How to Scale a Profitable Agency with 0 Employees (Using AI Agents)

24:59He like didn't have access to, you know, to the tools of technology, knew how powerful they would be. and would like find whatever way, probably working in like PC bongs or whatever, like in his hometown and like, to like just get access to the computer. It was like the same thing that like, you know, when people were like spending time at like the research labs in Silicon Valley to like get access to their first computers. It felt like he was going through that like hero's journey. Right. Just to get access to compute. As a kid in Jordan. As a kid in Jordan. And then like, you know, and then he was obsessed with like spreading it to everybody.

25:30So he was like one of the first guys at, what's it called? Code Academy. And like, you know, he was like the mixture of true believer, technical enough to build it, knew what the pain points were for him and for like everybody else who was coming up, has like real mission to like make a billion. Like there's going to be a billion developers. And if he has anything to do with it, he's like going to get to that end point. And then he's almost like an endurance athlete in the sense that he's willing to wade through like decade of boredom. Like it's like, it's sexy now. Cause like there's a replic agent and like, you can build your idea and you can vibe code.

26:06And he's like, it feels like a wild rollercoaster ride right now, but it was like years of wading through like school, like going to schools, building tools for teachers to teach kids how to code. And like the infrastructure needed to full stack it and a religion around the fact that you had to full stack it. You couldn't outsource these things. And it was like all of that minutia would like, there's a lot of people out there who are like, I'm going to build the ultimate vibe coding platform it's like you know this whole moment we're in and like where it's like the idea guy's time and like everybody's like yeah the time for the idea guy it's like the idea guy like now you get to skip like what was the first six months to validate the thing but it really just gets you to the the entrance of the maze right and it's like now you've got to go through like what's up idea guy welcome welcome you ready yeah you up for this because the maze sucks and you're gonna tear apart every idea it's all that matters is like the number of iterations on the experiment you can run and like ripping that idea you had in half and like telling you like the world telling you your idea is garbage and like giving you the feedback that like is brutal and honest from your customers that they hate your idea and it's like maybe there's a kernel of something from that idea that leads you to the next one it's like the idea guys time has come and that like we can validate ideas really fast but it's like i don't know if you've experienced this but like just because you can build the thing like and we've moved from like your apple notes to like rebels with the ideas fully, the MVPs built doesn't mean that you want to spend the next, you know, decade eating glass for that world.

27:31I have a lot of friends who are like idea guy, builder, product people who are like, I'm just looking for the person who wants to take this idea over. Right. Like, no, that's actually the job. Yeah. It's like the job is the, you know, going and spending time, like courting a dentist to sell them a product. It's like the same thing with people who are like, um, taste is all that matters now. Oh dude, the taste copers are even more it's even they're obscene of the idea guys they're like no no i don't even make the idea i just taste i just judge the idea i hear another person talk about taste in this market you know you ever read the articles of lisa doll for from a decade ago do you know this story oh my god it's it's an epic story lisa doll is like the korean master of go okay do you understand this moment that happened a decade ago with alpha go it's like everybody was the best at go chess chess is a known thing but no one will ever get to alpha go and it's like there's more possibilities in alpha go than there are atoms in the universe was like the quote i remember hearing that yeah this is the quote it's like at least it all's you know we're safe and it's like you know at least it all plays alpha go and at some point alpha go makes a move and it's like this absurd move that nobody's like this is a alpha go made a mistake right you know all those possibilities it made a mistake and it's like 78 moves later the alpha go beats the shit out of the human and like he's sitting there looking at the mirror he retires it's like a sad story like he retires and it's like you know the quotes are things like, I never truly scratched the surface of go.

28:51And it's like, you know, I'm embarrassed and I feel helpless, like the feelings of helplessness. And it's like, I feel like everyone, you know, is going to have that moment. And it's like, all those people who are talking about VC safe, it's like, it's all about taste and psychology. All those people are going to experience like a taste moment where it's like, where they're going to be least at all. And they're going to have a moment where it's like, you're going to present their taste and the AI's haste to the end consumer. Because ultimately, taste is in the eye of the consumer. It's in the eye of the customer.

29:21And it's like, they are the ones that are arbiters of taste. You think you're a tastemaker until you put like the burger in front of the person. Like, actually, I like this burger more. And it's like, but that's a McDonald's burger. You're like, yeah, I like the McDonald's burger. Billions of people like a McDonald's burger more than your like, you know, St. Charles, Fort Charles burger. And it's like, I prefer this thing. And so you might, you know, it might not win the award, but it wins the choice of the consumer. And so I think all these people who are like, taste is our salvation are going to get leased at all.

29:54It's going to hurt real. It's going to hurt real bad. They're going to run into the brick wall of consumer choice on taste. Well, dude, this just happened. Like, remember, I don't know, rewind five, seven years ago. And it was like self-driving cars, what people working on. Yeah. What's going to happen to the truck drivers? it was like the truck drivers and the grocery store checkout people it was like you know we're just gonna have to find them new jobs and then all of a sudden like dolly and these other tools came out i was like oh shit it's actually us it's every oh no it's us first it's the graphic designers the copywriters the like what were the first things that actually chat gpt yeah and like the modern wave of tools were good at it was like writing they did like the fake podcast of joe rogan talking to steve jobs and i was like oh podcaster all right that's gone like you know it's just a matter of time, you know?

30:39And so I don't really think there's really any sort of like safe space, but I definitely don't think it's the, um, Oh, I have, I have unique taste. Cause you're right. Like whether the AI maybe has better taste or it takes 1 million shots on goal while you take one and it's just going to play the law, like the law of large numbers and get it, get it right. Just by doing so many variations. Like, I tried to write a movie script. I was like, oh, I want to write the opening scene of this idea for this movie I have. And so I'm like, sit down. I'm like, oh, shoot. Like the idea was really great. I told like five people the idea.

31:11They're like, that's incredible. This is great. You should do this. And then I sit down. I just actually have to do the work. I'm like, oh my God, this is so hard. How do I, what do I, where do I start? Are they in a cafe? Are there a bar? Where do the characters go? What do they say? And so I go to chat GPT and I upload a script of the social network. And I upload like all of Aaron Sorkin's like work. And I'm like, all right, you're kind of like Aaron Sorkin, but you're also me and uh you get here's the idea for the movie give me a draft gives me a draft kind of sucks i'm like give me another one gives me another one instantaneously with no with no uh ego about it gives me another one gives me another one gives me another one and eventually like it got pretty good at doing that scene and pretty good measured by your your taste by my taste as your taste of what you enjoyed right but what i'm saying is like even if let's say my taste maybe it's right or maybe it's wrong either way it did 10 attempts before i could even lift a finger.

32:00The volume was there. The volume is going to win in a taste game. It's going to take a hundred thousand shots on goal. Same thing with like ads, right? Like if you look at like fashion brands that do good with Facebook ads, go look at their ad library. It's not like they have one David Ogilvie sitting in the room and he just comes up with this one beautiful ad. They're running like a thousand ads in a catalog, quantitatively testing which one gets the highest row ads. And they're doubling down on that. It's so funny because like we've gotten over the idea of taste and all these like really fuzzy areas of like human consumption and it's like taste on video taste like turns out like people preferred the algorithm of bite dance and tick tock to like you're following your you know programming on television like your years of study of what people are you know enjoying got replaced like by like the algo um you know i can't tell you how many mistakes i watched that's not true the algo is literally the definition of taste it's And it's already proven that the algo dominates.

32:57That's right. You know, whether it's editors inside the company or it's me for myself, it's better than what I could do for myself even. It's funny. And we make these mistakes all the time. I mean, you could argue that Apple lost the entire podcast business based on their religion around taste. Explain that. Yeah, so like Apple started the entire podcast movement, right? Like they owned every podcast got launched on Apple, right? And they were like, we really, on the other side of Apple, they're like, we really need to own the future of entertainment. And they're like, what is the future of entertainment?

33:31It's like great shows. It's HBO. It's taste. That's tasteful creators, tasteful makers, like things that are just like. No slop. No slop. But on the other side of the house, the volume was being made by people that didn't look like the top Hollywood creators. and all of them, no product iteration, no help for monetization, no like featuring of them, no studio production, no tools, no budgets, no like give them metrics and data back. None of the things that you would do if you had like a million free creators doing things and building awesome audiences that turns out can now sway elections. And all of them start on your platform.

34:13And then you fast forward, it's like, where's the most of that consumption? It's like YouTube and Spotify. And you're like, they fumbled. And they fumbled because like they didn't think it was tasteful and they missed it. And it's like YouTube back in the day did the same thing. They actually had half a billion dollars for content. There was like the original. Red originals, right? The originals. It was like a half a billion dollars. And they came to all the agencies and say, we want your best creators. And we all went and pitched them$5 million channels and they gave a big budget. And then they gave like$5 million for the native creators like Phil DeFranco and Michel Fon got like little touches of like cashier in there.

34:49Like the only channels left standing were the creators, the native creators. It didn't match the taste profile of like the advertisers that were upstream of all of this shit, but they were the ones creating stuff that people wanted. I mean, Sam Altman's got like the initiation point for basically every new business that's getting built. Right. And he turns out he ran YC for a long time. We're not like that far away from him saying like, Hey, why not just build like a funding model into the next GPT and be like, somebody's talking about starting a business. I actually like that business. Like, do you think it'll make money?

35:20Let's provide them like credits. Let's provide them a little bit of funding to get going. And like, I don't know, does that change how investment works? Is that maybe like upstream of all of the tastemakers? So what do you think it looks like? Let's say AI just keeps getting better. Yeah. There's no, there's no, uh, life raft for the taste guys or the idea guys or whatever. Like AI is getting better at all these things and you're going to, you know, so what happens? What happens to us? What do you do? How do you think about that? I think you just keep creating things that people want and like, you know, use the tools to piece them together.

35:53And it's like, just get to the final, get to the answer faster. Like, do customers want this thing and give them, give the customers what they want. That's true north. Like build something people want. Like it's the YC mantra. It's like build a product people want. And it's like, how fast can you get the product to people that they want? And like, how many times can you iterate on the thing so that eventually you get the thing that people want? And it's like, just laser focus on that and cut everything else out of your life. And like, that's how you build most of these like scaling businesses.

36:18Right. And it's, to me, that's like, that's never going to go away. People are always going to want things. You can use these tools to provide those things to them. And there's probably a good arm for the next long while. Like, we got a long period of time before this stuff filters through the economy. Because it's not how fast the technology is moving. It's how fast people adjust their reality and their habits. And that's like the friction that actually exists here. Technology is mind boggling. But like my mom learning how to second brain is like, even you and I learning how to second brain is really hard.

36:47Do you have any other AI sort of theories or frameworks that are interesting that you've been noodling on? Yeah, I've only, I've made, I made three investments post-co-to as an angel. All of them follow the same kind of framework. One of them is to a buddy of ours in the travel space. And the other two are founders that I backed before. but all of them are basically agent platforms. One's called Cognition, which is like the maker of a product called Devin. And the founder, Scott, was a founder that I backed once before. And Scott is like - He's a genius, correct? Yes. He's an actual mathematical genius.

37:26Among many things, one of the things I was riffing on was like, it's possible that Devin is just Scott in the background answering all the coding questions because he's so good. And then another product is called Augment. It's Harish Abbott. And Harish was a founder of a company that I was on board of called Deliver, which was like third party logistics for everyone. It was like Amazon Prime for everybody. He worked at Amazon in fulfillment and then built Deliver and sold it to Shopify for a couple billion dollars. And like Harish is one of those humans where like if you could imagine what the ultimate like logistics hire would be, you would hire Harish.

38:00No detail escapes him. He doesn't mind staring into the abyss of like a warehouse and figuring out how to optimize every minute detail of like product comes in. Where does it go? What platform? How do you get optimized? What's the routing down to the minute? Like he's that brain. It's just his it's his gift. It's his dark gift. And so both of these people, actually, all three of these people have these dark gifts where it's like you could never in your wildest dreams hire Scott. You could never hire Harish to do your logistics. but what you can do now is they've like they've built these platforms that are agentic and so it's like imagine if like the reinforcement training was done by the ultimate employee and that was priced at tokens what does that actually mean so like they're building an agent that's going to be like let's say your logistics yeah employee but he himself is literally like kind of auditing the like the answers he and the team that he's building are saying like hey we know exactly what goes into building world-class fulfillment and logistics we've done it at amazon We did a deliver.

38:58Like I know all the details. Now you've got a company that's an SMB, it's an e-com. And it's like, you don't know the knowledge that I have, but I can program it into an agent. So that like all the workflows that you're eventually gonna have to do, this agent can help you with. And it'll give you the things that would otherwise take you a lot of time. Even if you were the best in the world at, it'll do those things automatically for you. And so I think we're moving to this world where like the best at a task will be able to productize themselves as these agents and delivered. So, you know, when social media came out, one of the cool things that happened, one of the reasons why there's this word influencer is because prior to social, the only people you knew who did a thing were the people around you.

39:42You were limited by your geography. And the internet, the superpower of the internet is that it vaporized geography. So, you know, like when we had a baby, we're following these like mom influencer types who are teaching you like how to like get your baby to sleep and like little tips on, you know, swaddles and diapers and all these little things. Like I'm getting the best mom coaching and dad coaching from like, not just my geography, but like the world. And those people became, so the best teachers were not teaching in schools anymore. The best teachers were teaching on Instagram and YouTube and other places like that.

40:15And they were getting millions and millions of followers because like the best teacher actually should have a few billion students. And so the best got rewarded in that way. and so that's what the internet you know like like last 15 years has done and now with agents it's kind of the same thing it's like the best employee you're no longer limited to who you can afford yeah or who's nearby you who you can hire locally but actually like no globally who's the best at travel planning and booking who's the best at logistics uh you know workflows planning and analysis who's the best coding who's the best who's the best engineer you know right it's actually not who's the best engineer who's the best engineer period yeah he can program himself in the same way that like content creators were able to like make pieces of content that's scaled.

40:56And, you know, I can go to sleep and millions of people can listen to this podcast. And now they're doing that with like a piece of software, a piece of code that's going to actually like take their brain and be like, yo, I got that guy's brain here in this piece of code. And do the digital work that they would have done for you. Right. And just like the best teachers have millions of students, the best employees now actually work for millions of companies is what's going to end up happening. Yeah, that's amazing. I want to do some stories with you. So I have here. Oh, this is scary. These are scary.

41:24We're going to draw a card. And then I want to, is there people that you've encountered in your life? I want you to tell me some stories. Or story time. Take a card. Yeah. All right. Show the camera. Who'd you get? I got Peter Thiel. Peter Thiel. Do you have any Peter Thiel, either lessons learned, funny encounters, interesting stories, seeing him in action. What you got on Peter Thiel? The only time I've ever encountered Peter Thiel was on the opportunity to invest in Replit. we were both going for the opportunity and i think when you go against somebody like peter teal um you plan to lose in most cases uh and i didn't i didn't end up uh losing the opportunity to invest in replet and i think part of it is like the realization that like any given sunday in in in a lot of games like a lot of people count themselves out but on any given sunday you have the opportunity to pull out a W.

42:17And I love that product. I love it authentically. Like I use it all the time. I love the vision of like empowering like a billion people to build the companies that they want to build. And to like, I feel viscerally like the tinkerer's dilemma of like, I'm not an expert, but I wish that I were. And I wish I could bring this idea to life. And that software is this like bicycle and I don't, I'm like, I'm on a tricycle. I'm on like training wheels at best. And like, this thing makes you feel like you're on a motorcycle. And I'm like, I love that feeling. And if you can tell that feeling to somebody and get them as excited about it as you are and use the product and obsess over the details of it.

42:58Like I would send Amjad, like every product thought I had every, like I'd have, like I'd have shower thoughts about it. I was like, you know, whatever. And it wasn't like work. It wasn't like, you know, the art of the VC deal. It was like, I just genuinely loved it. And then I think there was a moment where like, where he was like, I can have a guy who's probably the one of the best on, you know, investors of all time. Or I can have Matt. And Matt loves me. And, and, and that was his choice. Um, and so I think that's the, I think the lesson is like, if you, if you really do the work and you really love it, like you might not win them all, but any given Sunday, you could pull out the dub.

43:43Bondo. Who you got? David Bonderman. Okay. Tell his story. Who is he? And what's your interaction with him? David Bonderman, um, passed recently. Um, David Bonderman, uh, was the founder of TPG. David Bonderman was a guy I got to know later in life. He worked with a very close friend and mentor of mine named Rick Hess. And he was during my sabbatical, one of the things that I did was like, I'm just gonna go and try to spend time with people who I've always admired and never really gotten to meet. And David was on the short list. David had ultimately been part of the group that acquired a majority position in CAA.

44:22And I'd gotten my first exposure to him there. And he had just had this like incredible storied career of like how he, you know, he ultimately, you know, he was a huge investor in like the airline industry and, you know, had owned sports teams and was like a titan of industry and did it his way. And what was his come up, by the way? Because like, you know, that's the cool stuff you do at the top of the mountain. Well, he worked for the Bass family and he was like, he like helped build like the investment strategy for the Bass family in Texas. and ultimately like pivoted that into, I think the first investment was like Continental Airlines where he made his first real like Buku exit and ultimately ended up building TPG into like one of the titans of the private equity industry.

45:03And I got to spend a bunch of time with David, like hours at a time. He was like the kind of guy where like he was late in life, but he still had it. Like he'd have these days where he was just like as hot and fired up as anything. And so some days it would just be like, let's just spend time talking about his job and his career and like lessons along the way. And then other times - Sorry, how did you do this? So you're on your sabbatical. You're like, I want to spend time with this. But what'd you, you call them up. You're like, hey, can I just come hang for a couple days? What do you say? I called Rick Hess and Rick was building a new strategy for investing.

45:32I was just helping friends. And he was like, I was spending time doing, you know, doing, I treated like all of my friends and family kind of like, I was still in the portfolio VC mind. I was like, I'm going to treat them all like portfolio companies. I'm just going to go do things for them that matter and help. And so like I would help friends like start companies. I would like go over and clean out their garage. I would like just, I had time for the first time in my 20 years. And like, I just wanted to spend time with people that I loved. And I had a list. I wrote a list of all the people. And I like would say, Hey, I have time for the next couple of weeks.

46:03Can I help you on something? And so Rick was like, well, I'm building this thing and I'm partnering with David. And he's like, why don't we go over and talk to him about it? And one of those trips, he was like, Hey, David's really interested in AI. Will you like put together some thoughts? And I was like, a hundred percent. And so I got to go and spend like a three hour session with Bondo. And I was just like laying out where I saw AI going. I'm like showing him mid journey. I'm showing him like chat GPT, you know, and, and like just walking him through all the new products. And, and he's just silently like, kind of like riffing on it and like asking a couple of questions here and there.

46:35And, and at the end, he's like, so what are you going to do? I'm like, I don't know. I'm going to invest in a couple of friends who are smart and, and building stuff here. I'm I'm like, what would you do? And he goes, I'd buy railroads. And I'm like, okay, this guy's, maybe he's just gone crazy. Maybe he's gone crazy. I'm like, I didn't understand what he meant. I'm like, you gotta explain that to me. I don't know what the hell you're talking about. He goes, well, there's two ways to play it. One is this world is moving so fast that everything is changing. And it's like, if you built software today or you built a product today, it feels like it's moving so fast that it could be obsolete in six months.

47:12And so that's shifting sand. You can play towards the bleeding edge, but that's where everyone is going to be playing because it's shiny and it's fun and it's distracting. Or you can buy a railroad. And it's like, think about the things that in the times of most change are still going to be here. And it's like, focus on the industries that aren't going anywhere. And it was like this moment where you're like, oh, I'm talking to like business Yoda. And it was just like a really interesting framework. And it's like, I think it does apply as like the business that, that I've been, that I ended up spending a bunch of last year working on is in a really old, dirty industry that is like going to be around forever, but applies these tools to it.

47:53And so I kind of like met him in the middle, which is like, I was going to use the tools that are available today to help an industry that I knew would be stable in the face of all of this change. And so he was just like one of those guys where he could like pull out a, invest in trains and have it be like one of the most incredible business, you know, pieces of advice. Hey, quick message here because you know that feeling when you send a wire and it actually works? No friction? Well, I've used Mercury for years now and let me tell you, it just works. And that's why I use it for not one, not two, but eight of my companies.

48:23From credit cards to invoices, I have everything in one place. There's no janky dashboard. I'm never told, please visit a local bank branch. None of that tomfoolery. And a few months ago, I landed a big client. The first thing I did, I sent them a clean, branded invoice. Boom, deal closed, cash in the door. That's the kind of banking experience I want. And that's why I use Mercury. So if you're running a startup and you want banking that feels like it's built in this century, well, go to mercury.com and get started in minutes. Mercury is a financial technology company, not a bank. Bankless services are provided through Choice Financial Group, Column N, A, and Evolve Bank and Trust members FDIC.

48:58All right, we got three more. I think the thing that I pulled from Mark was like the idea that like where venture was heading and the institutionalization of venture. It kind of feels to me like we're at the almost the apex of that. Like when I joined this industry, like there was all of this tribal knowledge. There was like things that were hidden secrets. What's an example? Like how to write a term sheet was like unknown. Like how to do a closing process was unknown. Like how to, you know, the real mechanics of the industry were unknown, let alone like the metrics of like what is good, great, bad growth metrics or retention or net dollar retention.

49:37Like a lot of venture today feels like it's really like institutionalized. And it feels like even like further out, we're at this point of like the industry where it's like the knowledge is all shared. It's all public. People have like posted almost as much institutional knowledge about an industry as possible. We have like documents like the safe that like revolutionized it. Like YC created a whole process for like how to institutionalize a fundraising, the handshake protocol, like we protocol the industry. and it's like, we're at like the furthest ends, maybe not the furthest end, but we're like the mature part of this industry.

50:13Like when I got into it, there were like 10 seed funds in market that like, you know, you didn't have to be good. You just had to be alive to like go and find these things. And there wasn't a ton of competition. There weren't like mega funds coming in and doing seed rounds. It's like, you met a founder, you liked the founder, you went to YC, there were 50 other people in the room. And you kind of like said, hey, I like this one, let's do it. And you got to a handshake on a note. Mark, I think, saw where the world was heading on this. He's like, all these asset classes are maturing and we're going to build like a much bigger platform for it.

50:42And I think it was inspired by a lot of the CAA mentality early on of like CAA shifted the way that agencies had been done. It went from this like, I represent one client with one deal and it's like boutique, but also like strategically, like Ovid's had this insight that like, if I rip an agent away from another agency, all their clients come. and it was like, where is it CA? One client sat in the middle of 10 agents with each of their own like personalized expertise. And it's like in VC, the same thing kind of existed. You had one VC, you had this boutique. You're like, I've got this board member, that's my person.

51:18And then a Dresen comes along and it's like, no, you've got all of us. And we all come with this like value proposition and it's like recruiting and marketing and all of these services. And it was the realization that like VC was a service industry and institutionalizing of that, that like changed the way that a lot of venture was there, like had been done. And then everybody rushed to create platforms and teams and like structure because they were just beating people on that. Even if it wasn't like effective, they pushed the edge of that and they owned the brand of that, of like what a platform VC could be.

51:50And the other edge you had like benchmark and, you know, founders fund and like people who are like, you need me or founders fund where you're like, you don't need anybody, you know? So I think what I took from that was like, you can look at any industry, VC included, and like bring a new institutionalization to it. And I think they're still doing it. I think they just acquired Turpentine and Tornberg. And it's like the realization that like one of those edges that you're competing against is like distribution, media. And, you know, if you can bring customers, right? Like what do the startups really care about?

52:24It's like customers and attention, the scarce resource is attention. And so it's like, we're going to build attention into the offering. And it's like, that feels again ahead of like the customer first centric, like customer centric, like response. And it's like, most VCs were selling things that weren't necessarily like what the customer needed. Right. It was capital. What's that guy named Gilly something? He invests in whiz and like every security start. Oh yeah. Basically he was like, he unbundled the Andreessen model. He's like, cool. We're not going to help you with, uh, you know, marketing or recruiting.

52:55like we have a network of CISOs at the top 500 companies and you'll get to 2 million in ARR if you invest with us. Yeah. And then to those guys, he was like, Hey, you're going to own a piece of this portfolio while you're sitting in your job. You're going to also be a venture investor, a venture partner in our fund. Yeah. And like kind of created a little bribery network that like actually worked and actually it's like, turns out huge, huge results, like, you know, way outperforming results by figuring out that platform. Yeah. And I think like those are like what he's continuing to do is find like what those gaps are what the what the customer really wants right and it's like if you could tell me like oh i want revenue like i want that's what i really want and you can deliver that that's pretty incredible and part of what the startup founder wanted was like you know the brand a16c i want cool i want to be at the i want andre godala to be like at our i want to meet him like i want these different things that you know again just work backwards from what what actually resonates most vcs were selling cool right they were selling they were selling uh maybe not cool they were selling uh the promise of de-risked right credibility yeah the promise of credibility that we that we were something that had been like validated they were selling like if you got a sequoia investment like that's like this is a real business they've they've looked at billion like how many trillions of dollars of market cap or like from those people we're among the you said you felt the association with market cap All right, we got two more.

54:22Derek Jeter. I have one absurd Derek Jeter story. That's super funny. So one of the things you realize at a talent agency and being around like A-list stars all the time is that like a lot of people go a little bananas. There's almost no equivalent though for sports stars because something embeds in your brain when you are a little kid that these people are like larger than life. And so I am a young VC at Lowercase and Derek Jeter and his partner are starting like a media company, a sports media company. And they're like, we want to spend time. And like, I saw all of this, anything like media and tech, I was like, I saw for years.

55:12And so we like go out for a dinner. We go out to this nice restaurant in Beverly, hills and um we're sitting down it's the three of us and up to the table walks a guy and the guy this is like the thickest deepest new york accent that you have ever heard in your entire life he's like hey guys and like he sees jeter and he's like about to talk about the specials and his face melts the guy almost like he gets like time is a flat circle and he is lost and it's like one of those moments where you see him like like reverse age into an eight-year-old and he's like this is like the moment of his life and so uh he's going he's like captures him like mr jeter mr jeter like i'm a big fan he goes through the whole thing and at some point we all order the same thing we order like the special the guy recommends those like truffle pasta he comes back to the table a little bit later and he's like you know it's fresh truffle on top and he gives me a little bit of fresh truffle and he gives the his manager a little bit of fresh truffle and then he's over at mr jeter and he looks at mr jeter and he's putting the fresh truffle on and it and he just like he his brain freezes but his hand doesn't and it it gets to a point where it is it is so funny that we just start laughing as it's happening because it is an ongoing mountain of truffle on this plate it is the whole plate is black it is a it is it must have been hundreds hundreds of dollars of fresh truffle on mr jeter's plate and he's like he's just looking at mr jeter and he's like i think you got it and it was just one of those moments where you're like it's really funny to watch people in that moment of their life um i don't have i don't have like a good lesson from it at least have like a different level of cool it's like it's another thing it transports you to being a little kid and so you know i i've had one of those experiences myself um and uh yeah well this might be the one that is that is uh that is the one i grew up as the most diehard of diehard Lakers fans.

57:07I grew up in LA. I went to college during the Shaq-Kobe years and the high school in the Shaq-Kobe years. High school, you know, Christmas was like Laker game on TV. Like, that's what we did. He's one of those people for me that was like, I got to watch this guy. And then I got to be obnoxious at college, like watching this guy beat the crap out of the Celtics. And it was really fun. But as a, again, at Lowercase, I had an opportunity. There was a brief moment in time where I was managing director of a fund called Lowercase 13, which was a Kobe Bryant partnership. And it was like for a split second.

57:44How does that happen? Kobe reaches out? I had a friend who was advising Kobe. Her name is Betsy Skolnick. And Betsy said, hey, Matt, Kobe is, I think he'd been injured at the moment. He was like, he's thinking about what comes after basketball. And he's always been obsessed with tech and venture. and he really wants to learn. Will you come down and have dinner and spend time with Kobe and teach him a little bit about venture capital? And this is my Jeter like truffle moment. Like I'm like, let's go, I'm ready. Like, do you want me to come now in the car? I'll come right now and we can do it. And she's like, great, we'll set up a time in the next couple weeks you can come down.

58:20So Chris and I go down and have dinner with Kobe and we like sit there and he's like asking questions. And it was like one of these things where you can kind of tell some people like whether they have like the second gear of curiosity. Like sometimes they ask the surface question and then there's another layer of curiosity where they ask like every relevant follow-up question that you could imagine having been in the industry for a long time. You're like, oh, this person's gone through and like they have real depth of curiosity. They want to know the details. They don't want just the surface answer.

58:49They want to be like, but how? This is actually what makes you great at like podcasts and interviews is like you do the second question. You don't just leave it at the first. You do the follow-up. And he did it for the entire, It was like a three hour dinner. And by the end, he was just like, this was awesome. Thank you so much. I'd love to find ways to do this again. Will you send me stuff that I can read? And I was like, okay, I'll send him some stuff that he can read. So I put together like the essential reading list adventure. Every blog post that I ever loved. Like I'm going through all the girly posts and the Wilson posts and like all the stuff.

59:19And thinking that he would like never read it. 2 a.m. I get a text. I read that post and it was just like, whoa. he was like in it and he would like text and like we'd have these conversations in the middle of the night i was like what's this when is this guy sleeping it must be like going crazy because he was injured he's like just like texting and then eventually he goes i really want to go spend some time and meet like we'd suggested like you can come with us and go to san francisco and meet a bunch of the startup companies he's like i'd love to again thinking like he'll never do it he's like let's go when when are we going and so we take him up to san francisco and we go to see a couple startups and we spread it out.

59:56It's like early stage apartment startups. And then we go to Twitter and, uh, and we do like the tour of Twitter and Twitter had just bought vine. And we're like walking around, we're onboarding him to vine and doing the conversation with Dick and Adam, uh, Dick Costello and Adam Bain. And he's like, I want to see the whole place. So we go down to like the engineering floor and he's walking past one of the, like the hang rooms for the engineers. And there's a kid in there and, uh, there's Papa shot basketball and the kid, have you ever watched those people who are like savants at Papa shot? Yes.

1:00:25And they can like both hand it. And it's like, they go into like whatever the fourth gear of like the, the matrix, the other in it. And they're like both handing and like, yeah, they look like the Tesla humanoid robot. That's just like, yeah. You're like, this guy is that to the T and Kobe looks in and he's like, I got to do it. And he walks up behind the guy and he goes, I got next. And all the engineers see like Dick and Adam. And then they see Kobe and they're like, holy shit. Like Jimmy's about to play Kobe. And they rush in. And it's like Vine has just come out. So they're all like taking video of this thing.

1:00:55And like Kobe goes and he's like bang, bang, bang, bang, bang, bang, bang. And he hits like 80. And then like Jimmy goes and it's like bang, bang, bang, bang, bang, bang. He hits like 82. And the room like erupts. And it's like the greatest moment in this guy's life. He has never been like the whole, like it's like no one will ever believe this moment. Right. He'd be like, I beat Kobe. I pop a shot. He's that guy. And like you expect Kobe to be like, oh, congrats, dude. High five. and I just remember the look on Kobe's face where he was like legitimately pissed it was like no it wasn't like a fake piss it was like I'm buying one of these things right never fucking happen yeah I will destroy you the next time I see you never letting that shit happen again and he like walks out um deletes his twitter account yeah anyway so it I it was pretty incredible like getting to spend the time with him and then uh yeah we he was like hey I really want to build a shop um and so for a brief moment we had like a side fund that we were putting together with kobe and we made like two investments um it was like one of them was ended up being stripe out of that fund but he had a he had a business partner who ended up like trying to renegotiate and we don't do those kinds of things so anyway matt full of stories this is amazing super fun thanks for doing it i feel like i can rule the world i know i could be what i want to i put my all in it like my days off on the road let's travel never looking back

1:02:24All right, this episode is brought to you by Mercury. They are the finance platform of choice for over 200 ,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of, and then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you could tell that it's actually made by a startup founder.

1:02:52It's an entrepreneur. You could tell it's made by somebody who used other banking products in the past and didn't like all the different rough edges and annoyances and decided to actually fix it himself. And really, any type of entrepreneur you are, let's say you're an agency, well, one of the things every agency has to do is be able to send invoices, easily create them, send them to customers, and stay current on your balances with all your customers. Well, you can do that inside Mercury. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show.

1:03:17For more information, check out Mercury.com. Mercury is a financial technology company, not a bank. Check show notes for details.