Discord's Power Move, Slate's Modular EVs & the "Act for Private Gain" | E2117

Today's show: Jason, Alex, and Lon break down today's top tech and startup stories — from Slate Auto's customizable $25K EV truck to Discord's major leadership shakeup ahead of a potential IPO. They also cover Uber's self-driving push with Volkswagen, Perplexity AI's aggressive growth moves, and why value-driven products are winning in a tough economy. Plus, Alex sits down with Tailscale CEO Avery Pennarun to unpack how they grew from 5K to 10K customers — and why fixing internet networking could spark the next huge wave of innovation. * Timestamps: (0:00) Jason, Lon and Alex kick off the show! (3:26) Introduction and features of Bezos-backed EV truck company, Slate (7:55) Market impact and value proposition of Slate's EV trucks (9:48) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups (14:04) EV features and market potential discussion (17:42) Discord CEO steps down and IPO prospects (20:19) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (24:00) Uber and Volkswagen's self-driving car partnership (28:39) Superpower - The best founders know: better health = better business. Visit http://superpower.com/twist to skip the waitlist. (30:00) Pace of self-driving car adoption and regulation (37:20) Butterfly Effect secures Benchmark investment (38:37) Perplexity and Motorola Razr partnership (43:12) Jason's experience with Light Phone (45:39) New York Times and Ziff Davis lawsuits against OpenAI (50:09) Nonprofit structures and OpenAI's mission issues (54:01) Founder Friday: Pitchfire and TACTUN's two-year plans (1:02:28) Introduction to Tailscale and Avery Pennarun (1:10:17) Tailscale's enterprise adoption (1:21:13) Current Internet networking issues* 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 episode: Check out Tailscale: https://tailscale.com/ Check out Slate vehicles: https://www.slate.auto/en Check out Not For Private Gain:https://notforprivategain.org/ Check out the Light Phone: https://www.thelightphone.com/ Check out Oregon lawmakers article: ****https://www.oregonlive.com/politics/2025/04/oregon-lawmakers-to-decide-whether-big-tech-should-pay-to-support-local-journalism.html Check out Manus: https://manus.im/ * Follow Lon: X: https://x.com/lons * Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Thank you to our partners: (9:48) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(20:19) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(28:39) Superpower - The best founders know: better health = better business. Visit http://superpower.com/twist to skip the waitlist. * Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason's suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com * Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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

• 0:00Jason Calacanis?

  I came in here to a hostile environment. It was a road game. I bought courtside seats for me and my friends, Ben Stiller, Timothy Chalamet, and my brother Josh, and we all went to the game.

• 0:12Speaker 01

  What a squad.

• 0:12Jason Calacanis?

  I kid you not, I'm actually friends with Ben Stiller. I'm not with Timothy Chalamet. And so I was like DMing him after the second game. We're in the playoffs now. And I said, hey, are you going to the game? Because courtside seats in Detroit are basically like $17. So I was like, Ben, hey, let's go to the game. And I got these courtside seats. And he was like, oh, yeah, I want to go. And, uh, you know, they tried to block everybody from buying tickets here. So when you go on Ticketmaster, they said you had to have like your IP address and your billing address of your credit card has to be in Detroit and the surrounding area. Of course, they're like, you can't like do this. And I said, oh, I can't.

• 0:51Jason Calacanis?

  I said, I have a Hulk. I have a Hulk. You know, when they say that in the Avengers?

• 0:55Speaker 01

  Yeah, we have a Hulk. That's Loki's big line.

• 0:58Jason Calacanis?

  Loki, we have a Hulk. You know what I have? I have a Heidi.

• 1:01Speaker 01

  Yeah, she's not taking no for an answer.

• 1:05Jason Calacanis?

  You tell Heidi, uh, yeah, no, we can't do that for Jake out. You know what Heidi does?

• 1:09Speaker 01

  Finds a way.

• 1:10Jason Calacanis?

  Hulk smash. And so Heidi Hulk smashed and got me courtside seats. Shout out to Heidi. I'm gonna give her an even bigger bonus this year.

• 1:17Speaker 02

  This Week in Startups is brought to you by LinkedIn Ads. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to LinkedIn.com/thisweekinstartups. Lemon.io. Hire pre-vetted remote developers and get 15% off your first four weeks of developer time at lemon.io/twist. And Superpower. The best founders know better health equals better business. Visit superpower.com/twist to join and skip the waitlist.

• 1:42Jason Calacanis?

  Hey, everybody. Welcome to another episode of This Week in Startups with me again, Lon Harris, Alex Wilhelm, yada, yada, yada, at Alex, at L O N S, at Jason. Yes, those are all incredible premium Twitter X accounts. And apologies for me not being suited up. I am in a delightful hotel in a delightful city, dare I say. Detroit, New Roy. I am so taken with the city. So shout out Timothy Chalamet.

• 2:07Jason Calacanis?

  A new bestie for me. Kidding, I'll probably never see them again, but best dollar, our friends, we had a great time. And I wanted to hate the city. The city had so much love for me. I'm staying at the Shinola Hotel, which is like, I guess, based on the watch. Great hotel.

• 2:21Speaker 01

  Oh.

• 2:21Jason Calacanis?

  I went to this ghost place, had the best hamburger, literally of my life. I think it might have been literally top two or three burgers in my life.

• 2:29Speaker 01

  Wow.

• 2:29Jason Calacanis?

  And then I walked around the town. It reminds me of like when Venice, Brooklyn, you know, pick like a hipster cool town, Austin. Same vibes, incredible people. They were so kind to me, except for the one drunk guy who wanted to beat me up when I was walking back from the arena for my Knicks jersey and the bouncer.

• 2:47Speaker 01

  Well, you were, you were wearing, yeah, you were wearing.

• 2:49Jason Calacanis?

  I was in hostile territory of the Knicks one. Anyway, a great time was had by all. Shout out to the city of Detroit Knicks up to one. I have to get home to my family now, but, uh, you know, I gotta tape this show and get out of here. So I'm going to miss all in this week, but yeah, uh, I gotta do some things for myself and my soul. Alex, how are you doing, sir? You look great. I like the shirt. I like the blazer.

• 3:09Speaker 03

  Thank you, thank you. This is, uh, this is Saks Fifth Avenue, actually. I, I pulled it out of the deeper cuts of the closet.

• 3:14Jason Calacanis?

  Like.

• 3:15Speaker 03

  I'm doing good. I'm also very glad that it's Friday, cause I feel like this has been a busy news week and I could use a couple of days of peace and quiet.

• 3:21Jason Calacanis?

  Yeah, sure, that'll happen.

• 3:23Speaker 03

  Something, something amazing has arrived on the scene, guys. And I think we all want to talk about trucks. So I think we should just skip right into it and just talk about it. All right. So for everyone, a couple of weeks ago, TechCrunch wrote a story saying that there was a new Bezos backed EV truck company called Slate, perhaps slate dot auto. And everyone was like, what, what are they doing? Why are they doing this? There's so many trucks out there. Well, the wrappers have come off. It's a small, very modular EV truck.

• 3:50Jason Calacanis?

  I saw this and I was like, you know, you need to, you, you, you teed it up perfectly, Alex, for me, which is if you're going to launch a truck company in the age of Cybertruck, the electric F-150 and like Rivian. I mean, everybody's got a truck. There's a ton of EV trucks. You gotta have a specific angle. And I saw this and I was like, that's the angle. Let's play the clip. All right, let's go.

• 4:12Speaker 04

  This is a slate.

• 4:13Jason Calacanis?

  This is a slate.

• 4:14Speaker 04

  Slate seats two and can carry sheets of plywood.

• 4:16Jason Calacanis?

  Seats two people.

• 4:17Speaker 04

  This slate seats five and can fit tons in the front.

• 4:19Jason Calacanis?

  Ooh, a nice frunk.

• 4:20Speaker 04

  It's actually the same slate. This is narrated by me, Jeff. I work at Slate and just happen to have a great voice.

• 4:26Speaker 05

  He really does.

• 4:27Speaker 04

  That's Chris, our CEO. Chris thinks new cars are too expensive and too complicated.

• 4:31Jason Calacanis?

  Two cars, new cars are way too expensive.

• 4:34Speaker 04

  One sec, Chris. Actually, under 20 after current incentives. Go ahead, Chris.

• 4:38Jason Calacanis?

  Oh, it's easy incentives.

• 4:39Speaker 05

  That wasn't a car.

• 4:40Speaker 04

  That means no fancy screen, colored lighting, cooled seats, self-driving, self-parking, automatic cup holders. Yes, that's a thing.

• 4:49Speaker 05

  But you can add accessories like?

• 4:50Speaker 04

  Little screen, big screen, SUV kit, fastback kit, open air kit, one speaker, a bunch of speakers, big bumper, spare tire holder, slatelets, fun grills.

• 5:00Jason Calacanis?

  It's like a platform.

• 5:00Speaker 04

  Even funner lights, colors, any color, really.

• 5:03Jason Calacanis?

  And you wrap it instead of painting it. That's brilliant.

• 5:06Speaker 04

  Means you can add an accessory now.

• 5:06Jason Calacanis?

  Oh, and those studs mean you can add other things, yeah?

• 5:09Speaker 05

  It's like a potato head. Wait, maybe there's a better analogy.

• 5:12Speaker 04

  Actually, there is. Slate is the chameleon of trucks and SUVs.

• 5:16Jason Calacanis?

  That's not a better analogy. Potato heads better.

• 5:18Speaker 05

  There are three.

• 5:19Speaker 04

  A slate is not like other cars or trucks or SUVs. And slate is not like other car companies. Slate, we built it, you make it.

• 5:31Jason Calacanis?

  Genius. I mean, you and I have talked about K trucks or Kai trucks? What are they called in Japan?

• 5:38Speaker 04

  K trucks, K E I trucks.

• 5:40Jason Calacanis?

  These are little purpose-built trucks for small streets and they have a little cabin. Sometimes it's two seats, sometimes it has a backseat and there's a mini flatbed in the back where you can cover the flatbed. They're super cheap. They're narrow. In a country like Japan with cities like Tokyo, you know, you park it anywhere. It's got a tiny little engine and it's not meant to go like 100 miles an hour. It's got like... I don't know if it's a two cylinder, four cylinder, tiny little engine and people have been importing them to the States. There's a couple of websites that do this and it's amazing. And when I see this truck, I started to think of that, but people like affordable. People love these kind of project cars. I could see this becoming a bit of a phenomenon.

• 6:21Jason Calacanis?

  If you are, you know, a young person or you're not a person of means, or simply you don't want to put your money toward a 50 to a hundred thousand dollar car and you need a second car or a third car, or you're somebody who just wants a primary car. That's just dead simple. You don't want bells and whistles. They can make it for 25K. I think this could be a phenomenon. And what do you think, Alex? What was your take on it? Like, I want one immediately.

• 6:47Speaker 03

  Yes, bursting with excitement. Like I, this is exactly what I want. I want to be able to carry things because I have two different double strollers, Jason.

• 6:55Jason Calacanis?

  Yeah.

• 6:55Speaker 03

  I need some cargo space, but I also live in a town that's very, very narrow because it's made for horses, not cars. So what I need is a small, get around the city EV truck. And while I do see Rivian's, I've seen a couple of Cybertrucks here. I've seen a pretty good number of F-150 Lightnings. They're all way too big for my driveway. Like even if I wanted one of those very much, it wouldn't fit.

• 7:14Jason Calacanis?

  And they're 80,000 all in.

• 7:16Speaker 03

  Yeah. Yeah. This thing 25 before incentives, 20 ish after, even if you drop every single option they have, you're still going to walk away for essentially like a quarter. And I don't like to spend my capital on depreciating assets, frankly. So I, I would literally, if my wife was home right now, I would be like, honey, guess what?

• 7:35Jason Calacanis?

  I'm going to put a deposit down on it. And you know, this would be a perfect truck for me for like the ranch or like the nannies or like, you know, going and doing gardening. Not screw up the really nice cars we have. Which I know sometimes I gotta put like bags of dirt or chips or something in my back of my Model Y. And I'm like, oh God, you know, I gotta put like something down. Like it just could be a beater truck. Nowhere in this did they ever mention the fact that this is an electrical vehicle.

• 7:59Speaker 03

  That's interesting. That was not part of the pitch.

• 8:01Speaker 01

  That's not really. They're they're very focused on the like, it's a customizable platform, which I get like people like that. I think even the Cybertruck, we've seen how much mileage people who own it are getting out of like, you could wrap it, you could make it different colors, you could style your Cybertruck. It becomes a personal expression thing. And I think that's really smart of them to focus on that element of it, because I think people are going to love that. But they don't mention the the EV-ness and they really don't mention like, I, I, you guys made fun of the the Prius C that I drive, but it is great for cities because it's a little bit more compact. It's so maneuverable. That's what I like about it. And driving around Austin, all these guys in their massive trucks, like, it's hard to park your forerunner on the street in Austin. It would be much easier to get around in one of these.

• 8:46Jason Calacanis?

  Yeah, it's super cool. I wish them great success with this. More options, more affordability. And, you know, I think this is going to be, if this trade war with China continues, if we go into a recession, value-based products really do well. I remember this from two or three moments in my career when value-based products, not cheap, I'm using value. This feels like a in the category of value and also fun. And it also empowers you as the individual to make decisions. So when you start thinking about products and product design, there are luxury products. Now, luxury products, Steve Jobs, a Birkin bag, you know, the Aman Hotel, they craft

• 9:29Jason Calacanis?

  the experience. You pay a large amount of money to be in that person's world. And you have to be willing to trade a large amount of your money for the experience that somebody else has done for you. That is actually what you're doing. It is not about practicality. Luxury begins where necessity ends. Hey, founders, I want to share with you an experience I love. It's when I get an ad that is relevant and not some nonsense. Like the other day, I got an ad for a fund management platform, and it was like a new one I'd never heard of. I clicked on the ad because, well, I manage four venture capital firms. We scheduled a call with them, and it was amazing.

• 10:09Jason Calacanis?

  This happened. Well, I was on LinkedIn because I like to share links from the podcast This Week in Startups right on LinkedIn. In fact, we livestream to LinkedIn three days a week and we get a great audience over there. And I happened to be presented with this fund management platform, and it was a direct hit. Like, I mean, talk about hitting the bullseye. If you're in business and you're making a product or service, it's really hard to find customers in the business-to-business space. And doing B2B advertising is hard, but LinkedIn makes it so easy because, you know, their tools let you target people by job title, industry, company size, and more. So this fund management platform obviously was looking for people in venture capital who had a fund size and a number of people, maybe 10 people, maybe 50 people. And they found me. They got me. They

• 10:52Jason Calacanis?

  split the arrow. Boom, right on target. And there's two things you really need to know about LinkedIn going into 2025. First, they broke a billion members, and 130 million of those billion are decision makers, and 10 million of the billion are C-level executives like myself. Where can you get to those people? It's really hard. And the second thing you need to know, LinkedIn makes an impact. B2B marketers report two to five times higher return on ad spend, or ROAS, return on ad spend. You should know that acronym. Compared to other social platforms, 79% of B2B marketers say LinkedIn is the best platform for paid media. LinkedIn is going to let you build the right relationships. It's going to drive results, and you're going to reach your customers in a super respectful business environment. It's not a place where people are dancing around, saying inappropriate things, or debating politics. Nope. LinkedIn

• 11:36Jason Calacanis?

  equals business. Business equals LinkedIn. Start converting your B2B audience into high-quality leads today. We'll even give you a Hyundai $100 credit on your next campaign. Go to LinkedIn.com/ThisWeekinStartups to claim your credit. That's LinkedIn.com/ThisWeekinStartups. Terms and conditions do apply. Luxury begins where necessity ends. This is, we're giving you necessity. It's up to you what you want to do with the necessary components here. I knew this because I knew some people who are extraordinarily wealthy, like private jet wealthy. They would charter jets, you know, had owned jets, whatever. And you know, I was like getting on JetBlue.

• 12:18Jason Calacanis?

  And when JetBlue had its routes and they had like the Mint service or whatever, I'd seen somebody who was extraordinarily wealthy, like in Economy Plus, or like I would see them in Mint, which is like this great JetBlue service. And JetBlue was pitched as like, it's a great value. It has some of the feeling of a luxury product, you know, like it's thoughtful, but you could tell people like, I really love it. It's a good deal. It's really nice and a good deal. You don't feel like you're getting screwed. And so in a really bad economy, like feels like we're going into, consumer sentiment's very low. We could go into a recession at any moment. We might have been in a recession.

• 12:54Speaker 01

  Yeah.

• 12:54Jason Calacanis?

  The last year, as you know, Chamath has said, he believes we've been in a recession, but maybe government spending has made it feel like it's not a recession. So maybe the GDP had actually been a little under and the government spending had made it feel like, you know, we were over or, you know, on the borderline. It's recession technically is two quarters of negative GDP. So we might've had like zero GDP or negative, didn't feel like it for most people. But when it does actually become recession, everybody kind of gets into this frugality mindset and they just look for things that feel like value. The Prius was another one. When the Prius first came out, Leonardo DiCaprio, George Clooney, Julia Roberts, all these like, I guess it was the early 2000s. They were like, oh, it's good for the environment and it's such a deal. And when you pulled up to a valet in one, you kind of got more shine

• 13:40Jason Calacanis?

  and virtue signaling points.

• 13:41Speaker 01

  Yeah. Well, that was the South Park episode. You remember when they're all, they're all smelling their own farts because they just got their Prius. Yeah.

• 13:47Jason Calacanis?

  Yes. And there's something about value people like, you know?

• 13:51Speaker 03

  But how far have we come? I mean, from the era of just having a hybrid being something that was kind of risible to now this, this truck's coming out with admittedly a pretty stripped down EV package, Jason. It's just rear wheel drive. It's only 150 mile range. But here's the thing, if I'm going to buy a car that is inexpensive and easy and low maintenance, I want it to be simple to maintain and run. And like an EV is so much better than an ICE.

• 14:12Jason Calacanis?

  This is going to be everybody's second car.

• 14:14Speaker 03

  Yes. Yes. It's genius. Uh, the question is, is it a viable business? The company has raised, according to TechCrunch, I think 111 million, not just Bezos, but also Guggenheim Partners CEO and the guy who runs the Dodgers apparently. Uh, it's going to need a lot more capital, Jason, and these won't come out until I think late 26. So we're about 16, 18 months away from actually hitting the streets.

• 14:37Jason Calacanis?

  I'm going to put an order in for one, just for sugars and giggles. I think it's going to work. It doesn't need to have a huge margin and I think they'll make their money. From accessories and officially licensed accessories. So because it's got those bolts on, you can have like a ton of creativity, but they're going to be able to come up with all kinds of interesting accessories that you'll buy. Right now, there aren't too many in there, but because this is a platform and it's just very base, people might be like, you know what? I want to have a speaker system. They'll come out with a speaker system. That'll be $3,000 for the most kick ass, awesome speaker system. So when you have a beach party, you can do it. There'll be a four wheel drive or an all wheel drive or an extra battery pack. Like it's got

• 15:19Jason Calacanis?

  150 miles now, but they'll come out with a 300, 400 stackable battery pack. They'll do all kinds of interesting things. And you see this with Teslas because the owners also like to geek out about the cars. I almost bought this for my Model Y, but I waited because I'm gonna probably upgrade it. And I saw today they're letting people transfer the self-driving again. So that's like, was the blocker for me? Like, I have to pay another 8,000 for self-driving? It's

• 15:42Speaker 03

  Oh, transfer between cars if you buy a new one.

• 15:44Jason Calacanis?

  Yeah. So when you trade it in, you have to rebuy it. And I'm like, ah, you know, even me, I like a little bit frugal, even though it probably don't need to be. But they have a refrigerator. It's a refrigerator for the back of the Model Y that slides into, in the Model Y, because it doesn't have an engine, doesn't have a transmission, all this other stuff. You open up the back and there's like a little, kind of like the front, a little pit. Well, they made something that fits perfectly into it and then plugs into the power. You turn your car on, you get a little refrigerator in your trunk. So I was like, oh my God, I could put in water bottles. I could put in energy drinks.

• 16:16Speaker 03

  Tailgating.

• 16:17Jason Calacanis?

  And tailgating and you just go back there. And you know, the Jeep Wrangler has a lot of this kind of stuff. So I think they're gonna make a fortune on their store and you could get listed on their store. They could do all kinds of subscriptions. I love the fact that they took the, um, the screens out and they're just like, your phone's the screen. Genius.

• 16:33Speaker 03

  That's really clever, yeah.

• 16:35Jason Calacanis?

  And if you want music, I don't exactly like this. Like you have to bring your own little speaker. I mean, somebody will come out with an accessory, but there'll be a whole business in Doing this, the other thing I thought was very brilliant was the wrapping, which is kind of what Elon did with the Cybertruck, which is, hey, we're going to give it to you and stay on the steal. But by all means, there's a wrapping culture around it. I think wrapping, wrapping those might be two grand, three grand. So it's not cheap for a Cybertruck.

• 16:58Speaker 01

  You could do pop culture themed ones. Like imagine if you could make your truck look like the Jurassic Park truck.

• 17:04Jason Calacanis?

  Yes.

• 17:04Speaker 01

  Like make a Ghostbusters Ecto One truck or something. People would get really into that, I think.

• 17:09Speaker 03

  Yeah. And the company says that wrap kits will start around 500 bucks, Jason. So they're going to start pretty cheap now. I think if you want installation and so forth, it's going to be north of the $1,000 mark. But that's pretty affordable, frankly. And on the Tesla Model Y refrigerator, because Tesla has so many fans, Jason, there's actually a bunch of different refrigerators you can put into your Model Y. Some of them are hidden, some of them are larger. People love to accessorize, which underscores your point that there's going to be a lot of fat margin to be made there. But give me some knobs, give me an easy EV. Let me throw some dirt in the back for 20K. I'm in. So a company, Jason, that we're all pretty excited about to see go public is Discord. They make a social chat application popular amongst the gaming world.

• 17:50Jason Calacanis?

  Yeah.

• 17:50Speaker 03

  Yeah, I'm a big Discord fan. Our friends at Twit have a big Discord group as well that they used to run their subscription program. The news is that Jason Citron, the co-founder and CEO, is stepping down from his role as CEO. He's going to be just on the board. They're bringing in a new guy, Huma Sahini, Sackini.

• 18:08Jason Calacanis?

  Sackini, I think.

• 18:09Speaker 03

  Thank you. Previously of both King and Blizzard, so a gaming background more than a social or chat background. But the cool thing is, this is a company that we've been talking about as getting ready to go public. And so, Jason, when I see a major C-suite shift on a company looking towards an IPO, it just smells like traction and progress to me. So I'm pretty excited about this, though. Of course, I don't think we're going to see Discord file and go out this year, but very encouraging, I'd say, from a Deca corn, Jason.

• 18:35Jason Calacanis?

  Yeah, I mean, it's a, it's a great product. It's pretty sticky, very popular with young people on their desktops. And I use it because there's a podcast or really a YouTube show called Nick's Fan TV. My friend CP, the franchise, not franchise, franchise, the fans elected him as like. The number one Knicks fan and it's kind of true. And I went to game two of the Knicks versus Detroit Pistons at Madison Square Garden with him. So every time, you know, the season playoffs happen, I take him to a game. We go to a game together and we have a good time and talk about Knicks because he's like the uber super fan. It's very funny because, you know, on the street, I'll get like two or three selfies to everyone he gets. And then we get in the garden, he gets 10 to one because he is like, you know, in his elements was very funny.

• 19:19Jason Calacanis?

  We were, um, people were bugging out that the two of us were friends and, um, he uses Discord for call-ins. So we, there's a way with Restream to use their video and their audio. So he runs his show, the same way we use Zoom to go out to Restream and then a Restream goes out, I think. He uses, I think Discord and then he takes callers because it's a call-in show. So the Discord is better than using a phone system because it's really crispy, you know, nice audio. And so I called in last night to talk about the game. I, I do, I do, we do like a field report. So whoever's in the opposing team's arena, we call it a field report on Knicks fans TV. He had like 6,000 people watching him live. He's a, gonna break 100,000 subs, becoming like a real business.

• 20:03Jason Calacanis?

  He was able to quit his job at Cantor Fitzgerald last year and just do his YouTube channel, which is like really incredible.

• 20:08Speaker 03

  That's amazing. Not alone because Discord. Discord now has 200 million global monthly active users according to itself. So that is a top 20 online platform, Jason.

• 20:19Speaker 06

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• 21:01Speaker 06

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• 21:21Jason Calacanis?

  You guys use it at all for anything? You have like any fan community or a part of?

• 21:25Speaker 01

  There's a lot of like independent creators. They run their whole like their Patreon network, like all of their content goes through Discord. So that's been mostly my experience with it is like, you know, when you follow like a popular YouTuber or a channel, you sometimes will get active in their Discord communities or that'll even be where they stream from sometimes or do event things there. Yeah, I mean, it's, I feel like it's very intimidating as a brand newcomer. When you first use Discord, the servers, there's so many bells and whistles and features that it does take a few minutes to sort of

• 22:00Jason Calacanis?

  Totally.

• 22:00Speaker 01

  grapple with, but once you're in there, you realize like it's very robust. There's so much going on.

• 22:05Speaker 03

  Yeah, it's amazing how different our use cases are. Jason, Nix, Lawn, independent creators and media. For me, indie game studios often throw up a discord when they're building a game in early access. So I've been like 15 discords for different city builders and automation games and I can simply just talk to the developers because they're right there. It's fantastic and very good as a business, according to Bloomberg, the company Forex revenue from 2020 through 24 to 600 million on an annualized basis. Now, Jason, my take is a company that was valued at 15 billion in 21 probably needs to have at least a billion revenue to go public and defend that valuation. But again, probably four to six quarters, like it's not too far away.

• 22:43Jason Calacanis?

  So wait, they, did they announce they're gonna file? Did they say they're considering it? Or this was like a rumor?

• 22:48Speaker 03

  So everyone's talking about it because, you know, big company, big valuation, they turned down that Microsoft offer for 10 billion. Citron, in an interview with Venture Beat, did say when asked about whether Discord's heading for an IPO, he said, and I quote, "No specific plans, but as you can imagine, hiring someone like Homan is a step in that direction." So definitely on the way and God, we need the liquidity because Benchmark, Greylock, Spark, Index, Green Oaks and Dragon Year all led rounds into Discord, not just participated. So there's a ton of private market money just kind of crying for this thing to go out. And maybe Figma will kick the door open, you know?

• 23:22Jason Calacanis?

  And their business model's membership, you pay for like a premium membership and features? Or the person who runs the Discord pays for a premium or both?

• 23:30Speaker 03

  I think it's both. You can go like, what's it called Discord Octane or Discord Fire or something like that. And so you this subscription payments, but I mean, across 200 million people and given how much everyone uses like, and my nephew, who's a big, uh, he's like a senior in high school now, he only talks to me on Discord because he doesn't have a phone. Because he doesn't want one.

• 23:49Speaker 01

  I also want to say they're doing a, and don't quote me on this, but I feel like they have like a Twitch like interface too, where you could do super chats and you could contribute to creators. I bet they're getting a cut of all of that as well.

• 24:00Jason Calacanis?

  What else we have in the news? This is great for them. Uh, we're going to have some more IPOs. Maybe the market calms down. I saw big news from Uber. You know, a lot of people, because they know I'm affiliated with Uber, uh, the ride sharing company, kind of become a meme, actually. How many times I mentioned it was pretty funny.

• 24:16Speaker 01

  A little bit.

• 24:17Jason Calacanis?

  They're like, did you know Jason was, uh, an early investor in Uber? They're like, no. And they're like, oh, well, when you meet him, you'll know in the first five minutes.

• 24:25Speaker 01

  Yeah, it's like your, your version of being vegan.

• 24:28Jason Calacanis?

  Yeah, exactly. So.

• 24:29Speaker 03

  Cross the vegan Uber angel investment.

• 24:31Jason Calacanis?

  Absolutely. So, um, you know, and I'm still along the company. I have exposure to everything else. I got exposure to Waymo. I got exposure to Tesla. I got exposure to everything. So I'm not like talking my book here, um, all that much. I mean, I am technically, but Volkswagen is one of the top car makers in the world. They came out with an incredible car. It's not the car for me, a Volkswagen bus right now, but I was, because we, we have a Suburban, which is like the largest SUV you can have. So when we have like a big family trip with a lot of bags, like when we're going to Tahoe, when we used to go to Tahoe from California, we're going on a road trip. We needed to have like a big, big, big max size. Eight, seven, eight people in the car, or in our case, seven, five family members, one or two friends, or you know, a nanny.

• 25:13Jason Calacanis?

  Tons of bags, like it's the greatest car ever. Suburban, tank, love it. But the bus is so cute and it's all EV. And I've been looking at him like, huh, it's a very cute car. And it also has seven seats, six, seven seat configuration, four captains chairs in back row. So like slate, um. It's a bit of a platform and they have self-driving technology. Uber has a network, Volkswagen, tell me how many cars they produce. I don't, I think I remember hearing top five producer in the world, maybe even top three.

• 25:44Speaker 01

  It looks like number two. It looks like in 2024 Toyota number one Volkswagen number two Hyundai three GM four.

• 25:52Jason Calacanis?

  Yeah. So they're very, very large global auto manufacturer. Like if you go to South America, you go to Africa, like they're making stuff everywhere. And I don't know what all their labels are, but they got a big push here. They've been, you know, really trying to get into EV stuff and they're going to do robotaxis with Uber. I believe it's an exclusive, but even if it's not, I had said earlier, like, listen, there's like 20 people working on self-driving. Let's assume half get there. Now you got 10 people get there. Now, what timeframe do the 10 people get there? Well, Waymo is already there.

• 26:23Speaker 01

  Yep.

• 26:24Jason Calacanis?

  At a very high price. So Waymo's in the game. Tesla's almost there, imminently there. Um, and then you have We Ride, you have Zooks, right? So you've got arguably three or four people, like one really going for it. And then maybe three with operators or something. So we're, you know, we're on the cusp of this. It's going to be a long, you know, 10 year rollout. But Volkswagen has a unique ability to produce a lot of cars if they're the number two car maker. And Uber has the largest ride sharing network. You put those two things together and they took the right approach. I've been saying over and over again, my belief is that the second, God forbid, a kid runs in the street, your dog or your cat runs in the street and we get on video,

• 27:06Jason Calacanis?

  somebody getting hit by a self-driving car, whether it's a Waymo or Uber had one.

• 27:12Speaker 01

  Elaine Hersberg was her name. This incident happened in 2018. The first recorded case of a pedestrian fatality involving a self-driving car.

• 27:20Jason Calacanis?

  Yeah. And I believe that immediately shut down Uber and it was in Arizona.

• 27:24Speaker 01

  It was in Tempe, Arizona. It was an Uber test vehicle.

• 27:27Jason Calacanis?

  Yeah. And the woman was playing Candy Crush. So this was an operator caused problem. In addition to self-driving, right? Because the self-driving was like, you know, level two or something at that time. You needed to have an operator. The backup driver of the vehicle was charged with negligent homicide, pled guilty to endangerment and was sentenced to three years probation. Uber was not criminally responsible in the crime. That's very reasonable. Kind of feel like you should have went to jail for a year, I'm being honest. Like if you're on your phone and you kill somebody, like that happened to your family member to just get away with a warning. Anyway, I'm going to put that aside. Criminal justice is not our purview here exactly, but I think anytime you operate in a city, you should have to do one year and let's call it 10,000 successful rides. I'm just picking a number, folks.

• 28:11Jason Calacanis?

  But it seems reasonable to me that 10,000 trips of an average of five or 10 miles each gets you into 50 to 100,000 miles. I have a major concern about the rollout of self-driving. I'm super happy about Uber. When we get back from this quick break, I'm going to tell you my concern that could stop the auto industry from doing full self-driving for years in America and globally when we get back from this quick break. Your business is as strong as you are. And as a founder, you know, listen, maybe you're running on caffeine, four hours of sleep. That's not sustainable. Your startup moves fast and founders are pushing their health to the limit and it's going to catch up with you. That's just the bottom line.

• 28:53Jason Calacanis?

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• 29:36Jason Calacanis?

  Visit superpower.com/twist, unlock peak health today because better health equals better founder, which equals a better business. This is incredible news for Uber. Uber's really up on the news. I believe of the 20 people trying to do self-driving, half of them will get it done in the same.

• 29:58Jason Calacanis?

  Let me pick a number, 12 months.

• 30:00Speaker 03

  Oh, okay.

• 30:01Jason Calacanis?

  The same 18 months, I'll say 18 months, I'll be a little generous here. I believe 10 companies in the next 18 months will have these products on the road. And in fact, towards the end of that 18 months, without a safety driver, with just a remote watch driver in limited capacity, limited geofence zones, and it's going to be awesome. I have a fear, the stock market is obsessed with self-driving. They're obsessed with it.

• 30:27Jason Calacanis?

  And I know this because when you own these stocks and you see the moves, Tesla announces something, Uber goes down, Uber announces something, Uber goes up, Waymo announces something, Uber goes up, Tesla goes down. It's just, there's becoming, or Zooks and Amazon, there's becoming a little bit, and BYD now getting in on it, because they have self-driving technology, there's becoming, and you know how markets drive this, I think the teams running these self-driving efforts are going to need to come up with a standard for safety. And it does not, because they're done in local jurisdictions, cities, states, countries have all different jurisdictions, and there's also like in other places, regions, we're

• 31:11Jason Calacanis?

  going to need to come up with an industry standard. Like the MPAA came up with the ratings, this is a PG movie, oh, Indiana Jones is coming out, we'll come up with PG 13, it's going to be a little scary, but it's not quite an R, so, but if you have a 10, 9 to 12 year old, Raiders of the Lost Ark might have been okay, but definitely Temple of Doom, Call of Duty, with the heart, not good for 10 year olds, 9 year olds are too scary. So, I think we have to come up with an industry standard. If we don't have an industry standard, now you're going to get some upstart who feels like they're going to go out of business if they don't get the announcement. You're going to have a company whose stock is down, or whose stock is surging, and they, you know, they get pressure from their board, or from shareholders, or an activist shareholder,

• 31:53Jason Calacanis?

  go faster, go faster, go faster, we have to catch up with Waymo, we got to catch up with Tesla, we got to catch up with Uber, we got to catch up with BYD. There needs to be an industry standard, I think the industry standard should be. Any city you go to, you do one year with the safety driver. Everybody agrees to that. So there's not this pressure where, you know, Tesla's been giving mixed signals. Is there going to be a safety driver? Is there not going to be a safety driver? In what timeline? That's putting pressure, obviously, on Waymo to expand faster. Waymo is probably feeling like, oh, my God, Uber and Volkswagen, they have a deal. Okay, is Uber going to be the neutral platform? Okay, and then BYD in China is probably saying, you know what? We have to get this on the road in Europe and South America before Elon gets there because he's very capable.

• 32:36Jason Calacanis?

  One year with a safety driver, perfect record. Then you're allowed to do a 10 by 10 mile area where you had that safety record. If you want to expand, again, one more year.

• 32:47Speaker 01

  Yeah.

• 32:47Jason Calacanis?

  10,000 more rides.

• 32:48Speaker 01

  I think it makes a lot of sense because people, especially people of a certain age, they're, they're, they'll get into this technology. They'll use it, but they need to like dip their toe and they need to feel comfortable first. And so it's sort of almost a marketing strategy as well. It's like, give people time to adjust to the idea of driverless cars before you just throw them on the streets with them driving everywhere and make everybody feel sort of threatened at first.

• 33:13Speaker 03

  No, you guys are both so wrong. You should go faster. This is ridiculous. I've never seen such, such mealy mouthed, overly safety conscious. And here's why I think we can go faster. I actually agree with everything.

• 33:24Jason Calacanis?

  Oh, you're serious? I thought you were joking.

• 33:26Speaker 03

  Oh, no, I'm dead serious. I actually agree that we should have stringent standards. We should have rules and regulations about this. And for context, the Volkswagen Uber deal is going to have people in the cars and it won't go driverless till 2027 to have time, Jason, to get it right. But I think once you've proven yourself in certain markets and you know how to roll out to new areas, I don't think you should have that many strictures on you because you're not replacing perfect drivers. You're replacing idiot humans behind the wheels of dangerous weapons. And so to me, as long as it's materially better, I just think we can go faster because we're taking risk out of the system, even with that.

• 34:00Jason Calacanis?

  It is a valid argument that if they are. Even 10% safer than humans, you would want to adopt that technology. That is a very logical approach to it. However, on an industry basis, it does not matter. You will be judged so much harsher, 100 times harsher for a self-driving car than a human. A human could be on their phone, playing Candy Crush, be distracted, kill somebody, and we don't stop people from driving with their phones. And phone enforcement has not changed. I think they should have cars that ride up right alongside you, videotape you if you're using your phone, pull you over, and they should take your phone.

• 34:44Speaker 03

  Yes.

• 34:44Jason Calacanis?

  That should be the law. Your phone is confiscated and you get a ticket. Imagine...

• 34:51Jason Calacanis?

  Listen, we all do it, folks. Somebody calls, you fumble your phone, you got it in a... If it's not in a tray, like if you're holding your phone, I'm talking about if you got it in your hand and you're doing this, like we all see people doing. If you're not using hands-free, you got it in your hands, you should get pulled over, you get your $100 ticket. They take your phone, they put it in the police station, and in 24 hours, you can go pick it up.

• 35:09Speaker 01

  I'm like, this feels quasi-legal to me. Like, I don't think they're allowed to confiscate your property. I feel like there's a due process issue.

• 35:17Speaker 03

  I don't think so, because a civil asset forfeiture is an enormous problem with the American police force. If you have a lot of cash in your car, for example, they can just take it.

• 35:24Speaker 01

  They can, right. They could see it, but it's... But that's like, you know.

• 35:27Jason Calacanis?

  Okay, well, let's... I don't know the law. You're probably right. I'm gonna go ahead and say you're right. This is the new segment we're doing here called "J-Cow for President."

• 35:36Speaker 01

  Yeah, right.

• 35:37Jason Calacanis?

  And I already put my first J-Cow executive order. This will probably be Executive Order 6 through 10.

• 35:44Speaker 01

  Yeah.

• 35:44Jason Calacanis?

  So I'm just putting it out there. We have two executive orders.

• 35:46Speaker 01

  Are you gonna sign your executive orders and hold them up for the camera like Trump style?

• 35:49Jason Calacanis?

  I'm gonna actually do it on the show.

• 35:51Speaker 03

  Oh, okay, great.

• 35:52Speaker 01

  I love that, yeah.

• 35:53Speaker 03

  I thought Jason was gonna say, your phone gets confiscated and it gets crushed by a machine, so all the information is safe.

• 36:00Speaker 01

  Yeah.

• 36:00Speaker 03

  But I... No, I really think that if you're driving and texting, you should lose your license.

• 36:04Speaker 01

  Oh, I'm not defending traffic.

• 36:06Speaker 03

  You're driving a multi-time vehicle where there are children.

• 36:08Jason Calacanis?

  I like the idea of a forfeiture. I mean, they could take your car when you speed over a certain limit.

• 36:13Speaker 03

  Yeah.

• 36:14Jason Calacanis?

  I have a friend who's Corvette. Was put on a flatbed because they were going at a brisk speed.

• 36:20Speaker 03

  Was this friend going over a hundred perhaps in a 60s zone?

• 36:23Jason Calacanis?

  This friend of ours.

• 36:25Speaker 03

  Yes.

• 36:25Jason Calacanis?

  Was dumb, young, and had run into a little bit of money and needed to learn a lesson that he has carried with him for a long time now. And it was before he had kids.

• 36:34Speaker 03

  I want to add to the story, though. Waymo did drop this week an announcement that they are now doing 250,000 paid rides per week up from 200. There's a lot of noise Jason made about like, oh, Tesla did their thing and now Waymo is trying to step on them. It's Alphabet earnings week. Of course they were going to drop a new number. So I view that as more coincidence than anything, but I want to reiterate that Waymo going to DC, I still think is clutch because I think it does show that they're confident enough to put congresspeople in self-driving, which to me implies technology is advancing fast enough that we can go faster on the regulatory side because my lord.

• 37:06Jason Calacanis?

  What else we got in the docket?

• 37:07Speaker 01

  It's kind of what I'm saying. Yeah. You need to sell the old people on it. You got to show them that it works in front of them. They don't believe you.

• 37:13Jason Calacanis?

  Works in a controlled zone and controlled weather and, you know, just no accidents, please. And come up with an industry standard. Why not? Why wouldn't you have an industry standard?

• 37:20Speaker 03

  All right. Next up, we're going to the insect route. We're talking about butterfly effect, the Chinese company behind the viral Manus AI agent. We talked about this a couple of weeks back. Everyone was buzzing. It turns out Manus, which was a way to essentially automate tasks very easily, was using some anthropic technology. So some people were like, well, is this really a breakthrough? Is this just great repackaging? Whatever the case, Benchmark is in, Jason.

• 37:44Jason Calacanis?

  Oh.

• 37:44Speaker 03

  They led a $75 million round into butterfly effect with participation from other folks, boosting its valuation up to the half billion dollar mark.

• 37:52Jason Calacanis?

  Where is the company based?

• 37:53Speaker 03

  I struggled to track down butterfly effect. I was going through some, a lot of fire lanes.

• 37:58Jason Calacanis?

  Wasn't that a Chinese company?

• 38:00Speaker 03

  Yeah.

• 38:00Jason Calacanis?

  Or they were making this announcement from China? I'm a little, I think there is a rule against investing in China right now.

• 38:07Speaker 03

  Literally, my, my question, my first question was, how did they do this?

• 38:10Speaker 01

  I mean, I'm seeing Beijing based is what I'm seeing.

• 38:13Jason Calacanis?

  Maybe they're spinning the company out and put it in Singapore or Hong Kong or something. They could have redomiciled it. They might have an. Office in China, which would be fine. So, but there was a bunch of divesting occurring because the Biden administration, you know, during the Biden administration, they said, yeah, no more investing in China and China, you know, that's when that chippiness started. Uh, what else do we have in the docket?

• 38:37Speaker 03

  Perplexity has snagged a big deal with upcoming Motorola Razr phones. If you are not young enough to recall Razrs.

• 38:44Jason Calacanis?

  Razr? They still make Razrs?

• 38:47Speaker 03

  Yes, they've apparently they brought them back, their little folding flip phones with a screen on their front. And, uh, there's the new Razr, Razr Plus and Razr Ultras, which launched on May 15th, will come with perplexity pre-installed. Now, the context here is that Google's currently in a lot of trouble for having, uh, a blanket, essentially monopolies on people, you having search in their apps on their phones, if it's Android. Uh, so good for perplexity. My question for Jason is pretty simple here. Are they doing too many non-core things as a company? They feel like perplexity is always in the news and it feels, um, frantic to me, but I'm curious if I'm just being too conservative about how companies should approach partnerships if they can get major one.

• 39:24Jason Calacanis?

  So they seem to be very partnership savvy. I notice a lot of times you get a free year to perplexity. So like, I don't know if it's like podcasts or other software companies that are really into bundling and trying to tap into other audiences and quickly get people into the subscription funnel. When you get a year free of something, in order to get the year free, I think you have to put your credit card in and you get billed in month 13 kind of thing. I don't know exactly how they do it, but when you do that, you can then count paid subscribers. So your paid subscribers can go up even though they're on a trial if you have their credit card, but you know, and then you're expecting a certain amount of churn.

• 40:05Jason Calacanis?

  So you got to be careful with that. I don't know if they're doing that, but I have seen that, uh, startups do that kind of aggressive tactic.

• 40:12Speaker 01

  There is a deal, uh, you get perplexity for a free year if you are signed up to Comcast Xfinity cable and streaming, uh, TV platform.

• 40:23Jason Calacanis?

  So I don't know if you have to put your credit card in to get it for free. You might have to do that, who knows?

• 40:27Speaker 01

  Right, you have to be an Xfinity customer, so you would have to give them your credit card.

• 40:30Jason Calacanis?

  So then maybe they're giving Xfinity half of the money in year two if you do it. So these kind of commission-based deals are very popular with credit cards. If you get somebody a credit card, you can make, I don't know, fifty to two hundred dollars. If you get them to open a brokerage account and put a deposit in, you can get three hundred dollars. That's why a lot of you'll see, like if you have Sirius XM or you have Hulu or YouTube TV, when they have like house ads that they run over and over again, it might be for E-Trade or something because E-Trade pays them a little bit of money, but then gives them a spiff. So there's an incentive for them to just run the ad in any empty slots they have. But Perplexity seems pretty good at these deals. I do think Perplexity is going to have a differentiation issue.

• 41:15Jason Calacanis?

  When, you know, you start to see people get into the habit of ChatGPT, Grok when they're in Twitter, Facebook's, you know, AI when you're in those things. It's, you know, standing up and getting a hundred million, two hundred, three hundred million people to pay for a product, other people are giving away for free. It's gonna be hard, it's gonna be hard. Then there's been plenty of paid search engines that people have tried to take the ads out and give you a paid search engine. About five to twenty-five percent of consumers, depending on the category, like to pay for stuff. Most people like it ad-based, so it's just gonna be challenging, but I give them a lot of credit. So interest in ChatGPT over time versus Perplexity? Yeah, I mean, it's kind of unfair. ChatGPT is such a juggernaut. I might do a better one would be like all, everything but ChatGPT.

• 41:58Jason Calacanis?

  So if you did Perplexity, Claude, Grok, and Gemini AI or Gemini, it might be interesting to do this.

• 42:07Speaker 01

  As a sort of layperson in the, in the AI world, it really feels like ChatGPT, Gemini, and Grok are way more visible. And then there's, there's a ton of other companies. And I mean, Claude is like interacting with a lot of applications and like other kinds of.

• 42:22Jason Calacanis?

  Yeah, that seems to be their sweet spot, Claude.

• 42:24Speaker 01

  Right, but like by far, those three are like the most prominent. And then everybody else, I feel like, is in a whole level below.

• 42:31Jason Calacanis?

  Claude is such a good product, though. I mean, I use Claude all the time.

• 42:33Speaker 01

  Right, and Claude is interacting with so many other startups and so many other products that I feel like that kind of is.

• 42:39Jason Calacanis?

  So this is interesting. We're looking here at Perplexity, Gemini, Grok spiking there. And it looks like Gemini. Yeah, and Gemini might include other Geminis, like there's a Gemini Trust or something like that. So that's a hard one to parse if we're talking about the actual Gemini, but

• 42:55Speaker 03

  It's also a star sign, right?

• 42:56Jason Calacanis?

  Yeah.

• 42:59Jason Calacanis?

  There might be some baked in interest there if they're using a generic name. You know, I bought a Light Phone 3. I saw the former founder of Pebble wouldn't stop talking about the Light Phone. Have you guys seen the Light Phone before? You know that concept?

• 43:13Speaker 01

  I'm hearing about it for the first time.

• 43:16Jason Calacanis?

  Okay, so I got a Light Phone coming. And this is what it looks like. It's an Android phone. I think it's using the Android operating system. It's basically all the things you need, but without the stuff you don't. So if you need to get directions, you want to play some music, take notes, have a calendar, have an alarm, use your phone. It's got those basic things. It's black and white. You get rid of your screen. I'm going to try this. So when I'm out with my daughters, I have a phone with me, but I don't have like a global streaming YouTube device to watch, you know, Knicks games on and get totally distracted by it and no social media on it. And yeah, I can take my notes if I need them. But I think this could be another trend coming. It kind of is like the slate truck we talked about.

• 43:57Jason Calacanis?

  Less is more. This is a third of the price I think I pay for my iPhone at this point. I think my iPhone was close to $2,000, which I'm embarrassed to even say that because I always just, I'm just like, I'll get me max memory, get me max storage. And now I'm actually like, I'm an idiot. Wait a second. Do I need max storage? I actually don't. I have cloud. So I'm like, yeah, get me the lowest storage. I was just every, I'm an idiot. And then I realized Apple is like literally making their margin from the idiots in their group. And then I'm like, for memory, I'm like, that kind of does matter. So with like laptops, I always try to max out the memory because I feel like you get one extra year. So you have to basically say, what is the cost of the laptop? And if you have max memory, you can get one more year out of your MacBook if you have max memory. So for an extra $400,

• 44:40Jason Calacanis?

  if it's a 1500 and you like to keep it for two years, or let's say three years, you can get a fourth year from it. But I'm, I think on corporate with these MacBook Airs, I'm going to go to keep them for three years, sell them back for 500 bucks and then keep upgrading them. I feel like year four on a MacBook Air is not fun.

• 44:57Speaker 03

  No.

• 44:58Jason Calacanis?

  What do you guys do? How many years?

• 45:00Speaker 01

  Uh, yeah, I mean, I, I'm, I ride them until they're, the wheels fall off. Like, that's my philosophy in general. But yeah, it's, it's

• 45:07Speaker 03

  I stopped you from doing that.

• 45:09Speaker 01

  Once your past three years, you, you start to really notice the device is getting sluggish as opposed to when you first got it and it was Yeah, super fast.

• 45:18Speaker 03

  Yeah. I, I keep my smartphone until the battery is failing me and I change out my gaming PCs whenever I want to play something that I can't handle. I have max graphics. So it's, it, it depends, but probably three years is a good cycle. I just don't get people who still buy the new iPhone every year. Like, do you really need to have your camera, the back of the case, things change? You're not going to notice. I'm not impressed by it.

• 45:39Jason Calacanis?

  Well, I mean, the other thing that's in the news is, you know, the New York Times is suing OpenAI for copyright infringement. They got a heck of a case based on my assessment of it. I think it will result in, you know, perhaps a record-setting fine for theft of IP. Uh, and you know, these things almost always get settled. I think it could be a billion-dollar settlement. Blon, um, and I think that would be fair because I used to subscribe to the New York Times for Wirecutter. Now, I ask ChatGPT, which I pay for, or Claude, which I pay for.

• 46:14Speaker 01

  Yeah.

• 46:15Jason Calacanis?

  Actually, it doesn't come up on Claude, but it definitely came up on OpenAI. But I, I will ask, what did the review site say is the best air purifier? And I'll specifically say, what is Consumer Reports and Wirecutter? I used to subscribe for Consumer Reports. I used to subscribe to Wirecutter. And I'll just ask them, what are their best ones? And they wind up giving you the answer.

• 46:32Speaker 01

  Yeah.

• 46:33Jason Calacanis?

  And it's like, well, that's behind a paywall. And then I'm like, well, how did they get the answer? And it was obvious they were scraping it. Now they're not. They should have paid for a license. They should have done it in advance. And now they're saying, oh, we're going to lose to China if we don't respect IP. Uh, but Ziff Davis has now joined the fray, I see. And Ziff Davis has a lot of content, a lot of like real technical content. So what's going on with that?

• 46:53Speaker 01

  So Dick, Ziff Davis says that, uh, OpenAI has, quote, intentionally and relentlessly reproduced exact copies and created derivatives of Ziff Davis works, which it claims are infringing on its copyrights and diluting its trademarks. Further claims that OpenAI use Ziff Davis content to train AI models and generate responses through ChatGPT. They're looking for nine figures in compensation.

• 47:18Jason Calacanis?

  I think it's going to be because OpenAI is the biggest and they're worth $350 billion and they're making 10 billion and they're making that 10 billion because they have the world's knowledge in there.

• 47:29Speaker 01

  Yeah.

• 47:30Jason Calacanis?

  And, uh, you know, it's pretty clear that they were fast and loose in terms of the early days. I don't know about today, but you know, they're trying to be more thoughtful now. Like in retrospect, I think they realized they did the wrong thing, which is great that they realized they did the wrong thing, but now you gotta make amends for it and they should have a licensing program. You should be able to come to ChatGPT and OpenAI. There should be a form where you say to them, you have my content. This is what my content costs pay me. So if they index this week in startups, I could say, you know what? As long as you link back to it prominently and you link back to the homepage and you link back to the YouTube page.

• 48:01Speaker 01

  Yeah.

• 48:01Jason Calacanis?

  Uh, and you use no more than 30 seconds of a clip. I'm okay with it. Like if they came to me with that offer, I might be like, okay, yeah, 30 seconds I'm fine with. Or if they said, we'll index, you know, 2,000 episodes or whatever, and we'll give you $100 per episode per year because it's great content. We'll give you 200,000 a year. If they came to me and said, I'll give you $20,000 a year, like literally that would be $10 per episode. I'd be like, okay, found money. $20,000. I'll take it.

• 48:25Speaker 01

  Yeah. And I mean, so many media companies, you know, companies that produce journalism, they're struggling so much now. They desperately need this kind of revenue boost. They probably would take a discounted deal if there were some kind of offer being made. And actually we already can see how it would work. Like if you use Notebook LM or you use Google's deep research, it shows you where it got every piece of information. It hyperlinks it. There are footnotes that you could follow. Like every, every AI engine should be doing that. Did you see this story we posted in the, the chat? Oregon state lawmakers are now considering a bill that would require big tech companies to pay money based on them using AI, feed that into local newsrooms and journalists. So it would like use some

• 49:09Speaker 01

  of the profits you're making off of these AI tools to fund professional journalism and provide a financial lifeline to Oregon newsrooms, which is I think a great idea. Like that's exactly how, you know, like when Netflix wants to go into a new market like Turkey or France, the local government will sometimes say, okay, but you gotta spend 15% of what you earn from the Turkish market, feed that back into Turkish original content.

• 49:36Jason Calacanis?

  It's pretty simple to just be generous. Everybody should.

• 49:38Speaker 01

  It's a no brainer.

• 49:39Jason Calacanis?

  All, you know, New York Times is probably going to want to go it alone, but I think Disney, New York Times, ESPN.

• 49:46Jason Calacanis?

  Ziff Davis, Conde Nast, like, some of these are major multi-billion dollar, hundred billion dollar brands. They should just all, tens of billion, they should just all get together and just pile these lawsuits on until OpenAI cries uncle and says, okay, here's the settlement and here's the go forward.

• 50:02Speaker 01

  Yeah, and these companies have such deep pockets, they could save the next 10 years of American journalism and barely even notice it on their bottom line.

• 50:09Jason Calacanis?

  Yeah, they don't care about that. What they care about is precedent, I think, and people in Silicon Valley, I'm not speaking specifically about OpenAI, they generally don't respect artists, they don't respect content creators, because content creators have been suckers and they're like, yeah, we'll build YouTube, we'll build Instagram, yeah, give us a fun playground, you give us some traffic and free software and we'll put it there. But over time, people start to say, you know what, enough's enough, we want some control over our content, it's our content, and, you know, they, they kind of do that. There's also, I don't know if you've seen it, and it's kind of like a, I think it's kind of a breaking story, I sort of come up this week, notforprivategain.org. A bunch of folks from OpenAI, and these are, you know, real experts, are doing one of

• 50:49Jason Calacanis?

  these, um, so they've written this open letter, and it's basically to this attorney general, or these attorney generals, about this nonprofit structure and what everybody bought into. And, you know, they want to understand these fundamental questions, so they, they really laid it out nicely, like, number one was understanding OpenAI's charitable purpose, why nonprofit control protects the mission, and, you know, they're using quotes from Sam Altman and other founders, you know, of OpenAI to kind of say, hey, this is what we all bought into, um, and they're really questioning if OpenAI is gonna solve the problem of profit-driven AGI and give it away for free to humanity. And it's very

• 51:34Jason Calacanis?

  interesting, because if you look at the signatories, these are some, like, pretty heavy hitters, people from OpenAI, but they also did a very smart thing, they went to all the law schools to talk about Nonprofits and nonprofits is like a very, I don't know how this concept actually came to be. And I'm going to try to find the history of it at some point, but I would like to understand why we have this nonprofit structure, why religions, you know, why rich people can pop up a nonprofit, hire their families to work for it, donate money to it and then use it, you know, for all kinds of purposes. And, you know, like I'm going to have a nonprofit golf tournament and like all the rules around it. It all feels like maybe it's unnecessary for us to have nonprofits.

• 52:17Jason Calacanis?

  Like if you're a rich person and you give a donation, would your donation change if you didn't get the tax break? And should nonprofits of a certain size have to pay taxes? And it just seems a little bit weird to me, the whole nonprofit structure, but you know, in order to preserve the nonprofit structure, allowing OpenAI or any company to just flip, flip, flip into for-profit.

• 52:38Speaker 01

  Right.

• 52:39Jason Calacanis?

  And take the original mission and get rid of it. It's as other people have said, well, if you can start with a nonprofit and I as somebody who, you know, I, let's say I made a million dollars in profit from a stock sale or from income and I get to give this million dollar donation. Well, then I get two for one dollars, let's say, if I'm in a high income tax bracket to donate to a nonprofit. I do that for three years. If it turns into a real company, I flip it into a for-profit company and then I was able to fund it at half price.

• 53:10Speaker 01

  It seems to purely violate the spirit of what we're talking about. Like the whole point of a nonprofit, we're giving you this tax exempt status, we're giving you all of these special benefits because you're not pursuing a private interest, you're pursuing the public good. So if you could just switch at any time, it's like, well, so this whole time you really have been serving your private interests, just quietly, you made it look like it was in the public interest. But so, yeah, that, that feels sort of ridiculous to me that you could just change it around at any point. It's like, no, you, you established this. It's, this is what you're doing now. It's a new organization if it's now for private.

• 53:44Jason Calacanis?

  Yeah, I saw the FT report also that Apple is going to shift all their US iPhones to India as soon as next year.

• 53:51Speaker 01

  Hmm.

• 53:51Jason Calacanis?

  Um, which is, uh, you know, China's not happy about it, but they had set this up as their escape hatch and here we are. This is their escape hatch.

• 54:01Speaker 01

  Yeah.

• 54:01Jason Calacanis?

  Let's do a Founder Friday. Let's get one. Let's get another pairing done.

• 54:04Speaker 01

  We got one more matchup left to go this week. We're in the midst of our Elite Eight. Last time, you'll remember Med Simple from Florianopolis. They are our first Final Four contender. Congratulations to the team from Florianopolis, Brazil. Today, we've got Pitchfire from Portsmouth, New Hampshire versus another international contender, Taktoon from Yerevan, Armenia. So first, we're going to look for, we're going to look at Pitchfire. They are a paid prospecting platform where potential buyers can earn money for reviewing and responding to sales pitches from B2B companies. And just as a reminder, we've asked the companies for this round. They're giving us an insight into their two-year plan.

• 54:44Speaker 07

  Eighty percent of B2B companies are missing their pipeline number, and everybody needs getting cold prospected. Let's give you Pitchfire's two-year plan on how we're going to fix this with our paid prospecting platform. Businesses pull buyers in by running paid prospecting campaigns at them over email, offering people money to respond to their sales pitches. Once a buyer responds and receives payment, they automatically join our marketplace, and we push them to install our inbox plugins. So why would they do this? Because it removes them from that sales rep's sales automation and gives them a shot at potentially making money for their retention. It also helps fund their sales team's paid prospecting efforts. A low-level B2B employee gets prospected about 780 times a year. They would push at least nine new sales reps onto Pitchfire every year. Pitchfire's path to average $100,000 in revenue in two years is all tied to generating responses from paid pitches. As Pitchfire grows, buyer-sourced pitches will be our main source of revenue.

• 55:29Speaker 07

  Over the next two years, we'll hire eight full-time employees, heating to $80,000 of burn every month in salaries. We'll start with growth marketing, another full-stack rep engineer, and a sales rep to push companies to do paid prospecting. Next, we'll hire a lifecycle marketing expert and another sales rep. Beginning of next year, we'll have a machine learning and AI engineer on staff full-time. As we get more volume, we'll need customer success to keep customers on over the next two years. Our product burn takes about $9,000 a month to operate at peak capacity. Our roadmap will start with adding SMS notifications for people that get pitches and user reviews to earn trust between buyers and sellers. A UI in our product for paid prospecting campaigns and a company wallet, an integration for marketing teams' hubspots and SOC 2 compliance, a chat in our

• 56:11Speaker 07

  That welcomes rebuttals and allows up sell opportunities then during buyer matching and user management to expand teams on the buying side in Q3 of 2026. We'll deploy an AI auto reply application that will automatically detect cold emails and send it to pitch fire. And by the end of next year, we'll have a buying agent answering pitches that come in from sales reps. We can get 7,937 paid pitches responded to with our 20% cut will hit a hundred thousand dollars in the last quarter of our two year plan.

• 56:37Jason Calacanis?

  What I like about asking him to do a two year plan is you can start to see if like they actually have a thesis and they understand how to budget money and that's what we got here. So your confidence as an investor goes up because if people plant that flag and say, hey, here's what we want. Here's the ask, we're going to raise two and a half million, we're going to spend, we're going to burn a hundred K a month. You can start to have a really granular discussion and look at the assumptions and then start banging on the assumptions and. You know, doing 8,000 intros, I don't know if that was a quarter or maybe it's a month. It doesn't seem like a giant number. If you remember, this was an interesting SaaS company. You get paid to evaluate a product. So I'm making Zoom. I email on, hey, we have this new thing. It's better than using Skype. It's better than using Google.

• 57:22Jason Calacanis?

  Whatever they call Google's one, Google Meet, it's better than Google Meet. Would you evaluate it for us and see if it's great? You, if you do, you get this $40. They evaluate, say it's not for us. Great. We take you off the list. You got 40 bucks in your account, but you work at Slack. And you evaluate it and then your Slack team gets whatever they get like 15 bucks. The other company gets 15 bucks and you, you kind of, then you can go take Slack and you can ask people at Zoom and other places. By the way, this is what happens in the startup community. People always ask their friends to buy their products. Certain accelerators are known for like trading. And I don't think the accelerators encourage people to do this. I just think it happens when you're in a cohort. Hey, you buy mine, I'll buy yours. Founders hack things.

• 58:07Jason Calacanis?

  So we always have to look at like, okay, yeah, tell us your top 10 customers or which five customers did you get this week? Tell us the names. How did you source them? And if they say, oh, we sourced them while in our accelerator, we say, okay, great. Of those five, we kind of, we'll just kind of laugh it off. Oh yeah, we know that trick. You know, that's great. Do any of them actually use it and get value? And then once they tell us that they got value, then we're like in a, in a great place with them. Okay. Let's hear our next one.

• 58:28Speaker 01

  All right, so from Yerevan, Armenia, this is Tactune. They're creating a platform that allows machine manufacturers to develop intelligent devices without having to write all of the complicated code themselves.

• 58:42Speaker 06

  Tact is a no-code automation platform that enables machine manufacturers to make the machines they build intelligent, connected, and autonomous. Over the next eight quarters, we're scaling from a working platform and initial pilots to a robust AI-enabled product deployed across the US and EU. Our journey starts with launching version 1.0 and securing our new paying customers. By 2026, we reach autonomous deployment capabilities and begin European expansion. We target 5 million in ARR by early 2027. Revenue accelerates quarter over quarter while expenses remain stable. We cross breakeven in Q4 2026 and stay profitable from that point forward.

• 59:25Speaker 06

  Our headcount strategy combines core human hires and full capability AI agents. As of Q1 2025, we have 11 team members. We add new hires quarter by quarter. By Q1 2027, the team includes 24 human employees and seven AI agents working across engineering, DevOps, support, and Q8. We track what matters: growth in customers, operating efficiency, and cost ratio. Metrics improve quarter over quarter as we scale showing strong fundamentals without exposing sensitive financial margins. Our operating plan is fully aligned with capital-efficient strategy. We plan to open 3.6-minute seed round later this year to fund execution for Q1 2027.

• 1:00:09Speaker 06

  The capital supports product delivery, go-to-market, and Series A readiness. Thank you very much.

• 1:00:15Speaker 01

  Huh, okay. What do you guys think? Which one is your favorite? And why?

• 1:00:20Speaker 03

  I'll start. Tactoon gets my win for a number of reasons, but the most interesting one is that they listed AI agents that they wanted to hire in their employee section. That's new to me.

• 1:00:29Speaker 01

  Very interesting. Yeah, I noticed that too. I thought that was really interesting. They're like, we're gonna have 24 humans working alongside seven AI agents. It reminded me, one of our founder U companies has created a virtual board of AI characters and they consult them every day. But like, they gave them different personalities. So like, this is our marketing expert. This is our, you know, business operations expert. I thought that was really interesting, too. Of these two, you know, I don't want to make it non-competitive, but Tactoon also, I think, is gonna get my vote. I just think it's such a smart idea for a platform and they seem to have the, you know, they seem to have already figured out how they're gonna grow it and expand it.

• 1:01:08Speaker 01

  And I just feel like that, to me, feels like the future. We're gonna have so many companies trying to make smart devices that work with their software. This just seems like a no-brainer to me.

• 1:01:17Jason Calacanis?

  Yeah, I think it's gonna be a clean sweep. You know, as much as I think Pitchfire did a better job on their pitch, and I thought their planning was better, I do think it's a bigger opportunity. So I think Tactoon. Congratulations, you're moving on.

• 1:01:30Speaker 01

  Tactoon in our second final four contender. So wow, they've, that's very impressive. Well done to Tactoon.

• 1:01:36Jason Calacanis?

  All right, everybody. Another amazing episode of This Week in Startups. A lot more coming on Monday. We'll see you at 12:00 PM, Texas time, 1:00 PM Eastern time, 10:00 AM, left coast time. If you're interested in Founder University, go to Founder.University and learn more. We'll have another cohort starting over the summer. And that's where we have three, 400 teams of two or three co-founders build their MVP and then decide if they wanna take a little bit of funding from us or maybe incorporate and take their, you know, business idea to the next level and go down the venture track.

• 1:02:10Jason Calacanis?

  We're doing a lot of great content over there. You get to hang out in 25 sessions with us. 25 sessions over 12 weeks. You're gonna learn a ton. Founder.University. He's Lon Harris. I'm Jason Calacanis and he's Alex Wilhelm. We'll see you next time.

• 1:02:26Speaker 01

  Bye-bye.

• 1:02:26Jason Calacanis?

  Bye-bye.

• 1:02:28Speaker 03

  Hey everybody. Welcome back to Twist. This is Alex. Today, we have another interview with an awesome Twist 500 company. Now, this startup is one that I caught wind of earlier this year when I read that it had gone from 5,000 corporate customers to 10,000 in less than a year after spending four years to get that first 5,000. I looked into the company, didn't fully understand the technology, but thought they were really up to something awesome, threw them on the list, got them booked for an interview, and then the company, TailScale, announced an enormous Series C right before we jumped onto an interview. So please join me in welcoming Avery Pinneran, the CEO of TailScale, to the show. Avery, how you doing? Hey, pretty good. Hey, how are you? I'm hanging in there. I love that you're here. And also, you guys are a Canadian company, yeah?

• 1:03:12Speaker 03

  We are. I'm sitting here in Montreal right now. Montreal. Now, is the company based in Montreal? I thought it was Toronto. It's a remote company. So basically, all the employees are remote. So my two co-founders, both named David, one of them lives in Toronto, and one of them lives in Berkeley, California. How do you handle having two different Davids? Do you just call one like California David and one like North David? We call them by their last name. It's Carney and Crosha. Now, that just got really complicated because the new Prime Minister of Canada is named as Carney. Yes, Mark Carney. Yeah, Mark Carney, no relation. Who got David at tailscale.com? Because I feel like that's going to be the hot domain name inside the business. You know what? I haven't actually checked that. I'm guessing it's Carney because he is

• 1:03:54Speaker 03

  sort of the operations-focused founder and loves administrative stuff. I was really unlucky. I got [email protected] as one of my aliases. That turned out to be a big mistake because accounts payable is AP. And so I get a lot of misdirected accounts payable-related emails. Well, that means you're always, you have your finger on the pulse of how much money's going in and coming out. That's not a bad place to be. All right, now, now, listen, Avery, TailScale works in the world of secure, I'm sorry, VPNs for secure networks. I want to talk about the technology behind this because I think it's very important for people to understand. But instead of me trying to butcher an explanation of what this is, I think it's best to let you explain, and then I'll ask you a couple of questions. So for folks out there who don't know, what does TailScale do?

• 1:04:39Speaker 03

  All right, so super simple answer is TailScale is technically a VPN. That is the like space in the technology world that it occupies. That doesn't really tell the whole story because VPNs have basically stagnated for 30 years before TailScale showed up. And so it doesn't work like IPsec or whatever you're used to. TailScale uses this new thing called WireGuard. And we can talk about WireGuard, it's an open source project, I really like it. And TailScale is a mesh VPN, which means it connects anything to anything in any location and all the locations at the same time. So instead of sending all your traffic through a VPN conservator or VPN server that you might be used to, you can just make a direct connection between point A and point B, things that are running TailScale. And so as a really simple example of what a lot of people use our free plan for,

• 1:05:23Speaker 03

  you can download TailScale from the App Store on your phone and on your laptop. You log into the same often Google account or Apple account or Microsoft account. And when you do that, those two devices use our servers to find each other, no matter how many layers of firewalls they're behind without opening any ports or anything like that. And now those two things can talk to each other. So you can access a web server that's running on your laptop. Or you can use a feature that we have called TailDrop, that is sort of like airdrop, but it doesn't depend on Apple equipment and it doesn't depend on physically being on the same network. And you can just send photos from one thing to another. So if you've ever had the problem of trying to send a photo between an Android device and a Mac, this solves that problem. Now, there's many, many other things it does, TailScale, like, you know, it was a VPN that enterprises use for multiple data centers.

• 1:06:07Speaker 03

  It's all the same technological problem, which is the VPN problem, but sort of expanded to the modern world. So people that are listening to this probably have heard endless ads from like NordVPN and the other kind of major consumer players that love to advertise on YouTube and other social platforms. So is VPN in this context the same kind of like underlying idea in which you can create essentially a, I was gonna say artificial connection between two things, but one that is distinct from the network that you're on currently? So similar idea, just a different application? Yeah, there's sort of two kinds of VPNs in the world. There's The classic original kind of VPN, which is take your stuff and be able to connect to your stuff when you're not physically right next to it. Right? So it's called a virtual private network. The idea is you had a private network. Now you have a virtual one.

• 1:06:50Speaker 03

  It doesn't depend on the physical location anymore. You connect to your private stuff. That term has kind of been stolen by these so-called consumer VPNs or privacy VPNs. That actually don't work like that at all. They let they let you take your your traffic and then you route it through them. Where they decrypt it and then send it out to the internet. And so it's more like a virtual public network, but I guess it's the same. I used the same acronym, yeah. Yeah. So Tailscale is the first kind. Use it for connecting to your stuff. Now, to to make things a little more complicated, we have a feature called Exit Nodes that allows you to voluntarily, if you want, route all your traffic through one of your other Tailscale nodes. Uh, and we have a partnership with Mulvad, which is the other kind of VPN. So you can subscribe to Mulvad through Tailscale. And use Mulvad as your exit nodes. So you can kind of do both things at once.

• 1:07:36Speaker 03

  All right. So I I got about eighty percent of that. So I think that's probably enough to go back to the the start of this. So. I was reading a lot of Tailscale material and you guys were talking about how the internet kind of hub and spoke model is just. Super inefficient because data has to be sent uh too far. For example, you had an example of going all the way across the United States and back, for example. Waste of time. Mesh networks allow for closer connectivity points. Can you just explain? How that technology works? And then I want to talk about security in a second, but I think mesh is probably a good thing to unpack a little bit. Yeah. So the really neat thing about Tailscale and and the WireGuard protocol that it's based on, WireGuard creates these super lightweight tunnels. So where traditionally setting up a VPN tunnel was like difficult and expensive.

• 1:08:17Speaker 03

  And so you wanted to have as few tunnels as possible. And you solve that problem by like having one tunnel between you and the center point. And then another tunnel from the center point to the other thing. And that's only two tunnels. And that's like pretty manageable. As opposed to what Tailscale does, which is like, if you've got a thousand nodes on your network. You've got a tunnel from each of those thousand nodes to each of those thousand other nodes. Uh, which is, you know, comes out to a million tunnels, right? That that is a lot of tunnels, but because they're so lightweight, it doesn't matter. But as a result, it means you get a direct connection between the two places. You don't have to go through a center point and it doesn't add latency and there's no. There's no place to get overloaded. So the more nodes you add to your network, the more capacity of the network goes up. And so overall, there's not a throughput bottleneck like you would get in a traditional architect.

• 1:09:03Speaker 03

  And the way that TailScale kind of does, works is that it sits in the middle, but it doesn't pass all the data through itself. But instead, it seems like pass, like Paskys and permissions to allow the mesh network to send things quickly without having the hub and spoke issues that we just described. Right. So TailScale, we divide the product into what we call the control plane and the data plane. And it's actually kind of clever. The control plane is very centralized. There's a SaaS product that you can log into. It's got a web console and stuff. And it, like you said, is basically an exchange point for the public keys that are generated on each node that you own. So the nodes that you own generate public-private key pairs. The private key never leaves the node, so you get end-to-end encryption. But they find each other by basically telling the coordination server in the center, it's like, hey, I'm

• 1:09:47Speaker 03

  node X. I'm over here. I have this IP address and I belong to Avery. Come and, and here's my public key. If you want to talk to me, come find me. Right? And that's basically all the coordination service does. Everything beyond that is a distributed system, right? With no single, with no bottlenecks or single points of failure. So this hybrid centralized distributed system is what makes TailScale so magical. I started off with notes about your massive growth in the enterprise space. So talk to me about, who are the customers that need TailScale in the corporate world? So, oh yeah. So businesses use TailScale and we charge them money because they, they, they're businesses. They have money and they get a lot of value out of TailScale. The way that works is all of these people use TailScale for free. The majority of them

• 1:10:30Speaker 03

  are kind of like semi or fully technical kind of people. Technical people have jobs frequently. And, and they find out about TailScale. They really get excited about TailScale. They solve their own problems at home using TailScale. And then they go to work and find out they have the same problems and the way they're solving it sucks. Right? And so they will complain to their coworkers and say like, how come TailScale at home, I mean, getting for free can solve this problem and this junk that you guys are paying tens of thousands of dollars for does not solve this problem. And that's basically how the conversation gets started. And then we sort of get, you know, either a small number of people using it at work on like some corporate credit card, or it turns into what we call a top-down sale. So it like flips, some executive gets word of it and decides to buy it for the company.

• 1:11:10Speaker 03

  So as a result, the way we sell tail scale is almost exclusively through inbound leads generated in exactly this way. And I remember like it's so funny on some of these calls that I'll get called in and there's like the CTO of a bank. I was thinking, you know, tens of thousands of employees and they're thinking of buying tail scale. And we always asked like, okay, well, what, why, how did you hear about tail scale? And they're like, well, my friend runs an Airbnb and to control the Apple TV at his Airbnb, he installed tail scale on the Apple TV. And he was really excited about how it works. So he suggested that I should buy this for my bank. So here we are. Right. It's always some weird story like that.

• 1:11:46Speaker 03

  This really gets at a question that I had because it seems like the technology you've built works from the hobbyist equivalent use case all the way up to the, you know, highly regulated banking use case. And I just, it's so rare to hear of a technology that works across that kind of scale. Was it hard to build it that way? Or is that just a facet of how tail scale works that it does function for people in their bedroom and then also people in the boardroom? Well, it's good that you mentioned the word scale because it's also in our company name. So the, the, the name tail scale is actually started out as a joke. It's the opposite of internet scale. And so the purpose of tail scale, we're like, look, lots of companies, everybody wants to sell the enterprise. Everybody wants to build something that scales to billions of users.

• 1:12:31Speaker 03

  Like those problems are like solved more or less, right? Might not be solved really elegantly, but there's some way to solve your problem if you, if you have billions of users and way too much money. Right. The, the problems that are not solved are the ones that like, we actually have to deal with on a daily basis. The long tail of problems that every software developer or a technical person needs to deal with. Like I want to start a dashboard and serve it to my 10 person team. How do I start a dashboard? It was actually turns out to be a nightmare. Like 90% of the work you have to do, make a little dashboard for your team, has nothing to do with making the dashboard for your team. Everything about like spinning up virtual machines and containers and opening ports and getting a DNS name registered. And what about a certificate? And how do I make the login process work? And how do I lock out the other people? Where should I open the firewall ports? And we made a list and we're like, this sucks. Why don't we solve that stuff?

• 1:13:16Speaker 03

  Right. So tail scale is like for solving the long tail of problems. So we're like, look, We are going to target the people that nobody else targets. These teeny tiny teams and companies at the very bottom of the scale. And some of these tiny teams are in big companies, right? Like, you know, your small team still needs to make a dashboard and your corporate architecture does not make that easier. What has happened in the subsequent years is that tail scale keeps getting pulled up market, which is a good way to go. We very rarely try to push up market, if that makes sense. We have actually been really resistant to taking on big contracts that are going to distract us too much from building like the core product that we know is good for everybody.

• 1:13:55Speaker 03

  But every now and then, the core product that we built is like just one little, you know, one little feature away from like, hey, my 10,000 person company can adopt it now. Could you just do like this one thing? And we're like, yeah, that seems like a good idea. So we build the one thing and then not only that company, but like a bunch of other companies suddenly can now use tail scale. And so we are now up to the point where we're seeing like million dollars a year contracts with very big companies with really high regulatory requirements. Then we got there just incrementally piece by piece by not chasing them, if that makes sense. We do very little of the actual chasing and that makes us pretty unique because the nice thing about starting at the bottom is that you can't build a product that is too difficult to roll out, that is too expensive and slow to get started because people are just not going to do it, right?

• 1:14:40Speaker 03

  The five person company doesn't have anybody with enough time to roll out an actual complicated VPN product. But they have enough time to spend the five minutes to install tail scale. And that means this really nice experience can go all the way up to the enterprise where they're absolutely not used to that. They're used to products that they buy that are going to take a six month rollout period and a whole team of people to roll it out. And they're just sort of like boggled when they try tail scale and it's like, hey, I'm done already. Hey, I mean, great, but I'm a little perplexed between the fact that you're being pulled up market, that you have tons of inbound demand, things are going well. Why raise a 100 and I think it was $60 million series? Because it sounds like you guys could have just kept growing without more external capital.

• 1:15:25Speaker 03

  A rare and awesome place to be in, but your GTM machine doesn't seem to eat 10 million a month. So why raise more capital now? Great question. So tail scale is a very efficient. Company and tail scale is a very product. So those two things together mean that we technically can, we can switch to a path of profitability whenever we want. And I try to run the company in such a way that whenever we need to, we could just say, okay, that's it. Put on the brakes on the like cost growth. And like get it under control and we can weather any storm. Right. And that's obviously been super valuable in the last little while with the like ups and downs in the market and so on. But I also have another saying, which is that the best time to raise money is when you don't need any money.

• 1:16:08Speaker 03

  So, you know, not needing any money has been a really good asset to us. So we actually haven't, at the time we raised our series C, which is we announced a week ago. And closed a few days before that. We're sorry, we announced it yesterday. Time flies. I was like, wait, can I really get my notes that wrong? Closed about a week ago. There you go. Yeah. But at the time we, that announcement, we actually spent less than half of the series B round that we raised three years previous. And so the question is like, look, if you're spending money that slowly, why do you need even more money? And, and the answer is pretty simple. Like first of all, it's the right time to raise money right now. Secondly, we are getting pulled up market sort of faster than we expected. And those opportunities getting up, appearing faster than we expected.

• 1:16:53Speaker 03

  So we talked about this, like, you know, we doubled from 5,000 to 10,000 paying customers, which does not include the free paying customers. By the way, it only includes organizations. In the two months since we announced that, we've gone up another 20% in terms of number of customers. Right. So it's just, it's, it's, it's going up really fast. And the customers that, that's the customers we're getting that we're making money from. There's also this like even longer tail of customers that we almost get. Right. But if only you had this, if only you had this, if only you had this, if only you had this. And it's a whole bunch of little things for the most part. Right. But if we just go after those little things, the revenue growth is going to be extremely high. And so this comes down to just the financial concept of ROI. Like, do I need to spend? Money? No, I can be profitable without spending the money. But if I spend this money,

• 1:17:37Speaker 03

  I can make even more money and everybody wins faster. It's a really like, you know, you do the do the formulas is like, oh, this is a really nice equation. You guys did mention AI essentially demand as part of your seriously. And I presume that I've been thinking too small because when I I'm learning more about, you know, high bandwidth memory and how people are using photonics inside data centers to get data moved around faster and so forth. But I presume you guys come into play when I have a data center talking to a data center versus inside of said data center. Uh, tail scale gets used in all of these situations, right? So like the the internet layer uh, does not provide authentication or encryption by default. Right? And people, especially in the AI world, are starting to realize, hey, you know what?

• 1:18:20Speaker 03

  Everybody's sending some incredibly ridiculously sensitive stuff uh, to these AIs. Maybe we should like encrypt it on the way there. Uh, also, AI companies have this uh, pretty much uniformly. They all have this problem. Their GPUs are in one place, which is the cheapest or only place they can get a GPU because GPUs are in extreme shortage. That place is probably not AWS, Azure, or Google Fab, right? The rest of their stuff is probably best hosted in one of the big clouds. And so they immediately have what's called a multi-cloud problem, right? And before AI, the general advice is like, just don't have multi-cloud problems. Uh, stick with one cloud provider and just be super loyal. Don't do it. It's horrible. Right? Just stay away from this. But now everybody's got to get a GPU from somewhere else. They find themselves in a world with multi-cloud problems.

• 1:19:06Speaker 03

  And so there is no product that makes your multi-cloud problems not terrible. Except tail scale, which doesn't care about the physical topology of your network. And so AI companies caught on to this very early. Uh, we're actually, I'm I'm remain a little embarrassed about it. We didn't notice until mid last year that most AI companies in the world were using tail scale. We didn't know we like had won the market. We there was no mention of AI or machine learning or GPUs anywhere on our website because we were just like busy with other stuff. Right? And then when we finally decided to investigate, it's like, hey, it seems like there's a lot of AI companies that are like showing up in our support ticket to should we look into this? We looked into it. It's like, oh, they all love us a lot and they all go to the same conferences.

• 1:19:47Speaker 03

  They all recommend tail scale to each other. Of course, there's lots of employees that jump from a own AI company to another. They'll leave a big company, found a new one. They bring tail scale with them because tail scale is the networking thing. Solve the problem so they can get back to their AI. If you had to pick a next project tomorrow and you had no choice and you couldn't say no, you had to do two things at once. What's another thing you would want to bring to the internet? That would improve the foundation for digital humanity the most for like the next fifteen, twenty, fifty years? So that's a big question. I don't know the most impactful thing that we could add to the internet. I know what I would add. One of my friends about twenty years ago, very insightful friend, he told me, even there's only three things in computing.

• 1:20:28Speaker 03

  There's compute, there's storage, and then there's networking that connects them to each other, right? There's many different kinds of compute. There's many different kinds of storage. There's many different kinds of interconnects. But those are the only three kinds of things, right? And if you look at the way the internet works today, right? It works the way it does actually because we failed at the networking part. It stopped evolving thirty years ago, right? Therefore, we ran out of IP addresses. We had to create all these firewalls and things. Now, the only things that you can connect are like your device to the cloud, right? And then you can connect another device to the cloud and you can get data to transfer like by going to the cloud and back. But you just can't connect a device to another device the way the original internet was supposed to work.

• 1:21:10Speaker 03

  Because we ran out of devices and we don't trust people, so we had to make firewalls. And then we had to have nets. The fact that networking stalled meant that how we do compute and storage had to evolve. And it's like really inefficient direction where now I have to pay rent to Amazon for everything, right? Because there's only they have enough IP addresses, basically, right? So now that networking is fixed, right? Thinking ahead a little bit, obviously, you know, tail skills are in everyone's hands, but let's imagine a world where it is and it's time for everybody to launch a new product, right? And now that networking is fixed, you can start thinking, how am I going to do storage differently, right? Peer-to-peer storage.

• 1:21:50Speaker 03

  Is an interesting concept that like dies every time someone starts because how do you connect the peers to each other, right? And they start connecting peers to each other and you realize it's 99% of the work and you don't have time to work on storage anymore. Right? So I would love a world where you can just like, you know, I've got tons of free disk space on tons of computers scattered everywhere, but I can't use it. I have to go rent it at 10 times the price from Amazon instead. Right? Or Google or Apple or whatever. Oh, yeah. AWS is a stand-in for any kind of modern hyperscale cloud infrastructure. Yeah. And then I've got, and then, you know, if you've got storage, well, what about compute? Well, I've got lots of extra compute. I joke sometimes about the supercomputer in my pocket, like my phone is, right? And my phone is actually a dumb terminal in the same sense as an IBM dumb

• 1:22:33Speaker 03

  terminal back in the 1970s, right? It doesn't, if you unplug it from the cloud, it doesn't do anything anymore. Right? That's a really terrible thing to say about a supercomputer. It's like, oh my God, this thing is insanely powerful. It has evolved like hundreds of thousands of times faster in the last few decades, and I can't do anything with it without plugging it into some cloud and paying rent. Why? Because of compute and storage and network. Right? So we can solve that chiad, but only once we've really truly fixed the networking problem. Once we fix that, a whole bunch of stuff is suddenly going to start, sort of come un-unblocked. And I think that's where the magic can come in. An idiot question, because all that sounds great, but I want to make sure that I'm fully

• 1:23:13Speaker 03

  tracking you. So essentially, because we ran out of IP addresses, I can't have six different IP addresses for my six computers that I have here, and therefore I can't access their storage super easily from anywhere that I want. So I have to go to a centralized bucket, which is AWS, etc. So if we could get around our problem, then any spare compute, any spare storage with proper encryption and so forth, could be used levered and kind of brought online for general, oh, that's awesome. Yeah. And if you want to get a little more complicated, so the reason I use storage before compute, because both of those things benefit. From being we won't be located as soon as you stop using cloud for storage, you're going to run into the so-called durability problem, right? It's like, look, my storage is great. I have this really big hard drive in my house, but what if it dies?

• 1:23:55Speaker 03

  Right? It's no good if all my data disappears. That's like, that is definitely 30 year old technology stuff, right? If it's in the cloud, all my data is not going to disappear unless I delete it or somebody hacks it. But if you have a good distributed storage system, you can share storage with like your friends' hard drives in their houses, or even people you don't know. And then it's encrypted, right? Then when your hard drive dies, it still exists somewhere else. And this is why it's so important for peer-to-peer devices to be able to talk to each other. So you can like spread this content around so that in case the drive dies, your system doesn't die. The only people who can do that today are the big clouds because they have all this stuff in one place. And they're all doing these tricks with multiple hard drives in the background that you don't see.

• 1:24:35Speaker 03

  But we could do that with our own stuff at 10, 10 times cheaper prices with the same exact hardware, if only the networking worked properly. All right, I'm being yelled at by the production team to, to wrap it up. Avery, I could talk to you all day long. This has been such a treat. Thank you for teaching me a lot of stuff. Two things before you go, what's the URL and what is a role you are having a hard time hiring for? All right, uh, let's see. Well, tailscale.com is the URL. I'm sure you'll have it posted somewhere in the. It'll be in the section down below, show notes, et cetera. Yeah. Excellent. And I'd say the role that we are, of course, we just raised a bunch of money. We're going to be spending that money. So we are hiring for engineers in particular.

• 1:25:18Speaker 03

  The hardest kind of engineer to hire for is, is what I would call the networking platform engineer. People who really truly understand way down at layer three and want to make a difference down there. And I know those people exist, but they are hard to find and there's, they're not making more of them. Uh, so there's this sort of like limited number of these people out there. And I would, I would love if those people would apply for tailscale because we've got some really fun projects that we're working on. All right. Well, Avery, a real treat. Thank you so much. And for everyone else, it's tailscale.com. All right. We'll see you all next time.