Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344

This Week In Startups is made possible by: Plaud: http://Plaud.ai/twist CLA: https://claconnect.com/tech Sentry: http://sentry.io/twist Lightfield: http://sentry.io/twist Today’s show: Google once interviewed the entire Justin.tv (now Twitch) team and then walked away from an acquisition deal, saying they weren’t good enough. Seven investors passed on buying 10% of Airbnb for $150,000, a stake pegged at roughly $9.25 billion today. Lon Harris and Alex Wilhelm revisit classic TWiST interviews with Justin Kan of Twitch and Brian Chesky of Airbnb to find out what those founders understood that the market didn't. PLUS, how did a box of cereal win over Paul Graham and get Airbnb into Y Combinator? Flashback Guests: Justin Kan on X: https://x.com/justinkan Twitch: https://www.twitch.tv/ Justin Kan (@justinkan) on X Brian Chesky on X: https://x.com/bchesky AirBnB: https://www.airbnb.com/ Relevant Links: TWiST E900: Justin Kan, co-founder of Justin.tv, Twitch & Atrium (Feb 5, 2019) → https://thisweekinstartups.com/episodes/L3DP8VCE12s TWiST E1735: Airbnb CEO Brian Chesky on early rejection, customer focus & AI (May 4, 2023) → https://www.youtube.com/watch?v=aZ-BjJZxNoA Halo 3: the game that flooded Mahalo with traffic → https://en.wikipedia.org/wiki/Halo_3 Weblogs, Inc.: Jason's blog network, home of Engadget → https://en.wikipedia.org/wiki/Weblogs,_Inc. Instinct: the invite-only personal AI agent from founder Noah Shinn → https://www.instinct.co/ AMD to acquire World Labs for $8.2B in stock; Li becomes AMD chief scientist (Bloomberg) → https://www.bloomberg.com/news/articles/2026-09-28/amd-to-buy-fei-fei-li-s-world-labs-ai-startup-for-8-2-billion Lovable: where Lon says he'd rebuild a bad app in two hours → https://lovable.dev/ Y Combinator → https://www.ycombinator.com/ Paul Graham on X → https://x.com/paulg Obama O's and Cap'n McCain's: the cereal that funded Airbnb → https://en.wikipedia.org/wiki/Airbnb#History Stripe: what Paul Graham suggested they build instead → https://stripe.com/ Timestamps: 0:00 Justin Kan on episode 900 (Feb 2019) 3:44 When Jason and Justin realized people watch gaming 5:52 Mahalo, Halo 3, and betting a company on 3% of its traffic 10:21 CLA: Get started with CLA's CPAs, consultants, and wealth advisors now at https://www.claconnect.com/withyou 11:42 The "zombie startup" years and Google's rejection 17:06 Instinct: the AI agent built for venture capitalists 19:43 Sentry: New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26 28:08 Kozmo.com and the era of "make number go up" 30:06 Lightfield: Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you - it even prospects and books your meetings. Used by thousands of startups. Free at https://lightfield.app/ 32:57 Why AI companies have to monetize faster 34:00 Clip: Justin Kan on knowing yourself as a founder 37:24 An early rejection of "founder mode"? 38:33 Brian Chesky on episode 1735 (May 2023) 39:27 "I hope that's not the only idea you're working on" 43:27 What 10% of Airbnb for $150K is worth today 46:05 Obama O's and the Y Combinator interview 48:15 Why investors fund unkillable, attention-hacking founders 54:37 Clip: Chesky on AI, deepfakes, and authenticity 58:13 Is AI costing jobs or just making them busier? 1:05:04 Did AI create "millions of startups"? Subscribe to our newsletters on Substack: TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland 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

• 0:00Speaker 00

  Hey everybody, welcome back to This Week in Startups. I am Lon Harris. With me, not as always, on a special occasion, former co-host Alex Wilhelm. Thanks for being here.

• 0:09Speaker 01

  Oh, it's so good to come back. Friendly faces. I'm sweating in a blazer again. You know, just like old times, my friend.

• 0:15Speaker 02

  This Week in Startups is brought to you by Lightfield. Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you. It even prospects and books your meetings. Used by thousands of startups. Free at lightfield.app. Sentry, your team should be focused on shipping features, not chasing down bugs. New users can get $240 in free credits when they go to sentry.io/twist and use the code TWIST26. CLA, innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up.

• 0:57Speaker 02

  Get started now at claconnect.com/withyou.

• 1:01Speaker 00

  And much like old times, you will notice I am wearing my Plod pin. It is right here, pinned to my jacket, recording everything that everyone says, and then it will conveniently download it. A summary, a transcript, meeting notes, whatever I want, all organized. I don't have to do a thing. I just have to use, hit the button, tell everybody that they're being recorded, so you don't do it surreptitiously. And then it's all going to just be done and waiting for me when I am done with the show or the call. If your work depends on conversations, interviews, meetings, anything like that, we urge you to get a note pin for yourself. You can check it out. Find out more at plaud.ai/twist and be sure to use the code TWIST to get 10% off your order. Thanks to our friends at Plod. We applaud Plod.

• 1:45Speaker 01

  We do indeed, and Plod, Plod. The first good AI wearable is how I think about Plod. They cracked it. They actually got something together that people need to use and makes their life better. And the first couple of pendants just didn't hit the mark. So shout out to Plod for being early, frankly.

• 1:57Speaker 00

  Yeah, that AI pin, those people are like, why are we taking strays? Why do we have to take strays on the Plod ad read?

• 2:04Speaker 01

  I had to watch their launch video, Lon. That's why they're taking strays. They took five minutes of my life and I'm mad about it.

• 2:10Speaker 00

  Yeah, it's like, I don't, it just like, a pin is a weird form function. I think we can all agree.

• 2:16Speaker 01

  Well, anyways.

• 2:17Speaker 00

  The AI brooch.

• 2:18Speaker 01

  What are we here today to do? What are we doing?

• 2:19Speaker 00

  We're not here today to just talk about AI brooches. We're here today, we're doing another of our patented flashback episodes. We're going to look back at an episode of Twist from February 2019. Folks, this is episode 900. A landmark show. And it features Justin Khan as Jason's guest of Justin TV, later to be known as Twitch. The guy who once strapped a camera to his head and livestreamed his entire life around the clock. That 2007 stunt, Justin TV, soon opened up to anyone who wanted to broadcast and livestream their lives. And its gaming section later spun off as Twitch, which Amazon, of course, bought in 2014 for 970 million.

• 3:00Speaker 00

  And you could currently still use if you want to catch up on the hottest video games or get very, very angry about politics. By the time of this chat, Justin had moved on to Atrium. That's a legal tech startup that had just raised $65 million in their Series B. Atrium would shut down barely a year later, and Justin has since gone back to gaming. He had the NFT marketplace Fractal, and now he's doing Stash, a webshop and payments platform for mobile game developers. So let's go back to 2019. Alex, take a little trip into history and check out some of these classic clips featuring Justin Khan.

• 3:36Speaker 01

  Absolutely. Now, I have a number of things that I want to get to, Lon, but where are we going to start in this relatively long, and I would say luxurious, interview?

• 3:43Speaker 00

  Yeah, I'd like to jump. My first clip is at about five and a half minutes in. And they are talking about Justin and Jason both when they first discovered that people on the internet wanted to watch other people on the internet play video games. Let's take a look at this startling revelation.

• 4:02Speaker 03

  Gamers were a genre unto themselves. Cause I remember back in 2007, 2008, I was doing Mahalo, and we started putting video game videos on the YouTube, the YouTube. And they went bonkers, like millions of views. But when did you realize video games were what streaming was about?

• 4:22Speaker 04

  Yeah, so.

• 4:23Speaker 03

  How did that happen?

• 4:24Speaker 04

  Well, so we launched this site in October 2007. And anyone could stream anything. And people streamed. And there was a lot of like, people trying to make talk shows and a lot of social kind of broadcasting, like someone would just be hanging out. And then there was this nascent category, which kind of grew that, mostly focused on trying to get celebrities and things like, you know, more famous people to create content. The problem was they didn't really want to do it on an ongoing basis. And so a couple of years later, this was maybe in 2010, we'd grown to a fairly big website. It was about like the top 300 on Alexa or something like that.

• 4:58Speaker 03

  So you got over 10 million people a month, basically?

• 5:00Speaker 04

  Yeah, something, something around that. But the problem was it stopped growing. And we were like, we had no idea how to grow Justin TV, this web platform for anyone to stream. So what we decided to do was go back to the drawing board and basically sit in a room and try to brainstorm ideas. And my co-founder Emmett came with his idea, and his idea was, was let's focus on the gaming content on our site, which was only 3% of the content at the time. And so gaming was only, I think, a couple hundred thousand uniques a month on our site. But his argument was, this is the only type of content that I actually want to watch.

• 5:36Speaker 03

  Right.

• 5:36Speaker 04

  Starcraft 2 had just come out. And so that was driving a lot of interest.

• 5:40Speaker 03

  Absolutely.

• 5:40Speaker 04

  And that was driving a lot of YouTube videos, and who wanted to watch live streams? And mostly they were on other people's sites. They were on Ustream or Livestream or, but he thought we could focus on this and build a community around the gaming content.

• 5:53Speaker 00

  Teach people how to do the Zerg rush. I witnessed this personally. I mean, this clip stands out to me because I was working with Jason at Mahalo in this exact era, when we also made this discovery alongside Justin TV that if you're, I know it's hard to even conceive of if you are under like 35, but if you are of a certain age, the idea that people for entertainment wanted to watch other people play video games was very counterintuitive for a lot of people.

• 6:22Speaker 01

  Oh, it was incredibly counterintuitive, Lon. I mean, my parents used to make fun of me for driving to their office, because they had faster internet than we had at home. We had dial-up. And I would watch old Starcraft Brood War VODs from South Korea and the Proserket. And they're like, so you're gonna go drive to sit and watch someone else in the past play a game? I'm like, you bet your ass I'm gonna do that. 100%.

• 6:43Speaker 00

  Yeah, now it seems so, both because it's incredibly common and everybody enjoys doing it, and it is not that weird of a thing. But also, if you think about like sports, like you might enjoy playing basketball yourself, but then you'd enjoy watching professionals do it very, very, very well, or college kids who are also very good. So that it isn't really that strange of an idea that people who love video games would want to watch very skilled players play video games. But at the time, I'm telling you, we did not believe it. And at Mahalo, we built, Halo 3 was the first game we discovered this for. And we started building pages about like, how to find all 100 skulls that are hidden in the maps around Halo 3.

• 7:27Speaker 00

  And it was dwarfing all of our other traffic to the point that it was undeniable we had to focus on video games. And it really took a while to sink in in our Gen X boomer brains that this was where things were going.

• 7:40Speaker 01

  Well, I think one thing that happened during this time was the mainstreamization of gaming. I mean, if you think back to when I was a kid, and I was born in 89, just for context for everybody. So I grew up in the 90s and the early 2000s. I was in my teenage years. And gaming was still very much a fringe activity. It was still something nerdy kids did and the cool kids did not. That is now done. FIFA and Madden, and a lot of the games have really made gaming mainstream, COD, et cetera. So I just love the story because I think it shows how you can catch something early and turn it into something quite large. It was 3% of their traffic, as Justin just said. That's not much. But if you can read the tea leaves correctly, you can build a subsidiary product that becomes so big, everyone forgets what you were originally working to build.

• 8:20Speaker 00

  Right. There's also a little, a little tactical, practical Jason founder tip sort of hidden in there, which is trusting your gut. I mean, you know, Emmett, his colleague said, this is the kind of content I would want to watch. And so even though data-wise, it was only a very tiny percentage of their overall viewership, he was like, we should still focus on this because just my instincts are telling me that other people are like me and are going to want to check out video games.

• 8:47Speaker 01

  Yeah, but it's just such an orthogonal bet. Like even, even given everything that you said, think about if you're a venture-backed startup today, and you're going to say, hey, we're going to just focus on 3% of our user base. Like you would get laughed out of the room. So even like, after this happened, it's still a non-traditional approach to growing a startup. And it did yield a roughly billion dollar outcome, as you pointed out, but I'm just amazed at the courage it must have taken to devote scarce resources during a period of flat growth on a small user segment. Brilliant in retrospect, but bold and brave, I think, at the time.

• 9:16Speaker 00

  Yeah. And also, the last thing I would mention is, in the early days especially, now video game companies and publishers understand that people live streaming, except Nintendo. There's still, you still hear issues about Nintendo. But other video game publishers now realize, we need live streamers. That's our lifeblood. They're promoting the games to new users. But back in the day, when you would try to do this, you would constantly be hitting it with content copyright strikes by the publishers of the game. Like you're not allowed to show people what happens in my game before they play it themselves. That's violating my copyright. So there were legal harangues to worry about as well.

• 9:54Speaker 01

  I mean, what they should have just said was, is that we're using this for AI training purposes, and therefore your IP doesn't hold any water. And we're just going to dissolve your entire business. No, I joke, but I do love seeing how things change and they become like de facto over time. Like, you know, we talked about Uber on the show a couple of times. Uber was the same thing. Like when I was growing up, it was, don't talk to people on the internet. Don't talk to strangers. Don't get in their cars. Don't go in their homes. Well, you know, it turns out that was entirely wrong with a little bit of technology and a little more time.

• 10:21Speaker 03

  One of the themes we talk about over and over again on This Week in Startups is making sure you do your chores. I'm no expert on these things. I have some experience. Stephen Estes from CLA is an expert. Let's talk about being cash efficient. Tell us about efficiency and what you see in the, in the top tier startups in your practice.

• 10:41Speaker 01

  We're seeing kind of an interesting trend out there where companies aren't needing to raise quite as much as they had in the past. You really have to be careful as a founder to only take on as much money as you really need. You've got to do the forecast and you've got to do the modeling and you've got to dial it in and get it right. Otherwise, you're going to end up either not raising enough capital to get to where you're going and you're going to have to go get venture debt or go back, have an extender to the round, or you're going to give up too much of the company because you just didn't recognize how much money you actually needed.

• 11:10Speaker 03

  Yeah, very important to get this stuff right, folks. And that's really a bummer when startups don't do things in a button up way. Always have a great partner, a good partner to have on this adventure. While things change, my friend Stephen over at CLA. So if you want a trusted advisor by your side who will navigate you through taxes, accounting, and everything in between, it's time to take action. Visit claconnect.com/withyou. And don't forget to drop a mention that your boy Jake Al sent you. That's claconnect.com/withyou. Start today.

• 11:42Speaker 00

  All right.

• 11:43Speaker 03

  Give us your first clip.

• 11:44Speaker 00

  Yeah.

• 11:45Speaker 01

  Yeah. So this interview blew my mind. I was a Justin TV fan. I was an early Twitch fan.

• 11:50Speaker 03

  Who was he?

• 11:52Speaker 01

  Well, all of my friends. It did feel a little lonely at the time. I'm not going to lie. But one thing I really appreciated about this, this interview was that I didn't realize how long Justin TV team had spent in the wilderness, lost years, just not having the right product at the right time for the right people at the right price. And we're going to loop back to this, but compare what he's about to tell us to the current startup era of rapid growth and what I might call instant product market fit. Let's take a listen.

• 12:23Speaker 04

  Working on in a dark room on this, you know, programming something. And I would think, why am I doing this? Why? What is going? Where is this going? And it never felt like we were making progress. It never felt like there was an inflection where it was like, oh, my God.

• 12:36Speaker 03

  We figured it out.

• 12:37Speaker 04

  We figured it out. Yeah. And so, or maybe we had days like that, but then it quickly referred it back to the baseline, right?

• 12:44Speaker 03

  Now 100 days of struggle.

• 12:46Speaker 04

  Exactly. And so, I, you know, it was, it was that zombie startup feeling where we were 25 people, five years in, had, you know, weren't growing super fast. And we were like, how, where does this go?

• 13:00Speaker 03

  Right.

• 13:00Speaker 04

  We don't see an exit in sight.

• 13:02Speaker 03

  And you decide to call this meeting. When did you decide to call that meeting? What was that moment where you're just like, I need to shut this thing down and move on? Or I just need to challenge everybody? What was that, the impetus for deciding to sit everybody down to do that brainstorming meeting?

• 13:19Speaker 04

  All right. This is a good one. I don't think I've actually told this story very publicly before, but basically, Google came around and was like, we're interested in acquiring Justin TV. And it wasn't a very high price, to be honest. But they basically, long story short, we talked to them, we talked to them.

• 13:36Speaker 03

  What was their theory?

• 13:37Speaker 04

  Their theory was YouTube owns basically the entire internet on the video. And this is like internet video. And this is one sliver, small sliver.

• 13:45Speaker 03

  A feature.

• 13:45Speaker 04

  Yeah, exactly. We might as well buy the feature. And they had YouTube Live at the time. And so they came to us and, you know, Justin TV was a decently sized site. It just wasn't very profitable. And it wasn't like, you know, it was a small company. And so we, they, they came to us and they wanted to interview our entire team. They interviewed our entire team. We let them, which you should never, ever do. Never let an acquirer ever interview your entire team. Because they interviewed our team and then they were like, your team's not good enough. Goodbye.

• 14:13Speaker 03

  Wow.

• 14:14Speaker 04

  Yeah. Which was like the most demoralizing gut punch of 2010 or 2011, whenever I think it was 2010.

• 14:21Speaker 03

  Thanks for letting us come in. We regret to inform you, your team sucks.

• 14:26Speaker 04

  Exactly.

• 14:27Speaker 03

  Google's people are smarter than yours. We would never let you in the building.

• 14:30Speaker 04

  You would be like significantly lowering the bar for the people at Google, basically.

• 14:35Speaker 03

  Right. We would never let you on campus.

• 14:37Speaker 04

  Yeah.

• 14:38Speaker 03

  Like literally on a Sunday, the Justin TV team is not allowed.

• 14:40Speaker 04

  Like you have to work out of the sales office, except you're not good enough to work there. So we can't acquire your company.

• 14:45Speaker 03

  It's like how they treat the.

• 14:47Speaker 04

  It's like the contracting, exactly. It's like this, you could work in the cafeteria, but you have to work for another company that we contract with.

• 14:53Speaker 03

  Right.

• 14:54Speaker 04

  Yeah.

• 14:54Speaker 03

  You'd be like the cafeteria employees. We're going to contract you or the customer support people. We, we just don't want you to consider your team Googlers.

• 15:01Speaker 04

  Yeah. And like, you can't call your team Googlers and you have to live in Fremont.

• 15:04Speaker 03

  What, what is it like to go back to work with the team after this happens? What do you say to them when you've been left at the altar? You just say like, F Google?

• 15:14Speaker 04

  Well, yeah, it wasn't great. Actually, the team like took it very well, which is very surprising. So that was the impetus. We were like, well, we can't get acquired and we're not growing. So we need to figure something out. And so we went to the drawing board and we came up with these ideas. And that's when we had the meeting and we started figuring it out.

• 15:32Speaker 01

  The thing that I find staggering about that clip, Lon, is how long the company had to try things, figure things out, and essentially have its flop era. One thing I love about 2026 and the AI era and startups today is that they're going from zero to 100 million in revenue, zero to a billion dollars in revenue in record time. And frankly, as a business journalist, that's exactly what I want to cover, right? Like, that's the type of story that I want to go dig into. But I also wonder what we're losing, because I don't think today, anyone would let a, a high profile founder spend so many years essentially beating their head against the rock and trying to figure out a way through. They would tell them to go build something else or to, you know, change what they're doing. But they had time to figure it out, to find that

• 16:17Speaker 01

  little audience we talked about earlier. And I, I almost worry that we're missing something today.

• 16:22Speaker 00

  I mean, how could we not be in, in a way? I mean, I guess the argument would be, well, you know, you would just start your next company. Like the, we, the, the, the pace is still, was always relentless. It was just like, maybe you used to have three years with one company to pivot five times until you found the right thing. And now you would just like, start a company and it goes out, get, it's done. Or start another company, it gets acquired, start another company. And or you're starting three or four, your agents are building three or four different projects at once, and you're picking which ones find traction and getting rid of the others. So I'm not really sure if things are changing that much, or if it's just the tools that changed the journey.

• 17:06Speaker 01

  Maybe, but let me, let me throw this at you. So Instinct, right? This well-known agent that everyone's been talking about and using. I have not gotten an invite yet. Sorry. So I can't tell you how it is firsthand.

• 17:15Speaker 03

  Yeah.

• 17:16Speaker 01

  You know, Lon, one day we'll be at the cool kids table. Not today, but eventually, you know, down the road. Who was talking about Instinct first? Venture capitalists. Who got access first? Venture capitalists. The product was venture legible from the get go. Because what does it do? It helps you untangle your snarled family life and it solves your calendar and books your job. It's literally the venture capital toolkit.

• 17:36Speaker 00

  There was a post today about, about this exact thing. Like, it helps you do, like, what are the things that people keep talking about it helps you do? It helps you sort your, your luxury items and shop around for, for high-end items. It helps you book your lavish vacations and it helps you get the best reservations at the hottest spots in town. Are those everyday consumer concerns? Or are those very, very rich person concerns?

• 18:05Speaker 01

  I'm flying into Aspen tonight and I don't know where I should eat. Who has the best croissant soup on the mountain? Like, that's not, that's not me. I don't need that. What I need is someone to order pouches and paper towels because I forgot. Not really the Instinct use case. But this company was not that. Like, no VC wakes up and goes, oh, I can't live stream my esports. Dying. I need that. So that's why I think that you're correct that you can build faster now. You can pivot faster. You can try more ideas. But I wonder if we're building closer to the same bullseye versus throwing at the entire dartboard as we might have been back in the early 2010s.

• 18:38Speaker 00

  It's an interesting, it's an interesting question. I mean, I, I think it's a very, it's a very open question. And I just, it's so different. Every aspect of the founder journey was so different back then. AI has really upset the entire cart. And what we're looking at, like what investors are looking at when they're picking companies is totally different today. I mean, I think, you know, on our venture capital show, or when you hear VCs talking about it, it has since become reduced entirely 100% to you're making a bet on the founder. Nothing else. You can't rely on anything. Like, is there, is this moat going to exist in two weeks? Or is OpenAI going to invent this? Like, is this model going to become too expensive to run?

• 19:22Speaker 00

  And we're going to need to use this kind of model instead? Who, who knows? It depends on the next model to come out. Like, all of these things have become question marks. How big is the TAM? Like, what kind of audience exists? And, and so all of those questions are kind of unknowable now. And so the, they're, they're making bets 100% for like, I, I like the cut of this guy's jib.

• 19:43Speaker 03

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• 20:28Speaker 03

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• 20:40Speaker 01

  I think also the expectation of faster growth makes more sense if you consider it from the perspective of how quickly technology is changing, to your point. So think about the lifecycle of an AI model. You spend all this money collecting data, then you pre-train, then you post-train, then you find turn, then you do reinforcement learning, then you put it out there and you have X amount of time to monetize it before it becomes essentially moot. So the cycles of tech are much faster now, so there's less time to grow slowly, to stagnate or whatever, because by the time you find your footing, you'll be dead three times over. But back in 2019, pre- Claude Code, pre-agent coding, pre可以用AI, pre-ChatGPT, uh, very different worlds. Maybe that's what I'm referring to is just that no one could do as much, so people did less and we had more leisure time, perhaps?

• 21:19Speaker 00

  Well, and it's also like, if I had a great idea and I built the app and I released my app, even if my app sucked and somebody else used my app and was like, this is bad, I could make a better version of this. That's three months, four months of like, I gotta find a few other devs or a technical co-founder and we gotta actually build it and test it and make sure it works right and then maybe we can launch it. Today, if I was like using an app and it was like, this app sucks, I'm gonna go into Lovable and monkey around for two hours and maybe I'll make a version of it that I like better.

• 21:52Speaker 01

  Yeah, and I'll host it myself, I won't put the App Store tax, it'll work on all of my devices, not just iOS, et cetera, et cetera, et cetera. Well, I just liked the story of how long they stuck with it. I just don't think even startup employees would stick around that long today to build something that ended up being iconic, so.

• 22:08Speaker 00

  Yeah, everything develops the whiff of failure much more quickly now, to the point that if it hadn't taken off after like a year, people would be like, well, I'm gonna go work at that other company that took off after three months.

• 22:18Speaker 01

  Or if you're Jev from Typesafe, I mean, it went from zero to trillions of tokens overnight. And then a couple of weeks later, OpenAI at their developer day announced a competing product that might crush it, so we'll have to find out. I hope everyone made their money in that short window of time.

• 22:33Speaker 00

  Before I even had a chance to understand what it does, it's already outdated.

• 22:38Speaker 01

  I have gone deep on Jev and there's still about it, deep inside its architecture that feels like magic to me and I don't quite understand how it works. But I want to stay on this theme of what's changed, what's different. And during this interview, Justin and Jason, who have been around the technology block a couple of times, talk about how the earlier tech was more about doing things for passion. This is about the Web 2.0 phase and I think it's an interesting point of between that and today. So if we could roll the tape at about the 25 minute mark, we'll take a listen.

• 23:08Speaker 00

  There was no money in the system. So Weblogs Inc., when we built Engadget, or Movable Type, or Dig, or Delicious, or Flickr. These were all passion projects by small teams that just wanted to see those products exist.

• 23:22Speaker 04

  That's what I loved about Silicon Valley in San Francisco during that time, because people were just doing it not because they wanted to make money, because it was not a popular thing to do and it was not a good career path. They were doing it because they thought it'd be cool. It was like a cool experiment.

• 23:37Speaker 00

  Yeah.

• 23:37Speaker 04

  Yeah.

• 23:38Speaker 00

  Let's see if we can actually get this website to exist in the world.

• 23:41Speaker 04

  Yeah, and like, will people do it or interact with each other on this weird website?

• 23:44Speaker 00

  Will people dig or read at this story?

• 23:46Speaker 04

  Yeah.

• 23:46Speaker 00

  Will people understand what that even means?

• 23:48Speaker 04

  Exactly, and I love that, I love that sense of exploration and I feel like, I know this is gonna sound like the jaded, like sad guy, you know, old guy, but like, I feel like there's a little bit of that that's missing now here in San Francisco, because there's a lot of, the culture's changed, it's matured and people are coming here for their career now. You know, they're like, okay, I wanna like, be a, this is a good career move, you know?

• 24:08Speaker 00

  You know what's interesting about that is, I think it's cyclical, because that actually happened in the dot com era.

• 24:14Speaker 04

  Yeah.

• 24:14Speaker 00

  Like, towards the end of it, people are like, okay, I'm graduating, I went to Harvard, got my MBA, and I'm gonna go into dot com.

• 24:19Speaker 04

  Yeah, Pets.com, that's a good move.

• 24:21Speaker 00

  And, and everybody floated to Pets.com in every possible iteration. And the second it got hard, when the dot com boom, they ran back to Goldman Sachs. They ran back to Madison Avenue to get an ad job. They, and it's, I call it tourist season, like, we're in the middle of tourist season right now, it's high season.

• 24:38Speaker 04

  Yeah.

• 24:38Speaker 00

  And there's a lot of people here, like, who are building companies, and I don't know if their heart's really in it.

• 24:43Speaker 01

  Lon, what I, what I find really funny about this clip, well, one, history just repeats itself, apparently, we're always going through the same cycles. But, uh, thinking about the financial sector as similar in terms of like value creation as the technology sector, like, you can go to Goldman Sachs or you can go to Google.

• 24:58Speaker 00

  Right.

• 24:58Speaker 01

  Today, the most valuable bank in the world is JP Morgan Chase and they're worth about 890 billion. The next one is the China Construction Bank, 430 billion, or as we now call it, a Series B. So like, it's so funny to see how much these paramount of prestige, these mountains of money, now seem relatively unglamorous and small. It's, it's.

• 25:18Speaker 00

  Well, what's also interesting there is, remember that, I recall that era when like the smartest and the best and the brightest graduates from the Ivy League and the top schools were all going into finance. And there was a lot of like hand wringing, like, all of these people who should be our teachers and our scientists and our great thinkers and philosophers, they're all just becoming financiers because that's where the money is. You don't hear that today when we, the perception is that our greatest minds are now going into building things and making things again. So perhaps it's a positive correction.

• 25:53Speaker 01

  It is a positive correction, somewhat. It is not quite as good as taking our best and brightest and maybe putting them out into the rural schools to really power the next generation of minds that are gonna take us to the stars. But, but think about this, in finance, you're doing deals, you're structuring credit instruments, et cetera. You're really just playing Excel, right? That's what you're doing.

• 26:11Speaker 00

  Right.

• 26:12Speaker 01

  And at least in technology, you're often building something that does scale to an enormous number of people. Like, there's over a billion people that use ChatGPT, access a huge user base, Google searches you pay for this. So like, Goldman Sachs never gave me a tool.

• 26:24Speaker 00

  Right.

• 26:24Speaker 01

  JP Morgan Chase just gives me a fee.

• 26:26Speaker 00

  It's impossible to argue that these big AI companies are not doing more. I mean, like, GrokBot saves me hours of time every day. And like, there's no new financial instrument that a guy at Goldman could invent, like, a new kind of derivative or whatever, that would actually make my life better. Like, I'm sure there is a guy out there who's like, oh man, I wish there was a new kind of derivative today. But like, for me, I'm definitely benefiting a lot more from people going into tech and creating amazing tools than I am from people coming up with like, a new way to invest in a bet about what the market's gonna do regarding banana futures or whatever.

• 27:07Speaker 01

  Yes, yes, but the, the, the first part of that clip, when they're talking about the Web 2.0 era, which is really when I was starting to pay a lot more attention to startups over finance, because I was originally, I wanted to go to get an econ degree and go into banking, like, that was the plan. Those companies were idealistic, but also like silly in a way, that modern technology companies are not. Like, I don't know if this is the American dominance theme about defense tech and be the hurly-burly American, but like Delicious had a dumb URL, if you remember how to spell that with all the dots.

• 27:38Speaker 00

  D L dot I C I O dot U S, I believe?

• 27:41Speaker 01

  Yes, wow, I thought I was the last person who could do that one on command, shout out Lon. And like, Dig was spelled with two G's just because, whereas Instinct started off with Instinct dot com.

• 27:52Speaker 00

  Yeah, there was, all right, all right. I think it's Instinct dot C O, actually, that, not to, not to burst your bubble there, but, um,

• 28:03Speaker 01

  Instinct dot com.

• 28:04Speaker 00

  Oh, never mind, my, my mistake.

• 28:07Speaker 01

  And dot co.

• 28:08Speaker 00

  The, oh, they got, they got both, they got both, folks, they got both. But the, the other thing I was gonna say is, I think there was this idea that nothing mattered other than users, like, that, when I first, like, 2007 was when I first started working at, uh, in tech at Mahalo for a guy named Jason Calacanis. It was my very first startup and that was really surprising to me, because you, you know, I got out of college and I, I took a few econ classes in grad school and the idea, to my mind, was always like, a good company, it's like about margins, you know, it's about like, how, every time you sell a widget, how much are you making versus how much you spent to put that widget together? And the, the higher that margin, the more widgets you sell, like, thumbs up, you did a good business.

• 28:53Speaker 00

  And then I started working in tech and nobody ever talked, I never heard one conversation about that, about like, spend versus, it was just make number go up, how many people used it? Monthly active users, that was the only metric anybody was, was checking, that's all the investors cared about. They'd give you basically unlimited runway if you just kept growing fast enough and adding a bigger footprint. Cosmo dot com is always the one I come back to, you remember? K O Z M O, and it was, here was the pitch for Cosmo dot com. It was just, it was like Grubhub or DoorDash before those existed, but the hook was, there was no minimum order size. So you could order like a lighter and one muffin.

• 29:38Speaker 00

  And they would send a guy from somewhere, like, from Pink Dot or Circle K or something, a guy would go pick up your muffin and your lighter and then drive it to you. And I don't even think you had to tip, you would tip like a dollar, like, you didn't even have to tip. It was like the cheapest thing in the world, because all they cared about was one more person today used Cosmo and we can go back to the investment team and say, looky, look, it doesn't matter how much it cost us to go bring this guy this muffin, he used the, the.

• 30:06Speaker 03

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

• 30:21Speaker 05

  Great to be here.

• 30:22Speaker 03

  When people go to try Lightfield, do I need to talk to my CTO or my CEO? Or can I just start using it as an individual and, you know, like a bottom-up SaaS kind of solution? You can play single-player mode or multiplayer mode? How does that work?

• 30:35Speaker 05

  So you can absolutely start in a single-player mode, as long as your CTO or CIO will let you connect your mail-in calendar. It's really sort of the backbone connector of Lightfield. So we have some folks who try it out by themselves, and then eventually they move their whole company over.

• 30:52Speaker 03

  Lightfield is model agnostic, so if I want to use open source, if I'm super concerned, or I have an on-prem, or if I have an on-prem system and my CTO and my CIO are very militant about that, I can switch models and use whatever I want. It's headless.

• 31:09Speaker 05

  That is correct. You can use any model you want. All of our providers sign the zero-data retentative clause. They're all in America, but it is truly headless. You can use the model that suits you best.

• 31:23Speaker 03

  So everybody go check out lightfield.app.

• 31:25Speaker 00

  And so I think that led to a lot of just like incredibly dumb nonsense, because it was just purely, who's going to use it? Not, does this make actual sense as a company? And today, everything's super frothy around AI, but I do still think people pay more attention to that. Like, does this, what's the business model? Is this ever going to make sense as a company? I hear people talking about that with Instinct today, where they're like, it's always going to be free. Like, yeah, they, yeah, that's what Noah Shin from Instinct did that Invest with the Best interview, I believe, Monday. And he said, it's always going to be free, they're just going to take a cut of transactions.

• 32:05Speaker 00

  So if you buy book tickets for a plane ride trip on your Instinct agent, they'll take like 2% or 3% or something. And they said they're even boutique hotels that are offering them like a 30% cut if their agent makes a reservation. So that's, but people are already like picking this apart, like, does this make sense? And the app is like, you can't even use it yet, it's still waitlisted. It used to be years before people had that conversation.

• 32:31Speaker 01

  Well, you actually outlined some very good examples of why this has changed over time. Go back to Cosmo, think about what they're doing. That's not a pure software product. That involves real-world purchasing, involves people on bikes or cars, moving things around. There's no way to scale that without charging a lot of money. Now, contrast that to the Web 2.0 era, when you have Dig and Delicious and Weblogs and so forth. You could add a million marginal users at the cost of some bandwidth and some CPU time, right? Now, take that to the AI era, no longer the case. Serving customers has real costs. We are in a compute crunch, and every CPU or GPU cycle that you consume has a real cost to it. And that's probably why companies are monetizing today faster than they were in the Web 2.0

• 33:12Speaker 01

  era, because you kind of have to, or you're going to pull a YouTube and probably not find your Google.

• 33:18Speaker 00

  Yeah, if OpenAI existed during the Web 2.0 era, they would never have ads by now. They would just purely be about, we want every single human being in the planet to be using OpenAI. It's only because it costs them so much every time. I'm like, what's this plan? You know, that they have no choice.

• 33:35Speaker 01

  Whenever I replied, "Thank you" to my ChatGPT Codex instance, and realized that I'm using Astro, and it goes, "Thinking." I'm like, "Oh, man." It goes, "You're welcome." And I'm like, that was like half my.

• 33:45Speaker 00

  You boiled a puddle. How dare you?

• 33:48Speaker 01

  It's okay, I'm going to boil a lot of puddles before I'm dead, Lon. I love it.

• 33:52Speaker 00

  It's like, it's like a shirt a guy would be wearing on like a cruise ship, like, "I'm going to boil a lot of puddles before I die." All right, we're getting silly. One more clip before we wrap with Justin Khan. I love this one, it's for about 57 minutes, so towards, towards the end. He's got some great, very practical advice. Founders need to recognize their own strengths, is the observation. And boy, howdy, never working for Jason, who's a wonderful manager and founder, but I have at this point now worked for a lot of different founders across a lot of different companies, and this is very applicable advice that I feel like a lot of startup people should take to heart. Let's take a look.

• 34:31Speaker 03

  What have you learned now through these four companies, five projects, six projects? You've incubated stuff.

• 34:39Speaker 04

  Yep.

• 34:39Speaker 03

  What do you think is at the core of creating startups?

• 34:42Speaker 04

  Well, I mean, I think that.

• 34:45Speaker 03

  And being a founder.

• 34:45Speaker 04

  The most important thing, really, the kind of meta-level important thing is to know yourself. I think most people do not spend enough time understanding themselves and understanding, what are you good at and what are you not good at? And for the things that you're good at, how do I like focus on those things and do more of them? And for the things you're not good at, how do I either improve or how do I delegate those to someone else? I think most founders hit a wall because they're doing something, it starts working, and then they don't get out of their own way. You know, they are, they insist, they think, because I created the product and it worked, which there's a heavy dose of survivorship bias there, I am going to like, all my decisions are right, so I want to micromanage kind of all these other parts of my company, or I want to be, have to make all these decisions.

• 35:28Speaker 04

  Or my ego is such that I don't get out of the way of these other people I brought into the company to let them operate. And I feel like that's a very common problem that I see all the time, and it's a problem that I've had in my life, throughout my life, that I've, you know, kind of only, you know, in the last maybe five or six years, really understood deeply.

• 35:46Speaker 00

  This really stood out for me so much, because I do feel like you get a lot of startups where the founder becomes this kind of, not just, like, we think of bottleneck in terms of workflow, but they become not just a workflow bottleneck, but a creative bottleneck, where it's like, every decision has to go through this one person, and maybe they're not great at making every kind of decision. Maybe they're great at making this handful of decisions, but they should let this handful of decisions be made by the people around them who they brought in. And I just, as a quick aside, one of, other than Jason, of course, one of the other best founders I've ever worked for was Clark Benson over at Ranker, who had a very good sense of this. He was a product guy, or he is, I shouldn't say was, he's still alive and running Ranker. He's a product guy.

• 36:30Speaker 00

  And so he had very good instincts about how the product should work, how the app should work, how it should be designed, UX, UI. None of us would really question him there. But then when it came to like media especially, which is what I was doing, the editorial side, he would really let the team experiment and explore, try different things on social media, try different things on YouTube. You guys know that landscape so well, just go. And man, it worked really well, and we ended up being able to grow that media business a lot, because Clark kind of got out of our way and understood, I'm going to be over here worrying about the app and the product, you guys go worry about that stuff.

• 37:04Speaker 01

  This interview, and longer than just the clip we just played, I really do recommend that anyone listening to this who's enjoyed it, to go listen to the whole thing. I'm really glad that I did. Justin talks a lot about like being aware of himself and understanding what happiness is and creating distance from his emotions, just comes across as a very, very mature person who's done a lot of like experience and a lot of learning from that experience. But in this case, what I found very interesting along was a implicit rejection of founder mode. Now, not really, because founder mode actually came out as an idea later on than this interview was taped, but here we have an executive who's, you know, taking a company from zero to a billion-dollar exit, so they have done the thing, the most impressive thing you can do in Silicon Valley, talking about shared responsibility and letting, you know,

• 37:48Speaker 01

  smart people run their own game. And that was the conventional wisdom that I grew up in, in startup land. And today, very much so, it's now pivoted towards founder mode, you know, one person carrying the torch, providing the direction, setting the North Star, and being involved in the details. And that's a change. And so I know all of tech is bundling or unbundling or cycles and recycles, but this did surprise me as tonally different.

• 38:10Speaker 00

  I think, I think it is, it's a, it's a different approach, and it's, it's a, it's a better, it's a better approach in a lot of ways that doesn't necessarily assume one person has to be the keeper of the flame for like everything that a startup does. They can sort of set the, the larger vision and then let sort of everyone, everyone go. Really good flashback coming up today. This one comes to us from May 2023. It's episode 1735 of This Week in Startups, and your guest is Brian Chesky, the co-founder of Airbnb. This episode dropped the same week that Airbnb rolled out Airbnb Rooms, a return to the company's original rent out your spare room concept.

• 38:51Speaker 00

  So that was why co-founder and CEO Brian Chesky had agreed to be on the show. To go back to 2008, seven investors passed on the chance to buy 10% of Airbnb for $150,000. The founders famously kept the lights on by selling novelty politically-themed cereals. We're going to talk about that. Also in this conversation, Brian talks about early rejections, obsession with the customer, how Airbnb is organized, and where he thought AI was going to take the hospitality industry. We're going to look at some of those projections. So let's just dive in, no need for any further intro. The first thing, Alex, I wanted to talk about, right away in the interview, Brian starts

• 39:34Speaker 00

  telling the story about how investors did not like the idea for Airbnb. Now we accept Airbnb as like, obviously, that's a great business. I use Airbnb. When I went to Rome earlier this summer, we stayed in Airbnb, it was a wonderful experience. But back in the aughts, when Brian was first pitching this around, people were a lot less receptive. Let's take a look at that clip.

• 39:56Speaker 03

  Everybody, when they see you saying, "Oh, my God, I love Airbnb," how do you reconcile that as an entrepreneur?

• 40:03Speaker 06

  We came up, you know, obviously, I know Joe told the founding story, but I'll tell a little bit of the, there's a founding story, and then there's Jason's, the story of all the rejection. The first time we came up with the idea, it was October 2007. It was for a design conference that was coming to San Francisco. There was an after-party at the Fairmont Hotel. We went to the Fairmont Hotel. The first person I told about the idea, he looks at me with a straight face, he said, "Brian?" I said, "Yes." He goes, "I hope that's not the only idea you're working on." That's what he said to me. And this is like a design luminaire in our industry. And that was kind of the general sentiment. I remember in January, February 2008, Joe and I were living in San Francisco in an apartment, and we had a roommate named Phil.

• 40:49Speaker 06

  And Phil worked for this company called Justin.tv. Justin.tv was a precursor to Twitch and it was funded by this program called Y Combinator. Now, I didn't know anything about Y Combinator. I didn't know anything about Silicon Valley. I didn't even know what angels were. Somebody once told me, there are these people called angels. And I said, oh, my God, this person believes in angels. So I was really naive. I didn't know anything about Silicon Valley. I was a designer by training. And Michael said, I can introduce you to these angel investors. And so Michael introduced us to like 10 to 20 angel investors. Now, at the time, Jason, we were trying to raise $150,000 at a $1.5 million post-money valuation. So for $150,000, you could have owned 10% of Airbnb.

• 41:32Speaker 06

  And the majority of them didn't even reply to the email. I actually ended up publishing a bunch of the rejection emails, but many people said like, this isn't a good idea. Many people said like, travel, we're not like excited about travel. I remember one investor said, we love everything but you and your idea. In other words, we don't, I'm like, well, everything else is good. Unfortunately, I was like, I thought to myself, wait, what else is there? There's me, there's the idea. Yeah, I guess there's the name, but they don't, they didn't like the name either. So, and what they meant by they liked everything but us and the idea was, it was three founders, one software engineer and two designers. And they thought, well, you have like too, too many designers in your founding team, you know? Like people just associated designers as like non-technical and therefore like maybe not adding value.

• 42:15Speaker 06

  And I think they, I always felt like Joe and I, our ability as being designers, was actually part of the secret sauce of Airbnb, because it was not a pure technology problem. And also people said, this is crazy. Strangers never say hello to strangers.

• 42:27Speaker 00

  I mean, I, I will admit, I had, I was already working for Jason when Airbnb was new. And he, we talked about it probably on a podcast episode very much like this. And that was also my reaction was like, well, that sounds dangerous. Like, how do you, I'm going to go walk into some stranger's house? I'm going to leave my keys and some stranger is going to stay in my room while I'm gone? Like, it just feels crazy when you're not using it. And then when you're using it, like now, I don't even think about, when I go to an Airbnb, I don't even think about this as somebody else's home. It's just my home for the week.

• 43:01Speaker 01

  No. Yeah, yeah, yeah. But I think there is something to be said for generations growing up in a post-stranger danger world. I mean, think about the PSAs that you were getting when you were a kid. I mean, it was every person's going to try to offer you candy and stuff you into a van and take you off to, you know, Tuscaloosa or Timbuktu. And not really the case. As it turns out, most people are pretty cool. Most people are fine and you can get along just, just okay. But for fun, Lon, guess what 10% of Airbnb is worth today?

• 43:25Speaker 00

  Oh, my God. I don't want to think about it. It's like,

• 43:29Speaker 01

  I guess.

• 43:30Speaker 00

  Uh, like $500 million.

• 43:36Speaker 01

  $9.25 billion.

• 43:39Speaker 00

  Oh, my God. It's insane. How is Airbnb worth that much money? That's crazy.

• 43:44Speaker 01

  Airbnb is currently worth $92.5 billion. It's because it became a huge business. Those investors were not just wrong. They were phantasmagorically wrong because they, turns out, this is popular the world around. Now, what I want to say is that Airbnb has, over time, changed a bit. If you think back to the early days, especially if you knew couch surfing from before Airbnb, it was a pretty hostile-ish experience, if you will. It was not five-star. It was not Instagrammable, though we didn't have Instagram back then. But today, I do feel like Airbnbs are much more upscale. You rent a whole cabin, et cetera. Lovely. But I mean, back then, it was, it was great.

• 44:18Speaker 00

  It was more variable. Like, in the early days of using Airbnb, sometimes you'd show up at the place and it was amazing. But then other times you'd be like, eh, this one doesn't really look exactly like the photo. It was a little bit more of a shot in the dark, whereas I think today, they've got it basically locked down. You know, from the Airbnb page, if it's got like a 4.8 or up rating and you look at the pictures and it looks nice, like you're pretty much confident in what kind of place you're going to be getting.

• 44:47Speaker 01

  For sure. But I will, though, you have to want the quirk. Like, if you want a boring room with like a bed and a shower, then just go to a hotel. If you want anything else with a more personal, human touch, then I think Airbnbs are great. No hotel has ever given me free weed gummies in Texas, but an Airbnb has.

• 45:03Speaker 00

  I actually, I feel like it's when you want, when you're just staying somewhere and you just want convenience and it's just like, like hotel, obviously, when you're going to be busy or whatever. But if you're going somewhere and you want to get like a feel for the place that you're going, then you want an Airbnb because you're staying in a neighborhood and there's like a person who's going to leave you a binder that's like, go to this pizza place. It's really good. You know, like, that's what you want when you're like, it's like a great vacation option. I don't know if it was like business travel. I'm just like, put me at a hotel. I'm putting it on the ramp card. But for Rome, it was perfect. I would very much recommend an Airbnb.

• 45:41Speaker 01

  It's, I'm so startup-illed. I mean, you said Rome. I thought R-O-A-M, Howard Startup?

• 45:46Speaker 00

  No.

• 45:47Speaker 01

  Wow. All right.

• 45:48Speaker 00

  I mean, Rome's the eternal city, Alex. Rome, the eternal city.

• 45:51Speaker 01

  Yes, the place where they had the big circle. They used to flood and have shit battles inside the town. Yes.

• 45:55Speaker 00

  Correct. Gladiator 2 is historically very accurate, I'm sure. So our next clip for Brian, he started, you could, at the tail end of that other clip, he started to tell it, but we want to get the full story in here because it's such a good iconic startup story, is when he talks about it, I teased this a little in the intro, how they funded the company in part by selling parody political cereals during the 2008 DNC and RNC. Here's Brian.

• 46:22Speaker 06

  So we go to Y Combinator. We go to the interview. It's exactly what I expected. It's Paul, it's Jessica, it's Trevor Brackwell, and it's, I think, Robert Morris. And they're all like, basically, they all ask us questions same time, like all four of them. And I was like, totally bewildered. And the first question Paul Graham asked me is, people are actually doing this? And I said, yes. His second question was, what's wrong with them? And the interview at that point went downhill from there. He, midway through the interview, he basically tried to get us to create Stripe. He's like, you should create this like payments company or like an online bank or something. And we're like, that seems like a really good idea, but like, we have an idea. And we're about to leave the interview. It doesn't seem like it's going well.

• 47:05Speaker 06

  And Joe takes out a box of Obama O's. And he hands it to Paul Graham. And Paul Graham's like, looks like he just got a novelty gift. He's like, all right, thank you. And, and we go, we goes, what's the story? He goes, this is how we funded the company. And he goes, what do you mean? He said, well, we told him the story, how we like made the cereal boxes. And then the way we sold the cereal boxes, we mailed them to reporters and they put them on their newsroom desk and everyone buy them. And he said something like, I guess if you can convince people to pay $40 for a $4 box of cereal, then maybe you can convince at least some people to stay in each other's homes. And he ended up admitting us to Y Combinator. And I guess, we've never looked back since. I also want to give credit to Jessica, because I think Jessica thought,

• 47:47Speaker 06

  I remember Paul and Jessica said later, they thought we were like cockroaches. And I think they mean it in a good way, that it was like an investment in nuclear winter. And in a nuclear holocaust, the only thing that survives are cockroaches. And the only thing that would survive an investment nuclear winter would be the founders of Airbnb. We said, we won't die, no matter what happens. And so they basically funded us because we seemed resilient, unkillable. And like, even if the fundraising market was dried up, we would just go on. So.

• 48:14Speaker 01

  So a couple of things. One, I do love hearing about a startup struggling in their Y Combinator interview because it's kind of a famous test of time, a coming of age moment. You become a man when you go through this. But it just goes to show that not everyone's perfect and people still make mistakes, even the vaunted founders of YC. But Lon, I have to say, it does track with what I've learned about startups to know that the grit matters more than last week's traction. And if you do know that a founder won't give up, well, that's probably half the battle of backing someone right there.

• 48:41Speaker 00

  Yeah. And I mean, I think that, you know, it's just like I was saying a little bit before about the, you know, that you're funding the founder, not the concept or the company. That has, that has always been kind of a truism. And I think this is a real, you know, case where you could see that is like, it's not, it is resiliency, but it's also the creativity and it's the resourcefulness, I think, that, that Paul Graham was noticing from these guys, that like, they're just doing business. They're just making observations. They're seeing angles. They're trying things. They're not afraid to like, do something kind of goofy to try to get attention, to make something happen. And I think that, seeing that in a founder has got to be really encouraging as an investor,

• 49:26Speaker 00

  that it's not some person who's just going to like, sit at their desk head down and work on their one project, single-mindedly. They're as like, head on a swivel, looking for opportunities.

• 49:35Speaker 01

  Well, there's something about being a founder that is just sheer persistence and not letting anything stop you. And so if you find some people that have managed to somehow hack at the same time, the political cycle, the news, media and their funding crisis in one fell swoop, and to do it in a way that makes them look kind of cool in punk rock. I mean, seems like a pretty obvious thing to fund if you're an early-stage venture capitalist, because you want people, and we've talked about this on the show ad nauseam over the years, who are willing to look from a different angle or perhaps even a little bit outside the rules. Like, I don't think you're actually supposed to use Obama's name and reuse cereal and probably resell it and blah, blah, blah. But no one really cares, so go for it, you know? Off you go.

• 50:15Speaker 00

  There's, there's tremendous value. And this has always been true from the aughts to the present day. A person who has a good sense of like, how to get something to go viral, like how to communicate an idea that a lot of people are going to be interested in, there is always value in being one of those people. If you have that, like we were talking about Instinct moments ago, the viral assistant app. That, that is the same thing. It's like, the entire strength of it is how to create something, how to kind of have a comment, how to make a statement that is repeatable and shareable and encourages people to, you know, what they now call like, stop the scroll. Like, if you are that kind of person, that has been a marketable, useful skill for 25 years plus now in the internet age.

• 50:58Speaker 01

  And I think especially as attention gets more and more fragmented across platforms and shorter and shorter form content, being able to stop the scroll is going to become, I think, a core competency of pretty much any founder. I mean, think about how we've seen launch videos of startups go from being super dorky nerds staring at a camera, shout out Justin Khan, to now the slickly produced, you know, quasi Marvel's Avengers-style films that people are now putting out at the cost of like 50 to 100K. I mean, Airbnb was trying to raise 150 total.

• 51:27Speaker 00

  Yeah. I mean, we've seen it even extend beyond tech. I mean, like entertainment media now is also about like capturing those viral moments. And like, like the, like Backrooms, you know, like Backrooms was a viral moment long before it was like a cultural phenomenon. It grew in the telling because it was like originally like a person with a good sense of like, this weird liminal hallway video is going to get clicks. And, and so I think we're seeing that across the board. That is a marketable skill in every industry in 2026.

• 51:57Speaker 01

  Yeah. If you can hack attention, pretty much you can work in media, PR, venture, startups, tech, law, business. I mean, like, anything but coal mining, you're going to be fine. The Backrooms one's an interesting analogy, though, Lon. Can I just go off script here and just ask you if you liked that film?

• 52:13Speaker 00

  I did. I do like the Backrooms.

• 52:14Speaker 01

  Okay, okay. Why?

• 52:18Speaker 00

  I will, I will tell you this.

• 52:20Speaker 01

  Or to quote Paul Graham, what's wrong with you?

• 52:22Speaker 00

  I think as a movie, you can tell that's a first, it's a first time filmmaker. It's a young guy who's kind of figuring out narrative. Like, I think there are, there are some like dead ends narratively in it. And you could maybe make that same story a little cleaner. Having said that, I think the back rooms themselves are extremely compelling. And I, and I have since YouTube, like the idea of being trapped in this like sort of surreal, repeatable, like, like quasi-realistic environment. And I think that he invented like the, the original backroom shorts are from before the AI era. But I feel like in the AI era, it feels very like relevant.

• 53:05Speaker 00

  This like endlessly repeating environment that like degrades in realism over time. And like the text becomes unreadable and things start bleeding in. It's like a glitch burst in some ways that we become more accustomed to in the AI era. And I, I think that, that makes it sort of inherently just very compelling. I think it's a great setting, more than a great movie, but I did enjoy the movie.

• 53:28Speaker 01

  Repeating text, quick release cycle, slowly losing your sanity. Are you talking about Backrooms, the movie or AI in 2026?

• 53:35Speaker 00

  I mean, that, I think that's what's in part so potent about it is that without it, like the best AI metaphors are not like super on the nose. They're like, this is what interacting with AI sort of feels like. And I feel like Backrooms really captures that specifically. And so did, um, the other one like that is Pluribus, that Apple TV. It's not about AI, but it's like Carol's frustrating conversations with the hive mind are reminiscent in some ways of what it's like to interact with AI.

• 54:07Speaker 01

  I can't wait until my kids are older and I can catch up on like years of television and movies that I've missed.

• 54:12Speaker 00

  Late nights, make, make time to catch up on Pluribus over your late nights.

• 54:16Speaker 01

  My, my wife steals the television and watches HGTV and no offense, that's not what I want to catch up on. So I just let her have it. But on the point about AI and what's real and what's not, I want to take us all the way to the 59 minute mark of this video because we get into a very interesting conversation about AI and what's going to happen where it gets harder to tell what's real. I want to bring up the, this clip and the one that comes after it, not because this is the most technical, practical startup advice ever, but because I think today we spend so much time thinking about AI. It's like the thing, but in 2023, it's going to become out. It was a smaller industry. It was not the entire world. And it's good to see how smart, engaged minds consider the technology before it became the only thing we can talk about. Take a listen.

• 55:01Speaker 06

  And so that's where I think it goes. And I think that we don't have a search problem in the future. We have a matching problem. So we are going to use AI to match you to whatever you want. And I think that the other thing is I think we're going to be really good. I hopefully identity authentication. You know, the problem with AI is what's the first word in AI? Artificial. The biggest risk before machines come after us is they become us and we can't discern who is a machine and who is not. And I think that we're already seeing that. I mean, when that Pope photo circulated, I thought that was a real photo at first.

• 55:33Speaker 00

  I did too. I was like, that's weird. The Pope is going for it.

• 55:36Speaker 06

  Yeah, I was like, pretty awesome. He's got Balenciaga, go for him. But that's today's technology. So we're about to live in a world where someone can sound like me, they can behave like me. And as we spend more and more time online, it's going to be harder to discern what is real and what's not real. So I think in the age of artificial intelligence, the other thing people want is authenticity. And authenticity is whatever's real and whatever's authenticated. So I think our brand is kind of authenticity. Like, we're not going to ever be the most digitally immersive company. That's going to be social media or entertainment. Our value is really the physical world. We get you online, offline with people different from you all over the world. And that comes with starting with knowing who you are, authenticating your identity.

• 56:16Speaker 01

  Lon, I'm impressed by how prescient that was, although it was only a couple of years in the past. But still, I don't think I would have had that clear perspective of what's coming. But his point about AI can sound like you, look like you. We are seeing AI models in the voice category today advance to the point to which you can feed them a very small snippet of audio and ape someone's entire speech patterns. We're seeing people create, I think we used to call them deep fakes. Now we just call them realistic videos of people. You can actually have avatars kind of like stitched over yourself digitally. And we're seeing people's parents get called by fake callers that sound like their children. So everything he called for is coming true. And I do think that he's correct that we do want more authenticity. I just think it's funny that he was talking about the physical world in a brick and mortar sense.

• 57:01Speaker 01

  But today, when we talk about AI, the physical world, we're mostly talking about robots or embodied AI, if you will.

• 57:07Speaker 00

  I mean, I, I think this prediction in particular, we've been hearing since the early chat GPT era, which is like, this is going to lead to a revival in in-person experiences, authentic experiences, human experiences, like live music is going to make a huge comeback. And we're all going to start hanging out together and going to block parties more. And like, I, I really liked that, that sort of take in like 2021, 2022. Here in 2026, I feel like that's not, that is not so far. That, that has not really seemed like it happens. We've, we've put up a lot, a lot of people have become much more hostile to AI outputs where they insist on, I only want to read substacks that are a hundred percent written by humans.

• 57:52Speaker 00

  I don't want slop on my timeline. Like, there's definitely a thirst for authentic content, but I have not seen like, I'm going to go to five extra concerts this summer, or I'm going to host more dinner parties. Maybe I'm just not popular, but I don't feel like we've seen that as a society yet.

• 58:11Speaker 01

  You're absolutely right. And here's the problem. I think AI and the general erosion of trustable media would lead to more people being outside more and together. But the problem is we're all working more than ever to keep up with AI. So no one has time.

• 58:28Speaker 00

  Right.

• 58:28Speaker 01

  Like there's, in five years, maybe we'll all work a little bit less because agents will take on so much of our workload that we have more spare time to take a walk during lunch. Go see a friend. Lon, I could fly down and see you and take you out for barbecue. I'd love that. But right now you and I are both so far behind at work.

• 58:44Speaker 00

  Yeah.

• 58:45Speaker 01

  That there's not the, the capability to do it. And so I, I think that's the real sticking point of AI for me right now. You and I are both AI users, we're fans, you know, we're not far from haters. But I do think that all it has done for a lot of people like ourselves is ratcheted up the intensity and duration of work. And that is not quite, not quite what I had in mind.

• 59:03Speaker 00

  Yeah.

• 59:04Speaker 01

  When we got this amazing advancement in AI.

• 59:05Speaker 00

  Yeah, it is, it is one of the rare points of total agreement between myself and Jason's all in bestie, David Sacks. We don't agree, we don't agree very much. But one of the things we do agree on is that rather than costing people their jobs, at least so far, what it seems like AI has done is made everybody a lot more productive at their job and therefore a lot busier at their job. So you're getting three times as much done. You're maybe working twice as much, but you're not being replaced. So that, that on the plus side, you still have a job. It's just harder now.

• 59:41Speaker 01

  Can I, can I challenge that ever so slightly?

• 59:44Speaker 00

  Please.

• 59:45Speaker 01

  All right. So I was here at the, the Goodship launch, a long, a long period of time. Several years in podcasting time, you're doing three shows a week. It's, we did a lot of work together. So I've been through a lot of iterations of the show. And one thing that was a consistent thing when, during my time was, uh, I wrote the show most, most of the time. And it was a lot of work, prepare the docket, Jason would have new ideas, we changed the format. It was this evolving living process. And now Lon, that's no longer the case. And we've done the modern thing and allowed really agents to write a chunk of it for us. Cause it's just collecting information and putting it down on the page. And I, I don't think you would go hire someone to prepare the show notes in the way we did when I was, when I was brought on. And I think that's, that is a change in the example of less job.

• 1:00:30Speaker 00

  I, I mean, yes, but there's a guy, his name is Zach. He works for us now and he is the one who's making the dot. Like I used to write the docket by hand. It was my job. It took up a big chunk of my day. You would do it for different shows than me. Uh, and you know, I spent three hours putting this document together by hand with all the pieces of research or whatever. So Zach does that now. I'm freed up, I'm working on the substacks or whatever. Check it out, TWI startups.substack.com.

• 1:01:05Speaker 01

  Best headlines in the game. No one outshines Lon in the pun game. Read everything he writes, makes me smile every week.

• 1:01:12Speaker 00

  You're, you're very kind. But so, you know, Zach is now doing that job. Maybe he's spending an hour or less a day on it, but it's, the job is now not only putting the stories, you still have to pick the stories. Claude's not good at that. Still need a human to curate what we're going to talk about. You give the stories to Claude. There's a Claude skill that turns those stories into the docket. Zach had to write and brainstorm that and create that skill. And then every time we have feedback on the docket, he needs to go back and fine tune and improve that skill. And then he's the human in the loop. So whatever the skill comes out with, he's got to go through line by line and be like, they didn't nail this, nailed this, didn't nail this.

• 1:01:56Speaker 00

  It is probably like 20% less work over the course of the week, but it is still a job. And I don't think in two weeks, we're going to iterate our way out of that job. I think that's going to be Zach's job for at least the next few months. And then it'll be on to the next skill and the next skill and the next workflow that he can improve. Maybe there is, here's what I would say. In three years, in five years, maybe we'll reach a point where these models have gotten so good that we won't need a Zach anymore to fine tune them. We won't need a Micro One with all their experts to help the frontier labs make the models better. Or a Taste Labs and all their experts to help make the models better designers.

• 1:02:41Speaker 00

  Or maybe we'll be done with that. I don't know, maybe. And maybe then we'll be talking about, okay, now that all the architects and accountants and lawyers train the models to do their jobs for them, now nobody has a job. I, I don't know if that's going to happen.

• 1:02:57Speaker 01

  I, I don't buy the.

• 1:02:58Speaker 00

  But I don't think that's happening yet.

• 1:03:00Speaker 01

  No, no, I, I'm just seeing little bits of work get automated. Like just to put another example in this, I write a lot and I have created some skills inside by a Codex instance that helped me do what I call pair editing. So I abuse commas and I need someone to go through my, my, my drafts and just remove the commas. Like this has been a problem my entire life as a writer. I know it, but I never want to sound like AI because I do all my own writing. So I've made skills that edit my work, leaving the tone, the jokes, the, you know, the way that I write, but just solving the, uh, the grammatical issues that are, that pop up here and there. When I was at TechCrunch and I started off, I had to take my writing and bring it to a human and have them do this. And here's the thing that blows my mind. You know what's really

• 1:03:42Speaker 01

  good? Codex, we'll just chat GPT, I suppose. It's incredible. And so I do think that we will see a slow erosion of previously high-touch labor categories that are in the knowledge work game that will change the employment system, structure. It just isn't going to happen in 18 months like a thunderclap like everyone thought.

• 1:03:59Speaker 00

  Right.

• 1:04:00Speaker 01

  But I, I, I wouldn't go all the way, the Socks view that, you know, only more jobs, no job disruption. I would say more jobs net long-term, medium-term churn. And I, I think that's probably a great trade-off for what we're going to get down the road. I'm not worried about this. I'm just chewing on it as we go through it.

• 1:04:15Speaker 00

  Yeah, no, I mean, I, I think there's some wisdom to what you're saying. And we're, we're definitely going to see some movement in general, especially like I said, in the two, three, four-year time range, when all of the expertise and fine-tuning work that we're doing now on models is baked in and done. And like, maybe we don't need to keep having accountants look at the output and be like, oh, mess that part up again, the model will just know and benefit from the, their expertise and get that, get better to that point that we don't need them anymore. I, I think that is definitely, I think that is definitely possible.

• 1:04:52Speaker 01

  Now, one more clip before we go, sticking to the theme of Chesky being a little bit early to things that are now very obvious. We're going to play a clip of him talking about what's going on in the realm of AI software development. Now, of course, here in 2026, we are deep into our Claude code era. Everyone uses an agent to write code. Sure. But back in 2023, very much not the case. But here is what Mr. Chesky had to say then.

• 1:05:15Speaker 03

  On the side, a friend, few told me, hey, you gotta try this place in San Francisco, Cafe Okinawa that I've been going to to get Tonkatsu sandwiches. I told like three people about this and, because I love these when I go to Japan and they're just, everybody goes there and they're like, oh yeah, you're right. That was great. And now they spread to the next person. And that kind of word of mouth, I think like this AI is going to find little things like that where it didn't know that this was something that you would be delighted by.

• 1:05:42Speaker 06

  Totally.

• 1:05:42Speaker 03

  And this is such an opportunity.

• 1:05:44Speaker 06

  I think it's amazing. And by the way, I think I heard another one of your podcasts, you said something that really resonates that I think is worth calling out. The cost to develop software is about to go down. And maybe a good analogy, Jason, would be like the camera. 130 years ago, very few people could operate a camera. And so therefore, you had to be a specialist to take a photo and there weren't a lot of photos. Suddenly, computer programming is just basically telling a computer to do something in its language. AI means you can now tell a computer to do something in your language. The moment you don't have to learn a different language, you can use your natural language, English. Suddenly, kind of everyone in a way can be a programmer, like everyone's a photographer. You don't have to actually have a skill. Now, there will be programming skills, but suddenly anyone can do that. Now, when that's possible, there's going to be so much more

• 1:06:29Speaker 06

  software. We're going to live in abundance of software. I think in a podcast, you reference like a ski instructor or a ski company, like a niche business that couldn't have developed, hired great software engineers. But now they can, the equivalent of the best engineer you've ever had, developing their app. And so suddenly the skills start to differ. We have to understand skiing, human psychology, taste, design, and how to operate and have a conversation with that tool. But you don't have to necessarily build the infrastructure. Just like we never built servers because we had AWS. But if we launched five years earlier, we would have had to have been really good at like, kind of building out servers.

• 1:07:04Speaker 03

  Rack and stacking servers. I mean, your first half a million would have went towards a co-location facility.

• 1:07:09Speaker 06

  Yeah.

• 1:07:10Speaker 03

  And now it's like, you're just going to talk to this thing and it's going to make your software for you.

• 1:07:14Speaker 06

  So I think this is going to create, I think this is going to create millions of startups. I think that like entrepreneurship is going to be a boon. I think there's going to be millions more. I think anyone can essentially do the equivalent of what software engineering only allowed you to do only five years ago. It's going to be awesome for many people. It's going to be wildly disruptive for others. Albert Einstein used to have a saying, the best way to keep your balance in a bicycle is to keep moving. And I think the best way to keep your balance in the world of AI is to keep moving forward and just adopt the tools. Don't fight it.

• 1:07:42Speaker 01

  Uh, to put some context on this lawn, I, I looked it up. In, in mid 2023, the leading AI models were GPT-4, Claude 2.

• 1:07:52Speaker 00

  Yeah.

• 1:07:52Speaker 01

  And, uh, and Lama 2. So this was way before they were good at coding, but he was able to see clearly three years ago where this was going to go. And I think, I think they were dead on. Here's the question though, for you, because you are deep in the launch ecosystem, accelerators, you know, founder you, et cetera.

• 1:08:08Speaker 00

  Sure.

• 1:08:08Speaker 01

  So Chesky was saying, we're going to see millions of new startups. And on one hand, I do think we're seeing a lot of experimentation in the market, but I just feel like we're seeing that many more new companies come up. So I'm just curious what you're seeing and if that prediction from this Airbnb founder, uh, has borne out.

• 1:08:25Speaker 00

  I, I, you know, I'm always a little dubious of this prediction, especially because a lot of tech people tend to use it to advance the argument that like, as like a pushback against being anti-AI. Well, like, oh, but it's going to lead to massive job disruption. Like, well, those people are just going to start companies. And it's like, well, everybody can't run their own company. Like, some people need to work for other people's companies. Some, like, you need, uh, users who have their own money from other jobs where they work to buy your, like, I don't, I don't know if a capitalist society where literally every single person owns their own company is sort of functional. I don't think that's the way our society functions. So it always seems like it's missing a little gap there

• 1:09:09Speaker 00

  in some ways. But, um, I, I do feel like we are seeing an explosion in entrepreneurship. We are seeing a lot of new companies and we're seeing a lot of people who have started one company are now starting three companies or are now starting five companies. And so we're seeing that grow exponentially, where if you are already entrepreneurially minded and a builder, you are getting great utility out of this and using it to do a ton of projects. I think, I think what's missing is the non-entrepreneur people. The prediction I think that Chesky and others are making is that people who have never started a company, who maybe had

• 1:09:50Speaker 00

  ideas, but always like, I don't want to start a Squarespace. That's too complicated. Now they'll be like, oh, but with AI, I could start that bagel shop I've always wanted, or I could open my own dog grooming business like I always wanted. And I'm not sure we're seeing that yet. Maybe it's just that the word hasn't spread to those communities and those people that like, AI makes it that much easier to start your own company. But like, I think we're seeing a lot of people who are already in the, I'm going to one day start a company mindset, using these tools to do it faster and easier. I just don't know if that's become universalized yet.

• 1:10:29Speaker 01

  Yeah. Uh, on your point about not everyone can, uh, become a, a founder, I think it was, uh, Yo Gotti, who said that everybody want to be a general, but don't nobody want to be a soldier. And I think that does apply here that, you know, you can't have an entirely top-heavy organization in the economy. People have to have jobs versus CEO titles. Um, the thing that I've been thinking a lot about though, and just pairing off of what, what Chesky was saying, is that now that you can program in your natural language, your normal language, uh, people are building a lot more out of sight. Like, one thing that I, that I keep being shocked by is when my non-technical friends, people that I've worked for off and on for a decade plus, uh, say things like, oh yeah. So I was using Claude yesterday and I, I made this app and I'm like, what? You? You couldn't even open Google Docs five

• 1:11:12Speaker 01

  years ago. What are you doing? And they're making their own stuff, things that they need, little things. And so I'm always trying to figure out like, if we're not seeing this explosion of startups that we expected, are we seeing instead people at, with jobs, essentially making Microsoft for companies inside their own role for themselves? And that's maybe where we're seeing more of this, you know, impact and rubber hitting the road and so forth.

• 1:11:34Speaker 00

  But I, I'll tell you what else I think we're also seeing is people who are already doing things like they're a content creator making Substack posts, or they, they are a dog groomer with like a van that they drive around. Like, I think a lot of people who are already doing that are becoming much more effective with the help of AI tools. Like, one thing that I am always shocked by, as a person who's been doing this job for 15, close to 20 years now, one of the massive headaches and also advantages, like 15 years ago that I had, was I was pretty good with Google Analytics. Like, I knew how Google Analytics worked and I could look at the pages and make comparisons and be like, oh, we need to do this, or this page is doing really well. So we should make three

• 1:12:18Speaker 00

  more pages like that. Like, I learned how to do that. And that was a very like, not everybody had that skill who was making blog pages or whatever. And so that could put me at an advantage. And today, you could just download your Google Analytics or your YouTube Analytics or your X Analytics. I know because I do this all the time. And you could just give it to Claude or Grok Bot or whatever and say, what kind of post should I be making? Or what can you tell me? You don't have to know one thing about how any of it works. You could even go, I did this once too. You could go to Claude and say, I have a YouTube channel. I want you to tell me what kinds of videos I should be making. What should I do in analytics? And it will tell you exactly what charts

• 1:13:01Speaker 00

  to pull for it and what metrics it wants to look at to make you a full report. It takes all the inherited knowledge out. So nobody has to show you how to do that stuff. And I'm sure those kinds of processes are making people much more powerful at the tasks they were maybe already doing.

• 1:13:19Speaker 01

  Yes. As long as someone's already done it and it has been ingested and is, you know, chewable by AI, then sure. Ah, I'm always so excited about progress and then I, I think about that and I'm like, well, you know, I could just prompt my whole newsletter and I bet it would be 70%.

• 1:13:35Speaker 00

  I am, I, I will tell you as a side and then what we have to wrap. So I'm doing these Substacks for, uh, for launch now. We, we have a This Week in VC one. We have This Week in Startups and This Week in AI. 100% human written. I write every single word. I don't let AI do any writing for me, but I do have Grokbots helping me out at every step of preparing those newsletters and I am able to, I'm so much more, I, I would never have been able to churn out three well researched, fairly lengthy Substack posts in a day, five years ago, but I can do it today.

• 1:14:12Speaker 01

  Help people out Lon. What is Grokbot doing for you? Is it clicking the buttons to publish them? Is it doing research for you, pulling facts?

• 1:14:18Speaker 00

  It's that one. Uh, so, uh, I'll give you a great example. In the This Week in AI newsletter, thisweekinai.ai, if you want to check it out for yourself, um, we do a demo or a model comparison or a tutorial every day. Like what is like a hot piece of content about AI that's hands-on and practical that we can share every day. The old workflow would have been me loading up X and literally scrolling my For You, looking for like, what are people talking about today? Let me spend 15, 20 minutes just getting a good sense or, or that and then go to YouTube and spend another 10 minutes scrolling over there. What are the, oh, Sonic 5.5 demos are

• 1:15:00Speaker 00

  the thing today. Now I have the X API tied into a Grokbot and I just tell the Grok, I already have this process figured out because I do it every day. So I just come in in the morning and it, it, it doesn't even need to be prompted. It just tells me, here are the big trending demos. Here are the big trending model walkthroughs. And it, it doesn't even just pull the links. It actually summarizes for me. So it's like Lon, Sonic 5.5 demos are super hot today. I found three times as many of those as everything. Like it's doing a research report for me. So, uh, and then I can go through that. I could be like, what part of the transcript of this YouTube video does this come from? And it'll give me the time codes. I could take that. I could give that to my clip bot and I could say, make a video of this video between this and this

• 1:15:42Speaker 00

  time code and it just makes it. So all the ticky tack stuff is done and I just get to focus on the actual writing.

• 1:15:50Speaker 01

  No, I, I think it's a brilliant example and I'll, I'll, I'll leave everyone with, uh, one more AI hack while we're sitting here. Um, have you ever run into a very annoying paywall because you don't subscribe to that particular website? Well, go to your favorite friendly chat GPT or Grok agent and say, hey, can you find me a gift link of this article link? It will go onto X and find you one.

• 1:16:11Speaker 00

  Yeah.

• 1:16:11Speaker 01

  Perfectly legal, ethical, and a great way to avoid the paywalls.

• 1:16:15Speaker 00

  I'll, I'll give you one other producing tip with Grokbot. Uh, it's really good at surfacing people's contact info. So if you don't want to pay for like a, a service, you know, there are those services where you pay them 20 bucks a month. And if you're like a salesman, it'll help you find anybody's email address. Or just ask Grokbot and it'll get really good at it. And now I could just, if there's somebody we want to book, I can say, find me some contact information, but it won't even just, it'll like figure out their assistant's name and look up their contact information. It'll figure out their press context name and find them on X or LinkedIn. Like it'll go three levels deep and spend an hour, like what it would

• 1:16:59Speaker 00

  have took, taken me an hour of research and I can zero in on that person. And I'll, I'll, I'll tell you, uh, we're very excited. She's going to be coming up on one of the shows. Dr. Fei-Fei Li of World Labs. I've been trying to get her booked on a Jason Calacanis podcast for many, many months. With the help of Grokbot, I was able to find an email address I hadn't found before and got right through.

• 1:17:20Speaker 01

  Surely you mean, uh, AMD's Fei-Fei?

• 1:17:24Speaker 00

  I do. World Labs, a division of AMD. Exactly.

• 1:17:28Speaker 01

  Yeah, yeah, yeah. She's the World Labs CEO, an AMD company.

• 1:17:31Speaker 00

  Hmm. Chief Scientist of AMD is her new title, actually, I believe.

• 1:17:34Speaker 01

  If you don't know what we're talking about, uh, her startup was sold to AMD in an $8.2 billion all stock deal. I'm sure it was on the show.

• 1:17:40Speaker 00

  It was.

• 1:17:40Speaker 01

  But that's what we're joking about. So.

• 1:17:42Speaker 00

  All right. I think that does it. I think we've talked more than enough about Brian Chesky. Just we, we enjoyed getting together and then hanging out, chewing the fat a little bit. Uh, so thank you to Alex Wilhumb for being here. I am Lon Harris. Uh, check out our Substacks, please. TWIstartups.substack.com. Go take a look, give it a read, give us a subscribe and we will see you next time on This Week in Startups.