Spycraft in SaaS, Rabbit's Comeback, and Startup Pitch Madness | E2106

This Week in Startups is brought to you by… Kyte - TWIST Listeners: Go to https://kyte.com/ and download the Kyte app today. Use code JASON to save 10% on your first rental. Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months. Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist Today's show: Jason and Alex go deep into the shocking new details about the Rippling vs. Deel corporate espionage scandal—where a self-admitted spy fed confidential product roadmaps and sales data to a rival CEO for €5K/month. Plus, they interview Rabbit CEO Jesse Lyu about their bold comeback with their new "Intern" AI agent that builds entire apps from a single prompt - Jason calls it a breakthrough. And we kick off Pitch Madness with fierce Founder Friday pitch battles featuring AI podcast tools and women's sports communities. Spy drama, next-gen tech, and raw founder energy—don't miss it. Timestamps: (0:00) Teaser: Rippling vs. Deel Espionage Case(1:46) Podcast updates and listener engagement(2:31) Job openings at Launch and This Week in Startups(4:19) Rippling and Deel lawsuit details and espionage activities(9:58) Kyte - TWIST Listeners: Go to https://kyte.com/ and download the Kyte app today. Use code JASON to save 10% on your first rental.(11:31) Stolen information and the aftermath of the espionage case(16:21) Corporate espionage vs. corporate intelligence debate(19:38) Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months.(23:07) Board independence, whistleblower protections, and CEO behavior(25:10) Y Combinator's culture of rule bending(28:41) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:02) Jesse Lu's YC experience and launch of Rabbit(34:48) Navigating the hype cycle as a founder and RabbitOS demo(45:02) Estate management and technology with Rabbit(48:39) Conclusion of interview with Jesse Lu(48:51) Launching Founder Friday pitch offs(50:43) Pitch: Snipd - AI-powered podcast app(53:29) Pitch: MedSimple - Medical education platform(57:10) Pitch: Trova - Workplace connection platform(58:45) Pitch: Osprey - Community for women in sports and entertainment(1:05:30) Analysis and decision: MedSimple vs Snipped and Osprey vs Trova(1:09:23) Discussion on Osprey's business model(1:10:33) Tips for improving pitch presentations(1:11:02) Announcement of Twist 500 competition(1:11:46) Closing remarks and social media call to action Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Links from the show: Rabbit website: https://www.rabbit.tech/?srsltid=AfmBOorumixyS_kXbNPL2tDqLBsI08B4Hs3xUSZkOLS2nlKsatop5VG2 Follow Jesse:X: https://x.com/jessechenglyu LinkedIn: https://www.linkedin.com/in/jesselyu/ Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (9:58) Kyte - TWIST Listeners: Go to https://kyte.com/ and download the Kyte app today. Use code JASON to save 10% on your first rental. (19:38) Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months. (28:41) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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

• 0:00Jason Calacanis?

  I provided Alex, CEO of Deal, with a lot of Rippling confidential information, including Rippling's product roadmap, which indicated where Rippling was currently providing services and where it sought to expand. I also passed on the deal, quote, "battle card", a document that instructed Rippling's sales force on what arguments to make to potential customers about the superiority of Rippling's products over deals. I also provided Alex with many of Rippling's sales leads. Jason, in terms of like the crown jewels, right? If you're a reporter, the crown jewels is getting someone's income statement, right? But if you're a competing SaaS provider, this is what you want.

• 0:36Speaker 01

  This Week in Startups is brought to you by Kite. Looking to get out of the city? Rent a car with Kite. Kite delivers rental cars to your door. No counter, no lines, no hassle. Download the Kite app today and use code JASON to save 10% on your first rental. Atlassian. From MVP to IPO, Atlassian for startups provides your team the right tools to plan, track, and collaborate on work. Head to atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months. And lemon.io. Get access to lemon hire, a platform with more than 80,000 pre-vetted engineers that you can interview within 48 hours. Get $2,000 off your first hire at lemon.io/hire today.

• 1:15Jason Calacanis?

  Hey, everybody. Welcome back to This Week in Startups. I'm Jason Calacanis. We do the show three days a week, Monday, Wednesday, Friday. We do it live. When you watch the live stream with Alex and I, you get to get about, I don't know, 20, 30 minutes more content, a little bit of bantering as we record the show, and then those live feeds go away. We will be adding images onto the live feed of our sponsors for the day's program. So team, let's make sure we do that. You can follow along on the docket. thisweekinstartups.com/docket. If you go there, you'll watch Alex, Lon, and the team build out the docket, the stories we're going to talk about, and you can post comments there. And it's just a fun way to go along the show. In the show notes, we're doing really great show notes.

• 1:58Jason Calacanis?

  We're doing chapters, I hope, in the, for the podcast now. We're just trying to get our podcast game, you know, just really chef's kiss, if you will.

• 2:09Speaker 02

  Doing quite a lot of work on it. Of course, feedback's always welcome. So [email protected] If you have notes about things we can improve. But yeah, you can always drop comments in the docket. I see and read every single comment people drop in. So if you want to reach me directly, please do so. Context, things we've missed, the stories we might want to take a look at. We are always listening to everyone out there who's a part of the, I don't know, Jason Twist Gang, maybe.

• 2:31Jason Calacanis?

  Yeah, the whole, the whole group. And we also are hiring. We're hiring. If you're interested in being the venture business, we are hiring in Austin. That's the starting point. If you're out of school, maybe a couple of years' experience, or you're looking to do a career change. Basically, what does a researcher do? They research topics for launch, our venture firm, which produces two programs, Founding University, the Launch Accelerator, and of course, we do this week in startups. The researchers are just the critical role. They meet and sort through 20,000 applications for funding a year. We meet with probably 20% of those, about 4,000 of them, 5,000 of them. We put them into our database. We track those companies, the ones with the best teams, and

• 3:13Jason Calacanis?

  maybe the best execution as we see it. Just a great way for you if you wanted to break in. And we're also hiring. We're hiring another video editor here. We need somebody who is good at shorts. We're trying to figure out shorts, but I'll be honest, we've never gotten it right. We're kind of boomers. Producer Nick, who went over to All In, was great at shorts, but I don't have him anymore. I need, I think I need a TikTok native. So if you're a TikTok native, go ahead and pull up that link if somebody can. Let me put it over here.

• 3:45Speaker 02

  I got you.

• 3:46Jason Calacanis?

  Oh, you got it? Okay. Pull up the link. It's a job description on LinkedIn. You can go find it if you follow the launch account there. And this should be in the office with me, Lon, Chris, and the team. We have our just podcast producer editor. And yeah, entry level job. But if you have more experience, yeah, it could go up from there. So if you're an entry level and you're just doing TikTok on your own, great. If you want to, if you got a couple years' experience, that's okay, too. We just need somebody who's native. That's what we're doing TikTok shorts here and YouTube shorts. We're trying to figure it out. Okay.

• 4:17Speaker 02

  All right.

• 4:18Jason Calacanis?

  Big docket, Ted.

• 4:19Speaker 02

  Let's get to work. Things not to do. You should go out and learn things. You should teach yourself new skills, but if anyone ever offers to pay you, Jason, a couple of thousand dollars a month to learn how to be a spy, say no. So the news is that we have new information about the Rippling Deal suit. As everyone I'm sure recalls, Rippling and Deal are both Jason outsourced HR providers. They'll help you make sure your employees are paid both in your home country and abroad. They're both large. They're both unicorns. They're both well known. So when Rippling said that Deal had put a spy essentially inside of its operations to exfiltrate information, it was a pretty big darn deal. Things died down for a bit. We waited for more information and now we have it.

• 5:04Speaker 02

  The spy, the mole, has essentially come clean and put together a large, almost confessional that we have.

• 5:10Jason Calacanis?

  He got pinched.

• 5:11Speaker 02

  Well, he definitely got pinched, but he was still considering. Well, we'll get into the, the why he decided to come clean towards the end here, but I want to walk people through what we've learned today, Jason, if that's okay.

• 5:23Jason Calacanis?

  Yes, we should totally do this because corporate espionage is incredibly entertaining. Two high growth companies in a spat, both of which apparently now have, you know, let's call it sharp elbowed founders, right? Parker Conrad had an SEC violation against him. I'm kind of like on the periphery of it because I like Parker Conrad. I think he's like a cool founder and he's like a super aggressive founder who made a couple of mistakes, got an SEC claim against him, whatever. Um, you know, it happens. I'm, I'm not condoning it, but I'm also not saying young people who make mistakes should. Like he didn't murder anybody. Let's leave it at that. But Parker Conrad, you know, like pretty aggressive founder with SEC violation is now up against the Deal founder.

• 6:07Speaker 02

  Yep.

• 6:09Jason Calacanis?

  Who hired a literal Rippling employee to spy on the company and has been caught with his hand in the cookie jar.

• 6:19Speaker 02

  Yes.

• 6:19Jason Calacanis?

  They're both, I think, YC companies.

• 6:23Jason Calacanis?

  And this also speaks to a larger Silicon Valley and specifically Y Combinator rule breaking ethos.

• 6:34Speaker 02

  So Rippling was the winter 17 cohort and Deal was the winter 19 cohort. So a little bit ago, but both companies went through YC, well-known founders. And I'm going to show some screenshots.

• 6:47Jason Calacanis?

  Before we do that, I also want to put out a disclaimer. I have exposure to both companies through venture funds I'm in. And I think one of our companies, I won't say which, was acquired by one of the companies. I don't want to, you know, just create this, but you know, we invest in 450 companies. Sometimes a company, we've invested in 450 companies over 12 years. Sometimes a company gets acquired, we wind up with some shares. None of it is like enough for me to have like a horse in the race. None of it is, it's all de minimis in terms of its impact on me. It wouldn't affect my coverage of this, but as we say in the business, no conflict, no interest. I'm an investor in 450 companies and I'm an investor in 20 venture capital firms. Some of them are higher profile than others and you would know them and they have it. Okay.

• 7:30Jason Calacanis?

  So let's get to this case because in Ireland, the person confessed in an Ireland court for some reason.

• 7:37Speaker 02

  Because they were out of the Irish Rippling office, if memory serves. So this was a person based in Europe. So I want to start with how much money this person was paid. So Jason, here is two kind of combined screenshots from the release. And I'm going to go ahead and sportscast a bit here for folks who are on the audio version.

• 7:58Jason Calacanis?

  This is a news story. This is a deposition. This is a court document.

• 8:03Speaker 02

  Court filing from the High Court of Ireland.

• 8:05Jason Calacanis?

  Okay.

• 8:05Speaker 02

  But it's from the voice of the alleged spy. So he's, he's talking.

• 8:10Jason Calacanis?

  Thank you for adding alleged.

• 8:12Speaker 02

  Oh, yeah.

• 8:13Jason Calacanis?

  Is it alleged if he confessed?

• 8:15Speaker 02

  Uh, I think it's alleged until someone is convicted because I would like to avoid extraneous legal risk.

• 8:21Jason Calacanis?

  What about admitted spy?

• 8:24Speaker 02

  Self, self-admitted spy, alleged corporate mole.

• 8:29Jason Calacanis?

  Okay, go.

• 8:31Speaker 02

  All right. So he says Alex and Philippe, the founder and his father was also the CFO, said that I would be paid approximately 5,000 euros per month for spying on Rippling for Deal and that I would be paid around the sixth of the month. They established payment terminology. So when he wanted to get paid, he would quote, "Send a picture of a watch to the payment chat" and Philippe would say, "Send that watch to London." Then he would say, "The buyer is happy." I understood this to mean that Alex, the buyer of Rippling's confidential information, was happy with my services and the information I sent. Jason, as far as code speak goes, that sucks, but at least they were trying to obfuscate a little bit, I guess.

• 9:12Jason Calacanis?

  I mean, I don't want to critique spycraft, but here we are. Why not send or hand the person, you know, a thumb drive with tether on it? Like, if you're gonna pick a way to pay somebody, pick the one that human traffickers, money launderers, and terrorists allegedly prefer, allegedly preferred by human traffickers and terrorists everywhere, tether. So they should have just been giving this kid tether on a thumb drive, you know, or dropping a thumb drive to, you know, based on my spy novel and, you know, knowledge, they should have been putting tether on a thumb drive into a Dropbox.

• 9:58Jason Calacanis?

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• 10:41Jason Calacanis?

  I had my car waiting for me at SFO and I avoid waiting around and I had my own car so I could go to all these disparate meetings I had across the Bay Area. You can manage your entire trip in Kite's app, meaning you can avoid waiting around while someone else enters your data into a computer by hand, one slow key stroke at a time. It's like that scene from the movie with the sloth at the DMV. Anyway, Kite doesn't do extra fees. It operates in large cities around the United States and I've used it in both LA and San Francisco and love it. Here's your call to action. Download the Kite app or book online at K Y T E dot com. That's K Y T E dot com. Go ahead and download the app now so you have it ready to go. Use the code JASON at checkout. You get 10%

• 11:23Jason Calacanis?

  off your first rental, which could be significant. Don't forget to use the code JASON. Download the app K Y T E dot com right now. So here's the next quote. What is this?

• 11:31Speaker 02

  This is what was actually taken. So, uh, the spy continues.

• 11:35Jason Calacanis?

  Let's read the quote here. Yeah.

• 11:36Speaker 02

  I provided Alex, CEO of Deal, with a lot of Rippling confidential information, including Rippling's product roadmap, which indicated where Rippling was currently providing services and where it sought to expand. I also passed on the deal, quote, "battle card," a document that instructed Rippling's sales force on what arguments to make to potential customers about the superiority of Rippling's products over deals. I also provided Alex with many of Rippling's sales leads. Jason, in terms of like the crown jewels, right? If you're a reporter, the crown jewels is getting someone's income statement, right? But if you're a competing SaaS provider, this is what you want.

• 12:12Jason Calacanis?

  The product roadmap is extremely damaging. Um, if it was accurate, some of it might be obvious, but it would give you the ability to front run announcements. Um, and then it would give you the ability to, um, say to investors or to your team or to your customers. In other words, your constituents. Look, we released these three features. Rippling is just the fast follower. They copy us.

• 12:41Speaker 02

  Right.

• 12:42Jason Calacanis?

  So you could really damage Parker's reputation and Rippling's reputation in this case by making them look like a fast follower when in fact you're, if this is all true, I, I can't imagine that this is.

• 12:59Jason Calacanis?

  To fabricate this would probably be a bigger crime than actually doing the crime, right? Like if you were to say this about Deal and it wasn't true, this person would be in massive slanderous trouble.

• 13:15Speaker 02

  It's either truth or the biggest defamation case in the history of mankind. So yes.

• 13:18Jason Calacanis?

  Okay, great. So here we go.

• 13:21Speaker 02

  So keep in mind that we heard about a honeypot trap that they set up, Jason.

• 13:26Jason Calacanis?

  Yes.

• 13:26Speaker 02

  As it turns out, there's a little bit of commentary on that in the in the notes that we got. And essentially, yes, Alex did ask him to pull that up. And then he did. And then he said, wait, don't do it. It's a trap. And he already had. After he got caught, there was a amazing bit of drama in which the the spy was essentially accosted at the office. So we have that quote about what he did when he got pinched, as Jason said earlier. So on Friday, March 14, 2025. By the way, that's like two and a half weeks ago. I went into the Rippling office.

• 13:57Jason Calacanis?

  Yeah.

• 13:57Speaker 02

  Yeah, believing that I was there to pick up a compliance award from one of my coworkers. An independent solicitor served me with a court order requiring inspection of devices. He lies and says his phone's upstairs. They go up, gets his bag, comes back downstairs. Once we got back upstairs, after retrieving my bag, it started to sink in just how serious this was. I panicked. I went to the bathroom with my phone and performed a factory reset on it, erasing all of its contents, including apps and contacts. I flushed the toilet a couple of times. When I came out, I just wanted to get out of there, started to walk out, was told and warned that I shouldn't do that. And he and then I said, I'll take that risk and left. This matches what Deal alleged in the original suit down to a T. But the wrinkle here is that Deal thought he might have had to, sorry, Rippling thought

• 14:41Speaker 02

  he might have tried to flush his phone. Turns out he was just making some noise to have him pass the time in the bathroom. But I do love that they had to search the pipes by accident because they did. Again, I'm not a spy craft expert here, Jason, but this

• 14:54Jason Calacanis?

  I am. I am a spy craft expert. I people don't know this, but I did spend some time in a couple of agencies. My time is over now. So I can talk a little bit about my time in the Mossad CIA and some other three letter organizations. This is just very low grade spy. If you're gonna do spy craft, you gotta do it at a higher level, folks. You gotta watch Day of the Jacko. You gotta just check out what Mossad is doing, KGB is doing. There's much better corporate espionage techniques. This is just bush league. It's an embarrassment. Disgratia for being a spy. But disgratia.com had an even higher level for not being a great spy. If you're gonna be a spy, I just, I talked about this at the top of the show.

• 15:34Jason Calacanis?

  You should aspire to be an elite spy, be top 1%, top 10%. This is bottom 10%.

• 15:40Speaker 02

  This is bottom decile. This is negative IRR venture returns level crap. Um, I'm gonna run one little quote just before we scoot on. Asif, Deal's in-house lawyer, said he was speaking in a quote, "personal capacity," and that Rippling quote, "have nothing." They suggested flying my family and me to Dubai that night, saying we, quote, "all need a holiday." So they wanted to...

• 16:01Jason Calacanis?

  A holiday. I think it means a place without extradition that is a nice place to live. So, um, I guess we have to ask what happens now. Um, and then maybe talk a little bit about corporate intelligence versus corporate espionage. One is okay, one is not okay. But go ahead. You have something you want to add?

• 16:21Speaker 02

  I, I, I was gonna prognosticate what I think happens, but then I realized that you're actually going into deduction, so I'm gonna hand the baton back to you.

• 16:28Jason Calacanis?

  Okay, so, um, what happens next? Is this criminal? This is criminal. So where's the criminal case? It must be being built by the FBI and the Department of Justice right now? This is happening in Ireland. There's been a confession. This is a legal document. So we have to get, I looked online for this and I couldn't find it. This is moving very quickly in the last two weeks, but I don't think a criminal complaint has been filed yet. So I'm wondering...

• 16:55Speaker 02

  There's a suit between Rippling and Deal about this.

• 16:58Jason Calacanis?

  That's a private civil suit.

• 17:00Speaker 02

  Oh, oh, you referred, is there a, like a federal?

• 17:03Jason Calacanis?

  Criminal corporate espionage stealing, like Waymo versus Uber or Alphabet versus Uber. That was a criminal case when Lindowski was pinched.

• 17:17Speaker 02

  So I, I, I was thinking more in terms of startup and, you know, blowback versus criminal investigations.

• 17:24Jason Calacanis?

  Well, the startup blowback is going to be, he's going to lose his job. The reason he's still in his job and these people are still in their jobs is they don't want to admit guilt. By leaving or resigning. So the board needs time to process this, collect the facts. That's why you don't see things happen immediately. This isn't like he murdered somebody.

• 17:43Speaker 02

  Right.

• 17:44Jason Calacanis?

  These are allegations, so we keep that in mind. You know, it could be possible, it's not probable, that this confession is a CYA by this person. And, you know, it's all a big misunderstanding or something. They hired him as an information consultant. I'm just putting out what the logical defense here would be is we used an expert network. I get offered to be part of expert networks all the time. They pay $5,000 an hour for an expert network. What an expert network does is they obscureify who you're talking to and they say you're talking to somebody who's in the smartphone business.

• 18:19Speaker 02

  Ah, that's great.

• 18:21Jason Calacanis?

  Then you, as somebody working at Apple or HTC or Xiaomi or Google, can talk to five experts in the industry. Now, they might tell you the person hails from Asia or North America or Europe, and they're a senior executive, and then you talk to them, you pay 5,000 to the agency, and that person gets paid 5,000. These expert networks, if you look them up, have been pinched or, you know, they're a gray area of corporate intelligence. So there's corporate intelligence and there's expert networks. So I was going to bring this piece up. Because this is where the gray is in our industry. This, if the allegations are true and the confession is true,

• 19:04Jason Calacanis?

  this is like criminal, straight up criminal. And that means everybody loses their job. Some people go to jail. Some people get suspended sentences. It will be out of deal and, um, Rippling's hands if it becomes a criminal case. They no longer, there's no settlements that occurs. The government decides, oh, here's a CEO who's a billionaire. Here's their lawyer who's, you know, got a $50 million worth of stock. Hmm, chef's kiss. This is a Martha Stewart-like pelt.

• 19:38Jason Calacanis?

  All right. If you're shipping a product or rolling out an update, you're building a company, you need to be organized, right? We know that. Atlassian has exactly what you need to streamline your work and smash your goals. And the Atlassian for startups program is packed with all the tools you need, like Jira, where you can track every task, sprint, and bug. That's the industry standard. Confluence, another industry standard for team collaboration and documentation. And of course, Loom for quick video explainer creation. Now, Loom is really brilliant. My team started using Loom on their own. They started paying for it on their own. Why? They wanted to get credit on the investment team for communicating to me, the general partner of the firm, why they wanted to invest in a company.

• 20:19Jason Calacanis?

  So they would do a Loom where they recorded over a recording of an interview they did with a founder or visiting their website and going through why they want to invest in a company. And this was so great for me. I would be skiing in Japan. I would be on a flight to New York to see my parents. And all of a sudden, I get a notification from one of my team members, "Hey, watch this Loom." And I get the link for the Loom. I click it and then I can put comments at any time. So it's like doing a conference call, but on my time asynchronously. And I can communicate right there on the video. Also included in Atlassian for startups is Compass, Jira Product Discovery, Bitbucket, so much more, all powered by Atlassian Intelligence. That's their built-in AI.

• 21:00Jason Calacanis?

  Atlassian software helps companies like Canva, CloudFlare, and Riving keep growing and keep innovating. Whether you're brainstorming on sticky notes or scaling to the big leads, Atlassian is here to accelerate your startups' growth. Check out Atlassian for startups where eligible startups get up to 50 seats for free for one full year. That is absurdly generous. Why can they be so generous at Atlassian? Because they're the standard. Atlassian is the standard. And they are generous to startups because they were once a startup. I remember meeting them 20 years ago in Australia. What a great company. Head to atlassian.com/startups/twist for complete details. They love, they love, love, love getting FTX. They love getting SBF.

• 21:44Jason Calacanis?

  You know, they love Theranos. They love a billionaire pelt. Because, you know, there's so many kids in jail for selling weed or... Fentanyl or whatever and they get 10 years and then everybody questions, hey, what about the white collar criminal?

• 21:58Speaker 02

  I'm just really curious about how the board handles this from a purely selfish perspective. Failure of governance, failure to, you know, be the, the adults in the room. Can boards catch this sort of thing or is this below their line?

• 22:13Jason Calacanis?

  Nope. When you're on the board, you're meeting four times a year. You might have phone calls or text messages, chats, emails in between those and you're looking at the top level information. A CEO can do all kinds of things. They can absolutely pay their cousin in an LLC to be a consultant and it's buried in the marketing budget and you have no insight into it and you're screwed as a board member. And then that's why whistleblowers exist and that's why whistleblower protections exist. That's why lawsuits and drive by lawyers exist because if something went awry at the Christmas party and somebody, you know, I don't know, streaked at the Christmas party

• 22:57Jason Calacanis?

  across the front lawn of Veronos, somebody is going to report it to HR or somebody's going to email a board member or they're going to email whistleblower at deal.com, right? And there are whistleblower protections in place for this reason. And this is why boards should be have some independence to them. So I wouldn't blame the board here. They did not know this. There's no way they could have known this. If they did know it, they would have resigned and they had a lot at stake.

• 23:23Speaker 02

  They had so much at stake. Yes. Cause this is a really successful company.

• 23:26Jason Calacanis?

  This is the equivalent of somebody's Robin Hood comm or Uber for me or for Chamath, his Slack, right? When something like this happens and you've got a big stake in it, you're like, you know what? My LP stake in this, my personal stake in this, the employee's stake in this, the company's employees, jobs, the customers, they're more important than a CEO who is behaving badly. We've seen this happen when Steve Jobs got ousted, when Uber's founder got ousted. These things do happen and you see a board take action very quickly. And in those cases, those weren't even criminal things. They were gray or Steve Jobs wouldn't listen to anybody, or, you know, Travis was aggressive in interpreting the rules, uh,

• 24:11Jason Calacanis?

  ride sharing, whatever. They will all be out of the company in a couple of weeks. The board will announce an interim CEO, uh, or a board member will take over as interim CEO. The stock will take a 50% hit and then recover.

• 24:28Speaker 02

  Now, one last note about this before we move on to our guest, Jason. You're right. This company will survive. It will. Yes.

• 24:35Jason Calacanis?

  And it deserves to survive. You know, I would say.

• 24:38Speaker 02

  Yeah, but that makes the stumble here, the ridiculousness, the bad behavior, the poor choices, just all the more ridiculous. It's not like there was a founder who was about to like not make payroll and got a little spicy with things. It was like, here's a successful company just being a jerk.

• 24:52Jason Calacanis?

  This is a YC specific thing. There is a punk rock rule breaking culture at YC. They like rule breakers. In fact, they index for rule breakers. They ask people, I think in their application, if there are things they've hacked, et cetera. And so you like a rule breaker. You like somebody who hacks systems. Paul Graham always had an affinity for that. That's why he picked Sam Altman to run it. He liked Sam Altman, you know, maybe doing, you know, on the margins, some things that other people would be more thoughtful about. Oh, you know, I'm just trying to be charitable because I like Sam. Um, and then when Sam was going to be ousted from OpenAI, people said, oh, it's because of his double

• 25:36Jason Calacanis?

  dealings. So here it is. Naughty is the way he framed Paul Graham. Though the most successful founders are usually good people, they tend to have a paratical gleam in their eye. They're not goody two shoe type good. Morally, they care about getting the big questions right, but not about observing.

• 25:54Speaker 02

  Proprieties.

• 25:56Jason Calacanis?

  Proprieties. That's why I used to use the word naughty rather than evil. They delight in breaking rules, but not rules that matter. This quality may be redundant, though. It may be implied by imagination. Sam Altman of Loop is one of the most successful alumni. So we asked him what questions we could put on the Y Combinator application that would help us discover more people like him. He said to ask about a time when they'd hacked something to their advantage hacked in the sense of beating the system, not breaking into computers. So this is the kind of thing where you want people who, you know, are on the margins, willing to do things like this. And then people interpret that and they take it too far.

• 26:40Jason Calacanis?

  Parker Conrad took it too far by creating quote unquote, the script, getting the SEC violation against him. That's the culture of Silicon Valley. It is what it is. Do I disagree with it? No, I don't. I'll be honest, I like a rule breaker myself. I don't like criminal behavior and that's the fine art here is understanding when you're bending rules and when you're breaking rules. If you bend a rule and it's like in everybody's best interest, an example of that would be Airbnb, you're bending a rule, but who benefits? People who can't afford hotel rooms, you know, bottom third of society get to go on a vacation that they couldn't previously do and the hosts get to make money and pay their mortgage. You're doing it for the benefit of those two sides of the marketplace where you know you're doing wrong.

• 27:23Jason Calacanis?

  This is a test for founder is who benefits? What's the Latin word for that?

• 27:28Speaker 02

  It's cui bono.

• 27:29Jason Calacanis?

  Cui bono. Cui bono. Who benefits? In this case, the deal CEO benefits.

• 27:36Speaker 02

  Yeah.

• 27:37Jason Calacanis?

  Who loses? Everybody else.

• 27:39Speaker 02

  Yeah.

• 27:40Jason Calacanis?

  Only person benefiting here is the deal founder. And when you do cui bono on Parker Conrad's transgression, who benefited? He did. The company did. Did the people buying insurance from, what was the company?

• 27:56Speaker 02

  Uh, not, I just, I almost said Ripley. Zenefits, thank you.

• 28:01Jason Calacanis?

  Zenefits benefited and so did the company. That's why the SEC came down. So here's your filter. Who benefits? Let's talk to our, um, a rabbit, our friend from rabbit. He was on the program. I don't know, was it two Januaries or maybe 18 months ago when he was the belle of the ball at CDS?

• 28:21Speaker 02

  Belle of the ball. Yes, we're going to have Jesse from rabbit back on the show. Everyone recalls that the rabbit R1 device landed with a nuclear shock. Everyone was stoked about this device. Reviews were a little bit wrongy, but the company has been hard at work improving both the software and also its digital services. So please welcome back to the show. It's Jesse Low. Jesse.

• 28:42Jason Calacanis?

  Founders, let's be real, let's keep it a buck. Finding great developers is hard. It's like one of the hardest things you have to do in our industry, especially when you're trying to run and scale your startup. But here's the good news. I got a tip that's going to save you time, money and a ton of headaches. You need to check out lemon.io. Lemon.io has thousands of on-demand developers who can help you. They have done all the work to find and vet great developers who are experienced, who are results oriented and who charge competitive rate. Great developers we know are hard to find and integrate into your team. So lemon.io will handle all of that for you.

• 29:24Jason Calacanis?

  They're only going to offer you handpicked developers with at least three years of experience. And if something goes wrong, lemon.io will find you a replacement developer ASAP. A bunch of launch founders have worked with lemon.io and they have told me they've had a great experience. So here's your call to action. Go to lemon.io/twist and find your perfect developer or an entire tech team in 48 hours or less. And TWIST listeners get 15% off the first four weeks. So stop burning money, hire developers smarter. Visit lemon.io/twist. Did you go to YC, Jesse? Are you a rule breaker?

• 30:02Speaker 03

  Actually, I was in YC winter 15 batch all the way back in 2014, 2015. So that was a long time ago.

• 30:10Jason Calacanis?

  Who was running? Was it Paul Graham or Sam?

• 30:12Speaker 03

  It was, it was the last year. I think it was the first year Paul left. It was the first year Sam was running. And with Jessica, Gary Tan, Justin Ken, a bunch of like amazing folks. Michael Sebo, yeah.

• 30:26Jason Calacanis?

  Was it a rule breaking culture? As I was just discussing, break the rules, bend the rules, hacking culture at that time? Was it something they emphasized or was it just like an undercurrent?

• 30:36Speaker 03

  No, it was like super obvious. It was super cool. I think, you know, one interesting first lesson I learned. I still remember today is that the first lesson they told you is that 99% of startup will die. And I think a lot of the young founders, when they first go to the VC, you know, I was back then 22, 23. Um, I was under impression be like, okay, you know, I have so much ambition, I can build this and that. And they're like, if your product doesn't work in the first two weeks, you're die. So that's like, you know, a very different culture than if you just build by yourself. And I, I, I still remember it was a really, really good period of time where we had this office hours.

• 31:18Speaker 03

  But I still remember, uh, office hours for us, I just went to Michael Sebel's house. And he, he was just cooking and he was just making coffees for us. And we were just sitting on his counter and, you know, talking about the, the project progress. And obviously, you know, see Sam and other people running back and forth. Um, and it was like very intense, I would say, two, three weeks of preparing for that. Uh, you know, the final showcase, the, the final pitch, which I, I believe each company got like two, three minutes, really just. Yeah, it's very short. It was very, very short. Um, but you got to learn a lot of like, you know, other ideas, other people are building. And it was super normal. You have probably like, I would say 20% of people, they completely pivoted by the time they graduate. Right.

• 32:02Speaker 03

  Which is good, you know, um, it was a good time. Yeah.

• 32:06Jason Calacanis?

  So you launched the rabbit. We'll pull up a picture of it here. It got a lot of attention because you hit it perfectly timing wise. Everybody was really enamored by L L Ms and everybody loves hardware and everybody loves new hardware. At the time you launched, you had, uh, the human or humane pin, humane pin. You had these two pendant companies that were going to do AI pendants. And you generally had a belief in the world that AI plus device, new fangled device would be an incredible opportunity. You had Sam Altman supposedly doing a new phone with Johnny Ive or a new device and raising money for it. And like all technological hype cycles.

• 32:51Jason Calacanis?

  People get hyped up on it and then people get disillusioned and they go to the trial of despair. And then after that, people come out and they rise again. And you can look at that. Alex will pull up that trial of despair and the, and the, that whole chart. I'm sure you're aware of it. The hype cycle chart kind of thing. Are we in the trial of despair? And how are you getting through that? And let's talk about your progress?

• 33:14Speaker 03

  Yep.

• 33:15Jason Calacanis?

  And what it's like as a founder to go through the hype cycle?

• 33:17Speaker 03

  Um, so first of all, I think, again, we met a year ago, which it was just by the time we're just about to ship.

• 33:25Jason Calacanis?

  Yeah.

• 33:26Speaker 03

  The, the luxury for our team is that we did hardware before. Uh, I think first of all, if you ever done any hardware project, you would completely agree to that chart. And, you know, the timing is very interesting because the core reason for us that we decided to, to build this little orange box, it's not that we don't like our phone. It's that we know this technology is just very disruptive, very new. And there's a lot of things needs to be changed. Right? So I wasn't even, that was quite a different angle than, oh, I just want to build a new phone, or I just want to build a new glass. So I guess for us, it's always that reason that we decided to have this little device to be able to run whatever

• 34:07Speaker 03

  the latest technology that we can put into. We didn't even hype about ourselves in the beginning. If you remember, like, we, we weren't not officially in the CES. We recorded my introduction keynote in a hotel, like lobby or like a meeting room.

• 34:23Jason Calacanis?

  You hacked CES. You were punk rocking it. You were an official presenter. And all of a sudden, you win the product of CES, like the, or you get on a lot of lists as the best product, which I don't think you anticipated. And you hit the timing right. And then your phone rings off the hook, I suppose, investors, partners, et cetera. And then it dies down.

• 34:46Speaker 03

  Yep.

• 34:46Jason Calacanis?

  Humane shuts down. We don't hear about these pendants anymore. Um, the Apple Vision Pro had come out in a similar time. That got hyped up. Nobody's talking about that anymore. So let's talk about your conviction for your idea. Take me through emotionally.

• 35:03Speaker 03

  Yep.

• 35:04Jason Calacanis?

  How you as a founder?

• 35:07Jason Calacanis?

  You know, smooth out the chart we just saw, which is the hype, the trial of disillusionment. And then here we go. You've got to just grind it out.

• 35:14Speaker 03

  Right.

• 35:15Jason Calacanis?

  Did that affect you emotionally to have everybody want to take a meeting and then everybody disappears?

• 35:20Speaker 03

  Uh, no, I mean, uh, you know, again, I would consider uh myself as a veteran. This is not my first time building a company, you know, I've gone through this in my early twenties. And you know, it's just one more time. So I'm mentally fully prepared for this. But obviously, you know, I wasn't uh expecting the hype building up with all this AI product and AI hardware can be that big. So I think, you know, we all learns how to become, you know, quote unquote celebrity. You know, I told my team and myself, uh, what we really should do is just go there and fix things, you know? Because when people talk about it, that means they, they, they care about it, right?

• 36:03Speaker 03

  They want the product to work in their imaginary way. While there, it will be like huge gap between how the AI is ready uh right now versus how human wish the AI will be. But you know, as a company, we're super focused on just, you know, fixing a lot of the things. Uh, you know, in fact, I, I would love to mention in this podcast that uh we actually, I did just did a count. We shipped more than thirty, three zero OTAs.

• 36:31Speaker 02

  Jesse, I want to pick up there. I want to show people this uh Rabbit OS intern thing you guys launched today. Cause I, I feel like it's newsy, so we should at least give it some shrift here. So for folks out there who are curious, this is what it looks like. And Jesse, the first thing that I noticed was, ah, I've seen this before. This reminds me of things that I've seen from OpenAI and I don't know, Google and other people. So I'm curious what the goal here is for Rabbit. Is this a way for you guys to refine your agentic technology? Or is this also an attempt to kind of bull your way into a burgeoning market, which is, you know,

• 37:06Speaker 03

  Yep.

• 37:06Speaker 02

  Consumer AI agents?

• 37:07Speaker 03

  Do you mind if my, if I share my screen? Cause I

• 37:10Speaker 02

  Yeah, go for it.

• 37:10Speaker 03

  Yeah, I've run some interesting cases. Uh,

• 37:13Speaker 02

  Yeah.

• 37:13Speaker 03

  So. Uh, here we are. To better understand why we build this tool is that, you know, it fits in line with our mission. Our mission is we're trying to build cross-platform general agents. That means that we want agents that not only can operate on website, but also can operate directly on apps. And obviously, if you're talking about apps, there's computer apps, there's phone apps, there's a lot of like different destinations. What we observed from the capability of all these models, fastly growing since last year, is that all these models are quickly getting better at reasoning, planning, as well as code level execution. So if you link all these three things together, that makes all this use cases become a reality.

• 37:58Speaker 03

  So I can show you um my prompt that I just run. Literally, I started running this um before I joined this room because I was in the meeting room for like twenty minutes. Uh, so I just, you know, run this. I said, I'll be on Jason's strictly startups, talk about newly released Rabbit OS intern agent. Help me create a comprehensive media prep book and make into an interactive HTML web app. So to use an intern, you really think about this has a similar capability of a human intern level. You're not expecting, so set the expectation right. You're not expecting this to be the chief scientist, right? Or a superstar engineer that get paid one million dollars per year. So this is an intern, human intern level.

• 38:40Speaker 03

  But what's amazing about this is that this is an intern for every domain. It's not just an intern for coding. It's not just an intern for real estate research. It's an intern for every single possible domain you can think of. To use with this, you just, you know, need to use language. But what's more beyond tools like OpenAI and ChatGPT uh and Gemini and, uh, you know, um, perplicity for now is that it's directly end-to-end consumer-facing. So if you want this to work on a website, it will actually give you a website. If you want to generate a PowerPoint, it will generate a PowerPoint. Um, so for example, I, I, I really love OpenAI and Google and perplicity.

• 39:24Speaker 03

  I was uh trying the same prompt on.

• 39:29Speaker 03

  All these three different platforms. So what I did is I also include the media.txt, which is just basically information from our current media outreach, right? So I copy and paste this, put into TXT. And this is the OpenAI GPT-4O. So I said exactly the same prompt. And this is the, and OpenAI GPT-4O actually did pretty good. It actually generates a website. But let's take a look of what's the contents here. So that's basically the HTML code that generated by OpenAI. And it has, you know, some basic information. I would assume most of these are just directly pulled from the TXT. I tried on a Gemini 2.5 Pro, which is their latest stuff.

• 40:11Speaker 03

  It says, it has this, you know, markdown summary, which is really nice. And it says, regarding to your request on interactive HTML web app, I cannot directly create web applications. I tried this on Perplexity. It gives this sample HTML code. And when I open it up, it is basically a template. Now, here's an interesting backend, what's happening with all these agents? So I'll better explain this. So what's happening here is that if you type this prompt, the RabbitOS intern will have a master agent, as if the virtual CEO says, hey, guys, come together, let's build this task. And this master agent will basically create a whole

• 40:56Speaker 03

  action plan for the remaining agent. And then you can see the tasks start spinning up. And it basically is a bunch of coordinating agent following the master plan. So this agency is doing this, and that agency is doing that. And all these tasks are automatically assigned to a different agent. And you can see, you can click on the sidebar to see like what's happening on the backend, right? So basically, all these agents are doing things together. Some of the agents doing research, some of the agents start building the website. And it goes on and on. This entire task took us 18 minutes to finish, which is not too bad. But now, you got all this, you know, generated files. You can download as a zip. But here's the thing, let's go back to see, to have a refresh.

• 41:41Speaker 03

  This is the OpenAI ChatGPT-4O. This is the website.

• 41:47Speaker 03

  This is what we have.

• 41:49Jason Calacanis?

  Got it. So you're actually publishing and if you had a hosting company, you could probably publish it actually live to the web.

• 41:54Speaker 03

  Yep, that part is straightforward, but I want to emphasize on the, you know, context, right? So if you think about my prompt was I'm asking, hey, I'm going to join this podcast. I want a media preparation handbook. So exclusive summary.

• 42:09Jason Calacanis?

  Yeah.

• 42:10Speaker 03

  Everything is super relevant. It even built this section by itself says, hey, checklist. Make sure you get all this prepared before you join the call. And you have this audience analysis. This is basically agent search on your this week's startup. Audience demographics, you know, host style and format. And it even says, hey, you, you're like direct, you know, everything is super relevant.

• 42:33Jason Calacanis?

  Skeptical, skeptical toward overhyped claims. Preference for concrete examples over theoretical discussions. This is all true. I wonder how it got that.

• 42:42Speaker 03

  Well, it just pulled the information from the, the existing internet and, you know, all the public data. This also.

• 42:49Jason Calacanis?

  I wonder if somebody has a webpage where they described my interviewing style or something, you know?

• 42:53Speaker 03

  Yeah.

• 42:53Jason Calacanis?

  Well, we'd love to see the citation for that. This is great.

• 42:56Speaker 03

  So you also got this, you know, Q and A session, media training tips, you know, you can really see the intern actually understand and execute it, you know, even in human format. And then product overview gave me some notes, you know, just in case you guys ask about our stuff, you know, I can reference this. Even has a quiz. I didn't ask for a quiz. It even has a quiz, right? So this is, by the way, fully functional. I'm just trying to hit a perfect score here.

• 43:25Jason Calacanis?

  Love it.

• 43:26Speaker 03

  Okay, so we'll see. We'll see if I, there you go. I hit a perfect, perfect score. But, but you know, you really need to understand where we are right now in the whole generation of agent technology. I, for the record, I think every single product will soon have this kind of capabilities.

• 43:47Jason Calacanis?

  Which is an agent. Happening in real time to do jobs for you. And then the question is, how good are the results and how helpful are they? Absolutely. So if you were to ask it to get my interview style and prep you, that's doing as good a job, Alex, as I think a PR person would do because they would go watch Alex and I talk or interview other people and they would write it down. It would take them a couple of hours. Here it found that information somewhere on the web or maybe it analyzed a couple of clips or something.

• 44:15Speaker 03

  Yep.

• 44:16Speaker 02

  Entry level jobs are going to get automated away, Jason, because computers can now do the collection and aggregation that we pay people to do.

• 44:23Speaker 03

  Yep.

• 44:24Speaker 02

  It's just that's coming.

• 44:25Speaker 03

  And also, this this system can do something that really, you know, out of expectations, you know, this is obviously a very professional, serious prompt, but I also build this 18 bit sequencer by using one prompt and it's a fully functional little sequencer. I can get some of the the music going.

• 44:43Speaker 02

  Amazing.

• 44:43Speaker 03

  By just play with it.

• 44:45Jason Calacanis?

  Yeah, I think these agents, you know, are really getting close. One of the things I was just working on was trying to figure out, because I'm incubating a company that's going to be estate managers. I think I told you about this, Alex. One of the things I noticed when you reach a certain, you know, stature, not stature, a certain station in life, in other words, net worth, when you have a second home, estate management, managing multiple homes, like you can manage your home, then when your home becomes five, six, seven thousand square feet, it's too hard to manage.

• 45:22Speaker 03

  Yeah.

• 45:23Jason Calacanis?

  You need help. So, you know, you have a family assistant or, I don't know, a handy person, a handyman come by. And it just becomes arduous. When you get to a second, third or fourth property, I have four properties, or you're a property manager for Airbnb, let's say, now it becomes hard. Now you need a full time person.

• 45:43Speaker 03

  Yep.

• 45:44Jason Calacanis?

  And then what I realized was, the hardest part of the job was vendors. Managing vendors is the hardest part of the job. So now I'm on a little exploratory. Thing with my estate manager, which is I want to create an estate fractional estate manager powered by technology. So I had my Athena assistants. I have two Athena assistants. Go to Athena wow.com to get a couple of weeks free. They give you a great deal at Athena wow. W O W dot com. I'm an investor in the company. I'm a spokesperson for the company. I have the two Athena assistants working, I think, one hour overlap. So I have a 15 hour window from like seven to nine P M. Every day of my time, the Athena assistants are available to me.

• 46:24Jason Calacanis?

  So I had them. I want to put a solar thing in, you know, where I have solar at the ranch and batteries. Not just like solar on my roof, you know, Tesla power wall. I want to put up an acre of solar and have enough batteries that I could be sustainably off the grid on the ranch forever. Okay. I'm, I had my current estate manager, give me her process, share that in a notion page with the Athena assistants, and I'm watching them do it. And I'm wondering, how long before I can describe this and have an agent make phone calls, research it on the web, call them up, get the quotes, normalize the quotes, like, feels like next year, right? Next year, definitely. I was about to say next year, next year. Yeah.

• 47:07Jason Calacanis?

  So that's why I'm doing this. Like, I think the Athena assistants, having like assistance from Manila who can brute force it, but then studying what they do, then the Athena assistants could be doing this. You know, using Athena assistants will have agents and it's just going to become like this cascading efficiency to absurdity. So then my thought, Alex, for the startup is imagine you own a $5 million home. Sure. And you have a $3 million vacation home, you know, Manhattan apartment or Brooklyn, Brooklyn town home. $3 million doesn't go as far as it used to. Well, a town, I'm saying a Brooklyn townhouse could be a brownstone could be $5 million and then a a $5 million Hampton's home. You put the two together, you got $10 million.

• 47:52Jason Calacanis?

  Instead of hiring a full time person that you don't need, you hire essentially a 20th of a person, a 10th of a person for 50,000 a year, 50 basis points of the total value of the two homes, whatever. And they just manage everything about that home, the landscaping, the pool cleaning, replacing the pool pump, replacing the HVAC, all that kind of stuff. And I think. Human plus agents equals success, but obviously no house manager is going to be able to do this. So every category is going to be able to fix these things. It's gonna be really interesting future. Jesse, thanks for coming on. Let's talk again in six months. I want to, I want to see some more form factors. You're a really great guest.

• 48:29Speaker 03

  Absolutely.

• 48:30Jason Calacanis?

  Keep grinding. I know you have tons of runway to figure this business out. So I wish you great luck in the trial of despair.

• 48:38Speaker 03

  Thank you. Thanks, Alex. Thanks, Jason.

• 48:40Jason Calacanis?

  Cheers now. As we wrap here on this, there was somebody in the chat room who said they have the R1 and they love it. And they picked it up at a TWA party almost a year ago and they still love it. So that's pretty great.

• 48:51Speaker 02

  All right, let's do some Founder Friday pitch offs. It's time to discuss the bracket, my friends. We are talking about something that we are very excited about, which is showing off cool things from the Founder Friday world. Jason, here is our, not March-

• 49:07Jason Calacanis?

  Founder Friday, just to explain, FounderFriday.tech, six founders around a table. They get together every first Friday of the month. You go around the table, buy founders, four founders, no looky-loos at the event. You have to be a founder of an active startup. Founder one says what they're working on, what their big win, what their big fail is, what their big challenge is, what their big, you know, win is.

• 49:32Speaker 02

  Sure.

• 49:32Jason Calacanis?

  You do that for two or three minutes. You go around the table, six people, three minutes each, 18 minutes. Then you spend the other 40 minutes, each person goes around and says, oh, Alex, your big win. I want to hear more about that. Let me ask you a question about how you're acquiring customers using TikTok videos. And then you say to me, yeah, and I want to ask you about your challenge of acquiring customers. I'm wondering if you've tried, if you've done Google search and if you're retargeting. The person says, what's retargeting? So here's the tracking pixel. Here's how you do retargeting. Boom. That's the format. So we asked these teams, have your own competition between the six people, or maybe have three pods of six. And we're codifying this at Founder Fridays. You can go to FounderFriday.tech, great domain names, to create your team. And we're going to do March Madness. We're going to have-

• 50:17Jason Calacanis?

  Eight teams on one side, eight teams on the other. I'm not sure how we broke them up.

• 50:22Speaker 02

  Well, we have, just for folks who are on the audio version, this is done by cities. So we have Houston versus Boston, Austin versus Quincy, New York versus Philadelphia, go birds, Zurich versus Florianopolis. So Jason, what I'm going to do is play for you four clips, two competing pairs of companies from this. And then we're going to pick our favorites and we're going to scoot them forward and get this ball rolling. Are you ready?

• 50:43Jason Calacanis?

  I am ready.

• 50:43Speaker 02

  Okay, excellent. Cause too bad if you weren't, we're still gonna do it. All right. Here is the first one. This is Snipped. Let's hear from Snipped.

• 50:51Speaker 04

  Hi, I'm Kevin. I'm the founder and CEO of Snipped. Snipped is an AI-powered podcast app for people who listen to podcasts to become more knowledgeable. For me, podcasts and for many other people out there have become the most important source of knowledge. And I usually listen to podcasts while I ride my bike, but the problem is that whenever I hear an amazing insight, it's so difficult to write it down. So what we have done with Snipped is whenever you listen to a podcast on Snipped, and every time you hear an amazing insight, you can just triple tap your headphones. And our AI summarizes the insight that you just heard and saves it together with your original transcript and audio in your knowledge library. You can now review this, you can send it with to friends, you can even sync it with your favorite notes app like Notion. But actually, in the meantime, our app does much more. One way of thinking about it is really, we've become the AI-native podcast app, similar to how Cursor is the AI-native IDE for developers.

• 51:36Speaker 04

  So our app has AI-generated transcripts, AI-generated chapters. We identify the guests of a podcast, create a little mini bio about them. We identify all of the books that get recommended in a podcast. You can chat with an episode. We even generate small summaries for you, such that you can decide whether or not to listen to a podcast. So all of this together basically creates the AI-native podcast app experience for people who listen to podcasts to learn and become more knowledgeable. We have users in more than 210 countries and paying users in more than 149 countries. So really looking forward to the next country to get to 150.

• 52:09Jason Calacanis?

  Awesome. I love the idea.

• 52:10Speaker 02

  What do you think about Snip, Jason?

• 52:11Jason Calacanis?

  I know this. I've met the founder. I downloaded the app recently because I'm looking for Podcast 2.0 standard apps that have the live link in them. Shout out to Adam Curry, the Podfather. And I'm looking for ones that have the donate button in them. And I've been pushing Spotify to add the donate and the live button. So when we go live, we should be able in our RSS feed to just post it in there, have it ping Spotify, and then have Spotify say we're going live. So we don't have to do what we're doing right now is use Restream and have six different live streams going across every platform. We should be able to send a notification to our subscribers and say, this is our preferred live platform, YouTube, X, whatever. Putting all that aside, it's a great idea. The app has some challenges. I happen to have used

• 52:56Jason Calacanis?

  it because you have to pay in order to use all the features. So it'd be better for them to have some advertising in it and make it free up and or, you know, time gated or let you have three podcasts. And then after you get 100 notes or something, then it upsells you to charge you. But anyway, great idea. I think you would like the idea too. Who are they up against in the bracket? Who are they now going up against?

• 53:18Speaker 02

  That was Zurich. And now we are going to hear from Florianopolis, which is a city in southern Brazil. And their chosen champion is a company called MedSimple.

• 53:29Speaker 05

  Since I am from Brazil, Florianopolis, and I will present to you today MedSimple. There's medical school simple. It's one of my first times doing English. The first one was on Founder's Friday. Okay. And I appreciate you guys watching me today. Our proposal is to improve medical education in Brazil. Why? Because it changed our lives. Who? Me and my co-founders. We both met on med school admission test and we got approved together. When we went to medical school, we faced a problem, lack of active study in medical school, difficulty memorizing large amount of information. Okay. And lack of specific questions that we missed from the admission tests. And we created a solution when we was on med school. A SaaS where you choose a subject, diabetes, tuberculosis, hypertension, you choose a study mode, questions, flashcard videos, and you do have to recall these informations. And why now? Because a lot of new medical schools in Brazil, new students, and maybe

• 54:13Speaker 05

  you're going to have a Brazilian medical proficience test like the USMLE for United States. Done. In terms of work, we Have more than 100 billions in global market share education. In terms of Brazil, we have a quarter of a million medical students with a ticket of 120 USD. We could reach a 30 million ton, but you can improve that doing another products and going up to the residency model. Ton of 40 millions, okay? Other players in the market, we have strong brand, like a pro, extreme improvisation, a residence model, we are working on that. We are a SaaS, BTOC, 120 per year. Our revenue, we are, here we are in medical school and we started very small, you can see here. And now we are more than half of million in revenue per year with an MMR of 50,000, okay?

• 54:55Speaker 05

  The team, we both are physicians and our dev is Gabriel Bozzi, give up contributions of him.

• 55:02Speaker 02

  So, I love this.

• 55:04Jason Calacanis?

  I love them both, this is a problem, it's too strong. Give me your, what you love, what you love about each really quick and then which one you pick.

• 55:13Speaker 02

  Okay, so Snipped, I adore because, I mean, you might have heard of this, this week in Star Wars podcast, Jason, big fan. So I live in the podcasting world, I love anything that lets people extract more from audio. I love the application of AI to popular consumer formats. Okay, Medsimple I adore for two reasons. One, I know the market very well, I've watched my spouse study for boards and different step exams through medical school and residency. So I know how much work that is and I recall how much money we spent on stuff. Like books, courses, mnemonics, like there is so much studying that goes into this work. So I know the pain is huge.

• 55:52Speaker 02

  Uh, Medsimple because of the revenue growth, love it.

• 55:55Jason Calacanis?

  Okay, I was going to go with the podcasting app because I think it's amazing and it's innovative. The Med app isn't super innovative, I think anybody could build it, it's built on other people's LLMs, it seems very basic, it seems very simple. But then I saw their traction and if it's true, they got to over a half million dollars in traction already. And he did that product velocity, which panders to me, I too fell in love with the medical one. But I, my, I probably would obviously use the other one and I think one's more innovative than the other, but the other's got traction. Both of them are amazing, I would love to invite them both to the accelerator, but I think they're beyond it now in terms of revenue and money raised. I'm going to give a slight edge to Med.

• 56:41Speaker 02

  Simple.

• 56:42Jason Calacanis?

  Simple. So all right. Now you and I are in agreement on that one. So that's an easy one.

• 56:47Speaker 02

  Yeah.

• 56:47Jason Calacanis?

  Next one. Let's go.

• 56:48Speaker 02

  Turn it up to Brazil over Zurich. All right. Next up, we are going to talk to

• 56:51Jason Calacanis?

  This is incredible.

• 56:53Speaker 02

  All right. Isn't this fun? Osprey, the company from the Houston group. And then we have Trova from the Boston group. So we're going to start with Trova, which I have pulled up right here. And we are going to hear from a man who looks like he's going to sell me a pharmaceutical. Doesn't he look like?

• 57:10Speaker 02

  Oh, I'm sorry. I'm just kidding.

• 57:11Speaker 06

  All right. Let's hear it. Quickly think back to your first job, the friends, the mentors, the experiences, all of those things that shaped you in your lives and made you the success that you are today. Now think about this next generation of workers. Chances are they'll be onboarded remotely, which means that their office is actually in your house on the computer. Their mentors will probably be chatbots. Instead of going to the dining hall or catching up at the cafeteria or restaurant with friends, they'll just doordash. This next generation is on a path to loneliness and isolation. That's bad for their mental health and our companies. There's a thousand statistics that back that up. That's why I'm super excited to introduce myself and my company, Trova. My name is Mike Federa and Trova is a platform that's bringing real authentic human connection back to the workplace. We've anchored on three pillars. Trust, which you get from working in the same organization.

• 57:56Speaker 06

  What we call who you are or full self, that made you bring your whole self to work, your interests, your background, your skills, and then common ground. So now if two employees on different teams, both like playing poker and rucking, Trova would make that connection for them automatically. So therefore you have a chance of finding a new bestie. Last year we did $60,000 in ARR and we're on track to triple that this year. We're a small, scrappy, two-person team that's never raised venture funding. Work used to be the cornerstone of human connection and with Trova, it still can be. We know what it's going to take to scale our business and we'd love for you to be part of that journey. I can't wait to share more about what we're building and get a chance to introduce myself to you all. Thank you.

• 58:34Jason Calacanis?

  All right. That was all pitched. No website, no product, unfortunately. So I had to imagine it. We'll pull up the Trova website in a moment, but let's hear our second pitch.

• 58:42Speaker 02

  All right.

• 58:43Jason Calacanis?

  And make a decision.

• 58:43Speaker 02

  Pitch number two.

• 58:45Speaker 07

  Hi, I'm Lydia Davies, the founder and CEO of Osprey. Osprey is a community for women in sports and entertainment. Our nest houses over 100 members with a collective following of 17 million plus and 15 brand partnerships. Our members are Olympic athletes, DJs, news anchors, high-profile executives in sport and entertainment, and college athletes. It's a Venn diagram. All of the groups work together and collaborate to support each other, to network, and to sometimes create startups, which we really try and push. We offer them different opportunities via our speaker sessions with lawyers, wealth experts, and more. We're also doing an athlete and STEM program with an activation at SpaceX in a couple weeks.

• 59:27Speaker 07

  Last year, we had five sold-out large-scale events, from women in football at the Super Bowl to women in motorsports at the Indy 500. You'll find us everywhere. We do women's summits and retreats, and we have already got off to a bang for 2025 with two sold-out events. So, what do the brands do for us? Well, we bring in these amazing brand partnerships that have the same core values as us, and they offer our members opportunities and discounts, and our members market them. Most of the brands see over 100 million-plus insights at each one of our large-scale events. That's amazing. We also provide a Big Sister program for our college athletes, which is now heading out of our beta stage, where we give them a member from the community as a Big Sister

• 1:00:10Speaker 07

  mentor, and will help support them along their journey. We are expanding so fast, and we grew 10x last year, projected to grow another 10x this year.

• 1:00:20Speaker 02

  All right, what do you think?

• 1:00:22Jason Calacanis?

  Um, God, you can see the difference when they show the product and they walk through a deck, and they don't. It leaves, it's just so hard, because I'm trying to figure out what it is. Trova, you know, these are both... Touchy feeling and Trova, I understand people want to try to make it less boring to work from home in front of a computer and create mentorship. I've talked about this countless times. I'm literally in the process of addressing this. We have, I think we'll have 10 people in an office here in Austin very soon. I'm only hiring people in Austin going forward. And then extremely high performers can be extremely high performers remote. That's where

• 1:01:02Jason Calacanis?

  I came to after three years of work from home, which is like, I think 10 or 20% of people can work from home. Extremely high performers, self motivated. Everybody else needs to be in an office. That's just my personal belief. So, looking at their websites, if you pull it up, we look at Trova, you know, if I criticize a website, I think you need to show the product, not just do like, here's logos, etc. You have to have like a very quick, not just these illustrations. I understand that's what people think is the best practice. For me, the best practice as a startup is to show the product with the founder walking through the product in a video. I think a product video and a product demo on a website explains everything. And

• 1:01:47Jason Calacanis?

  this doesn't. So it's just hard for me to conceptualize the product without seeing it. But I get it. When we look at the top of the page, to transform your workplace with meaningful relationships that drive engagement, innovation and results. So if this was in our accelerator, I would destroy it. I would be like, what does it even mean? Right? Define your community, build your community, like foster collaboration. This is all soft hippy dippy language. Inspire your people. I hate this. What you really want to do is say, Trova is a Slack plugin that increases team collaboration by helping

• 1:02:30Jason Calacanis?

  You know, employees get to know each other, remote employees to get to know each other. And you just try to say one thing and then you show it. And if you showed it and it was two people answering a quiz, boom, so you got to show, don't tell. Show, don't tell is one of my key reasons or key insights of presenting companies. Show, don't tell. If you tell us, we have to imagine it. If you show us, now we're on to the next issue. Tell me about the business model. Tell me about the growth. Are you raising? Here, we're still in, what is it? Same thing if we pull up the next community and we go to their homepage and I'll just criticize the homepage. Elevating women in sports and entertainment. The fastest growing community for women in sports and entertainment.

• 1:03:14Jason Calacanis?

  Vetting members, vetted members, 20 plus brand partnerships, 17 million followers, 30 plus, 12 grand. This is all like, um, like, uh, peacocking and not explaining the value. So I would say here, join, you know, uh, uh, an online community of 1,272 women who support each other, who support and inspire each other. Learn more, right? Like boom, and then I would have exactly how that happens.

• 1:03:47Speaker 02

  Yeah.

• 1:03:48Jason Calacanis?

  You know, uh, so if we scroll down, empowering women globally. Again, that's like hippy dippy language, empowering globally. I hate these words because they're just like trigger words for not a real business. And I, I try to get more specific in what the value proposition is. Welcome to a collection, a collective of collaboration. This is words out. Osprey empowers women in sports and entertainment through network events, opportunities, leadership, resources. Again, you're doing the whole list. Too much. Make it bullet points. Make it simple.

• 1:04:25Jason Calacanis?

  Network with powerful women online in a chatroom by categories, including sports, entertainment, personal development. Two, come to monthly events. So when you heard me describe Founder Fridays, I was very specific about what it is. Alex, what happens at a Founder Friday?

• 1:04:49Speaker 02

  Six people get around a table and share their wins and struggles so that way founders can support one another.

• 1:04:54Jason Calacanis?

  Boom. The reason you know that is because I am a master at explaining things simply and defining them.

• 1:05:01Speaker 02

  I also spent a lot of time listening to you, so I feel like I'm cheating. But no, you actually, I realized you talk in bullet points, which is interesting.

• 1:05:08Jason Calacanis?

  I talk in bullet points when I'm trying to communicate stuff because

• 1:05:12Speaker 02

  It's effective.

• 1:05:12Jason Calacanis?

  People are busy. I literally just did it. Too much word salad, not enough actually showing of the product. So both of these aren't as good as the first two presentations. So this is like one of those brackets where like the people who should be in the Eastern Conference Finals met each other in the first round. The first two companies would have beat both of these companies, but if I had to pick here, I think that the Women's Collaborative can charge $1,000 a year, $5,000 a year. There are a bunch of communities doing it. Who's the guy from My First Million?

• 1:05:47Speaker 02

  Oh, I'll talk about that.

• 1:05:49Jason Calacanis?

  He's a great founder. He had done Hustle.

• 1:05:52Speaker 02

  Sam Parr and Sean Perry.

• 1:05:54Jason Calacanis?

  Yeah, so Sam Parr has a new community and there's a couple of these going around that are 5,000 or 10,000 a year. So they put up a $5,000 or $10,000 gate so it can only be CEOs who can expense it or venture capitalists who can expense it or, you know, otherwise successful people. So the dollar amount you spend is to create scarcity. Then those people interact with each other, support each other, and they get to be part of this. I was thinking about doing this. This was like my other idea for Founder Fridays was to make it elite, to charge a fee. And I might still put a fee on it so that it's you're committed, right? So for Founder University, we put a $500 fee on it.

• 1:06:33Jason Calacanis?

  And then when you finish the course, you get the 500 back if you submit your weekly updates 12 weeks in a row. You have to submit 12 updates. And can we make a note, Matty, that in order to get the $500 back, we can change this for the next one if we communicated it differently. You have to come to the weekly on Monday and you have to submit your weekly update. Your weekly update is your attendance and your attendance is your attendance. But that's what we're looking for anyway. So you can't fill out 12 updates that you're getting paid 50 bucks each or 40 bucks each for them. Like, okay, you could have just filled out the form and gotten 40 bucks. So here, we don't know how much they charge. Did they mention how much they charge?

• 1:07:13Speaker 02

  Osprey was jumping into live checks. We are doing this live, of course.

• 1:07:16Jason Calacanis?

  Oh, great.

• 1:07:17Speaker 02

  They say, quote, "We do charge that." So I think you're probably actually-

• 1:07:20Jason Calacanis?

  How much? Didn't say. How much do they charge? I mean, that, this would have made the presentation. This is why I'm good at what I do. Because I have seen so many pitches that I can just tell you how to make it literally two or three times better instantly, just with two or three tweaks. If you said it's a $5,000 a year program and you get X, Y, and Z, then we wouldn't have to play this crazy game of trying to figure it out. How much is it?

• 1:07:46Speaker 02

  We're waiting for them to respond. But while we wait for that information, I want to, I'm going to weigh in on my selection here.

• 1:07:53Jason Calacanis?

  Yes, go ahead.

• 1:07:54Speaker 02

  First of all, I think the idea of making remote work a little bit less lonely is awesome.

• 1:07:59Jason Calacanis?

  Yes.

• 1:07:59Speaker 02

  I've been both in-office and remote and hybrid. And let me tell you, I get the most done by myself, but I miss people's. I love the idea of having a closer knit team. Love that. I'm also an enormous believer and supporter of women and women's sports. So to me, the idea behind Osprey and just women entertainment as well is fantastic. Big fan of that. And I, I just don't understand the model as well, Jason. So to me, even though I like to think of myself as someone who would be a big supporter of Osprey, I'm going to go with Trovok's. I better understand the economics of a Slack plugin.

• 1:08:31Jason Calacanis?

  Okay. $3,100 a year is what Osprey charges. Therefore, I'm picking Osprey. Tie goes to the founder of the pod. So Osprey makes it to the next round. If we had Lon here, I would go with majority.

• 1:08:44Speaker 02

  No, no, no. That's, that's imminently reasonable. I was just curious how we were going to break the tie. And the answer is-

• 1:08:48Jason Calacanis?

  I just decided in that second that tie goes to the founder of the show. It goes to whoever's done the most episodes. That's me.

• 1:08:55Speaker 02

  That's not fair.

• 1:08:56Jason Calacanis?

  Okay, whoever's invested in the most unicorns.

• 1:09:01Speaker 02

  Whoever has the most children named Ada.

• 1:09:03Jason Calacanis?

  Okay, there you go.

• 1:09:05Speaker 02

  No, that's fine.

• 1:09:05Jason Calacanis?

  So we'll go with Osprey. And I do like these expensive membership things. And then, you know, again, if you want to like, get all precious about it, oh, my God, you can afford $330, $100 a month. It's $10 a day to be part of this community.

• 1:09:23Speaker 02

  Yes.

• 1:09:23Jason Calacanis?

  It's $10 a day. So what I would do is I would do for every 100 members, five scholarships based on merit that are discounted to $2.

• 1:09:35Speaker 02

  Oh, I like that. So you still have skin in the game, but it's much more affordable for everyone who wants to take part.

• 1:09:40Jason Calacanis?

  And we only, it's only 10% of the membership and we don't tell you which 10%. And you have to tell us what you're doing, how much money you're making. So if you're only making $50,000 a year, running your startup and you're bootstrapped and you're not rich. We know that you're living in an apartment, you tell us your sob story. Okay, so $500,000 a year. Well, let's say you make $50,000 after taxes.

• 1:10:02Speaker 02

  Sure.

• 1:10:03Jason Calacanis?

  Would you put 1% of that into being in a community, 500 bucks or 2% of that, $1,000? If you're not willing to put 2% of your take home pay into it, it's obviously not the right thing for you. You have no skin in the game.

• 1:10:16Speaker 02

  Right, no interest.

• 1:10:18Jason Calacanis?

  Yeah. And if you're making 150K a year as the CEO or venture capitalist or partner at a venture firm. Okay, 2% of that is 3,000. So I think four great companies. I love the format. The punch up is do a loom, walk through your deck where you are in front of your thing. It'll go much better for you. And then let's make the cap 75 seconds. So when we do the next one, 75 seconds. And if anybody wants to redo their pitch between now and when they're going to be on, I'm going to allow them to redo their pitch. We can send this clip to folks because you'll have a greater chances of advancing if you show those things. Let's add to this.

• 1:10:58Speaker 02

  Okay.

• 1:10:59Jason Calacanis?

  A version of this for the Twist 500. So next month, let's do one for Twist 500, where you present the company, the three of us discuss it. The founder doesn't have to come on, but we do it based on the highest known valuation. So we sort by valuation and we do twist the top. How many is it? 16? The sweet 16 of Twist 500 by last valuation.

• 1:11:25Speaker 02

  So spicy given OpenAI's latest because that's gonna see

• 1:11:29Jason Calacanis?

  OpenAI, you got SpaceX, you got Andro, shout out to my guy Palmer Lucky. You've got so many great people who will be in that, right?

• 1:11:35Speaker 02

  Stripes on there. And by the way, there's now more than 300 companies in the first 500. So everyone should take a look and see what we might be missing. We're working on our next batch of 25. So keep your ears and eyes peeled on to that.

• 1:11:46Jason Calacanis?

  All right, everybody. Another amazing episode of This Week in Starb's a long one, but sometimes we can go to 90 minutes, you know, 100 minutes. And you get what you pay for. It's free. Enjoy. He's Alex, X.com slash Alex. I'm X.com slash Jason. Monday, Wednesday, Friday, we go live. What platforms are we going live on? Instagram and TikTok? Need a favor from you all. Please go follow it. Obviously, that would be great. But go ahead and go in there and like it. So how many followers do we have there on the Instagram?

• 1:12:14Speaker 02

  We have 30.5K.

• 1:12:17Jason Calacanis?

  30,500. And then if you hover over these, how many views are we getting on these posts? Like if you go down and just hover over it, it should tell you how many views we're getting. I think we're probably getting low hundreds or something.

• 1:12:30Speaker 02

  It's only got four likes.

• 1:12:31Jason Calacanis?

  Too light, too light, folks. And so

• 1:12:34Speaker 02

  26 likes.

• 1:12:35Jason Calacanis?

  Likes, four comments, 24 comments, six. So it's, we just started doing this. I really need your help. Go in and like it, but more importantly, write a comment and just say, what's up, Jake Al? What's up, Alex? All right. This has been another episode of This Week in Starb. So see you next time. Bye bye.