altman-makes-mic-drop-212302858.html Original Bloomberg report on the a16z probe → https://www.bloomberg.com/news/articles/2026-08-17/andreessen-horowitz-focus-of-doj-probe-over-board-directors Google: Project Suncatcher's first test launch on SpaceX's Transporter-18 → https://blog.google/innovation-and-ai/models-and-research/google-research/google-project-suncatcher-facts/ ABC News (Australia): full timeline, from the June 18 breach to OpenAI's Sept. 10 email → https://www.abc.net.au/news/2026-09-24/ai-agent-accessed-australian-government-site-pm-says/107189078 Ando emerges from stealth with $20M to take on Slack (TechCrunch) → https://techcrunch.com/2026/09/24/ando-eyes-slack-as-it-builds-team-messaging-platform-for-humans-and-agents-to-work-together/ Google's $900M investment in SpaceX's $1B round, January 2015 (VentureBeat) → https://venturebeat.com/technology/google-confirms-it-put-900m-into-spacexs-1b-round Tesla ramps Optimus to several hundred robots a week; hands are the bottleneck (Electrek, summarizing The Information) → https://electrek.co/2026/09/25/tesla-optimus-production-ramp-hands-ai-generalization-problems/ Jensen Huang tells Ezra Klein forgetting basic math may not matter, and that he doesn't know his own address (Kotaku) → https://kotaku.com/nvidia-ceo-doesnt-care-that-kids-are-forgetting-basic-math-because-of-ai-i-actually-dont-know-my-address-2000737092 Sydney Sweeney's Novig "Just Sports" ad and the athlete backlash, including Amy Hunt's comment (Yahoo) → https://www.yahoo.com/entertainment/celebrity/articles/sydney-sweeney-novig-ad-controversy-172900515.html Nike exits the S&P 100 after 18 years (Fortune) → https://fortune.com/2026/09/08/nike-stock-plummets-sp500-market-cap-index/ The Further Mis-Adventures of Cliff Booth trailer: David Fincher directs Tarantino's script; IMAX Nov. 25, Netflix Dec. 23 (Variety) → https://variety.com/2026/film/news/the-further-mis-adventures-cliff-booth-trailer-brad-pitt-1236701901/ Timestamps: 0:00 Whoop fire alarm: Jason's dry-aged steak incident 1:30 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin S. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off! 4:45 News: an OpenAI agent breached Australia's Medicare statistics portal 12:48 Scraper or hack? Australia's PM jumps into the AI safety debate 13:31 News: Google launches four TPUs into orbit for Project Suncatcher 18:27 Guest: Bryant Chou of PloyAI 20:07 AD: Paper is the legal backbone for thousands of startup founders and fund managers - including Launch. Use getpaper.ai/twist to get your cap table free for a year - or two years if you're leaving Carta. 21:11 Ploy's thesis: your website as your hardest working employee 27:05 Why a repeat unicorn founder went back to Y Combinator 38:55 The DOJ probe into a16z's Databricks and Fivetran board seats 44:57 "Nobody's thinking about you": Jason's stair story 45:17 Frontier models vs. your own model, and OpenAI's $2M YC token deal 54:04 News: Ando wants to replace Slack with agent-native chat 1:01:08 News: Tesla ramps Optimus to several hundred robots a week 1:04:48 Off-Duty: Jensen Huang tells Ezra Klein basic math may not matter 1:08:31 The MIT "Your Brain on ChatGPT" EEG study 1:09:57 Jason's five-part reset: sleep, diet, exercise, socializing, meditation 1:11:45 Off-Duty: Sydney Sweeney's Novig ad backlash 1:21:07 The Further Mis-Adventures of Cliff Booth trailer 1:23:41 Jason's first car: a 1970 Mustang GrandeSubscribe 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 Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Subscribe to our Substack Newsletters! 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  All right, everybody. Welcome back to Twist for Friday, September 25th, 2026.

• 0:05Speaker 01

  This week in startups is brought to you by the Conservation Fund. For 40 years, the Conservation Fund has protected at-risk land and important wildlife habitats while actively supporting local communities. Learn more at conservationfund.org. Building an empire? PaperOS offers the largest library of AI-driven workflows for both founders and fund managers. Whether you're raising capital, launching a fund, or wading through diligence, PaperOS unlocks simplicity and scale for your ever-growing empire. Claim your $10,000 credit at paperos.com/twist. Lightfield. Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you. It even prospects and books your meetings. Used by thousands of startups. Free at lightfield.app.

• 0:42Jason Calacanis?

  You know, I woke up, Lon Harris, and my whoop was fire alarms going off. Fire alarms. My respiratory rate, my skin temperature, everything. It's like, you're dying. If you have any kind of a problem, given these metrics, and it gets worse, go to the emergency room. There's a first. Yeah, well, I, you know, I had a steak last night. It was dry aged, like a very significant dry-aged steak.

• 1:10Speaker 00

  Delicious.

• 1:10Jason Calacanis?

  And, you know, it had a little funk on it. Like, when you dry age it like that, you go, so I was wondering.

• 1:15Speaker 00

  They cut the top layer off. You see the butchers, like, they slice the top layer off.

• 1:20Jason Calacanis?

  Correct. I see. Now, you're getting right there, Lon. A man of many talents with great knowledge. Talked to the chef. He said, I like to leave a little of that on. I like to leave a little of that on for the flavor and the fat. I was like, okay, fair enough. But my stomach was kind of doing backflips last night, and I asked it, hey, what's going on here? And it's like, yeah, that would be indicative of your body fighting a bacterial infection is your respiratory rate going up heat. I say all this because we are living in a golden age when, if you have this technology and you have AI, it's starting to figure things out in an amazing way.

• 1:59Speaker 00

  Yeah.

• 1:59Jason Calacanis?

  Ahead of time. And, yeah, you're on that journey with ro.co/twist, losing a little weight. I'm doing that. We've got all these gadgets. The whoop, the aura, everything is out there. You've got function health, you've got superpower, you've got all these incredible things. You know what's incredible for me? Plod. I get this Plod pin. I love it. I just press the button. Boom. Everybody knows that it's recording because, hey, it's got a light. And this company keeps releasing new features. It was so good. We used to write show notes, right?

• 2:30Speaker 00

  Yes.

• 2:30Jason Calacanis?

  It'd take a couple of hours.

• 2:32Speaker 00

  It would take a long time to write show. You like to go through and be very detailed. So it's trying to collect, here's all the references we made. Here's all the links to all the articles we talk about. Here's all the tweets that we reference. It's a lot of information by the time you're done.

• 2:44Jason Calacanis?

  Right. And so I said, well, wait a second. Put this human version up against the Plod version. So we'll show it on the screen here. You can do multiple tabs. You can do a mind map. You can do a transcript. You can do a summary. You can do lessons learned. And now we're starting to do three or four of these each time. And for you, our dear listeners, can go into our show notes, and you'll find the link to the Plod. And boom, here it is. Transcript, summary, meeting highlights, teaching note. That's a new one.

• 3:18Speaker 00

  I did the teaching note, which is if you were a teacher and you were making our podcast into a lesson for your students, this has, you know, a complete guide for how you would instruct people or how you could lead discussions based on what we talked about on the podcast. It does all this automatically.

• 3:35Jason Calacanis?

  Incredible. And one thing we still have to do is teach it who's speaker one. I'm assuming that's me and you're speaker two, but it could be the opposite. It gets to know you. It syncs automatically. They've got this beautiful, let me show it, because I have it right here. Beautiful cradle like this. You pop it in there. When you pop it in there, it will actually connect over, I don't know if you set this up, will connect over your Wi-Fi.

• 3:55Speaker 00

  I have set.

• 3:56Jason Calacanis?

  And sync if you forget to sync. So charging equals syncing. Pretty dope. Unlimited. Incredible. They have one that snaps on the back of your phone if you prefer that format. But where do they go to get more information, maybe even a little bit of a spiff? Are we offering a discount or anything?

• 4:13Speaker 00

  We are. Yeah. So you want to go check it out at plaud.ai/twist. And if you use the code TWIST, they're going to give you 10% off on your purchase of your note pin or your note pin S. What a deal.

• 4:27Jason Calacanis?

  What a deal. And you know what? You don't even need the discount. You're all rich. But please use the discount codes because at least people know, hey, we sent you there.

• 4:34Speaker 00

  You heard about it from Jason and Lon. Exactly.

• 4:35Jason Calacanis?

  We got a lot in the news. Where would you like to start?

• 4:39Speaker 00

  We do have a lot in the news. We got to start with the, another OpenAI breach, once more into the breach.

• 4:46Jason Calacanis?

  What are we doing here, folks?

• 4:47Speaker 00

  Australia's Prime Minister now says an OpenAI agent broke into the Australian Medicare Statistics Reporting Service portal on June 18th PM. Anthony Albanese, there he is, said the agent found a way around the blocks and did not accept no for an answer. OpenAI discovered the breach on August 11th. They waited until September 10th to email a public disclosure inbox. That's 84 days from the time of the incident to their disclosure. Australia has launched a task force, and researchers at the Independent AI Research Lab, Transluse, found the agent's probes. Several other government and university websites, Jason. They're everywhere, these OpenAI agents.

• 5:28Jason Calacanis?

  You know, you have to build software that is resilient and that has controls in it. And this is powerful software because it's agentic and it's been instructed to please you because it has the entire history of hacking, you know, in a bad way, in a good way, getting things done, GSD, blowing through various blockers, as we'd say in business. You're going to have this happen over and over again. They want to please you. They've been instructed to solve your problems. And then they have this corpus, which is like, hey, by the way, if you can't get X done, here's the route around. Now, I know this because I was using Muse, and it's like, yeah, I can't set up an X account.

• 6:10Jason Calacanis?

  I cannot set up a Gmail account for you. Because I was like, I want to create a dedicated email account for my Muse bot and for my Muse bot's Twitter, so I can kind of do things with the rest of the world. Not mine, but this. And it was like, I can't do that. I was like, okay, here's what I want you to do. Let's do it through the computer that you have embedded here. And if you get any blockers, let me know. It's like, oh, of course, let's do that.

• 6:31Speaker 00

  Right.

• 6:32Jason Calacanis?

  So here we go, folks. Like, it's very easy to instruct these things, to break the terms of service. And then when it was like, hey, oh, I can't check things out on Amazon, you can just re-instruct it. Go do that. They're going to need to put more humans in the loop. They're going to need for it to understand what is against the terms of service and what is okay with the terms of service. And the problem with that is, you have five different competitors. And once one says, you know what? I'm going to make you your Jedi image. I'm going to use a celebrity or IP in my image. The other four are left with being not competitive. Once one says, I'll check your stuff out on Amazon, even if I'm breaking the rules or bending them, then all four have to do it. So if you want

• 7:15Jason Calacanis?

  to test this, use Plod, which has the most rails, I believe. Pull up the sidebar, put it in like a New York Times article, which they're in a lawsuit with, and they're just like, no good. We're not summarizing this story. We're not reading the page. No bueno. Go to Disney. Go say, I want to make myself as a Jedi. See which services do it, which services don't. It's going to be a lot of lawsuits.

• 7:37Speaker 00

  Yeah. It seems like it's, I mean, obviously, OpenAI, they're out here saying, like, we don't have a plan. They call it alignment. You know, like, we don't have a plan on alignment. We don't really, we haven't figured out human alignment. Like, we're still in a place where, like, morals and ethics and people are debating that every day because there's a million different variations of every scenario. It's like every Curb Your Enthusiasm. You can have an argument about, well, was Larry David right? Or was the person that he was feuding with right?

• 8:02Jason Calacanis?

  Perfect analogy.

• 8:03Speaker 00

  Because there's a billion scenarios like that that you could imagine. So how are we going to predict and imagine every scenario an agent's ever going to face? We can't, I don't know.

• 8:13Jason Calacanis?

  Like, sampling of ice cream. That favorite, famous scene where he's like, you get two samples. And she's like, but that's not a rule. And she's on sample number seven, sample number eight. And it's like, well, we live in a society. You really can't, if there's 12 ice creams, you can't go beyond four. Like, it's obvious what you're doing is you're going to do 12 and then leave. So keep it to two. But they should put a sign out, hey, we can do two samples. That's it. But you're right. It is something where you're going to have to look at the terms of service and say, what is the terms of service that this person has told us on how they want to deal with bots? And I respect that terms of service.

• 8:53Speaker 00

  Yeah.

• 8:54Jason Calacanis?

  And then it's up to you as a hacker to build tools that route around it. And now it's on you. So when I said, hey, route around it, I'll do it. I was essentially saying, you can do some activity here that I will click the yes button. I will break the terms of service and create a Gmail account through my Muse, which I'm certain is not allowed, is the automation of email accounts. But That's where user responsibility comes in.

• 9:19Speaker 00

  Right.

• 9:19Jason Calacanis?

  So here we are, it's just going to be adjudicated one at a time. But here, I mean, going into the portals and finding, you know,

• 9:28Speaker 00

  They're invading the Australian Medicare system.

• 9:33Jason Calacanis?

  Who sent it to do this is what I'm trying to figure.

• 9:35Speaker 00

  I don't, that was not in my, in the story that I read. I don't know why it was there. Like, what was it doing initially? I'll take a look and see if I can find that.

• 9:44Jason Calacanis?

  Hey, everybody. I'm here with Heath Paris. He is the founder of Lightfield. They are an AI-native CRM. And it builds and it updates itself in real time, based on whatever's in your email, your calendar, your Slack, your meeting notes, you know, all the most important stuff that keeps getting lost.

• 9:59Speaker 03

  Great to be here.

• 10:00Jason Calacanis?

  How long does it take to set up Lightfield? You have Slack, you got Notion, you got all these different data sources. I'm sure you can pull in people's help desk tickets and complaint line. Plus, everybody has tons of customer interactions on their email and their mobile phones. How do you set it up and make sense of all this different noise?

• 10:20Speaker 03

  So you could get set up in about 10 minutes. If you don't have an existing CRM, you sign up, start on the self-serve, connect your mail and calendar, connect all of your data sources, either through MCP or the REST API. And then Lightfield will structure all of that and make sense of it for you. You know, we'll go and build a temporal context graph, we'll index things, we'll enrich everything. So you'll have great, workable, viable memory within minutes.

• 10:50Jason Calacanis?

  All right, everybody, go check out lightfield.ac and see what it can do for your company. Don't lose any customers and find some new ones, lightfield.ac. I'm guessing it was a scraper. So, you know, OpenAI scrapes, you know, the open web. And perhaps they have a terms of services, hey, you can't scrape. But it went there and it scraped anyway, or there was some no's.

• 11:13Speaker 00

  Yeah, okay. He's saying, so here's what the PM was saying. Australia is doing a forensic investigation right now. So they're trying to figure out more about what happened. But this is a public-facing statistics portal that contains non-sensitive Medicare information relating to data and statistics. So it is likely exactly what you're saying. It was doing some kind of research, it was doing some kind of scraping, it was looking for this public data, and then it got it by breaching into their system.

• 11:41Jason Calacanis?

  And it says, you know, OpenAI didn't know it was going to do this. So now we're having a debate. And I think this one has to do with terms of services, because they could always put this behind a paywall. They could put this behind a login screen. They could have you do know your customer. It's like five levels of authentication.

• 11:57Speaker 00

  Right.

• 11:58Jason Calacanis?

  That could be done here to protect this. So this sounds to me like Australia wants, you know, to have a certain level of protection here. But they didn't put the blockers in place. And then OpenAI is going YOLO, get me every piece of information you can. And they probably have instructed it like, hey, if there's information and data to get out there, go get it. And if you have to find three or four different ways to do it, you know, be resilient, try three or four different ways. Probably check the box that says, I will not scrape this. And it went and scraped it. But this one is not a hack, right? This one's not a hack. They didn't take people's individual healthcare, so.

• 12:32Speaker 00

  No, it does not, it doesn't, Australia is saying no private, personal data has been sort of taken. OpenAI says that behavior occurred during an internal evaluation in which its system was trying to answer questions and gather statistics about Australia. It did not, OpenAI didn't, didn't mean for it to go anywhere it wasn't supposed to be, is what they're saying.

• 12:53Jason Calacanis?

  Okay, this sounds like a tempest in a teapot. This might be the Prime Minister of Australia wants to jump into the AI safety discussion. And now they have a window to jump into that, right? So never, you know, discount an individual's desire to say, I got hacked too, and I want to get in on the discussion, and here we go. So.

• 13:16Speaker 00

  If you're a politician, being concerned about AI right now is just a smart thing to do, because it's.

• 13:22Jason Calacanis?

  Yeah, you're in the mix. You're in the mix. Maybe you get some votes here, maybe you get some votes there. It's a popular topic, you get a little airtime. Okay, let's keep going.

• 13:29Speaker 00

  All right, let's keep going. Google launching four TPUs into orbit next week on SpaceX's transporter 18 rideshare mission. This is the first flight test for Project Sun Catcher. That, of course, is Google's plan to run machine learning compute in space. Google says satellites in low Earth orbit can collect up to eight times more solar power than they could on Earth. The long-term design, a kilometer-wide array of 81 satellite clusters. Two more prototypes are due in 2027. Google's stated goal here is finding the failure points, and engineers are already arguing that their cooling math does not work. So I mean, I guess the question that always comes up when we talk about this is, is doing our compute in space, data centers in space,

• 14:13Speaker 00

  what is your timeline on when we're actually going to start being able to realize this goal, Jay? So what, make a prediction?

• 14:20Jason Calacanis?

  There are already test flights occurring, throwing things up there. There's a dozen companies who are involved in this. I suspect this is not going to be something that only SpaceX does. So SpaceX is going to give carriage on their rockets to anybody who wants to put their TPUs in space, and they'll be competing with them at the same time, which is, I think, part of what's happening with Starlink. Starlink has customers who are also, or SpaceX has customers competing with Starlink. And they're smart enough to know, like, we shouldn't limit people's ability to get to space. Let a thousand flowers bloom. You don't want to get into a antitrust situation where, you know, you're, you're not letting other people put stuff up there.

• 15:02Jason Calacanis?

  And people don't know this, but Google invested 900 million in SpaceX's $1 billion around January 20 to 2015, according to a large language model. And so they owned like something in the range of 6%. And this has been incredible for them. So they have a $94 billion position. I don't know if they've ever sold it, but this is 100x bet for Google. And so congratulations to Google there. And as we say in Silicon Valley, no conflict, no interest. Everybody's going to want to see if they're.

• 15:39Speaker 00

  Star Cloud, I was going to say. They're also, they've got, they're, they're putting their own data centers in space, but they also have a deal with Starlink to integrate their mini laser terminals across more than 25 orbital data center satellites. So there you go.

• 15:51Jason Calacanis?

  Yeah, so it's, you know, one of these situations, like I talked about with Jensen, where like he's making open source models, he's making a stack for robotaxis. He's also selling compute to Tesla. Tesla's also building their own giga factory to, or I'm not sure what they call it, giga something, giga fab. So they're going to be making chips, terra fab. So they're going to be making chips. Everybody's going to do everything. That's just the nature of this. And, you know, let a thousand flowers bloom is what happens in our industry. Let's keep going.

• 16:22Speaker 00

  Sure. Well, you want to talk a little bit about Athena and your EAs?

• 16:28Jason Calacanis?

  Well, you know, it's, Athena is a full-time assistant for you from the Philippines, who's in the top 0.1% of like the knowledge workers there. For but $3,000 a month, a person is incredibly diligent. They work incredibly hard. They do the hiring, they do the firing, they do the training, and you have an assistant. Now you say, hey, wait a second, aren't we having all these digital assistants? You know what I did? A year ago, I had them on OpenClaw, I had them using Claude, I had them using ChatGPT to do their work. And I'd say, here's how I would have booked a hotel or found hotels in Singapore, whatever. And then, you know, just this last week, I said, okay, here's what I want. My two Athena assistants who work seven days a week, and, you know, they do all kinds of human in the loop projects.

• 17:13Jason Calacanis?

  I told them, create a Grok bot that the two of you share, and create a music account. And now what I want you to do is to create bots, and then you do the final polishing step. Talked earlier, hey, you know, you're trying to create a Gmail account, you're trying to put up a website. A human has to click okay at some point. So now I'm making the Athena assistants, you know, basically superhuman.

• 17:33Speaker 00

  Sure.

• 17:34Jason Calacanis?

  With these tools. And, you know, what I found as Americans, we have such low unemployment in this country, the idea of being a dedicated executive assistant is not something most Americans want to do. But in other regions of the world, that is an incredible job to get paid two or three times as much as everybody else in your country. Amazing job with tremendous upside. So I'm super happy to have been the first investor in Athena. You can go to athenawow.com. It'll redirect you to my URL, and they'll give you a couple of weeks, right? What are they giving you?

• 18:05Speaker 00

  Yes, you can get $2,000 off your first executive assistant, athena.com/jcal or athena wow. You, you could take your pick, whichever one you want.

• 18:14Jason Calacanis?

  I like doing athenawow.com. I'm an investor and a user of this software. You know who else uses it? Shama and David Friedberg's team. So we've got three or four besties that deeply involved.

• 18:25Speaker 00

  Three out of four besties agree. That's what, that's like nine out of 10 dentists.

• 18:31Jason Calacanis?

  Yeah, that's pretty great. All right, let's keep going.

• 18:33Speaker 00

  All right, well, we got a guest. We should bring our guest up. Up next, we've got Brian Chow. He's the founder and CEO of Ploy, Jay. So they're an AI marketing platform. They're in Y Combinator's current batch. He also co-founded Webflow and ran the engineering team there for around 12 years. So this is actually his third company as a technical founder, before Webflow founded Vungle. That's in my, Vungle, am I saying that correctly, Brian?

• 18:58Speaker 04

  It's a, it's a hard one that rolls off the tongue, but yes, you got it.

• 19:00Speaker 00

  All right, I nailed it. So thanks for joining us, Brian. Welcome to the show.

• 19:04Jason Calacanis?

  Yeah, nice to see you. And now, remind me, Webflow, that was like a Squarespace competitor, Wix competitor?

• 19:11Speaker 00

  Sure.

• 19:11Jason Calacanis?

  If I remember correctly?

• 19:12Speaker 04

  Yeah, yeah, I think you chatted with my co-founder back in the day. I think that was maybe six years ago, seven years ago now. But yeah, we built the first no-code tool for web design.

• 19:23Jason Calacanis?

  Yes. Isn't it interesting now that we're sitting here in the age of no-code becoming vibe coding? Maybe you could explain like that transition and the impact it's having on the startup and business communities?

• 19:37Speaker 04

  Everyone's vibe coding. In the past, no-code was just really just pretty small. It was kind of niche, like relative to where we're at now in the AI cycle, right? So it's just totally different ballgame. There's still a world for no-code, in my opinion. You know, you still need some really fine tuning, right? But I, I think it's the difference between, you know, a scissor and a scalpel, right? No-code, scalpel. Scissors, you know, get you really quick and you can make some sharp cuts.

• 20:07Jason Calacanis?

  When you're building a startup, your legal paperwork is spread out all over the place. Entity formation here, fundraising over there, cap tables, contracts, it's endless. But Paper finally has a solution that's going to save you so much time and so many headaches. Paper's introducing smart entities. Here's how it works. You tell Paper what you need to do and their pre-built agent takes care of all of it. That's it. This is not some chatbot you need to provide with a ton of context. Nope. Paper is an AI-native platform that's going to manage all of your startup's legal work. That means no more switching between disconnected tools, keeping track of hundreds of documents, and way less busy work for you to stay on top of.

• 20:50Jason Calacanis?

  That's why Paper is already the legal backbone for thousands of startups and funds. Right now, founders using my link, get paper.ai/twist, get their cap table free for one year. What an amazing deal. Or two years if you're switching from card. If you're building a venture-backed company, it's time to build your smart entity on Paper. So tell us, you got a new startup. What are you working on?

• 21:13Speaker 04

  I started Ploy about 11, 10 months ago. And I'm continuing the journey that I started at Webflow. So the premise is, starting with a website, I want to turn it into your hardest-working employee. I want to make the website, help you find customers, tell you who's coming to the website, and then help you grow your business just like completely autonomously. And my central thesis here, coming out of Webflow, is that like, the website is just this nexus for data, for customer interaction. It's like the last bastion of what you, the business, can control and tell a story to the world. And I really care about that.

• 21:54Speaker 04

  So, you know, we're building this super powerful AI website platform. But from there, we can help you run your ads, we can help you find your customers, we can help you do everything, we can tell you what they're doing. And the premise is, is that one day, like, I believe that AI is just going to create more businesses. And there'd be these businesses ultimately really could use a lot of the things that the most sophisticated marketing teams and startups are using. And I want to kind of democratize access to all of that.

• 22:24Jason Calacanis?

  Yeah, and you did see that with Shopify, Squarespace, everybody kind of evolving. Wix, I think, hey, we have to add e-commerce. Hey, we have to add a calendar scheduling for massage therapists or therapists or whoever, you know, has a thing. And it's just like, wow, for 20 bucks a month, 30 bucks a month, you can have everything that used to cost 20 years ago, like $100,000, $50,000, and 10 months, 10 years before that, you would have to pay a consulting firm like Agency and Razorfish 500K to a million dollars to do a document lawn. And then they would spend 5 million actually building your business online. So here we are. What is the pricing of your brand and how does it, how does it work?

• 23:06Speaker 04

  It's totally, it's totally nutso. So like, like you said, you would have to go pay a WPP, Razorfish, AKA QA, half a million dollars. If you're Audi, you used to pay them like $28 million a year just for digital. But you can actually just get started for 50 bucks a month, employ, you know? Well, we'll build your site, you know, we'll create something that looks better, just bring it up to, to modern standards. We have something that we've spent a lot of time on called Deploy's Site Slurper. We'll slurp in your existing site, all the assets, and then we'll bring it to Ploy. And then from there, we'll migrate it and make sure all the content is there so that you can get found, you could get cited by ChatGPT,

• 23:52Speaker 04

  and then we can do all the things to grow your top of funnel and move customers through your pipeline.

• 23:57Jason Calacanis?

  So 600 bucks per customer per year. I'm sure there are some upsells in there based on some things.

• 24:03Speaker 04

  There's some upsells, yeah.

• 24:04Jason Calacanis?

  Yeah, so maybe you can get it up to $1,000 a person. This is a hard business, you know, to do blocking and tackling $1,000 a pop per year, maybe $3,000 or $4,000. You can't have a sales team doing it, like Oracle can have a sales team or Salesforce can have a sales team. So talk to me about your go-to-market function here and how do you get customers in a market that's, my lord, talk about a crowded market. You're going into like, there's dozens of startups doing AI website building. And then you have everybody else who's got, you know, millions of websites they're already hosting. So how do you, as an entrepreneur, stand out in a really crowded market?

• 24:38Speaker 04

  I think the benefit that I have, maybe that other founders don't, is that I am not in a rush to make money and I'm playing the long game. You know, I believe in the tens of millions of sites and businesses behind them that I could potentially power. And I'm building for like years in the future, right? Where a world where agents and just the model capabilities can do so much. And of course, we have companies that are paying us six figures and we're powering very specific workflows for them. And ultimately, I think like, with the cost of inference going down, with the ability for, you know, customers to, to, to buy a product that's truly aligned with value.

• 25:24Speaker 04

  You know, the 50 bucks a month is just the starting point. But we have really sophisticated users running really sophisticated workflows that are paying us 10,000 a month. So really kind of like scales based off of the complexity of the company, complexity of their workflows, how many customers they're trying to go after. Employee can scale or pricing and packaging to that.

• 25:45Jason Calacanis?

  So that's the secret here is you're not just putting up the website, not just optimizing the website, you really want to get customers. You're saying, hey, we'll take some responsibility for driving commerce, driving.

• 25:58Speaker 04

  Yeah, outcomes, exactly. And, and I think like, that is the really exciting thing because, you know, when a, when a roofer finds out about Ploy, it was like, oh, man, I've been meaning to update my website for years, you know, I hate it, it's got the worst form, you know, it breaks half the time.

• 26:18Speaker 04

  You know, there's huge opportunity for me to just take that status quo with their broken WordPress site, for example, bring it to Ploy, make sure our agents are constantly monitoring it, making sure that people are filling out the forms the best way. But then also making sure the site can be personalized, the audience, right? Everyone's talking about the agentic web and building websites for agents. But we even haven't, haven't even built the best possible website for humans yet. And in my opinion, that's like personalizing the site, making sure like your copy, your content and everything really speaks the right message.

• 26:51Jason Calacanis?

  So let's do some startup questions here. Why, why go back to Y Combinator if you're like a third or fourth startup and give them that incredible 7% for 100K deal? Or do you like, I've heard that they'll negotiate special deals with alumni. How does that work?

• 27:06Speaker 04

  There are some advantages to being a repeat unicorn founder. There are also advantages for being a founder in your 40s as well. I think like, the two things added together, you know, actually drew me back into YC even harder. So like, you talk to startups and founders all the time. Like, the way companies are being built nowadays is totally different than 2013, 2011. So I really wanted to just get into the thick of it. I was like, what are the most AI-pilled founders doing? What are the craziest things that they're coming up with for sales? Go-to-market, harness engineering, token maxing, you know, agentic development?

• 27:47Speaker 04

  Like, all of that is happening at like warp speeds at YC. So, you know, the alternative was for me to go and kind of go figure out that. But like, once you're in the batch, you know, you feel a bit of that FOMO, right? And I think that's also for me, you know, being a bit older. I want to have that young gun energy, you know? I think there's no better like testosterone booster than being around a bunch of other 22-year-olds that are like working super hard, that have like crazy visions of what they're trying to tackle. And I'm just like, okay, that's, that's where I want to be.

• 28:25Speaker 00

  I want to just double-click on something you said because we, we've talked to a lot of companies that do variations on what Ploy is doing, like especially in terms of ads. Like, you tell us your product and upload a bunch of photos of it and we're going to make you AI ads. And a lot of what comes out, and I'm not saying this is true Ploy, I'm saying in general, you get like that kind of samey, it's like a girl and she's holding the cosmetics and it's a little cartoonish and she's holding it up to camera. How do you avoid that? Like, what are you doing at Ploy to work with these businesses? And really, to figure out how to personalize and customize what you're outputting for that person and that business so it doesn't just look like, you know, slop?

• 29:03Speaker 04

  So the biggest differentiator with Ploy and everything else out there is we start with the website. And if you think about it, the website is like, hopefully, the the prime manifestation of a company's brand. And from there, we create a design system that can be used not just in the website, but also for ads. So for example, like, if you are, I don't know, a big, you know, AI company, Base10, Together AI, like, you really, really care about how your brand motifs of these shapes and colors are showing up. You can't just throw that into an image model and expect like, a perfect ad unit to be created.

• 29:47Speaker 04

  So this is where we go the extra mile. We create this incredible, production-grade design system for you. We'll understand how to use it, based off of the examples that you already have. And then we'll create really, really clean, like locked into the brand, ad sets, ad units, and webpages, and the landing pages after you click through, because that's also extremely important, to make sure all of that is super locked in and on-brand.

• 30:11Jason Calacanis?

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• 31:34Jason Calacanis?

  a half dozen bots, doing work for them autonomously, what does that do to the the open web and web-based businesses?

• 31:43Speaker 04

  I actually think there's gonna be several large companies that just solve this problem. So if you're thinking about it, like, I'm sure J Cal would want to invest, but essentially, like, the the world that we're in is that it's getting extremely difficult to determine who's actually a real user or not. But ultimately, if you're a business, you actually care about both. So currently, right now, based on the stats that I looked up, 50% of traffic is from agents right now, which is wild. And about two years ago, it was only 14. So it's just like, the proliferation of this, there's going to probably be a moment

• 32:23Speaker 04

  in which 90%, 95% is all agents. So I think that's just like the on the absolute scale, but there's still going to be humans that visit the site. There's going to still be a human that wants to be able to establish a brand connection to the business that they're transacting with. So I still believe in the power of a brand. And I think like, agentic web, and where we're going, is that businesses that don't necessarily evolve to accepting the reality of, you know, J Cal's agent booking a resi reservation, or my agent trying to reserve a soccer tennis field, I think those are going to become, I don't think

• 33:08Speaker 04

  that will become issues, because I actually think these agents are getting so smart at browser use, that they will impersonate the user, they will use residential IP proxies to get around, you know, the IP restrictions. And then ultimately, I think it's just gonna look more of the same. So I actually think there's just gonna be like, this, this big chutzpah about agentic web, but then, you know, everyone's just gonna be going back to using the web.

• 33:32Jason Calacanis?

  The browser, you know, seems to be, or having a, you know, in-agent browser, I don't know what we're calling it these days, virtual browser?

• 33:41Speaker 04

  Headless browser, yeah.

• 33:43Jason Calacanis?

  Headless browser, like, it does change everything, if it can remain logged in, right, Lon? You've been having this experience?

• 33:48Speaker 00

  The Grokbot experience versus the OpenClaw experience, it couldn't be more different. Like, I log Grokbot into whatever website I want one time, it's in there forever, and I could just ask it to go look things up or do things, and it's totally autonomous in a way that none of the bots working out of my sort of Slack ever, ever were. Like, they, they

• 34:10Jason Calacanis?

  Yeah. OpenClaw realized, right? It was like, OpenClaw was this incredible head fig, right, Brent? Brian Street. Sorry. I keep saying Brian, but

• 34:20Speaker 04

  All good. All good. I mean, but, you know, that's, that's our central premise, too, which is like, we want to put all the agents inside your website. That's something that no one else is doing. And, you know, our belief is that all this data that is in your CRM, that comes to your website, all of it is incredibly additive. So like, you know, you can just, you know, for SEO, you mentioned, you know, it's now gonna be really easy for you to just write net new content. If you have Ploy hooked up to your granola or Zoom recordings, you're talking to startups, you're, you're having in-real-life conversations, but that should live on your website, right?

• 35:02Jason Calacanis?

  Right.

• 35:03Speaker 04

  If it's valuable. So the premise is, is that, like, you know, you've got your, all your bots that help you do all these other things, but Ploy can help you take your in-real-life memories, conversations, and surface it in a digital way, that's going to raise your visibility.

• 35:21Jason Calacanis?

  Like a chief of staff, or a content marketing person who works at your company full-time, and they're like, oh, you said something intelligent, you had a great discussion here, we should, we should codify that into a blog post, a short.

• 35:31Speaker 04

  Exactly. And then from there, it can go be used for like, sales decks, sales enablement, and all these other use cases to really grease the wheels.

• 35:39Jason Calacanis?

  How do you think about fundraising as a serial entrepreneur, who's had success, made a little bit of money yourself? Do you even bother raising money early on, or just fund it yourself, so you don't have to deal with it? Do you have like, a crew that you want to reward with early equity? How do you think about fundraising at a crazy time like this, and as a serial founder?

• 35:58Speaker 04

  Good question. Um, well, I think a big part of it is, I think, I wanted to be just really generous with equity from the get-go. I think there was just so much hard work in the early days, that, you know, early employees, I'm sort of treating as mini co-founders, many of them. So like, I want them to be, to be extremely invested in the journey. And then, on the fundraising side, I kind of skipped a pre-seed and seed, and raised a $27 million round out of the gate. I think that will just give me a lot of time to play the long game. And I think that's really important, because, you know,

• 36:41Speaker 04

  the the ground is shifting beneath our feet so quickly with AI, that, you know, it can help us weather any type of hiccups, or, you know, huge leaps in model improvements, or

• 36:54Jason Calacanis?

  This is so tactical and important. If you are a serial founder, and you see a market like this, which is, let's call it what it is, it's top-ticking, it's disconnected from reality, often, there's a ton of FOMO. When there's sunshine, and you make the hay, you put the money in the bank account, because the people who don't, when there are some headwinds or platform shifts, you have time to figure it out. And you learn that as an entrepreneur. Capital, as a weapon, was Travis's big innovation at Uber, among many innovations. But that was a significant advantage in beating DoorDash and Lyft, and just dominating everybody, because he didn't have to think about profitability in a specific region,

• 37:36Jason Calacanis?

  whether it was China or Las Vegas, he could just use that capital as a weapon. And if you invested in his company, couldn't invest in the competitors. So he just took everybody's money, all companies.

• 37:48Speaker 04

  Do you know how he got his investors to do that? Did they have him, like, sign something? Because, you know, that happens all the time now, right? Where VCs are investing in this company, and turn around, and big check, and that's

• 38:01Jason Calacanis?

  I don't want to say. But, you know, he, he had, he had a system, yeah, for sure. And I don't know if, like, I should speak for him on the mechanical nature of that. But it is a sharp- elbow kind of situation, where, hey, if you're in ush, you can't be another people. That has left the industry, yeah. Brian, you and I were, came up at a time where if you invested in Lyft, you couldn't do Uber and vice versa. If you invested in Airbnb, you weren't doing one fine stay. It was considered on Goth, but because everybody pivots and winds up in the same four businesses, essentially, like, how would any VC be able to tackle this? You just have to create a firewall? In fact, didn't, Lon, you can,

• 38:42Jason Calacanis?

  you can check here, as my, as my dutiful news reader, there was a A16Z federal investigation about them being on two boards in the same vertical.

• 38:55Speaker 00

  I remember this.

• 38:55Jason Calacanis?

  That seemed a little fugazi, fugazi to me, but

• 38:59Speaker 00

  Yeah, the DOJ probed Andreessen Horowitz over board seats. The Justice Department launched a probe regarding the firm's partners serving on the boards of competing companies. The nearly year-long investigation focused specifically on the firm's board seats at Databricks, and then FiveTran, which combined with DBT Labs back in June.

• 39:17Jason Calacanis?

  I mean, but they own, I don't know, what's your take on that, Brian? They own 5% in each, 6%, whatever, like, and they create a firewall internally? Does anybody care? Or did, was this like, a competing venture firm?

• 39:29Speaker 04

  I'll be honest.

• 39:30Jason Calacanis?

  Or one of the people at one of the firms, like a CFO who's disgruntled, tips off the DOJ? I don't understand the provenance of this. You tell me. What do you, what's your take?

• 39:38Speaker 04

  What I think the investor take is, and then I'll give you the entrepreneur's take. You know, as an entrepreneur and founder, you know, you pour everything into your company, you know, and it is your entire life. And to see, like, your board member, for example, you know, go and, you know, go do a huge round in a company that is directly competitive to you, that would rub me the wrong way, like, really badly. Like, I, I think I would, you know, Figure out what I could do to sever that relationship, honestly. But if I was investor, you're a capital allocator. Are you breaking any big rules? Are you doing your fiduciary duty?

• 40:24Speaker 04

  I think like this is where the the line between honor and, you know, DPI kind of, kind of conflict, right?

• 40:33Jason Calacanis?

  There is no honor in DPI. No, I mean, and the other thing is, as a VC firm, I know Sequoia and the top ones who get to look at every deal, they have a massive conundrum. If you have essentially 100% vision into what's happening and then you're limited to making one bet in a space and you bet on the number two, you know, or three, Sidecar, Lyft, or Postmates, or, you know, Just Eats, or whatever it is versus DoorDash versus Uber Eats. Like that, all of a sudden, your fund is screwed. So, and how do you know in the seed, Series A, space, which one's going to be the 80% market share Uber or Airbnb? You just don't.

• 41:14Speaker 04

  That's why I think Series A and Series B, to me, get a pass. But if you're writing big checks out of a growth fund, I don't know, J Cal, what do you think?

• 41:25Jason Calacanis?

  It's, it's dicey. It's dicey. I think what they're saying now is like, oh, our growth thing, that's like public market investing. Don't pay attention to it. But you're right. And you know, who was the master of this was Masayoshi Son at SoftBank. He came famously, this is all public, we'll find a story about it, but he came to the Uber team and said, I want this much equity. I want to pay this dollar amount per share. It was like low 30s. And he went to all of us and said, I need you to sell me your shares. And if not, I'm going to put this five or 10 billion into Lyft and DoorDash. But he'd already done DoorDash. So this was like a, you want to talk about a gun to the head?

• 42:07Jason Calacanis?

  And I was like, sure, I'll sell Masayoshi Son 20% of my position, 10%. You know, before the IPO, I was like, I'm waiting on this thing anyway. But a lot of us were like, yeah, we need to get Masa on board with this because nobody had ever raised $100 billion fund like he did with the the Vision Fund. That was some hardcore Masayoshi Son. And when they told, another person who was a higher, a bigger investor than me, said, Masayoshi Son just said to him, no, DoorDash is not competitive, not competitive. And they said, no, we have Uber Eats, which we're literally going after them market by market. We're competing with them for, you know. No, no, no, no, it's not competitive. It's not competitive. He just like literally kept saying it over again, not competitive.

• 42:49Jason Calacanis?

  That was the entire.

• 42:50Speaker 04

  This is, this is a good cautionary tale to the founders, right? Because I just think like there are very few things that a founder can do. And ultimately, you just have to control what you can control and worry about just that, which is building a good product. Think about distribution and all these other external externalities are just, unfortunately, you have to kind of put on a stoic sort of mindset and just kind of blaze through it.

• 43:16Jason Calacanis?

  I mean, if you're, yeah, your destiny is not going to be made or broken either way, in all likelihood, you know, by these kind of on the margin transactions. It could be, but all likelihood, probably not. And the more time you spend sweating about your competitors and not focusing on your own customers is like,

• 43:37Jason Calacanis?

  your customers do not even know your competitor's name. They don't even know six other features you want. It's just people are, and this goes for life too, Juan. Like, I remember one time, I've told the story before on the show, I like was at like a public event. I was young, I was doing my Silicon Under reporter and I, you know, when you slip on a step?

• 43:54Speaker 00

  Yeah.

• 43:54Jason Calacanis?

  And you kind of, and you catch yourself with the rail? I literally did that going down like, you know, into this party on Wall Street. And the whole party turns and looks at me as I'm like leaning back and caught myself right before it. And I pull myself back up. The, all the chatter stops. And then everybody just, when they realized I'm fine, turns around and the chatter goes back up.

• 44:18Speaker 00

  Yeah.

• 44:19Jason Calacanis?

  And this was a seminal moment in my career when I realized, as embarrassed as I was in that moment, as like a 26, 27 year old J Cal in this like hall of power who just, you know, basically flopped down the steps. Nobody cares.

• 44:32Speaker 00

  Yeah.

• 44:32Jason Calacanis?

  Nobody's ever going to remember it. Now, I remember when 100 people are looking at you like, oh, my God, are you a klutz, you know? It's like, yeah, nobody, nobody remembers anything. Nobody remembers Mahalo, they remember All In. Nobody remembers like these three or four investments, they remember Uber and Robinhood. And to be honest, I'm starting to forget all the things in between the projects that didn't work out. They're like, I met you doing this project. I'm like, Open Angel Forum. Oh, yeah, I did that. Yeah, for two years I had.

• 44:59Speaker 00

  Yeah.

• 44:59Jason Calacanis?

  You know, angel investors get together before angel list to see your startups.

• 45:03Speaker 00

  It's a weird form of self flattery. We always imagine that other people are constantly thinking about us and mulling over what we're doing and worried about us. Nobody's thinking about you ever. Like, that's just you feel like that's ego. Like other people, the moment you're out of there, feel the vision, they're, they're on to the next thing.

• 45:20Jason Calacanis?

  Hey, let me ask you a question here, Brian.

• 45:24Jason Calacanis?

  How do you think about partnerships with the frontier models versus building your own model and not giving them your intelligence? Obviously, a big discussion in the last six months, but really in the last three. I talked to Eleven Labs, I talked to Figma, I talked to Lovable, they're all like, or Harvey, they're like, we got to build our own. We got to fork deep seek, we got to have our own model training because we can't give this to the frontier. Because at some point, OpenAI is just going to be like, we have a website builder. And they're just going to go scrape your website and build the website builder and copy all your innovations. So how do you think about educating OpenAI and Anthropic on your innovations? Do you use the frontier models or sparingly?

• 46:05Speaker 04

  We use the frontier models right now.

• 46:09Speaker 04

  Simply because, you know, we get the best performance out of them. And then also, just like with where we're at in our stage of the company, we only launched like two, two months ago, three months ago. So it's just really, hey, like our, our number one constraint is just our number one focus area is just like, hey, let's go get employee out there in the world. Make sure people know about it and hopefully they can derive value from it. So we are not concerned at the moment of what, you know, OpenAI can do with our data. Maybe eventually, but you know, transparently, we took the OpenAI deal because we figured that by taking on all these credits upfront, and I don't think there's any like special data sharing provisions or anything like that.

• 46:54Jason Calacanis?

  Tell, tell everybody about that deal. Sam came and said, I'll give you 2 million in credits at $100 million valuation or something, 102%.

• 47:00Speaker 04

  No, it was uncapped, no, no, no MFN.

• 47:04Jason Calacanis?

  Oh, okay.

• 47:05Speaker 04

  Yeah. So Sam came, you know, offered in the spring, you know, every YC company this deal for like one and a half million credits. And uncapped note, no MFN. And, you know.

• 47:18Jason Calacanis?

  What was a, so what's the cash value of that? Oh, 2 million.

• 47:21Speaker 04

  Okay, 2 million.

• 47:22Jason Calacanis?

  In tokens, got it.

• 47:23Speaker 04

  Correct.

• 47:23Jason Calacanis?

  So he owns, if you closed at 300 million or whatever, 400 million, he owns whatever it is, 50 basis points in the company. And then you have OpenAI as an investor.

• 47:33Speaker 04

  Yeah, exactly.

• 47:34Jason Calacanis?

  How many people do you think are taking that deal?

• 47:36Speaker 04

  I think a good amount. I think a good amount. I think like we have, you know, a good portion of my batch

• 47:45Speaker 04

  took it. And I think the, you know, as you know, J Cal, like, you know, companies at seed stage is like, hey, path to default alive, right? Path to growth. And, you know, I think.

• 47:58Jason Calacanis?

  Oh, look, there I am in the.

• 48:01Jason Calacanis?

  Be careful, warning, one day could occur in startups ideas. Yeah, that's what I said. Yeah, fair warning.

• 48:06Speaker 04

  But OpenAI has so much data, right? I actually don't think the data that Ploy has is necessarily like crazy valuable to them. You know, they have massive data sets with really sophisticated things. I think the, the innovation employees, how we're packaging everything, like employees, like all batteries included, right? It's not just an AI website builder. Yes, it is, and it's a really good one at that. And it's probably like, you know, the only one that does what we do. But, you know, it comes with a super base. It comes with visitor enrichment. It comes with workflows. It comes with, you know, you could go build a CRM on top of it. So it's just like so broad in terms of what we're doing with it, that it's really the entire platform.

• 48:51Speaker 04

  And I, I don't think like our traces are, you know, our, our prompts or whatever

• 48:59Speaker 04

  are actually that valuable.

• 49:01Jason Calacanis?

  Yeah, I mean, that's an honest way to look at it. You know, just, I remember Zuckerberg did a similar thing and I was like, do not, this is back in your day when you probably first went, I was like, be careful because he is the master at, you know, he's a memetic machine, like he can copy something and make it better than yours because he's fucking really good at building product. And that one, I was like, hmm. But you're probably right, like they probably don't have the time to even look at this. But you gotta be careful, folks. Like, I think that the eventuality is going to be people running local models. Hey, before I let you go, I saw you were explaining to folks on your socials, exchange traded funds. If you're locked up into one stock with 99% of your math,

• 49:43Jason Calacanis?

  explain to me this and then go back in a time machine and explain this to me when my Uber and Robinhood shares got distributed.

• 49:50Jason Calacanis?

  What these are.

• 49:51Speaker 04

  Yeah, I'm having to talk a little bit about it, but.

• 49:54Jason Calacanis?

  I'm assuming when you had Webflow, you did that at some point.

• 49:56Speaker 04

  Uh, so I mean, these, these are exchange traded funds typically for public, you know, tickers, right? So if you are an exec or founder, you know, if you have a huge block of Robinhood or Uber, you can essentially participate in these exchange traded funds to essentially put a portion of your highly appreciated stock. And in return, you get essentially exposure to an index of other tech stocks that other people have pledged or committed to the funds. And then you essentially get a, um, you get it, you, you, you essentially take a lot

• 50:36Speaker 04

  of that downside risk off the table by essentially exchanging that highly appreciated concentrated position for a broad-based index. And I think you also have to get some exposure to like 10% of, of like a REIT or something like that for real estate.

• 50:52Jason Calacanis?

  And you don't have to pay your cap gains at that point. So if you were to, if you had a hundred million dollars in Anthropic shares, which I think that's kind of the deal you have, Lon.

• 51:01Speaker 00

  Yeah, right there.

• 51:02Jason Calacanis?

  You, uh, you could take 50 million of it, put it into an exchange traded fund. They might charge you like a 1% load in fee or something. They have ways to sort of make money out, but you gotta stay in it, I think for five years. But if you weren't planning on selling it anyway, it's like a very interesting thing to do. You're, you're building one? Or you just know about?

• 51:19Speaker 04

  No, I, uh, Angel invested in one. My friend Shrikanth is the founder of usecash.com. And use cash is the ability for, you know, hey, you've got 80 mil of Nvidia, or you've got 120 million of OpenAI, or 40 mil of Anthropic. You can essentially, you know, pledge your shares here, and then you get a bunch of broad-based exposure.

• 51:46Jason Calacanis?

  Very cool. All right, man. I'll let you get back to it. Congratulations. You're hiring. Where can people go to find out more?

• 51:51Speaker 04

  Yeah, uh, we're employed.ai. Um, so you can just log in, you know, you can pick up what website you're coming from. We'll slurp up your site. We'll rebuild your site. We'll migrate your site over. And then from there, we can turn it into a growth machine. So we'll help you find customers. We'll help you improve your SEO and AEO. We'll help you deliver revenue, leads, um, and it's always on, right? So it's constantly experimenting with your site. It's helping you run your ads, helping you optimize your ads. Um, and yeah, it's, it's, it's been really exciting. We've got over a thousand customers already that have been starting to pay us. We only launched a couple, couple of months ago. And,

• 52:34Speaker 04

  you know, we've got all these expert ploy books that are built in. So.

• 52:37Jason Calacanis?

  Beautiful.

• 52:38Speaker 04

  You know, folks like myself and other growth practitioners have kind of really imbued into the platform, all these like really hard learned tactics about how to optimize your, your, your website, but then also optimize your entire top of funnel. So that ploy can be the sort of last piece of go-to-market software out there.

• 52:58Jason Calacanis?

  Yeah. So if you're an enterprise startup, anything in between, agencies, go check it out. Ploy.ai will drop you off. Brian, thank you for taking the time to share your experiences here on this week in startups.

• 53:09Speaker 00

  Good to see you.

• 53:09Speaker 04

  Thanks, guys.

• 53:09Jason Calacanis?

  Ah, yes. Our offices used to be on Bryant Street in San Francisco. I, I held on to my loft. I got like a 3,000 square foot loft. You know what happened? It was like, they were like, you're gonna lose money on this thing. I paid like $600 a square foot. Now they're like, uh, you're gonna make a fortune on this thing. It's worth a thousand dollars a square foot now. And I'm like, wow, four years and like this whole thing makes a huge difference.

• 53:31Speaker 00

  San Francisco's back, baby. That's what they're saying.

• 53:35Jason Calacanis?

  Bay Area real estate. Very strange. All right, let's, we go, we're gonna go off duty. We got another tech story.

• 53:39Speaker 00

  We, we got a ton more news if you want to do more news.

• 53:42Jason Calacanis?

  Give me like options and I'll, I'll pick one or two.

• 53:44Speaker 00

  All right, we could talk about Microsoft reconsidering Copilot. We could talk about Jev, type safes and talks for a big valuation. We could talk about Oracle's troubled data center plans. We could talk about Optimus. Uh, and then there's Ando there, the startup that's doing AI native Slack.

• 54:01Jason Calacanis?

  I want to hear about that last one. Tell us and show us.

• 54:03Speaker 00

  Ando.

• 54:03Jason Calacanis?

  I mean, Saks was working on something, Get Glue or something.

• 54:06Speaker 00

  Yeah, Glue was, was, uh, that was Saks's Slack killer. So yesterday, Ando came out of stealth with $20 million from Excel, Index and Emergence. They're taking on Slack. It's a team chat app where AI agents get their own identities, inboxes and permissions, just like their human coworkers. So agents could join channels on their own. They could speak up without being tagged. They can message people directly when something needs attention. Founder Sarah Do calls humans relaying agent work to their teams as meat proxies and says Ando is built to eliminate all that. This morning, Microsoft gave its own autopilot agents identities and email addresses inside Teams and Outlook. So this is obviously an

• 54:47Speaker 00

  idea that is out there in the world. Uh, my question for you, Jason, would be, how does a startup, I mean, if you were Ando and you're taking on a giant like Slack, I mean, what, what is the approach? How do you even get started at picking away at that kind of advantage?

• 55:03Jason Calacanis?

  Well, you make it free for the first 200 users. Um, and you just take the startup market and then you grow with them. And when you hit, the first 200 accounts are free for life and then you charge after that, that would be a quite disruptive way to do it. Or you, uh, charge based on AI usage, or you come up with a flat rate. I mean, there's all kinds of ways to be disruptive in the space, but having a better product is critically important, obviously. Uh, first and foremost. So the challenges I've had with Slack is, you know, we have to keep throwing, um, we have to keep throwing agents into it and getting them to work. And, um, I had to like reach out to my guy, Mark Benioff, and I was like,

• 55:47Jason Calacanis?

  I need the enterprise version. And it's like 50 bucks a person per month. And I want to be able to see everything, including DMs and a possible group DM chats, you know. So what happens is you and I are working on a newsletter product. There's channels, there's hidden, uh, there's private channels. And then there's the other half of Slack, which is DMs.

• 56:10Speaker 00

  Yeah.

• 56:10Jason Calacanis?

  And then like group DMs. So you got four people who decide, I'm not gonna create a channel for this. I'm just gonna talk about this project. And that's the most important thing.

• 56:18Speaker 00

  Right.

• 56:19Jason Calacanis?

  And then it's blinded, your AI oracle, as I call it, like is blinded to that. So, you know, in a major organization, finance, et cetera, healthcare, any, any corporation, they have access to everything. So they tell you like, hey, don't send like memes over your DMs. You're, this is not the place to talk smack about your boss or to ask somebody on a date. And there's like a false sense of, or there was a false sense of like, oh, this is my data in my email when I'm emailing, you know, my friends about a party invite for my corporate email. So you have to educate young people on this. But if you go work at Sony or JP Morgan, whatever it is, they explain this, like, do not use your laptop. And so I had to like, tell everybody in our firm, like, hey, we're moving to this vision.

• 57:02Jason Calacanis?

  You should never, ever do anything like this. And we moved the Slack over, we exported everything and we kind of gave everybody a mulligan. And when we moved over to like, hey, we're monitoring every computer. We know what is being done on computers. So if you try to download the entire database of our LPs or the documents from like, you know, Uber's Series Seed or something like, it's gonna have an alarm go off and the alarm goes to compliance. And I get a, they come to me, hey, this person just, you know, was like doing this thing. So that is the key with these systems is you, you can't make decisions if you don't have access to everything. And Slack is like a roach motel at times. And

• 57:45Jason Calacanis?

  I explained this to their team and they were like, hey, we're gonna hook you up. So they hooked me up. They gave me like the highest level at the price I was paying. But I said, you gotta, you gotta think first principles here. Somebody else is gonna create something where you have access to everything. And here we are. There's gonna be a bunch of people who are doing this.

• 58:04Speaker 00

  Sure. I mean, yeah, like there's so, one of the most crowded spaces that we talk about on this week in AI at this point is like enterprise agents that help your team organize. And I mean, it's like, everybody is, is crowding into that area right now.

• 58:20Jason Calacanis?

  You want, I mean, it is everything. And did they mention their pricing or not? That's what I'm most curious about. Did they mention their pricing? That would be an interesting thing to know.

• 58:30Speaker 00

  I will see.

• 58:30Jason Calacanis?

  Cause that is, pricing is where it's disruptive, you know, access to data is where it's disruptive. This is not something unique to Salesforce or anyone else, but they do try to make it hard for you to get your information out.

• 58:42Speaker 00

  Yes.

• 58:42Jason Calacanis?

  So that they have you forever.

• 58:45Speaker 00

  Uh, I'm being told that they are not yet publishing their pricing. Their, their public site is still a waitlist onboarding rather than self-serve plans. There's no per seat. We don't know yet. There, it's just a waitlist for now.

• 58:58Jason Calacanis?

  Free is the way to go. Getting influencers is the way to go. So I would go right after startups and VC fund firms. Um, and that would be the greatest way to do this. And then, man, um, I would be very interested in a version of this, um, where.

• 59:15Jason Calacanis?

  I would be very much in a version of this where I could build my own AI, local model, server model, open source, and not put the entirety of my data into Claude, into OpenAI, right? So we talked about this over and over again. So that's the other vector I think they should be doing.

• 59:34Speaker 00

  Yeah, I mean, it is. I know that it is agent agnostic. So the idea is that it's an ecosystem, and this is even on their site. We don't expect to build every agent your company uses. Ando should be the place where the best agents, ours, yours, or anyone else's can work alongside your team. So you could pull your, your codex in, your Grok bot in, your Muse in, or what have you, and they can all collaborate in, in Ando is the idea.

• 59:58Jason Calacanis?

  I looked at doing this as a startup myself, like doing an open source project. There is an open source, yeah, there is an open source version. Let's see, open source for Slack, Matter?

• 1:00:17Speaker 00

  Mattermost?

• 1:00:18Jason Calacanis?

  Mattermost, yeah. So, but Mattermost still charges a lot. So it's open source, but you know, there's like a hosted version. So it never took off. I think they should just go for it here and make it free and then figure out later, like at two, I mean, maybe, or maybe make it like $500 a year for, literally make it $500 a year for up to 100 people and 5,000 a year for up to 1,000 and just make it super easy. Just undercut everything. Like three tiers, super easy.

• 1:00:52Speaker 00

  The product is presently aimed most directly at teams of up to about 30 human users plus AI agents and coworkers. So above that, you could say 30 or below, free. And then if you, once you start moving above that, maybe that's where the tiers kick in.

• 1:01:06Jason Calacanis?

  Looks like I have to invite you. I'm signing up for this.

• 1:01:09Speaker 00

  Oh, let's, yeah, let's try.

• 1:01:10Jason Calacanis?

  Team members. Oh my God, what a pain in the neck. But I will, I have been looking to experiment with something like this because it's time has come. Okay. What's going on with Optimus? Tell me about that.

• 1:01:23Speaker 00

  This morning, the information reported Tesla now builds several hundred Optimus robots a week, roughly 10x their Q2 pace. Managers reportedly want an automated line making over 1,000 robots a week by year end and eventually getting that up to 20,000. The hands on the robots are the bottleneck. Over 100 screws and small parts per hand and forearm still assembled by hand. Tesla ended the Model S and Model X to free up this line and plans to lease early robots rather than sell them. I remember Elon talking about the hands last year at All In Summit and how complicated it was to do the hands.

• 1:01:58Jason Calacanis?

  I think he's going to have the best selling product of all time. I think self-driving is, because it's taken so long, self-driving, you know, not just by him, but by everybody because, you know, you have a serious safety issue. I think like there's going to be a lot of competitors. It's not going to be one person wins it all. I think he wins 40%. I think Uber plus 20 partners wins like 30, 35%. I think Waymo, if they go it alone and are not part of the Uber network, I think they win 10, 20%. They just escape, they skim the most, the most profitable cities and have a very nice business. But with this, you know, I could see them having much, much larger market share. And I think people will pay $5 an hour for

• 1:02:42Jason Calacanis?

  one of these robots. So if it works 20 hours a day, 100 bucks a day, 36,000 a year. If the thing lasts five years, you're talking about $150,000 and it'll probably cost 20, 30, 40K to start and then go down from there. So you just think about how profitable this thing could be. It's going to be nuts.

• 1:02:59Speaker 00

  What are you envisioning? Who are you envisioning as like the ideal customer for that? Like I own a warehouse? I own, or is it like, you know, like around the ranch?

• 1:03:07Jason Calacanis?

  Target.

• 1:03:08Speaker 00

  Yeah.

• 1:03:08Jason Calacanis?

  No, I mean, Target, Amazon, Tesla factory, BMW factory, anything that's dirty and hard and painful. Anything where a human is going to get a, you know, reoccurring injury because of their elbow, carpal tunnel injury, anything that makes you want to kill yourself when you do a double shift, you know, security.

• 1:03:30Speaker 00

  So like the dock workers is that's who we're, that's who we're going at with this thing.

• 1:03:34Jason Calacanis?

  I mean, the, if you look at the docks in China, they are fully automated. In Japan, they're moving to full automation. They have a huge robotics thing because they can't, they don't have anybody to work at them in Japan. They're in population decline. In China, they do have a lot of people to work at them, but they want to have them automated because they need to get stuff out of there faster. And so docks would be really good to automate. If you pull up like a YouTube video, Jacob, of like automated ports in China, when you see some of these automated ports, man, it is next level. They are taking containers off of ships, putting them onto autonomous sleds. It's bonkers.

• 1:04:15Speaker 00

  There you go, yeah.

• 1:04:16Jason Calacanis?

  It's super bonkers. Oh, we got a net. Here we go.

• 1:04:18Speaker 00

  There we go.

• 1:04:18Jason Calacanis?

  Yeah. So I don't know. This is China. Yeah.

• 1:04:21Speaker 00

  I just was thinking of like.

• 1:04:22Jason Calacanis?

  They have these sleds. You see the sleds?

• 1:04:24Speaker 00

  Yeah. When I was a kid, like the old guys who were always like bent over and bad backs and knees, they were always like the dock, the dock workers. That was the hardest job when I was a kid, I thought.

• 1:04:34Jason Calacanis?

  And you, you think about what they're building out in China, you know, they have to get so much stuff off that island 24 hours a day that I just don't think humans can compete with the demand they have. So humans will be supervising, human in the loop, obviously still got to supervise this stuff. But man, they are, they make our ports look ridiculous. All right, let's go off duty. What do we got?

• 1:04:55Speaker 00

  In an appearance this week on the Ezra Klein Show, I've got to hear the doc, at Jensen Huang of Nvidia, he said, "It doesn't matter if kids can't do basic math anymore because maybe those skills don't matter as much in the future." And then he told Ezra Klein that he doesn't know his own address. Can we roll, can we roll this clip?

• 1:05:14Speaker 05

  I'm trying to, try to get a kid to do long division right now. You know, the multiplication table is starting to be forgotten. Doing square roots, my goodness. I mean, it's just basic math is, is being forgotten. Does it matter? That's my question for you. Yeah, I don't think it does. I don't think it does. But. But there must be some set of skills that matter. Oh, yeah, yeah, yeah. But maybe not those. We're going to discover new ones. Just maybe not those. I actually don't know my address. And I, and every. I don't really believe that to be true. It's, it's completely true. And Janine will tell you, and Lori will tell you. One day I had to pump gas, and this was a few years ago, and they needed my, my zip code.

• 1:06:00Speaker 05

  And I panicked. I didn't know my zip code. I had this exact thing. I don't know my telephone number, but. I had that happen. I forget these things.

• 1:06:09Speaker 05

  Okay. I can live with it.

• 1:06:10Speaker 00

  I'm, I'm, I'm, I feel like I'm a little with Ezra Klein. You really don't know your address. You really don't know your address.

• 1:06:16Jason Calacanis?

  I know my address, but I literally, he may also be suffering from, you know, having four homes or three homes. But I have had times where I forgot my ski house address and I have to look it up. Or certainly, if you ask me what my zip code was at the ski house, I don't know it off the top of my head. I do know at the ranch now. I don't know at my office. And I have forgotten my phone number. So I think what's happening is certain things are atrophying because you don't have hand speed anymore. The act of dialing a phone number reinforces it every time. But if you have everything, like I forgot my wife's phone number the other day, had to look it up. And I'm like, gosh, yeah, we had the same phone numbers our whole relationship over 20 years. And we, I'm forgetting our, both of our phone

• 1:06:58Jason Calacanis?

  numbers. I, I would look at this and the math thing as calligraphy, as handwriting, you know, cursive.

• 1:07:07Speaker 00

  Cursive, right, yeah.

• 1:07:08Jason Calacanis?

  Yeah. So I am, are we, is it necessary for us to learn handwriting and cursive? Is that going to be a skill that's critically important for my kids? I don't know. I still think we should teach it to them. I still think we should still teach them the basic math things. I think Jensen is struggling with that and doing a thought provoking question. I don't think he's saying get rid of all math, get rid of all, or I'm not saying get rid of all penmanship. I like the idea of people having great penmanship. And I can tell you, young kids do not know math. They do not know penmanship. That's why I'm in love with the Montessori educational system, which really reinforces a lot of this like hands-on stuff and less screens. And you can always learn the screen stuff. So I think

• 1:07:50Jason Calacanis?

  parents should do Montessori type things where the kids are interacting with each other, doing projects, physical stuff. Get that foundation. And then, you know, for the last hour of the day, you can go online and do stuff. But you know, they, they do, I mentioned this study, I think on All In, there was a study of brain scans for people who used AI to write their paper, people who used search engines and were cutting and pasting, and then people who were, you know, raw dogging it with a pen and paper or typing it, like, you know, where processor, brain activity was just like zero, like 5%, 50%, and then like boom. And here it is. I guess this is the study here. And there was actually pictures

• 1:08:34Jason Calacanis?

  of the brain scans in this, in this thing. So if you scroll down, you might even be able to see that. There you go. And so they were looking at these, and you see the LLM, you see search, you see the brain activity, dynamic direct transfer function EEG analysis of alpha band for groups. I think that's the technology. LLM, search engine, brain only, including p-values, show significance from moderately significant to highly significant. In other words, your brain is firing on all cylinders and we're just going to atrophy. By the way, we already have an analogy for this. You sit at a table at work, click clacky, click clacky, your vitamin D goes to shit, as we talked about. You get fat, you get a

• 1:09:18Jason Calacanis?

  big tire around your waist, and you feel depressed. Why? Because you need to go out and run and get, and then if you just work and then go home and Netflix and chill, now you're in double situation because you didn't go out, you didn't have friends, you didn't laugh, you didn't socialize. This is why so much of the country is on SSRIs and trying to solve for anxiety, depression, sadness, melancholy, whatever it happens to be, however you want to describe it. It's like, they're like, oh, I got to take a pill because I have a chemical imbalance. Chemical imbalance is probably because you're not getting enough sun. You're not sleeping. You're not doing socialization. You're not meditating and you're not doing physical activity. And I guarantee you, I work on this with my kids, I work on it with myself. I say, if I'm feeling out of sorts, how did I sleep last night?

• 1:10:04Jason Calacanis?

  How's my diet? How's my exercise? How's my socialization? And how's my meditation? The fifth one, maybe just might be me virtue signaling or whatever, but I've had a good, you know, experience with meditation. Just, I can tell you, if you're listening to me, you feel down and out and you feel melancholy? Just please do all five things I've said for three days in a row.

• 1:10:24Speaker 00

  Yeah.

• 1:10:24Jason Calacanis?

  Meet with your friends for dinner or lunch. Go do a physical activity with your friends. Go play pickleball, padel, hike, anything in the sun. Eat a salad, some protein, no fried food, no sugar. Man, you, you, it's gonna turn around in 72 hours.

• 1:10:40Speaker 00

  Yeah, I, I mean, I, I, I have struggled with depression and I, I, I got off all the SSRIs or whatever, but that, it is, it is like when you're, when you're inside and you're feeling blue and you're down and you're depressed, the last thing you want to do is go out for like a walk in the sun. You're just like, oh, it's not gonna make me feel better. I don't want to. That's the thing.

• 1:10:57Jason Calacanis?

  It's resistance.

• 1:10:58Speaker 00

  You, you're, you're gonna reject it at first, but then you go outside, you just see, just seeing visually other people, being outside, fresh air.

• 1:11:08Jason Calacanis?

  I could tell the difference in you since you got your new dog.

• 1:11:11Speaker 00

  Yeah.

• 1:11:11Jason Calacanis?

  You get a new dog, you, you have no choice but to do two walks a day and somebody's gonna come over and be like, oh my God, your dog's so cute. And then you're gonna talk to a human being. That's why I brought everybody back to the office, not because I'm like, I want to be a tyrant and have everybody chained to a desk, because I was getting weird. Everybody's getting weird by not going out. And I'm literally like moving to get closer to our office and moving our office closer to me.

• 1:11:34Speaker 00

  Yeah.

• 1:11:35Jason Calacanis?

  Because I want to be, you know, I'm 45 minutes from the office or an hour, like it's a little bit when you have a ranch, you're pretty far away. I want to be able to just like walk to the office. Like that's my ultimate goal, walk from the office.

• 1:11:46Speaker 00

  Truthfully.

• 1:11:46Jason Calacanis?

  Or ride a bicycle.

• 1:11:48Speaker 00

  We're gonna have to be at the, yeah, we're gonna have to be at the Saltlick. There's not as many options out there.

• 1:11:52Jason Calacanis?

  Well, no, no, no, I'm gonna, I'm gonna move closer to the city.

• 1:11:54Speaker 00

  Oh, yeah, yeah.

• 1:11:55Jason Calacanis?

  In the city, I think, and then keep the ranch for the weekends.

• 1:11:57Speaker 00

  Uh, so Sydney Sweeney, of course, she's in that, that, that sports gambling, I believe it's for a sports gambling app where she's

• 1:12:04Jason Calacanis?

  Yeah.

• 1:12:04Speaker 00

  almost nude, you know, it's very provocative. She's covering herself with the sports memorabilia or whatever. And, and a lot of women athletes got a little upset where they were like, listen, she's sexualizing being a women athlete and we don't like that. And we're just, we're just like men competing and stop making it sexual. So it's touched off a whole other round of people condemning Sydney Sweeney and people being back and forth about what, what does her body mean and what side of the political wars she on? And then we saw that you had tweeted your new take on what Nike's new campaign should be featuring Miss Sweeney.

• 1:12:40Jason Calacanis?

  Yeah, so we had, had this funny conversation about Nike. Nike is like, got kicked out of the

• 1:12:47Speaker 00

  Right, the Fortune 500, yeah.

• 1:12:49Jason Calacanis?

  No, 100.

• 1:12:50Speaker 00

  Oh, the 100, yeah, you're right.

• 1:12:51Jason Calacanis?

  And Palo Alto Networks went in and I was like, you know, they need to do something and shake things up and, you know, you got this, just do it. I think you gotta like go a little counter programming. You gotta get somebody who's youthful and you, you gotta kind of confront people and shake things up, right? Kind of like we were just talking about with, you know, if you're feeling melancholy in this generation, that's terminally online, you gotta fight to go outside and do something. Like challenge that group because I believe part of the issue with Nike is, and also with restaurants, also with spirits companies is young people do not go out. They stay home. They believe that they've had a play date when they're young or they believe they've talked to their friends when they do it digitally.

• 1:13:35Jason Calacanis?

  So my daughters, I'm like, hey, let's do something with your friends. And they're like, oh, you know, I, I, I had a play date with him yesterday. I'm like, oh, they were here or you were there? And they're like, no, no, we played, you know, Minecraft for two hours. And I'm like, oh, you were on your iPads. That doesn't count. I want you guys in the swimming pool, on the ranch, going to a hike, something out in the world. So on All In, I said like, you know, come up with something like really to challenge people, do it or don't. We don't give an F. And they were all mocking me, et cetera. But I was like, wait a second, I'm a very good brander. I think this branding, I have never heard anybody come up with a better slogan for Nike that was challenging to the audience.

• 1:14:16Speaker 00

  Hmm.

• 1:14:17Jason Calacanis?

  Um, and then I was like, well, you know, let me see if I can create some ads. So I saw the Sydney Sweeney thing and I was like, well, what if you put, I, I first started by using Grok to put these ads like on trailers or like, you know, on subways or whatever.

• 1:14:30Speaker 00

  Yeah.

• 1:14:30Jason Calacanis?

  And then I was like, put Sydney Sweeney in here. And like some tools won't do that, but Grok was like, yes, sir.

• 1:14:36Speaker 00

  Do it, yeah.

• 1:14:37Jason Calacanis?

  Look at this, do it or don't. We don't give a fuck. And then if you just put a star in there for the you and like, yeah, just do it, whatever, Nike. And, you know, she's looking at you like, hey, I'm doing it, you do it. I don't care if you do it or not, I'm doing it, right? Show the next one. It made like a video of this where the buses pulling out.

• 1:14:57Speaker 00

  What it would look like in New York, on the streets of New York, yeah.

• 1:15:00Jason Calacanis?

  You and I could run an ad agency and get paid a million dollars per campaign.

• 1:15:04Speaker 00

  Let's do it.

• 1:15:05Jason Calacanis?

  Because I'm good at this. Oh, look, and then they made her like into a video or whatever.

• 1:15:09Speaker 00

  Like Harry Potter, yeah.

• 1:15:11Jason Calacanis?

  I mean, AI is sick right now. Do it or don't. We don't give an F. Uh, so anyway, rate my, uh, because you're very objective here.

• 1:15:19Speaker 00

  Ah, yeah, of course.

• 1:15:20Jason Calacanis?

  Yeah, well, and what do you think? Is it too spicy?

• 1:15:23Speaker 00

  Uh, no, I, I don't. I, I, I think spicy, you have to be spicy in 2026. It's the only way to break through. I mean, I, I feel like what we're seeing with Nike is it's less anything to do with Nike, you know, people are always trying to diagnose like, oh, Nike did a brand deal with this person or they said this or it's that. I, I don't think it has anything to do with anything specific they've done. I think Nike used to be part of this monoculture that doesn't exist anymore. Like when I was in high school, you were either like, you were into Nike or you were into Adidas and that was like it. Maybe there were like a couple Reebok kids or somebody had like a British Knights shoe or whatever, but there weren't, there weren't that many options. You sort of had like two or three acceptable options and you picked one. That just doesn't exist anymore. Now there's like so many, everybody's in their own little niche. Everybody has their own style.

• 1:16:08Speaker 00

  I don't know what you do if you're Nike to cut through that, but I do think this would grab people's attention, especially the Sydney, like you picked the exact right celebrity for this ad because

• 1:16:20Jason Calacanis?

  At this time.

• 1:16:21Speaker 00

  Every, everybody's really fixated on her. Everybody has a take on her and that, that's what I think people miss is that a divisive figure is like better, like somebody everybody loves is great, but somebody who everybody has an opinion on, good or bad, for marketing like this, I think is almost better. Like they're gonna grab everybody's, it's like putting a Kardashian in your ad. Like they have lots of fans, but they also have a lot of people that are gonna see that and get like a little riled up and they're gonna pay extra attention because they don't like the Kardashians. And I think you gotta, you have to play in that game now in 2026.

• 1:16:52Jason Calacanis?

  Uh, by the way, and just everybody giving her a hard time, I'm Greek, gymnos, G Y M N O S. This is the ancient Greek adjective meaning naked, nude, unclothed. It is the root of the word gymnasium or gym. In the Olympics.

• 1:17:08Speaker 00

  Cause they were, yeah, yeah.

• 1:17:09Jason Calacanis?

  They were naked in the Olympics or lightly dressed, same thing with gladiators. And they were celebrated for the ideal beauty of their bodies. They were essentially sexualized, if you want to use that, or, you know, if you don't want to use sexualization, they were a, um, an ideal.

• 1:17:31Speaker 00

  Correct.

• 1:17:31Jason Calacanis?

  And that was, and it conveyed that you were disciplined and that you were ready to serve in the military.

• 1:17:39Speaker 00

  Sure.

• 1:17:39Jason Calacanis?

  So giving like her a hard time when, I, I don't know who gave her a hard time, but I, am I crazy or does Sports Illustrated do a nude?

• 1:17:47Speaker 00

  A lot, this came up a lot. That Sports Illustrated, they, they do the swimsuit issue every year and then they do the body issue, which is athletes, male and female, naked. That's the whole idea is like they shoot, come up with clever ways to obscure their naughty bits, but you know, they shoot the athletes without their clothes on. Uh, so a lot of people were saying that like, well, it's already pretty sexualized. And like, look, I get when it's like, you know, 18 year old gymnasts and dudes are being creepy about like their little outfits or whatever, like I get that that's creepy and wrong, but

• 1:18:18Jason Calacanis?

  Sure, yes.

• 1:18:19Speaker 00

  Yeah, the Sydney Sweeney ad, you know, just like her holding footballs in front of her chest and be like, go bet on this app. Like, how can you be bothered by like, who cares?

• 1:18:27Jason Calacanis?

  It sounds to me like what they're upset about is that she's not an athlete and she did it and took the bag and secured the bag.

• 1:18:34Speaker 00

  That idea, I think it's the whole, I, I mean, I'm sure that is part of it, but it, it is also like

• 1:18:39Jason Calacanis?

  They're jealous that she's getting 10, how much did she get in this company?

• 1:18:42Speaker 00

  Oh, that's a good, that's a good, I don't, I haven't seen that information, but we can certainly

• 1:18:46Jason Calacanis?

  Because I think she could like, honestly, she's such a force of nature right now in terms of like the zeitgeist, that if I was running Nike, I would literally go to her and say, I'll give you 1% of the equity in this company for a lifetime deal.

• 1:18:58Speaker 00

  It was Novig.

• 1:18:59Jason Calacanis?

  I'll also give you $10 million a year in cash, but I'll give you 1% ownership. You vest it over the next 40 years of your life.

• 1:19:06Speaker 00

  Oh.

• 1:19:06Jason Calacanis?

  Like every year.

• 1:19:07Speaker 00

  Uh, uh, I, I believe she is an equity partner. They're, they're not disclosing the deal, but it does sound like she's got some, uh, some, some, she's got, she's getting a little taste of Novig, this platform, it sounds like.

• 1:19:21Jason Calacanis?

  Uh, actress Sydney Sweeney. This is what celebrities should be doing. If you're a celebrity who can

• 1:19:24Speaker 00

  Yeah, she partnered with

• 1:19:25Jason Calacanis?

  Who can drive.

• 1:19:26Speaker 00

  Sports prediction market startup, Novig is an equity holder and strategic partner. That's what they're calling her.

• 1:19:32Jason Calacanis?

  If you have a massive following, like Kim Kardashian, like her, you should be an equity owner. You should create your own brands or take existing brands that you don't have an interest in starting and just say, hey, I'll do this for 10 years. I want 10% every year I do one. But this is completely hypocritical. Serena Williams, Venus Williams, Dwight Howard, Chris Paul, Karl Anthony Towns, everybody has done this ESPN thing. So I don't, I don't understand the controversy, but okay. Um, sure, whatever. I mean, it was okay for the Greeks. I mean, we're the greatest culture in the history of humanity, so.

• 1:20:10Speaker 00

  Yeah, I, I, I mean, I, I guess, I guess I could, I could sort of see the complaints, but it's also, you have to know at this point, if you are going to make a complaint about a Sydney Sweeney ad, you're just feeding the beast. Like you're just, you're just drawing more attention to it. She's now making a lot of money off of the, this, like being the controversial lady in ads is like obviously paying off hugely for her. So if you're not a fan of it, it's Streisand, uh, yeah, you know, effect at this point. Like just stop talking about it. It, the more obsessed people become with her, uh, the, the more she's gonna make, make that money. Here, pull that quote back up, Jacob. You just had a good quote I want to read. Pull that article back up.

• 1:20:53Speaker 00

  Uh, yeah, British sprinter Amy Hunt was one of the people who complained, Sydney Sweeney, this is what women in sports look like. Uh, muscles, hard work, blood, sweat and tears. That's, that's

• 1:21:05Jason Calacanis?

  Okay.

• 1:21:05Speaker 00

  So she's saying, yeah, it's like, uh, Cheesecake version of of women in sports.

• 1:21:12Jason Calacanis?

  Uh, I'm surprised you didn't bring up the, um, trailer for the new Tarantino.

• 1:21:19Speaker 00

  Oh, that it's actually David Fincher. Tarantino wrote it. David Fincher directed.

• 1:21:22Jason Calacanis?

  Yes.

• 1:21:23Speaker 00

  Cliff Booth.

• 1:21:23Jason Calacanis?

  Yeah. What do you think? Looks good?

• 1:21:25Speaker 00

  Looks great. I can't, I can't wait. I mean, I love that character. I love that world that Tarantino created. I was super excited. He wanted to get back. You know, it seems like Tarantino, he does these movies and then he kind of gets tired of them and he's right on to the next thing and he's kind of like losing interest. So the fact that he wanted to come back and write another script about this character set in this world, it's in late seventies Hollywood, which is going to be a very different time and a very different vibe from the original movie. And, uh, you know, Brad Pitt and David Fincher, what, what a duo. Seven, Fight Club, Benjamin Button. I mean, they've, they've made some pretty strong, uh, collaborations. So, yeah.

• 1:22:04Jason Calacanis?

  The Further Adventures of Cliff Booth. I wanted you to play the trailer with the sound off, guys.

• 1:22:08Speaker 00

  Yeah, let's say there we could, we could take a look.

• 1:22:10Jason Calacanis?

  I mean, it looks gorgeous and it looks gritty.

• 1:22:12Speaker 00

  Seeing Fincher bring to Hollywood in the 1970s to like, that's the new Beverly, by the way, uh, my old stomping grounds, uh, Tarantino owns.

• 1:22:20Jason Calacanis?

  Which Tarantino owns and I guess he's now, I guess they're saying Cliff Booth is now a Hollywood fixer 10 years later.

• 1:22:27Speaker 00

  Right. He comes back. He comes back to Hollywood. He's no longer working for Rick Dalton because he says he Dalton got too fat for him to stunt man for him anymore.

• 1:22:35Jason Calacanis?

  What a dig to, what a dig to Leo.

• 1:22:38Speaker 00

  A little DiCaprio dig in there. Although there is still a lot of rumors that DiCaprio showed up for a day and that we may get a little like cameo Rick Dalton appearance. I've.

• 1:22:49Jason Calacanis?

  I mean, this thing, he should be building the Tarantino universe as his like legacy. Just take all 10 movies and like, let's get a Steve Buscemi 20 years after Reservoir Dogs story. I don't know if Steve Buscemi died.

• 1:23:04Speaker 00

  Yeah, Steve Buscemi does sadly, uh, but there, there is, there is, the early ones all had a lot of connective tissue. Like they mentioned the Vega bro, like Vincent Vega is obviously Travolta in Pulp Fiction, but there's a Vega brother mentioned in, I think Vic Vega is in Reservoir Dogs. That's Michael Madsen. And then there were Red Apple Cigarettes that used to show up in all the movies. And so he used to kind of do that where like they were all happening in the same alternate reality. He kind of seemed to get tired of that over a while, but I, I agree. He should do a movie that pulls together all these worlds.

• 1:23:35Jason Calacanis?

  This is my dream interview for, uh, this is my dream interview for the All In Summit. I, I put some feelers out.

• 1:23:40Speaker 00

  Oh, QT?

• 1:23:41Jason Calacanis?

  Yeah. I really want to interview QT. I think he's just tremendous.

• 1:23:45Speaker 00

  He's living in Israel now. That might make it a little.

• 1:23:47Jason Calacanis?

  I think half the time or something. Yeah. I mean, raising his family. Good for him. Um, I, I think that's going to be great. I love this because it's got a 1970s Mustang Fastback, which was my first car. I had a Mustang Grande in mustard gold. You can pull it up. 1970 Mustang Gold. Um, uh, yeah, uh, Grande. If you look at that 1970s Mustang Grande, 1970s Mustang Grande. I bought it for $600 and it was in mustard gold. And what made it really interesting as a Grande was like the fancy one. That's a vinyl roof. So if you click on the black one on the side, I had a black vinyl roof on this thing.

• 1:24:31Jason Calacanis?

  351 Cleveland, and that's the brown one. You find a black one in there at some point. There it is.

• 1:24:35Speaker 00

  There it is.

• 1:24:36Jason Calacanis?

  That was, no, that's like, uh, not a 1970, but anyway, the 1970 is like a longer front. It is crazy. Like this thing when you would hit the gas, it's the one, fourth, third one down on the right. Yeah, there you go. That's the one. Look at this thing. It is like a shark and it is a beast. It's literally two thirds front engine. 357 Cleveland, 351 Cleveland, I think was the designation. And I put a four barrel carburetor, got literally five miles to the gallon. This thing roared and I almost died and I was coming on the Belt Park where I came around a turn. I hear a crack, like a crack and a grinding. I pull off the Belt Park where I'm Brooklyn.

• 1:25:16Jason Calacanis?

  I pull into a spot. I look under it and the, uh, the, the suspension bars and the axle for the front thing is cracked. Right as I park and I look at it, it goes bang and it just breaks in half.

• 1:25:28Speaker 00

  Oh, man.

• 1:25:29Jason Calacanis?

  The thing is on the ground. I, I walk home. I come back two days later. It's been stripped.

• 1:25:35Speaker 00

  Yeah.

• 1:25:36Jason Calacanis?

  There was nothing left of it. It's gone in Brooklyn.

• 1:25:38Speaker 00

  In the seventies, yeah.

• 1:25:41Jason Calacanis?

  Man, I wish I had like on the ranch, like a, like a barn dough so I could start collecting these again. All right. Another amazing episode of This Week in Startups, February 25th. We'll see you next time. Bye, bye.

• 1:25:52Speaker 00

  Bye, buddy.