Jony Ive Joins OpenAI, Waymo Hits 10M Rides, and How to Launch a Marketplace from Scratch | E2129

Today's show: Jason and Alex dicsuss Jony Ive's $6.5B deal with OpenAI and what it means for the future of AI hardware, Tesla's push into robotaxis vs. Waymo's 10M paid rides, and Microsoft's latest move partnering with xAI. We dive into the GENIUS Act and what it means for stablecoin regulation, explore practical, gritty tactics for launching and scaling a marketplace from scratch, and debate the ethics of AI-powered smart glasses and always-on recording. Plus, Jason reflects on the legacy of Scott Adams and the power of systems thinking. Timestamps: (0:00) Episode Teaser(2:00) A broadcaster-to-broadcaster moment for Scott Adams(5:18) OpenAI teams with Jony Ive, and why wearables are banned from the J-Ranch(10:16) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(16:11) From Partnership to Purchase: The M&A Story(20:09) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www. Squarespace.com/TWIST(25:42) Robotaxis EVERYWHERE, and thoughts on the continuing self-driving car rollout(30:12) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/banking-solutions(34:41) Should we trust stablecoins now? And who is actually monitoring this?(42:54) Polymarkets: Checking in with some of our favorite market(49:58) REDDIT QUESTION: How do I build a marketplace?(58:53) Customer feedback's role in product iteration(58:55) Every piece of SaaS advice EVER Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Links from episode: Polymarket: https://polymarket.com/ Polymarket for AI Leaderes: https://polymarket.com/event/which-company-has-best-ai-model-on-june-30 LMArena: https://www.lmarena.ai Real Coffee with Scott Adams: https://www.youtube.com/RealCoffeeWithScottAdams Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (10:16) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist (20:09) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www. Squarespace.com/TWIST (30:12) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/banking-solutions Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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

• 0:00Speaker 00

  So instead of like the pie being static and being the ratios of who owns what being changed, the pie is going to get larger and there'll be a healthy mix of both human and autonomous drivers. That extends the longevity of human drivers for another five years. But I still see this going to an eventual point in which we're not driving. But it sounds like that'll take, ah, I just want to go faster, Jason. You're probably right.

• 0:23Jason Calacanis?

  I mean, there's a group of people who will never drive an autonomous car. It might be a third of people ultimately just do not want to be in an autonomous car.

• 0:30Speaker 00

  I think that's high.

• 0:31Jason Calacanis?

  Yeah, sure. I mean, huh, how many people do you know who were like, refused to get a smartphone for 20 years? How many people do you know who refused to do email or get an Instagram account? I mean, it took, yeah, those things took 10, 20 years to boil the laggards and finally push them into it.

• 0:49Speaker 02

  This Week in Startups is brought to you by Vanta. Compliance and security shouldn't be a deal breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. Twist listeners can get $1,000 off for a limited time at vanta.com/twist. Squarespace, turn your idea into a new website. Go to squarespace.com/twist for a free trial. When you're ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. And Brex, the financial stack founders can bank on. Unlike traditional business banking solutions, Brex has no minimums and no transaction fees. And you get 20 times the standard FDIC protection. Get the business account trusted by one in three startups at brex.com/banking-solutions.

• 1:32Jason Calacanis?

  All right, everybody, welcome back to This Week in Startups. I'm your host, Jason Calacanis. With me, Alex Wilhelm, and we do this three days a week, Monday, Wednesday, Friday. 12 o'clock Texas time, I'm out here in the hill country at Austin, Texas. Big docket, there's a lot going on, so we'll do a little big tech, little medium tech, and some tiny tech as well. Breaking news as we're sitting here. Oh, and before we start, I just wanted to broadcast broadcaster, everybody knows in the tech community, and may or may not agree with his positions on certain topics, Scott Adams. He is a vocal Trump supporter and podcaster, he does a daily show. And as a broadcaster, just unbelievably consistent, an iron man, 365 days a year, Christmas, Thanksgiving, he just.

• 2:20Jason Calacanis?

  I'm in awe of the effort he puts in. Now, I was on his show. We had a little debate before the election and he is super brilliant when it comes to specific topics. He's got great insights and tragically, he has the same cancer that Joe Biden has and it's terminal prostate bone cancer or prostate cancer spread to the bones. And yeah, my dad has prostate cancer. He survived for many years and he's still alive and thriving. You're Scott Adams, broadcaster to broadcaster, and as a guest on your show and friends online who trade DMs once in a while. You did a great job and what an epic life, creating Dilbert and your podcast and you inspired a lot of people

• 3:04Jason Calacanis?

  with your books. And I always tell people inside my company or startups, hey, systems over goals. And I was always a systems guy from the early days, doing Lotus Notes, Alex, and trying to make processes. But I never added that part, like, oh, people have goals, but they don't create systems. And I heard him say that over and over again. And I was like, oh, yeah, I'm a systems guy, but I never told people why the system is important. And you know, systems are important because if you create a good system, the goals take care of themselves. And he has really helped a lot of folks without knowing it, the people who are founders or who work for me, people I touch, I always tell them, hey, listen, create a system for that. I understand your goal. Goal's pretty clear. You want to reach a million customers. What's the system by which you'll, you'll collect those customers and get them to not turn? Have you created any

• 3:49Jason Calacanis?

  systems around them? They say, I don't, I don't know what you're talking about. And I explained it to them. Yeah, he says he's going to die this summer. And it just got me thinking, my gosh, we do all this broadcasting, we touch a lot of people. And I just wanted to let him know he touched me. And have a great final lap. And what a great life lived. Dilbert touched so many people. You got a little bumpy there along the way. He got canceled. There was a lot of brouhaha. He had spicy opinions, but none of that matters. At the end of the day, I think the totality of the person matters and their intent matters. And I always thought his intent was to help people.

• 4:24Speaker 00

  He kind of raised me in a way because I read so much Dilbert growing up. I had like, like a stack of like the compendiums.

• 4:32Jason Calacanis?

  Yeah, sure.

• 4:33Speaker 00

  And I learned words like paradigm from him because I thought it was pronounced paradigm because I'd never said it out loud. So I used that word out in the public once and got, got wrecked. But I used to be like the world's biggest Dilbert fan. And then I kind of grew out of my comic book space, but like I read. Thousands of his of his trips. And even though I don't agree with him at all politically anymore, there's an impactful person who touched the law of the world with his art. We don't have to only judge someone on the last act of their life.

• 4:59Jason Calacanis?

  And what who cares about political differences at the end of the day, right? Like it's a it's a team sport. Everybody. It's like a blood sport. So, yeah. Anyway, broadcaster broadcaster. What a career. What a career. All right. What's in the news? I know there's a breaking news story. I don't know if you want to start.

• 5:15Speaker 00

  Yeah, let's let's just get that out of the way. So as we were sitting down and literally hitting go, everybody, we saw a headline from Bloomberg, which is that OpenAI is going to buy Johnny Ive's company Love From for $6.5 billion. This is an all stock transaction. And if you don't know Johnny Ive, he's the guy behind a lot of the kind of iconic, maybe even seminal Apple products, Jason, known for his design sense, understanding of aesthetics and usability. And the thought here, as far as I can tell from the last couple of minutes, is that he was working on some hardware for the AI game and what does OpenAI do? Well, some of the biggest, some most popular models out there. So put the two together and you could see a very interesting hardware device

• 5:55Speaker 00

  from OpenAI. Just given how far Apple has dropped the ball on hardware AI integration compared to just, for example, this week, Google and Android. This is actually very exciting to me. My first thought was, yuck, what a waste of money. Do you really need this? It's a lot. But then if they nail it, what's the value of the iPhone today for Apple? It's it's like, what?

• 6:15Jason Calacanis?

  Oh, I mean, it is the it is the company. Yeah. So I'd say it's 80% of the value of the of Apple is the iPhone, right? It's got to be 90% of the profits or something along those lines, you know, taking out like maybe the Google deal. Yeah, Love Now or Love From. Is it Love From? Love From.

• 6:32Speaker 00

  Love From, yes.

• 6:32Jason Calacanis?

  Yeah. And, you know, that was his design studio. So he was doing jobs for other people, no pun intended. So he was kind of acting like for any startup that wanted to do something. And I think everybody realizes there'll be a pendant. A physical device that incorporates AI and maybe creates a new format. Most people think it's glasses. I just got the, um, the Ray-Bans from Facebook and I see Googles coming out with their new glasses that will be augmented and I was gonna play with them over the summer on vacation, take some videos, etc. with the kids, thought it would be a fun thing to experiment with. And so this is very interesting. I bet you Johnny Ive is gonna make more from this than he is from his tenure at Apple. It's 2% of the company he's basically getting.

• 7:16Jason Calacanis?

  And you have to ask yourself, as a founder, will Johnny Ive's designs make OpenAI 2% more successful? That's the bet you're making when you give him $6 billion. And I'm, I'm certain it's not 6 billion in cash. I'm sure it's five-

• 7:33Speaker 00

  It's all stock, according to Bloomberg.

• 7:34Jason Calacanis?

  Yeah, I was about to say, I mean, I could see like $100 million or $250 million in cash or something if they got cash laying around. But I think he believes, probably correctly, that it could be a trillion dollar company. So if he gets 6 billion now and it triples, this could be an $18 billion opportunity. And $18 billion is a lot of money. So congratulations to Johnny Ive and his team over there. And I, I think this was a more of a collaborative, um, organization. I don't know how many employees there are on LinkedIn for love from, as a company, or if they're even allowed to put themselves on LinkedIn.

• 8:09Speaker 00

  Yeah, that was my, my thought. Like, I don't know if that's gonna be the right number.

• 8:12Jason Calacanis?

  Well, I mean, the, the really interesting thing, I think, about this is you're, you're making some sort of a bet. And if you think in bets, as, um, Annie Duke would say in the poker world, thinking in bets is her book, you know, what are the odds that Johnny Ive doesn't make the company 1% more valuable? I think it's zero.

• 8:33Speaker 00

  Low.

• 8:34Jason Calacanis?

  Yeah.

• 8:34Speaker 00

  Yeah.

• 8:34Jason Calacanis?

  I mean, he's gotta make the company 1% more valuable. Now, what are the chances he makes it 10% more valuable? That's, that's probably not gonna happen. So the truth might lie between 1 and 3%, 4% more valuable to have the world's greatest designer of the last 30 years or one of the top five, certainly, uh, on your team focused only on the ChatGPT app or a piece of hardware. I was at dinner the other night and somebody had one of those pendants. And it was on and he showed it to me and he showed me the app. And he said, do you have a problem with it on? I'm like, at dinner? I said, if you weren't my friend, I would punch you in the face if I found out halfway through dinner.

• 9:14Speaker 00

  You were recording me the whole time?

• 9:16Jason Calacanis?

  No, when we sat down, it was on and creating summaries and you know, I had my friend Adeo from Founders Institute. You know, he also was wearing that life pin. Remember the life pin that would take a picture every second? And then you would have life casting. Just a piece of advice, man. Do not wear this stuff around your friends if you want to have friends in the world. Honestly, if somebody were to record me like that, now I assume as a micro celebrity, which is the form of celebrity, Alex, that exists below the lowest rated reality show that just got canceled.

• 9:52Speaker 00

  So D list, and then you're kind of like bringing up the pinnacle of the E list.

• 9:56Jason Calacanis?

  Okay, precisely, precisely. I am the tip of the spear of the E list. And the D list would be like, yeah, Bravo or E network just canceled.

• 10:04Speaker 00

  Real Housewives of X. Yeah.

• 10:06Jason Calacanis?

  Well, no, that would be a successful one. I'm talking about one that got canceled after one season. Uh, yeah, that's where the podcasting tech celebrity exists.

• 10:17Jason Calacanis?

  All right, founders, I know you're building something amazing and you're going to change the world. And now, hey, the big logos, they're taking your calls, right? But here's the catch. If you're not SOC two or ISO 27001 compliant, these deals won't close. Now, some of you are saying, I've never heard of those terms. Some of you are saying, I've heard of them, but I don't know what they are. And that's where Vanta comes in. They're going to be your partner. And they are the all in one compliance solution that helps startups get audit ready. And that's going to build a strong security foundation for your company, which you want. But they're going to do it quickly and painlessly. Vanta automates the manual security tasks that slow you down. And that streamlines your audit. So here's your call to action.

• 11:00Jason Calacanis?

  Whether you're closing your first deal or you're gearing up for growth. Vanta is going to make compliance easy for you. Join over 8,000 companies, simplify your compliance and get a thousand dollars off at vanta.com/twist. That's V A N T A dot com. Yeah, don't wear these things, folks. It's absurd. You know, even in a Zoom call, you know, I now have to think that every Zoom call I have is recorded. So now, you know, sometimes I'm out here on the ranch and I just did something, you know, I mowed the grass or, you know, I went to feed the chickens and I'm disheveled or I did a workout in the barn. I assume I'm being recorded. So then in terms of Zooms now, sometimes I'll just say, yeah, I'm not going to be on camera today

• 11:45Jason Calacanis?

  because it's enough with the on camera stuff. And then I'm like, maybe somebody's recording this and like I look disheveled. I don't need a recording of me on a board call or whatever. And then I see people recording their board calls. By the way, board calls are not intended to be summarized by AI or recorded. Talk to your counsel, but you're supposed to just take very top level notes. So you don't open yourself up to discovery in a lawsuit where, you know, when you have an opposing attorney with an axe to grind and they had a transcript, they could just twist somebody's words around as you've seen when people are on the stand who have had a phone call recorded or something. So anyway, they're always on recording stuff and those designs are really pernicious. And I think we are going to have laws around them, which will be similar to guns.

• 12:28Jason Calacanis?

  So in Texas, people can request that you don't have a gun on their property and you can put up a specific type of sign that they're not allowed to. And I think it can be like you get a penalty if you went on somebody's property who has that specific type of sign that they don't want you on private property to have a gun. Point is we need that analogy for recording devices. There needs to be a standard. It should be a federal standard of recording devices in public spaces. And although the assumption is you're being recorded, there needs to be a penalty for this. There needs to be new legislation. It needs to be reasonable, but it should be a bright blinking red light if you've taken a photo in the last 30 seconds and before you take a photo.

• 13:10Jason Calacanis?

  So if photo, 15 second warning of a blinking red light before the photo is taken, 15 seconds after, if in public, maybe that's reasonable. I don't know, or maybe it blinks three times or something.

• 13:22Speaker 00

  So this is what it looks like on the Meta Ray-Ban. Jason, just going to show everyone this so they can get kind of a feel for it. But I really want to talk about the title of this video, which is can you hide the blinking light on the Ray-Ban Meta Glasses? And I believe the answer to this is yes. So let's hope that we don't have to get to the point of legislation for this and we can sort it out.

• 13:46Jason Calacanis?

  Even in that picture, that white light, see, they made it white, which is like, yeah, Zuckerberg once again. And when you look at some of these pictures, like, it really doesn't feel like a very strong light that's being lit in my personal estimation. It should be red and it should stay on when you're recording.

• 14:06Speaker 00

  Here's another example, this one from our dear friend Lon, who is slightly under the weather today. We love you Lon, feel better soon. This is a little better to me, Jason. I think this is the snap spectacles. Yeah, this is, but this is the yellow rim and I can see that being a little bit

• 14:19Jason Calacanis?

  Why not red?

• 14:20Speaker 00

  In your face.

• 14:21Jason Calacanis?

  There's a reason. They're trying to get people away from the universal red that means recording. There's a reason it's blaring red because people don't want to be recorded. So I think there's going to have to be legislation because the first two people up the hill are not doing a good enough job.

• 14:37Speaker 00

  Bringing this back to Johnny Ive, though, and OpenAI is, it's actually really fun. I was reading Hacker News as I always do, and there was an interesting discussion about OpenAI's new Codex Coding Agent. And I was reading the reviews and the conversation about it because I thought we might talk about it on the show at some point in time. Love to get the developer perspective, people who are actually testing this stuff, who know what they're doing and would really kind of struck people was the UX was criticized. And so I wonder if a little bit of Johnny Ive magic across the OpenAI organization might help them file off some of those kind of rough edges and just help make all their products work a little bit better because the Johnny Ive era of Apple is famous for a reason, Jason. Like it's an earned reputation from a lot of really just great work.

• 15:19Jason Calacanis?

  The way they do what they do, the secret was they would make many design ideas in a studio and then Steve Jobs would come and have a discussion with him and go have lunch with him or whatever. So they'd be like, here's a table filled with pendants and the pendant team is working on this. Apple never released a pendant. Here's the team working. On televisions, they famously were going to release a television. I had heard that that was like a fait accompli. That they were going to release it and then they never did. For whatever reason, they was released the box for Apple TV. Long story short, 99% of what Johnny Ive did there with this incredible design team never saw the light of day. It was all an exercise and then they would just skim the cream. Most startups, you know, a design's an afterthought. They make a bunch of stuff and then they produce it.

• 16:03Jason Calacanis?

  So you really basically have to produce 10 times what you need and then skim the cream of the best. That's my best advice for design. Let's keep going through the docket here.

• 16:11Speaker 00

  I want to talk about Brex and Zip. So Brex, Jason, I think we all probably know is a corporate spin startup, famous for their corporate cards that were startup friendly back in the day. They bought out all the bus stops in San Francisco. Big buzz, low budget, now quite a large company. There's another firm called Zip and I was less familiar with Zip. Turns out it's actually worth about $2 billion and what they do is corporate procurement orchestration, which is very fancy words for helping companies buy stuff and pay for it without losing track of POs, making sure it's going into the right budget. If you're a large company that buys a lot of stuff, it's actually a pretty big deal. So the news item here is that Brex has teamed up with Zip instead of competing with them directly. And they do have some shared customers, so there's some overlap.

• 16:54Speaker 00

  But it does feel kind of interesting to see Brex, a company that I think is worth more than 10 billion, partner up with Nirvan, previously TripActions, which is, you know, kind of like corporate travel management, if you will. And now with Zip, who also kind of overlaps a little bit with them. I'm still very bullish on Brex and its competitor Ramp, but I'm kind of, this almost feels like politeness and kindness inside the startup world versus combativeness. I just kind of wanted to get your take on why Brex is making this choice.

• 17:19Jason Calacanis?

  Some people understand they have a lane and they want to stay in that lane and be the best at that. And then let other people plug in as a platform. So the example of that might be in today's market, DoorDash doesn't do cloud kitchens. Cloud kitchens, Travis's new company, provides cloud kitchens. Those people who rent space in a cloud kitchen, then they go put their food on DoorDash, direct websites increasingly and on Uber Eats.

• 17:48Jason Calacanis?

  Postmates, whatever. And so in each of those cases, Cloud Kitchen's saying, you know what, there's enough work to do here. We don't need to compete with DoorDash and Uber Eats. Uber Eats and DoorDash are like, we don't want to be in that business. That's going to be a lot of work to stand up all these things and Travis is going to do a better job. So, you know, if you stay in your lane, you can create a lot of partnerships and get to market quicker. The best example today would be that one, or what's happening in self-driving cars with Uber, Tesla, Volkswagen, et cetera. So Waymo's like, we make this stuff. We have an app. But suddenly they were like, well, we have an app, but Uber's got, you know, 20,000 cities and 150 million or 250 million customers, whatever it is, and 30 million of them are Uber One. We don't need

• 18:32Jason Calacanis?

  to recreate the wheel here. Let's have them, let's go into their distribution system, their network. And then Uber sold famously, big question if they should have, still juries out. They sold their autonomous because they said, hey, there's going to be 15 providers of autonomous to be a commoditized service. It turns out it is going to be a commoditized service. Now, there is a chance, never bet against Elon, that he will create this robotaxi, the specific two-door one, and be able to produce 10 million of those a year, and he will take the number one position. That's, that's possible. Some people might say probable. There's a big bet going on. Will Uber, having Volkswagen the number two carmaker, Waymo the number one leader in this, Waymo providing to Toyota, Toyota providing here, will that

• 19:14Jason Calacanis?

  whole consortium where everybody does their best work beat, you know, somebody who's a verticalized player? Time will tell. I think in this case, it will not be winner take all. It will be three winners take most, and those three winners will be Waymo, Tesla, and Uber. That's my belief. And then I think there'll be mergers and acquisitions in it. So that's probably what's happening here is Brex is like, you know what, we have enough work to do here that we don't want to do the corporate backend. Let them do the corporate backend. They don't want to do corporate cards. Then they could go to everybody and say, hey, we're not in your business, but we are in this business. Do you want to partner with us? When people are in your software, they can click this button to create an account with us. You'll get credit for that. When they're in our software, they can click over to you, we'll

• 19:57Jason Calacanis?

  get credit for that. And they will probably monitor account creation and then say, together, we can beat other people who are trying to full stack it. That's the concept.

• 20:08Jason Calacanis?

  All right, founders, let's talk about your website, huh? It might be a little bit of a sensitive subject. You might be a little embarrassed about it. Let's fix that right now. If you're launching something new, give your brand the refresh it deserves. You're working so hard on your company and your website looks terrible. Do what I do, use Squarespace. It's the all-in-one platform to make a stunning professional website. And it's ridiculously easy to use. It's going to work for everything. If you're selling products, it's got all that e-commerce built in. If you're selling services, it works perfectly. And they have a new AI product called Blueprint. Want more control? Well, of course, you can choose one of the award-winning templates and use the intuitive drag-and-drop tools to make it your own. Easy peasy.

• 20:50Jason Calacanis?

  Squarespace equals the most functional and beautiful website on planet Earth. Go ahead, Squarespace.com/twist to get a free trial. And when you're ready to launch, go to Squarespace.com/twist to get 10% off your first website or domain purchase. That's Squarespace.com/twist.

• 21:08Speaker 00

  The cross-selling element of this makes perfect sense to me.

• 21:11Jason Calacanis?

  Yeah.

• 21:11Speaker 00

  My question is kind of what comes next? So, Brex was last raised at seven, valued at 7.4 billion. Sorry, everybody not over 10. And then Zip was valued at 2.4 billion. Post, if this partnership goes well, Jason, is there a heightened chance that they decide to link up? Kind of like Coda and Grammarly did? Does this, is this a first step in that process or just a potential?

• 21:31Jason Calacanis?

  Yeah, I don't know if Coda and Grammarly had a partnership previously, but if they did, yeah, that could be what we call a partnership to purchase. So with Weblogs, Inc., I started a partnership discussion with AOL and Jim Bankoff, who was like EVP of whatever at AOL at the time. And they wanted blog software. Maybe they wanted to engage its inventory. They were going to make a small investment. And then after like but six weeks of discussing this, Ted Leonsis called me on the phone and said, "My Greek brother, I'm going to make you very rich and your family's going to be taken care of forever. We're buying your whole company. It's going to be great for you." And I said, "Thank you, Mr. Leonsis." And, you know, that was that. So, yes, and that's why being a good partner and being professional in partnership.

• 22:16Jason Calacanis?

  Is a better way to pursue M and A than, you know, asking to be bought. So if you solve a major problem for a major player, then they will, in the partnership, say, wow, what a great management team. Oh, great engineering team. Oh, product design is great. We don't have that. Which, by the way, OpenAI was with Johnny Ive, a previous story, working with him.

• 22:38Speaker 00

  And then bought the company.

• 22:39Jason Calacanis?

  And then bought the company. So there it is. That was a, you know, consulting deal that resulted in a purchase, right? So that was partnership to purchase in the previous story. This is an awful lot of announced M and A. Two companies bought by DoorDash, two companies bought by OpenAI, right? They bought, or they're in the process of buying. We told them not to buy it, that the company doing a programming co-pilot.

• 23:04Speaker 00

  Wind surf.

• 23:05Jason Calacanis?

  Wind surf. Yeah, something's happening here. I think since Trump gave up on his, or folded, or slowed down his, slowed his role. Yeah, that's why I don't trigger any of the TDS people in the audience, the Trump dedication syndrome sufferers. We have both in this audience. Trump derangement and Trump dedication syndrome. We're in the middle here. He stopped barrel rolling the plane known as America, the American economy, and all of a sudden, M and A is back. So this is great. I think this is why we're starting to see the stock market come back. I think this will be amazing for venture firms who two out of three went out of business. And this is why I haven't given up on venture. I'm like, I think that this is where venture capitalists are made.

• 23:48Jason Calacanis?

  When you're forced to survive four years, four years of no M and A. That's going to make you, if you get to the other side of it, that's like going to the new world, Alex. Like, you know, everybody went on these ships. People didn't bring enough lemons. They didn't have the resiliency. They went crazy, jumped off the ship, got eaten by sharks, scurvy, cannibalism, whatever. And we'll see who's left after this, you know, boom bust cycle. It's kind of like a pond where the fish get too big. They eat all the small fish, then there's not enough fish to eat. The algae goes away. You have these boom bust cycles in nature. That's just what happened in venture and startup land. The startups don't have to worry about it because they can always raise money. But venture has been.

• 24:31Jason Calacanis?

  You know, this is the Ice Age. That's probably the best analogy. We're lived through. Who survives the Ice Age right now, right? And I can tell you, I'm sitting here with like a lot of saber tooth tigers, you know, coming at me and woolly mammoth pelts around our team trying to stay warm while we wait for DPI to arrive. And sure enough, the secondary markets have started to wake up. Hey, are you interested in buying more of this company? Are you interested in selling some of this company? The prices are anywhere from a flat to 90% discount of the peak. But transactions are occurring. So green shoots, folks.

• 25:08Speaker 00

  Just to understand, Jason, 90% lower than the peak?

• 25:13Jason Calacanis?

  Yes.

• 25:13Speaker 00

  Or 90% of the peak?

• 25:14Jason Calacanis?

  90% lower than the peak. So if somebody had a, let's say a $2 billion valuation, they might be a 200, 300, 400, 500 million dollar offer for the common shares of those companies. Why? The employees selling common are behind the preference stack. So the preference stack might be what the company sells for if they raise too much money. That whole conversation of did you raise too much money? And is that, are you ever going to get past a preference stack? And what happens to comment? That's literally what's happening now, quite literally. Okay, let's keep moving.

• 25:42Speaker 00

  Let's talk about Waymo reaching 10 million paid rides. I think this is very important. Waymo is a company that sits kind of in between the public and private markets, but certainly is one of the leading kind of American AI companies. And Jason, the latest news from them is that they have reached 10 million rides. And the reason why I think that matters is not just the big round number that we all love, but because they did half of that in the last five months, which implies about a million rides a month that are paid, which to me is like real commercial viability because I have not heard a resurgence in Waymo runs over your dog or whatever. So it seems to me that as this ramps up, the technology really must be maturing to the point in which they can take on this much volume, which frankly, I think bodes well for Elon and company because if the tech has gotten this far,

• 26:26Speaker 00

  maybe it's the right time to do something bigger.

• 26:29Jason Calacanis?

  The real question is, how different are these two technologies? And how big of a part is LiDAR in Waymo's success? And how big a part of Tesla's success is their generalized driving technology? Waymo started with constrained areas and really trying to solve a constrained area problem where they were, let's just say bespoke solutions, right? In a lot of cases for how to deal with this traffic circle. Now, large language models. Reinforcement learning and just generalized AI is the route. Elon has gone without Lighter. And so that's the big question. There's a lot of hand wringing. And Elon restated yesterday, hey, we're going to have these Austin testing units out at the end of the month.

• 27:12Jason Calacanis?

  Wisely, it seems there will be safety drop remote drivers. So that's unclear. If those people will be one to one. In other words, there'll be somebody sitting there with a joystick. They're like literally with a Nintendo joystick or a steering wheel at Tesla HQ. One to one, just so there's not somebody in the car. So you get the feeling of a Waymo. But there's literally somebody in an office somewhere driving it. Now, Waymo says, we don't do that. We will, when there's a problem, tell the AI how to solve the problem. So if the AI was stuck because it's behind an ambulance, they say, okay, is there ability to make a U-turn here? Is the ability, is there an extra lane to go around it?

• 27:56Jason Calacanis?

  Is there, you know, whatever. And sometimes they will draw, from what I understand, a line of which way it should go.

• 28:03Speaker 00

  Oh, that's cool.

• 28:04Jason Calacanis?

  In this case, I think Tesla's going with the, because they're all 5G cars LTE a driver, but the latency is there. So, you know, this is going to be a very consequential month. I would say July will be the consequential month. It's only opening up 10 cars to 20 cars. With in a closed beta. This is also a very smart decision. If I was advising Elon, and I am not, or Tesla writ large, which I am not. I would have put the safety driver in for the first year, just so regularly. For the whole year. I would just say, listen. You're going to get in the car. There's going to be a person there. You're going to watch them use the software.

• 28:43Jason Calacanis?

  They're not going to touch the wheel. But if something does happen, we're, you know, a little kitty, you know, or a. You know, baseball and a football goes, soccer ball goes running into the street. We're, we're going to take over just out of an abundance of caution. And you get to talk to the person and they'll explain to you the virtues of the Model Y, of which I just ordered my second Model Y, which will be

• 29:04Speaker 00

  Oh, you're going to get the, uh, the updated

• 29:06Jason Calacanis?

  The Juniper update. Yeah. The new one with a light beam on the back. So, uh, yeah, congratulations to Waymo. This is going to have zero impact on the drivers. Uh, now, why would I say that, right? Cause you already have like a certain number of rides in San Francisco are being done by Waymo. I have a new theory and based on data. I think what we're going to see is the same number or a growing driver base of humans for years while the autonomous ones get put into the market. And we're going to see the humans do the routes that the autonomous ones can't.

• 29:46Jason Calacanis?

  So Ubers and Lifts will be coming to the suburbs more doing, you know, so it'll expand the area of ride sharing. What's that going to do? People in the suburbs who couldn't wait 15 minutes for a ride, uh, get it down to five, they're going to start using it and they're going to start using it for commutes.

• 30:05Jason Calacanis?

  As a founder, you can't be putting business expenses on your personal card. Oh my God, that's a disaster. You should be taking those as business expenses and paying for them with pre-tax dollars. Brex has built the killer banking experience, which will take your dollars further. They're going to protect your cash while extending your startups runway. It's not just the Brex card, although people are over the moon. I'm literally looking at my new Brex card right now. Amazing. All the other great banking things you need. A checking account, treasury, and of course FDIC insurance. Nearly 40% of startups fail because they run out of cash. A hundred percent of startups cannot afford to make financial mistakes. It's hard enough to get product market fit. So get a great banking partner like Brex. That's the one I use.

• 30:50Jason Calacanis?

  20 times the standard FDIC protection through program banks, industry leading yield on your cash. Yeah. Earn a little cheddar, wet your beak and the ability for you to send money worldwide. At lightning speed. Brex is used by one in every three US startups. So get the financial stack that founders trust, including me, your boy J Cal, at brex.com slash banking dash solutions. And that's going to be super powerful. At the last Uber demo day, they did a week or two ago. They have a new system where you can say, this is my commute. This is the time I leave. And then it sends you active alerts. Hey, if you're, if you normally leave between 7:30 and 7:45, here's the cost, the cost is going up, the cost is going down. And this is when you should leave.

• 31:34Jason Calacanis?

  So they created this like very elegant product for daily commuters, which means Uber believes daily commutes are coming. The second thing is many parents are sending their kids to school in Waymos now. I think what we're going to see is autonomy takes over the city centers, 50, 60, 70% of that in the next couple of years. Moving the other drivers out, the other drivers move out and get more rides that move faster. That'll net, net make them as much money because there'll be longer rides.

• 32:00Speaker 00

  So instead of like the pie being static and being the ratios of who owns what being changed, the pie is going to get larger and there'll be a healthy mix of both human and autonomous drivers. That extends the longevity of human drivers for another five years. But I still see this going to an eventual point in which we're not driving. But it sounds like that'll take, ah, I just want to go faster, Jason. You're probably right.

• 32:23Jason Calacanis?

  I mean, there's a group of people who will never drive in an autonomous car. It might be a third of people ultimately just do not want to be in an autonomous car.

• 32:31Speaker 00

  I think it's that high?

• 32:32Jason Calacanis?

  Yeah, sure. I mean, huh, how many people do you know who were like, refused to get a smartphone for 20 years? How many people do you know who refused to do email or get an Instagram account? I mean, it took, yeah, those things took 10, 20 years to boil the laggards and finally push them into it. Like if you're a laggard, the only reason you got a smartphone was because there were some things you could not do. Like it literally like you couldn't get an Uber on a flip phone. So there was this like, There were use cases that force people into it. So eventually there will be a use case that forces people into it. All right, let's keep going.

• 33:06Speaker 00

  So in the same way that we like to see Waymo and Tesla competing to grow the market and prove the products, I'm also very excited to see that Microsoft has added XAI's Grok models to their Azure AI Foundry business, which is essentially the place where you can run models on top of Azure's compute systems. The reason why this is important to me, Jason, is because I feel like OpenAI, DeepSeek and Anthropic, which we'll get to, just control too much of the market. I want to see more players, more competition, more steel on steel. And so to see Microsoft say, we are going to host every major commercial model, period. To me, just speaks well for everyone's having lots of competitors and also just people having the option to pick and choose and tinker. You're not locked in to just one thing.

• 33:48Jason Calacanis?

  This is also has to speak to the ChatGPT, OpenAI relationship. You know, if you're running Azure, you need to support everything, obviously. And if you're Satya Nadella, you probably want to have a strong relationship with Elon in the chance that his model becomes better than ChatGPT's, which is a significant chance. I'd be betting against Elon has been a fool's errand for a long time. So he's definitely going to be number one, two or three. And, you know, that could flip, so keep your relationships open. Why would you limit yourself to having a relationship with just the top, you know, model right now?

• 34:29Speaker 00

  It's just topsy-turvy to me. Like, I remember so vividly the era of Microsoft that was like anti-open source, didn't want to work with other people, wanted to crush all markets. And now Satya is like, we want everybody to come party with us, come on in.

• 34:39Jason Calacanis?

  Okay, let's keep moving.

• 34:40Speaker 00

  So the Senate just advanced the stablecoin bill, the genius act. Now, this is not passed yet, we'll get to that in a second, but the context for everyone here is just this. If you take a look at the chart that I have on the screen, this is from our friends over at DeFi Llama. It shows the current aggregate market cap or just value of all the stablecoins out there in the world today. And it peaked in early 2022 and then entered kind of a long trough, Jason. And that was a bit dispiriting for folks like myself, who thought the stablecoins were awesome and we're going to have Big future. Things have dramatically changed since kind of early 2024. And now there's about $250 billion worth of stables out there.

• 35:17Jason Calacanis?

  Yep.

• 35:18Speaker 00

  Really great growth over the last year and a half. Very positive. And I think that's really pushing Congress to get its act together. Now, on the compromise point, there was dissension in the ranks for both Democrats and Republicans. The GOP lost a couple of votes. Democrats lost more, mostly over concerns about the Trump family and their crypto efforts. But what matters is that, and we can always debate about the fine points here, but the big picture is we're going to probably get a strong, industry-friendly set of regulations for having stable coins here in the US. And that means that I think every single technology company is going to be able to spin up their own stable. And there'll be some sort of liquidity between them all, and so they'll be fungible. But it's going to be kind of interesting to see every company managing.

• 36:03Jason Calacanis?

  So people didn't want to do it because they were concerned about the Trump meme coin or Trump's family's connections to stable coins. That was the reason? Or was it because they didn't have other nuances in this legislation around tether and offshore? And know your customer. What was the actual reason people dissented? Do we know?

• 36:23Speaker 00

  I think it's not just one answer. I think some people are anti crypto. And I would loosely put Elizabeth Warren, Senator, in that group. Some people felt that the World Liberty Financial Stablecoin Deal to fund Binance from, was it the UAE? Was indicative of that stable coins need to have more structure and stability around how they're regulated. And that certain action shouldn't be allowed. But I think also just some bad blood there between Democrats and the Trump family.

• 36:51Jason Calacanis?

  The key thing here is that American companies based in America that have a big four accounting firm auditing them as opposed to Tether, which has had attestations. And I guess Howard Lutnick's previous firm, Cantor Fitzgerald, is trying to work with them to clean things up. I'm interpreting maybe their involvement in it. And I think a lot of this has to do with Lutnick. And tether. That's not being spoken about here, but in my estimation, Howard Lutnick stands to have massive gains at his firm. Now, I don't know if he's sheltered from them because he's part of the administration or cabinet, I guess. So I don't know the

• 37:35Jason Calacanis?

  exact details there, but I do think there's probably Democrats as well, looking at the tether issue. And they had that congressional hearing, I believe, where tether was sort of taken to task because of the attestations, the history of the firm, and then how people are using the stable coins. If stable coins are going to exist, I think we should not allow offshore companies to operate without an onshore entity, without a board, without insurance, without regulation. It should be an onshoring, American only. So this genius act, which I don't know, and I have some questions about that, maybe we can answer in the next episode, or the audience can help us out with. I really want to understand offshore companies. I really want

• 38:17Jason Calacanis?

  to understand, know your customer and how people use these. Of course, the tethers of the world will claim, well, we can track how people use them. But typically, when people burn their tethers and they've traded them 10 times, yes, there's a trail, but whoever was at the start of that trail is long gone and absconded and done human trafficking, terrorism, etc. There needs to be very tight regulations on who's trading stable coins, how they're trading them, know your customer. And that's really the offshoring I want to understand. That's the details that needs to be in this genius act that I don't think are.

• 38:55Speaker 00

  There's a little bit of a weirdness that we should talk about because when we think about the genius act, which by the way, if you don't know, stands for the Guiding and Establishing National Innovation for U.S. Stable Coins Act, which is the most hilarious backronym ever. There's kind of two tiers of regulation, Jason. There's stable coins that have more than 10 billion AUM, so 10 million like $1 units on the market. And if you're over that level, you're privy to the federal regulations. If you're under that state level, or you can choose that. My concern is that some states may have overly Standards to attract smaller stable coins and that we could then run into some of the KYC offshoring, just the stuff that we don't want to see pollute the USD ecosystem because most

• 39:39Speaker 00

  stables are USD backed and so forth. So I almost wonder a little bit about the distinction between big stables and little stables and the different regulatory regimes they go into under. I'm also sympathetic to it because less regulation for smaller products makes sense. But when it comes to finance, it gets sticky. So

• 39:55Jason Calacanis?

  It's so interesting. I have been pushing for regulation over and over again for years that there should be a safe harbor for small projects and then increasing regulation as they get bigger. And, you know, who's permitted to do this? And the audits and transparency are the details we're going to need. And, you know, I think there's some certification and people putting their names on things and outside auditors putting their names on things that has not happened with Tether. You know, I don't want to see like Tether previous was like, here's an attestation from, I don't know if it was like the BVI or something like that, British Virgin Islands. It was like, hey, guys, if this isn't done in New York by Ernst & Young or KPMG, I'm not interested.

• 40:36Jason Calacanis?

  Like, and it this whole attestation thing as explained to me was like by accountants and people online was like, it's like here, we took a picture of a bank statement, essentially. We know there was money in account, but we don't know all the underlying transactions and how you got there. These things need to be regulated. There needs to be feds inside your office, looking at these transactions all the time, in detail. Yes. There's way too much, it's just way too dangerous to have this be the Wild West anymore. And you know what? For Tether, that's making, you know, tens of billions of dollars a year on the float, that business is going to collapse because there's also regulation. This is a little bit detailed. You, they want

• 41:21Jason Calacanis?

  You to be able to buy stable coins and then share the interest with you on them. So an interest bearing stablecoin account is the next piece of dialogue you'll start hearing because I was talking to some people off the record. And they're like, short tether, they're not literally short tether, but they're short theoretically tether because

• 41:41Jason Calacanis?

  instead of your tether is making five, six, seven percent, whatever it is off these treasuries and other devices they have with people's deposits. What happens when you say, I'll give you 5%, I'll keep one point. You get five points, I get one point. Well, why would you ever use tether?

• 41:56Speaker 00

  Yeah.

• 41:57Jason Calacanis?

  So you'll have 85% contraction in the revenue generated here, which is what should happen. Like what idiots are the only people who would leave like a billion dollars in a stablecoin are probably people and let tether take 5% to make 50 million on that are probably people who have some shaky relationship in their transactions. That's my interpretation and I'm no expert, but this industry needs to get cleaned up. And of course, when you hear people, and I'll end on this.

• 42:24Speaker 00

  Yeah.

• 42:24Jason Calacanis?

  Alex, whenever you hear people saying, well, criminals do this and this, I mean, you can bring a suitcase with hundred dollar bills. Whenever you hear people talking about like how criminals do stuff and that's a justification for them being marginally better than them. Those people are typically criminals.

• 42:40Speaker 00

  Oh, yes, yes.

• 42:42Jason Calacanis?

  Experience, I'm not saying tether is criminals. I'm just saying, in my experience, the people who are like, you know, there's criminals who have done far worse. I'm like, probably should get a magnifying glass on whoever said that.

• 42:54Speaker 00

  Jason, we need to talk about polymark.

• 43:03Speaker 00

  We have a

• 43:04Jason Calacanis?

  Partnership.

• 43:04Speaker 00

  Bet that I want to talk about and a partnership too. So why don't you walk us into this and then I'm going to pull up some really cool data.

• 43:09Jason Calacanis?

  I love polymark. I can't stop thinking in bets. Shane from polymark is a friend of mine. We decided to do an exciting partnership here, which is I'm constantly talking about the odds of something happening as a poker player. That's how I see the world, right? And we just had a conversation about this earlier in the show. So what I asked the team here to do is to integrate a market. Into the show. Now, I don't know which ones. I asked the team to go there and surprise me with a couple of markets. So hit me. Hit me with a market here from Polymarket.

• 43:40Speaker 00

  This is what I was absolutely fixated by. This is the market for which company has the best AI model on June 30th. So the midpoint of this year. And if you're watching the video version, as you can see, the people that have taken the lead recently are Google. But if you go back in time just a little bit, you're seeing earlier this year, OpenAI far ahead. Now, Google has absolutely soared. And I think this is partially because the Gemini model family has improved quickly. I think Google has really managed to build out a series of technology products in the AI realm that people are impressed with.

• 44:12Jason Calacanis?

  Yes.

• 44:12Speaker 00

  And, you know, they just had their Google I/O event this week and they started talking about their new, oh man, what the hell is it? Google Gemini Pro Ultra Max, whatever. That's supposed to be quite impressive. But the market here has essentially given OpenAI and XAI the same chance, Jason, of having the best model on June 30th, which is low. And Anthropic is basically a zero. So Google.

• 44:32Jason Calacanis?

  Yeah. Here's a great idea. Go take a look at the rules. This market will resolve to yes, if any model owned by Google has the highest arena score based off the Chatbot Arena LLM leaderboard. So when making these markets, they resolve, how you resolve a market is critically important. And we've been doing them on All In and we have a partnership over there as well. So you just have to, when we look at these, or we're going to create some of our own. So I think an interesting one would be to do on self-driving and Uber. Pretty interesting. And then if you start thinking about who has the most robo taxis on the market by the end of 2026, or 2025.

• 45:13Jason Calacanis?

  If you did that, Waymo is going to win. So you maybe would say who outside of Waymo will have the most number of robo taxis? Or the largest number of cities, right? You can come up with something. And then you say, how many cities will Uber have robo taxis on the ground at? And today, you know, you have the We Ride folks, Pony AI, Waymo, and then Volkswagen's coming. And then you have to define robo taxi with a driver, with a safety driver or not. And so I would like to know just even with safety drivers. How many different cities you have? That's like a very interesting wager. It's a very interesting market, I should say.

• 45:55Jason Calacanis?

  And as a market, what's interesting about that is then people could say, well, yeah, I mean, maybe Waymo is going to just go very wide, but not deep. Or maybe Uber is going to go really wide, not deep. You know, you kind of start to have to think about things in order to pick which outcome you think is going to happen. The reason these outcome markets are very interesting to me is if you had a large position in Uber, you could place a wager, you could pick a side that would be Uber not winning, which would then hedge you against your Uber stock. Or if you were a Tesla shareholder and you were like, okay, Tesla has a million cars on the road next year. What are the chances of that happening?

• 46:38Jason Calacanis?

  If you bet against it, but you're a Tesla shareholder and they don't hit it and the share goes down or Tesla's flat, you would win this bet.

• 46:44Speaker 00

  Right.

• 46:44Jason Calacanis?

  So you could place a wager. I don't know exactly how they phrase these, but you could pick which outcome. And when you pick which outcome, that could be a hedge against other things happening. This is what people were doing with climate and climate change. Farmers would do this. Oh, if there's going to be a frost, there's a 5% of chance of a frost. I will put some money in that 5% chance. So if I lose, if it's a one in 20 and I have a million dollars in oranges coming and there's an orange frost, I'll put $50,000 on it. If my oranges freeze, I still make the same amount of money. It's $50,000 in insurance.

• 47:20Speaker 00

  It's interesting how a wager on an outcome can have the same vibes as an insurance policy and also a hedge. Cause it feels like you just went through several different ways you can kind of approach this. Now, we did talk about how the market we showed resolved. I want to show everyone what we're talking about. So it's using the LM Arena leaderboard, which is actually really, really cool. So take a look at this, Jason. This is the new UI for the LM Arena leaderboard. But you can see why Google's currently leading on the market because well, they're crushing everywhere. They're on top of the leaderboard for text, for web dev, vision. And search, not copilot, but text to image, et cetera. So very, very, very strong models from Google today.

• 48:03Speaker 00

  And I brought up the Ellen Marina Jason, not just because it's cool as a data source, but also Bloomberg reports that the company, we talked about them spinning out, making their own kind of actual company about this. Turns out they've gotten around, put together, and it's going to be a hundred million.

• 48:18Jason Calacanis?

  Wow.

• 48:19Speaker 00

  Because of course it is. And Jason Horowitz, the UC system, and then also some capital from Lightspeed, Felices, Kleiner, and others. Valuation? Take a guess.

• 48:29Jason Calacanis?

  I mean, seven hundred fifty million.

• 48:33Speaker 00

  Six hundred, but still, that's a lot of money.

• 48:36Jason Calacanis?

  Fifteen percent, yeah. I, I, I thought, well, twenty percent might be a lot, you know, that'd be a billion dollars. Five hundred, five hundred would be twenty percent, ten percent would be a billion. I just picked in between those two numbers.

• 48:48Speaker 00

  But remember when Instagram sold for a billion and we all kind of collectively crapped our pants?

• 48:51Jason Calacanis?

  Different era, different era, man. Different, a different number of people online, different amount of revenue per person, different amount of e-commerce spend per person online. Everything just keeps growing thirty percent, ten percent a year. There's big prizes here. And if you place a bet, and we don't know what the actual pitch is under this. Okay. Any startup stuff? I think there was a couple of startup items here where people ask me questions or I answer them. Rapid response, maybe with one or two of them. And again, when we do Reddit rapid response, I don't know ahead of time the question, but I am Jason Calacanis on, so I'm you slash Jason Calacanis on Reddit.

• 49:33Jason Calacanis?

  Follow me, say hi, DM me, whatever. And go look for me answering questions in anti-work. I love anti-work. I love engaging with people who hate capitalism, because I want to convert them in some ways. But I also want to understand their hatred of free markets, competition and capitalism. Just helps me sharpen my position. Yeah.

• 49:54Speaker 00

  A secret vegan going to the barbecue. That's Jason in anti-work.

• 49:57Jason Calacanis?

  Yes.

• 49:57Speaker 00

  All right. So from, from lawn and the r slash startups subreddit, I absolutely love that place. I read it every single day. There's a great question that I think we should talk about. So how can I build a marketplace from scratch? Jason, people talk a lot about the chicken and the egg problem, how to get early momentum going. They want to know what's the best way to launch a marketplace? I know you're supposed to have supply before launching, probably do that. But I'm not sure about how to reach the first customers apart from people they know. So for the Reddit user Elon Jr. Musk, what you got?

• 50:30Jason Calacanis?

  This person answered their own question. When DoorDash started, they picked one or two restaurants in Palo Alto. They put up phony websites, they bought some ads and sent people to this, I think, Indian restaurant. If the story is correct, then they took their personal credit card, ordered from the Indian restaurant, picked it up with their personal credit card and then ran to the person's house and dropped it off. And the person thought, okay.

• 50:53Speaker 00

  Right.

• 50:54Jason Calacanis?

  They didn't even question it. They had no idea that this marketplace was glued together by literally you taking the name of a restaurant. Let's call it Palo Alto Dosa. And they didn't have a website, they didn't have online ordering. You put up Palo Alto Dosa, you put the menu, you say, pick what you want. They, they, you know, vibe coded something or in that case, you know, actually coded. And then they bought ads against it and said, Indian food Palo Alto delivery. And then finally got somebody to order. The order came in, they were like, what? An order came in and then they went and just called the order in on the phone and got it to the person. So there's your example. When you get going, you could offer people some amount of a base guarantee.

• 51:38Jason Calacanis?

  That's a more advanced technique when you have funding perhaps. And you really want to be in a certain geo or a certain vertical. So let's say you wanted to do all home services, painting, you know, painting cabinets. I don't know, gardening, pool cleaning, just start with pool cleaning.

• 51:57Speaker 00

  Sure.

• 51:58Jason Calacanis?

  Find 10 pool cleaners. Do phone calls and interviews with them and say, I'm making a marketplace for home services, pool cleanings, what we're going after. I just want to understand what you charge. And I was wondering if I could send you the ability to get a customer and I'll text message you, the customer, what they want. And we're trying to achieve 24 hour turnaround, if not same day, and we'll pay a premium for that. Might you be interested in being part of this? And they'll be like, yeah, sure. Here's my phone number. We're done. And so that's how these things all get together. They're done in ways that don't scale and your friends and your sweat equity are part of that equation. Yes. If you DoorDash used the four DoorDash founders as the first four

• 52:42Jason Calacanis?

  DoorDashers, the end. So you are the supply. Go clean the pool yourself in this analogy.

• 52:49Speaker 00

  Or if you're a banker, go drive Uber for a bit to get the deal. Elon Jr. Musk does talk about in his Reddit post, the importance of marketing and so forth. And you did touch on the supply side, Jason, but on the demand side, when the DoorDash guys were putting together their ads to get their first couple of orders in, what do we know about that? And what do you recommend for founders today who might be cash strapped that are looking to build out that other side of the marketplace?

• 53:11Jason Calacanis?

  Yeah. I mean, it's super easy. You can, if you're in a specific geo and a specific vertical, you would be surprised how affordable Google search ads are. Yeah. You could be paying a dollar or two a click. So you know, you might only need a hundred to $500 to run this task. If you can't get a hundred to $500 together, you probably shouldn't be a founder. So there's pretty easy ways to do this. And of course, you could make a mailing list of everybody on your campus and you know, test it there. If you were doing like the DoorDash example, or delivering people or doing a laundry service, you could, you could just find the first 50 customers amongst your friend group in a neighborhood.

• 53:54Jason Calacanis?

  Or you could offer people $10 off your, you know, let's say this is the pool cleaning service. You just go on Google Maps. You find everybody's got a pool by looking at satellite photos.

• 54:06Speaker 00

  You literally just see them. Yes.

• 54:08Jason Calacanis?

  Correct. You then print out flyers. You then hang them on people's doors and slide them under their things. And if the person happens to open the door when you enter, you say, hi, I'm an entrepreneur. I started this company. Please don't kill me. And then you get that person 100% as a customer. I put a laser printer from Brother for like 150 bucks and paper's free. It was like 100 bucks for 1,000 pieces of paper. You just laser print the offer and you hand sign them. Say, hi, my name's Jason and Alex. We've started a new marketplace for pool cleaners. We want to save you money and we want it to be on demand and easy breezy. Just text us if you need your pool serviced anytime and we'll put you on a weekly thing and here's the price. Boom. And you can trust us because we live in the area. I would say the door hanging flyer thing, door to door thing, a lot of founders don't

• 54:51Jason Calacanis?

  do. It works. Emailing people next door, if you were doing again in a geo, next door is a good place to do because you can find all your neighbors.

• 55:01Speaker 00

  Yeah.

• 55:01Jason Calacanis?

  And so once you find all your neighbors, you can start messaging them or you can literally just fake it. So if your marketplace was a marketplace for, again, we'll go back to pool cleaning in a geo, you could very easily just go in there and say, hey, I'm looking for a pool cleaner. And then Alex says, I found this great one. And you reply to yourself. This would be in the gray hat area.

• 55:21Speaker 00

  Yeah.

• 55:22Jason Calacanis?

  You're not committing a crime, but you are doing something that some people would be like, is slightly unethical. I'll say it's clever.

• 55:29Speaker 00

  Everything you've said thus far though, is just doing the work the hard way. Like the DoorDash folks delivering the food themselves.

• 55:35Jason Calacanis?

  Yes.

• 55:35Speaker 00

  Going around the neighborhood, passing out flyers, getting a cheap Brother laser printer, which you can keep until it runs out of ink and then you throw it away. Like, I mean, none of this is expensive. This is a thousand dollars, $2,000.

• 55:45Jason Calacanis?

  Why don't you pick a category for me? Pick a category of marketplace. Think about your own life. I picked like food and I picked pools, but you pick one that's kind of random or out there that I wouldn't think of.

• 55:56Speaker 00

  One that's near and dear to my heart are home visit arborists. So we have people that come and take care of our trees.

• 56:04Jason Calacanis?

  Sure. Tree marketplace. Great. If I went onto Facebook right now and I typed in arborists, or I went to the Austin subreddit and I typed in Austin arborists and you know, I'm going to find.

• 56:25Jason Calacanis?

  Arborists threads, and the first one I found in Austin was Arborists are going to be raking it in, no pun intended, from two years ago, right? And I guess this is when they had the big freeze here and a bunch of trees die.

• 56:38Speaker 00

  Oh, okay.

• 56:39Jason Calacanis?

  And so now if I go to Facebook and I type in Facebook, just do this right now, I'm just doing a search here, you can do it as well.

• 56:47Speaker 00

  Well, Jason does that. I did the same test for Providence, typed in Arborist, and I immediately found best Arborist in Providence, which I guarantee you get search traffic.

• 56:54Jason Calacanis?

  Yes.

• 56:55Speaker 00

  You could just drop a comment there and get some gorilla.

• 56:57Jason Calacanis?

  Facebook Arborists, Brooklyn, and you're going to find Arborist of Brooklyn. And so there's your supply, folks. There is a Facebook, a LinkedIn, a subreddit for every group, and there's message boards and forums. So if you append to that, you know, Brooklyn Arborist message board, back in the day, people used these different message board software, you know, before Facebook and subreddits kind of took it over, and you'll find, there's Brownstoner, this is something in Brooklyn, that's a message board in Brooklyn forum archive, tree removal company, right? So because these things have ranked on Google in search or DuckDuckGo in search, that means they had some validity. So literally, that's like having an intern go find those things for you.

• 57:40Speaker 00

  Yeah.

• 57:40Jason Calacanis?

  You infiltrate those groups, you'll be honest about it, like, I was looking for ranch hands, and, because we're going to probably get a ranch hand here eventually when we get the horses, and I had no idea what they get paid. And it turns out if you provide them a tiny home, there's like an infinite number of people in their twenties who didn't go to college, but who love horses, who, if you put them up and give them three squares a day, or some food and a thing, they'll work for minimum wage to just be around horses. It's kind of crazy, right? Like, ranch hands are pretty affordable.

• 58:11Speaker 00

  People love horses.

• 58:12Jason Calacanis?

  So they're, and it's a global thing. You've got people in Germany, people in Australia, who just want to be ranch hands, they just want to teach horseback riding and, you know, equestery and stuff. So I had no idea. I did my research just for that in 10 seconds. So, and I was going to create one for domestic staff, like estate managers and stuff like that, and I never got around to it, but. Marketplaces are great. You can build them with three or four people. You can hack the inventory. You can hack the supply side. And then, once you get going, then you can say, I know I'm going to make a lifetime value of this amount per customer. Therefore, I know how much inventory drives, how much supply, and you can do a little bit of math, right? And those math formulas are online, pretty easy for you to figure out.

• 58:53Speaker 00

  Jason, do we have time for a funny joke about startups before we go?

• 58:57Jason Calacanis?

  Sure. I mean, I, Alex, you're gonna tell a joke. Okay, here we go. Maybe this is gonna be a dad joke.

• 59:04Speaker 00

  I'm not telling a joke. Lon found the best thing I've ever seen in my life, which is this. It reads, "Every piece of SaaS advice ever, all at once. Roll with me here. Advice goes as follows. Validate before you build. Build before you validate. Launch fast, but make sure it's polished. Don't waste time, but also don't run. Talk to users, but then don't build what they say. Ship fast, but don't break trust. Cool. So I'll just build, unbuild, relaunch, and question my life choices in a nice little loop. Feels like the advice self contradicts. You know what? I kind of feel for this person because I've read a lot of SaaS advice, and a lot of it goes in kind of contrasting directions.

• 59:44Jason Calacanis?

  The reason for this is because people will look back on a successful startup, and they will attribute some technique to the success of the startup when really, it was just, maybe there was a market need, and it just, man, everybody needs Uber or Lyft, and it's just gonna get sucked up. So people think, oh, it's the mustache on the front of Lyft that made them popular. And I was like, well, the mustache had nothing to do with it. Oh, it's a talkative driver, having character. No, it was about utility, Uber's approach. So, you know, in a vacuum, you can get all kinds of advice. And my advice to founders is to write it all down, and then you will pick which way you want to do it. There are multiple ways to get to the new world. Some people got to the new world by, you know, going through the Bering Strait, right?

• 1:00:29Jason Calacanis?

  When it was frozen over, they would walk across it supposedly and come down into North America. Other people risked their lives going across the Atlantic. Many different ways to, you know, get there. And some people will have their Startups succeed because they build something, show it to customers and customers like, oh my God, I never thought about staying on renting out somebody's house and staying there. I always stay at a hotel. This Airbnb thing is incredible. Other times you're like, look, there's all these people couch surfing on Craigslist. If we made a gorgeous website and had more inventory, so it wasn't random, that would make, remove friction and we could just tell everybody to go from couch surfing to Airbnb. Both of those approaches could work and have worked for Airbnb. So that's why you do get contradictory

• 1:01:12Jason Calacanis?

  advice. So once you've, you know, got the early adopters, what's the advice for the massive middle? And what's the advice for the laggards? The advice for the laggards is going to be super different, right? Like than the advice for, you know, the people who are the true vanguard of using products. The vanguard is like, tell me about the features. How much RAM does it have? You know, and then the laggards are like, what colors are available? You know, when you buy an iPad today, there are people who pick their phone or their iPad based on the color. And then there are, that's you. Okay.

• 1:01:46Speaker 00

  I mean, I kind of get it. I keep my phones for like four years. So like the color.

• 1:01:50Jason Calacanis?

  I mean, but if you, if a new color comes out, would that put you in the upgrade cycle? I'm always wondering.

• 1:01:54Speaker 00

  Hell no. Also, I forget what color my phone is. Oh, it's this color.

• 1:01:58Jason Calacanis?

  When I see that, I'm like, yes, whatever that is. When I see people buying based on the color, I'm like, what's going on here? And it's like, I get it. You know, like you're, you're a mom or you're a teenager and you love red and the red came out and it gets you to visit the store and reminds you, maybe I should get a new phone. For the rest of us, we're like, what are the specs? Is anything, it's a tool for us, right? So you have one group of people who's buying it based on aesthetics and forgets about it. And the other group cares about this. There's, that's like the perfect example of like, people have different motivations to engage at different times in your startup's life. Write all this advice down, take it all in. The most important thing is to get close

• 1:02:42Jason Calacanis?

  As best as I can tell, if you, this is why I narrow advice down to three things. Best team possible. Product velocity, keep iterating on that product and bear hug and understand your customers and delight them. Because all the advice you'll see, there'll be tactics that are on the periphery of that. But most of the advice, if you pull up that list one more time and you put it through my sort of startups are about three things. Rubric, I think you're going to find that they fit into those three things. So validate before you build has to do with product and customers. Build before you validate, that has to do with building a product that you validate with customers. Launch fast, that has to do with product and having a team that is capable of launch. But make sure it's polished, that has to do with your team and your product.

• 1:03:24Jason Calacanis?

  Don't waste time, that's on the periphery, but don't rush, that's on the periphery. Talk to users, that has to do with your customer. But don't build what they say has to do with your customer ship fast, that has to do with your product and product velocity, which is driven by your team. But don't break trust, that has to do with your customer relationship. So if you look at all this advice, it almost comes down to those three core principles. If you're wondering what to do today, talk to a customer. And ask them about the product or look at the product's metrics and look at your competitors' metrics. Or go look at an award winning product that has nothing to do with yours and then think, how might that influence me here?

• 1:04:01Jason Calacanis?

  So if the car of the year is the, you know, Tesla Model Y or the Corvette is the best one or the ID Buzz is the best family car. Go take a test drive it and then look at it and say, why aesthetically are reviewers losing their minds over these cars? And how does that apply to my product? You could like open your mind up, right? And have like a really interesting moment or look at your team and say, is there anybody in this team who's not bringing it? I can do some professional development or should I replace a team member? Or should I add a team member? Or should I stop them from doing some repetitive work and give them some more interesting work to do? All right, it's been another amazing episode of This Week in Startups and happy one year. First reality, Alex, you made it to a year. Well done.

• 1:04:43Speaker 00

  I know. It cost me all my hair and half my sanity, but ladies and gentlemen, year two, let's do it.

• 1:04:48Jason Calacanis?

  Let's do it. Let's, uh, let's, let's double down here. Let's get focused. X.com slash Alex. I am X.com slash Jason. The show is at TWI Startups. If you love the show. Hey, we have a, we have a subreddit. Go to TWI Startups in Reddit and you can find me again. I'm Jason Calacanis, one word over there and we will see you next time on this week of startups.

• 1:05:10Speaker 00

  Bye, everybody.

• 1:05:11Jason Calacanis?

  Bye bye.