How to retire with millions (and pay $0 taxes)

25:21Like they have my health records now in a beautiful website. They pulled all my medical history, which like I could, if I wanted to go look at my own medical history, I couldn't have even done that before. So like that, that was a change that happened. So you have all these different things sort of stacking on top of each other that like Anker said, like a cultural movement towards status, status being associated with being healthy rather than being a degenerate, right? Like before in my circles, the more you partied, the cooler you were, right? The more sort of bad for you your lifestyle was, the cooler you were.

25:54Now, the more good for you the lifestyle you have, the better, the cooler you are. And I don't know if it's just I changed or culture changed. Tell me, how were your results? Oh, you didn't see my tweet about this? Yeah. What did you say? I said, oh, I just found out that my chronological age, 37, is different than my biological age, 40. But long term, I'm not concerned because I'm just going to go ahead and kill myself now. because you never see someone share their results where their age is worse than their actual age it's always like oh look i have the body of a 23 year old you know russian gymnast uh cool thanks for i'm so happy i use this app why were you so i'm the only person i'm the only person i've ever seen with a higher bile literally never i've never seen anyone i think i broke a record what what was so old about you um well so it's pretty cool because actually the next thing that happens is they go, there's a concierge doctor who basically is going to, in a week, give you kind of an action plan.

26:51So it says, oh, okay, look, we did these 30 tests in one, in a single blood draw, they do these like 30 tests, right? And they say, look, right now, let's say, I don't know, let's just pretend it's like your, whatever, your LDL is high or low, whatever, whatever the, something is wrong. And then they'll basically start to talk to you. So there's a little concierge, a little chat here where somebody is going to then work with me to develop maybe an action plan, things I could be doing, eating slightly differently, whatever, walking more steps, whatever, whatever you people do, go to cold plunge for six minutes, all those things.

27:23And you come up with a, an action plan. So, you know, whether this is like life-changing or not, they're probably just gonna be like, yo, like delete DoorDash off your phone. Like, you know, that'll probably do the trick. Like there's, you know, there's a few different ways that you can help somebody. But again, like this is not how normal medicine works. Normal medicine is a car, you know, mechanic. You go there when you're broken, they try to fix it. And most of the time they're like, yeah, it'll never really run the same, right? Like we're in maintenance mode from here on out. Whereas at least this operates under the assumption of being proactive rather than reactive.

27:57And that there's actually something you could do. There's, there's actual lifestyle steps you could take and not simply like medicines you can get on to improve your health. Yeah. I also think in addition to all of that, I do genuinely believe a lot of people are sicker than before, particularly like in the US. And some of my other ideas have to do with that. But I do think you look around whether it's like fertility, gut health, allergies, like shit's kind of falling apart in a lot of places. And people are reacting to that. But by the way, the upsell in this thing is crazy, because the initial deal is super good, right?

28:32So it's like 500 bucks, and you're going to have like a 10 times better version of your annual physical. It's like, okay, that's actually like a good trade that you don't need to be super wealthy to do like you can pay 500 bucks and get a better version of your physical but when you're in there it's like you want to know how that gut's doing on a microbiome test i'm like yeah i'd love to i kind of dude i had to click next the upsell page on function health i did function health i clicked next i'm not joking 15 times i didn't even click next i clicked yes i was like yep give me an allergy test give me a toxins test in my blood give me the gut test i basically did every single test except for the like blood like cancer test one and i just i just said yes to all of them so they upsold me like a couple thousand dollars worth of tests but honestly like great i wish my doctor had been offering me these like why doesn't my doctor like offer me these either these tests they do it they do it the other way around they're like oh you want to get your testosterone checked you look fine yeah what's your wife say to you i'm like what why is this so personal

29:33so what's your idea here so a lot of these services are doing really well i think you cut out the motivation a lot of times for people is the aesthetic side of it too people want to look good i think if you had a function health but for your physical appearance it would completely crush so it's like you come in it's like wow sean your hairline has receded two inches and you tie in a DEXA scan to it. But basically like a concierge service to elevate your experience, like two of my college roommates are plastic surgeons, right? And I've heard a little bit about that side of the business, but marrying these two ideas, basically concierge lookups with improving your aesthetics, I think is a fantastic business.

30:22This is actually a great idea. We had Justin Mayers on the podcast and his skin was glowing. Yeah, he's telling us about his inner health, and we were just like, he's handsome. I was like, dude, your hair is full. Your skin has a glow. Your teeth look nice. Can you just tell me about that? And so, yeah, I'm on board. We went out to breakfast, Sam, and literally everything he ordered, I just said, whatever this man eats, I need to eat. So he ordered this drink. The waiter looked at me. I said, did you not understand the instructions? Whatever this man eats, I eat. and so I had an identical meal to him.

30:58But I think you have to. Like Stam and I are investors in a testosterone company and if the founder was not jacked, I would not have invested in the company. That's true. Sean's in on that too, by the way. It seems like we've all invested in the same stuff. Yeah, so you have to look the part in order to do it. So I think, yes, I think businesses focus around the aesthetic part of it would crush. I mean, you already have concierge medicine in Turkey, stuff like that. But secondly, I think anything that helps us break out of the U.S. food system will do quite well. And again, probably more so in cities like New York, but it's kind of funny.

31:33Like every Friday evening, I go and meet my like raw milk dealer, which is super sketchy. It's this like Amish farm that like drives in. It's illegal. So, you know, they literally park on the side of the street. You make this little transaction. But I have a lot of people that just want to break out of the U.S. food system. And I think businesses that enable people to do that will go quite a long way. And so how did you find this Amish farm? Like, what was your process to find this alternative? So it was word of mouth. A lot of my friends were all talking about it. And then someone's like, oh, I get my beef from this place.

32:10And it actually started out with like, you know, you buy beef and then you get upsold on all the other products. And now before you know it, my like soap is made out of goat milk and shit. That's probably not even relevant or helping. But, you know, they have a pretty nice business. But yeah, they go straight from farm to like they drive out to New York City. They have this little truck. They park the truck on the side of a street corner. You have a 30 minute window to meet them. And as much as I joke about it, it's actually pretty cool. It does improve the quality of my life. I do think the products taste well.

32:41Raw dairy is more of a novelty. you know that's something that like sure i'll add four dollars for the for the raw milk uh but i think breaking out of the u.s food system at least you know we'll see what rfk does but in the short term i think there are a lot of people that will pay quite a bit of money for do you get all your meat from this uh this amish fellow i do it's so good like like dude i don't like chicken in america like as someone that's traveled a lot most chicken here at a grocery store tastes like nothing to me like you can't really taste anything but here it actually you know again but such a big difference if you have the same stuff outside the u.s we all need one of these amish guys isn't this what a farmer's market is supposed to be by the way it is it is what a farmer's market is supposed to be this feels more authentic right this feels this feels more real well feel the way you describe it's more like a drug deal and i actually that kind of appeals to me in a way like farmer's market it's a little bit like a cute date on a sunday morning but like i kind of like an element of danger with my groceries this is this is contraband this is contraband exactly not only that when you like you like buy something and all the signs on it will very clearly say not for human consumption but it's like wink wink oh man can we ground it up and inject it in my veins that's usually what i do when it says not for human consumption yeah for for cats and dogs only does it make you feel better by the way this stuff it does i mean of course you have to like control for placebo effect and stuff but generally yes i do feel better when i'm when i'm eating this and or don't control for placebo placebo is the best placebo is a mess right yeah yeah whatever i read about these i'm like wait so you have to like study like when we talk about placebo we act like it's um like it's an issue and i'm like wait a minute you're telling me i take a fake thing and it gives me the real result give me all of the fake things that's all i ever want it's the fake thing no it's i mean the only reason i even went down this rabbit hole is i remember i've had multiple times in my life where i'd like live a very healthy new york life like cook my own food or whatever and then i'd go to like argentina for a month live like a degenerate and i'm like i i feel better like my physical body feels better and um i don't think it was the addition of the alcohol.

34:54I think it was just the food system. It could have been that. It could have been some of the other stuff you're doing on there too. Yeah, it could have been never.

35:04All right, next idea is a travel agent bought for credit card points. Again, we already talked about this, right? I'm on the cutting edge of a lot of personal finance shit. I still find it a pain in the ass sometimes to actually find the right flights. Like right now I have 250 ,000 MX points, 100 ,000 chase points. I'd pay a good amount of money for someone to go find me two first class tickets to someplace warm in the summer. How do you want this to work? I want this to be a concierge service. I want to tell people exactly what I have, like what are the points or whatever I have and where I'd like to go, including like, like, hey, like for a lot of times I don't even care where I want to go it can be you know a warm destination in a certain part of the world so and they just do it for me Jack Smith is a friend of all of ours I believe Jack Smith very um when he suggests something uh you you take it seriously even though he's uh one of the strangest people ever but there's like you know that he's like thoughtful enough that there's some unique reason why he uses this he only books his flight via flightfox.com and I've used it a couple of times, but basically you sign up and at the time, I think it was free.

36:23Now it looks like it's$20 per ticket. You tell them like roughly when you want to do something. And there's a human on the other end who goes and books it for you. And they spend like two hours per flight, finding a flight for you. Their business doesn't make sense. Like what's their margin on in on this? I have no idea, but I have booked three or four flights on this and it is amazing. It works every time uh it just can you enter like your credit card points and stuff or is this just dollars yeah so you they'll either just pay for it and book it for me or they'll give me the exact flights to book and then i go to delta.com and book it let me tell you another crazy thing have you guys ever heard have you ever bought another bought or sold another person's miles uh no but that's the kind of stuff that like i think businesses had made that easier there's so much value to be unlocked there.

37:13Have you ever heard of this, Sean? I've heard of it. I've never done it before. Have you done it? I've done it. So I booked a flight where I had a friend who spent roughly 10 or$15 million a year on advertising with his Amex card or some credit card. And he is like, I have all of these points. If you wire me the money, I will book the plane ticket for you and I will take a small fee and you get the discount. And I did. And I think the flights, I think I saved 40 % or 30%, something like pretty significant because I was buying like six first class flights. It was very expensive. And it was like thousands of dollars that I saved.

37:53So who's this friend? Basically what they're doing, but as a true sort of professionalized service is how I would like it to work. And I think you can now automate a lot of the backend with smart tech and stuff. This is highly, not illegal, but it's against the terms and service of all these airlines. And so if you get caught doing it, I think they take your ticket. I feel like a disproportionate number of my ideas are turning out to be illegal. Yeah. Yes. So what were you saying about the financial services company that you currently run? All right. Illegal raw milk. I don't want my chief compliance officer to message me after this.

38:38I should add, nothing shared here should be considered as legal advice, investment advice, or tax advice. Everything is for informational and educational purposes. Or health advice. That's fine. That's not that regulated in this country. But you're right on the points thing. So I use seats.arrow, I think, which is basically you plug in what points you have. And it's like a search engine, but it's very slow. It's very hard. And I have to do it myself. You're absolutely right. I want either a human or I need AI to be able to do this where it just knows. I just say what I'm trying to do. And sometimes it's as fuzzy as what you described.

39:09Like, I just want to go somewhere warm in the summer. Like, it's okay if it's Puerto Vallarta, and it's okay if it's Hawaii, right? Like, I'm not as dead set on, and sometimes I am dead set on a date and a place. Sometimes I'm not, right? But either way, be able to make use of these points because I think I have 7 million Amex points. Yeah, exactly. There's so much arbitrage. Wait, you have 7 million? Yeah, at least 7 million. How does that convert? Is that like$70 ,000? once you get good at it the value is so much more than the dollar amount but finding the person but the average person is not going to get good at it so finding the intermediary that's good at it extract some value off the top even though you're incredibly wealthy do you still uh so you still use airline points like crazy dude naval destroyed me on twitter like i like posted some like point pack and he's like i thought you sold a company ratioed the hell out of me um yeah do you still credit card churn i i don't credit cards and i don't do things that are like high effort but like the basics like oh if i'm spending money on shit like yes i'll use a credit card yes i'll get points um and i still struggle like if a flight is over ten thousand dollars like i i still struggle even though mathematically you're like oh you can afford to spend that do you still mostly buy on sale items not on sale idea like now like like there'd be a time where if i'd go to e-commerce and you know you'd get a 20 new customer discount i'd create another account now i don't do that now i'm like that's that's that's that that's too much effort you quit doing that yesterday yeah but credit card points i think if you spend a bunch of money it like just helps a ton also as a brown kid it's very helpful to allow me to buy things for my parents my parents will not accept me buying a ticket for them but if i tell them the ticket comes from points they have no problem accepting it so it's like i do the same thing weird psychology like yeah exactly i told my sister i was like just tell her it's points yeah and then don't bother with the points it's gonna be too confusing just get her the ticket could you tell me i read somewhere that you've built a few things with ai to like personal software software for your own life um what did you build and also like what do you see as the opportunity there?

41:29So I was someone again for context I had a computer science degree I wrote enough code to launch the first version of Teachable and have not written a line of code in like 10 plus years so I understand enough but I just felt like everything kind of went away for me until now with AI where it's again become super fun to play around with stuff and build small little apps. So I started by building things that like just like annoying workflows I have to do. Like every time we host a webinar, we could download something from someplace, re-upload it somewhere else, started building these sort of internal tools.

42:06But now it's reached a point where I have all these annoying, we're talking about home ownership, all these annoying things I need to do for my house. Building like a very simple sort of task management app just for myself is super useful. I think you're starting to see more and more people realize this both for their business and for themselves. What did you make? So for now, it's a very simple task management app where there's certain things in my house I have to do at a different cadence, property taxes, you pay quarterly to change the fucking water filters once every X months. And you enter all these sort of tasks, as well as in some cases, if there's another person attached to them.

42:47And it kind of pulls it all automatically. It's like, oh, it's been, you know, like this month, here are the things that you should do and here are the people that can do it. And again, this is something just for my own entertainment, amusement, whatever. But you can extrapolate how any local business can do it for whatever annoying things they have to do. Sean, whenever I hear, so Ankur's single, I think, well, you're not, you're unmarried. Whenever I hear a single guy, sorry, that sounded like, you know i'm not your mother i'm not trying to diss you this is this already sounds like condescending no it's not type statement listen listen listen dad's like well it's so simple for you you'll understand but go on no what i'm saying is it's the opposite what i'm saying is when i hear you describe this stuff i think to myself if i didn't have a wife or she just like walked out on me i have no idea how i would handle any of this stuff like i don't understand how a lot of our bills are paid they're just kind of magically paid uh and so when i have a bunch of my single friend so like uh sophia maruso one of our mutual friends she tells me about like all the time she has to spend doing all this and i'm like dude i'm used to having two of us you know i wash she dries like i'm used to having two of us to hear to have one person manage all of this as part of a household when you own a home and when you have like responsibilities that it sounds so hard you know what i mean sean can you imagine like having to do this stuff uh like everything i just wanted to see if you could land the plane on that one and i would say i landed yeah he did he did it was like a southwest like you know there was a bump there was like a little bump on the way down but you did you did what i'm saying is it's so much work i don't understand how people do it especially when you add in the dynamic of home ownership especially as someone that grew up outside the u.s so i have no actual life skills like i feel like people in america like know how to do shit they don't like they don't need a plumber they like they've like learned it somehow but growing up outside the country, I'm not handy.

44:40So running a house is quite a hassle. Wait, is that a stereotype that Americans know how to fix toilets? Yeah. You don't think it's true? Well, I do think that amongst all of my brown friends, my brown Asian friends, all of them hate Home Depot. Yeah. Like self-reliance was not a status symbol. In the US, it is a status symbol. Like you are higher status if you can actually fix stuff. In India, it's like, oh, you have someone to do all this stuff for you sam it's not true if you go if you go to home depot on the first saturday of every month it'll be filled with indian people do you know why no what are they doing because that's when they host the free home depot class where you your kids can come build things and it's totally free they give you a kit and they build it it's amazing it's like a free educational thing only indians in the store during uh first saturday of the month and it's by the way it's amazing if you're not using this you should use this is that a true stereotype ramit has told me He was like, my rich life, he like explains all this stuff and he ends it with like, and also to never step foot into a Home Depot.

45:42Yeah. No, I mean, it definitely, at least when I first moved to America, it struck me as like strange how one, how handy everyone was, but how much pride they took in it. Growing up, it was the opposite. It was weird to like, you know, even change a light bulb, maybe an exaggeration. But yeah, I definitely think being a homeowner here, as someone didn't grow up here, you're not prepared for it. that's awesome that's funny all right what tell me about uh tell me about uh this like pickleball thing that you're you're writing about oh dude this is so i've so i was like in terms of things i spend money at after food my second biggest expense in new york right now is a sport called padel um it's pretty crazy it's like is it not it's not paddle paddle padel whatever same thing same sport so i want to say it right it depends like latin america versus u.s either one is fine And it's spelled P-A-D-E-L, not P-A-D-D-L-E.

46:38So Paddle, Paddle, whatever. It's incredible. It's become, in New York, it's sort of, there's a place near my office. It's like the closest we have to a country club because there's not enough space here. But you see, like a lot of our mutual friends are there. We go there all the time to hang out. But I think it's a bigger thing than that. If you look at the Google trend for the word, we're at a point now in the U.S. where we're super, super early. There's like 2 ,000 cords here. And there's like 20 ,000 in Spain. It's on a fantastic trajectory upward. Incredibly fun sport. Demographic with a high propensity to pay.

47:14What is the difference between this and pickleball? It is substantially more athletic. So a lot of people who play this are like, well, pickleball is a game. Paddle is a sport. Nice. I like that. I do like a little bit of snobbery. Pickleball is uniquely American in that like it's like it's like, I don't know. It's so slow compared to anyone who's actually played sports. Like, Paddle has a lot of, like, ex-D1 tennis players. But you're not exactly explaining the attributes of the game. You're more so just insulting them. Yeah. Is it a bigger court or smaller paddle? Like, what's the difference?

47:48The difference is that paddle ball is just a bunch of fat, disgusting pigs, and they're slow, and they're athletic. And Paddle's the same thing. It's just Division I ex-athletes. Yeah. So imagine a slightly smaller yet wider tennis court with a back wall. It's a depressurized tennis ball. So it's quite fast because you have the back wall. So instead of hitting the ball out, it hits the back wall, bounces back, and you kind of go back and forth. It was really big in Latin America and Europe, and it's finally coming to the US in a way that I think you can go to any tier two city, spin up a location, and probably do quite well for the next few years.

48:28I think we're in this unique sort of arbitrage opportunity. In New York, courts are about$300 an hour and booked out over weekends. And again, New York is probably the most extremely expensive market in the US, but it kind of cascades all the way downward. Don't you have like an app? I was with you one time and you're like, oh my God, someone just took my spot as the leader. Dude, it's the worst. It's the game within a game. There's a rating every game you play. and it's insane because I'm playing with people that are all in their 30s sometimes 20s and 40s insanely good at their professional life but they have this like unmet competitive need so everyone is so aggressive about their rating about their ranking like and like a buddy of mine was texting me after we lost our match and we're both in a really bad mood and he's like he's like I don't know why I'm so upset I'm just thinking about my life I have a wife that loves me I have a beautiful daughter why am i why am i so angry about but is it like a is it like a is it a self-reported system how's the ratings yeah so like we all have scores let's say i beat you i entered that in the system and the algorithm is like oh i'm with 3.9 sam is a 2.6 but you only beat him by a little so actually went down despite beating him it's like an elo score exactly and it's the most insane thing because you have all these people taking this way too seriously right everyone has like real life jobs and responsibilities, but people get so cranky about this.

49:56Is this a social network, basically, that somebody's built? So there's a company called Playtomic that's built this in Europe, and they've white-labeled it. I bet that that's also, by the way, a fantastic business. It's just, I don't know how big a market it is, but this one company has a monopoly on this little paddle, tennis, all these apps. Hey, this episode is brought to you by Mercury. They're the fintech of choice for over 200 ,000 companies. I myself use it for eight different companies. The reason why we all choose it is because it has everything you need under one roof. So like my e-commerce company, it's super important for us to be able to easily wire transfer, pay all our different vendors and suppliers all around the world.

50:34And the old way with our more traditional bank that shall now be named, I try it online. It would say no. It would freeze my account. Then I'd have to go in, book an appointment, speak to a specialist who would try to upsell me on something I didn't need. And then finally, after 30 minutes there, then they charge me 50 bucks for the pleasure of that terrible interaction. And now with Mercury, I just go online, push two buttons, and I'm done. It's such a seamless experience. It's very intuitive. Everything's under one place. They basically took all the things any company would need for their financial tech, and they made it super easy to use and put it into one platform.

51:05So highly, highly recommend it. If you're not using Mercury, I question your judgment. So that's it. You've heard it on My First Million. For more information, check out Mercury.com. Mercury is a financial technology company, not a bank. Check show notes for details. you said that new york has a thousand courts and there's 20 000 in spain in the u.s there's 1 000 only in the u.s and there's 20 000 in spain correct wow that's pretty crazy and again the google trend for the sport like just look it up or i can drop a graph it's like straight up into the right and picking up momentum so dumb question here because squash and racquetball almost an identical game to this what are they just like how mad are they that they just like sat there they're pretty mad i mean but squash squash has been on the fringes for a while in the u.s it's like either an immigrant sport or like rich white ivy league like connotation there's there's no there's no in between paddle is also any different it's it's it's become it's i mean it's globally it's growing really really fast and i think it's it's all a case of like catching the right timing.

52:11And it's a sort of sport where you can play the first time and can kind of play it like tennis, you play the first time, you're pretty terrible. It'll take you months to get okay, but you can keep playing and keep getting better. So the community that's formed around it, I think has been awesome to see. I think even Andrew Schultz was talking about it on Joe Rogan. And it's starting to become a thing that we're still early. I don't think it's anywhere hit mainstream consciousness but like i don't know it's may 12 2025 come back to this in two years i think it's gonna see a lot sean last year i went to a my friend held an event at the padel court and i wasn't sure padel was a sport or a brand i didn't i wasn't sure what it was but when i went there i think it was the same place on her that you go to the whole place was all black like black walls like as if like berries or soul cycles like it had that vibe and it was like everyone was like hot and cool and like it was definitely a scene were you good i didn't even play i was like at an event but i was like watching these people and like i got the vibe when i got like when i got there i was like oh they're like this is like a they're like you know they want to exclude people from coming here like that's like the vibe that i got like if i don't wear a college shirt they're gonna kick me out like that's like that was the vibe that i got like i can smell the racism you either pickleball or paddle?

53:34I, no, I try to play like real sports. I don't want to play those things. No, I don't order. Yeah. That's a game. No, I don't, I don't really like, I feel silly playing paddleball if I'm being honest. The one thing, the one thing I dislike about New York is it's so hard to have a country, like a country club or a place you go and can have all the sports. So I do think, smaller spaces like this are potentially one of the answers. Because I, again, I have a bunch of friends that are like dads for the first time. A lot of them don't know how to make friends as an adult dude, right? Like they're like, hey, I've moved to a new city or I've like, I don't like my old friends.

54:17And how do I actually make friends as a man that is not dating, not drinking, not going out? What do you do? And I think places like these are the answer quite often since people come there, hang out, chill out and some community forms around it and all that how do you meet friends sean no new friends baby no new friends i'd try to keep i'm trying to do a good job keeping in touch with my existing friends rather than make new friends now there's a lot through the school actually so like once your kids get into school the priority sort of shifts to like well i'm gonna be around these people anyways let me just find the coolest people of this group because i'm I already have like three things a month that I have to do with, you know, this set of people.

55:02So is there anyone here who I get along with? And then secondly, if I can, then I get the double win because I get the play dates for my kids while I get to hang with somebody cool. So that became like the focus for me rather than like, you know, going and individually making a friend. And then, you know, I got three little kids under five years old. Like if I'm going to go do a hangout with my friends, that's a pretty hard, like that's just like a choice that's only benefiting me. It doesn't really benefit like the whole, it doesn't integrate with the rest of my life. But I do, I do play in a basketball league that I treat like uber seriously like this.

55:34Our friend Ruben runs a basketball league called SF Hoops. He's been doing it for like a decade. And we play one game a week and you would think like, oh, it's just like this wreck ball. Who cares? Pick up basketball basically. But no, like I take it so seriously. Like basically the six other days of the week are just preparation for the one big game night. And then after that, you know, we come home and I basically get the footage off the AI camera. And then I start sending clips to the team. And I'm like, hey, like, you know, partially funny, like, you know, just commentary, but also like, yo, we got to correct this for next week.

56:11We're not going to, we can't do this again. And so we take it very, very, very seriously. It's exactly the same in our groups because it's a 2-on-2 sport. People are sending coaching videos back and forth and the whole thing, the whole thing is pretty insane. You bought a piece of a cricket team? I bought a piece of a cricket team. What's the story here? So again, flashback, I don't know, age 8 to 14, cricket was the only thing I cared about. I wanted to play professionally. I played internationally for the country I grew up in. It was sort of my first love. And I think we've all felt this, where the older you get, the more you're like, I want to do what the 8 or 9-year-old version of me thought was dope.

56:49and then I got in touch with someone who said one of the shareholders in what is the most valuable cricket team in the world they're like worth roughly about a billion dollars in the Indian League was selling a stake and I was like like this is the whole point of having money right to be able to do things like this so I ran so I put in a bunch of dollars myself also put together dollars from other investors we now own a small piece of the team but in time the idea is can keep buying a bigger and bigger piece since I joke about this a lot but like you got to be like the non-douchey chamath the douche part is uncertain for now yeah so which team is it and you like ballpark we're talking like six figures seven figures eight figures how much did you put in um I put yeah so I put in seven seven the the group we represent put in high seven figures of which I think I was 20 % was my own dollars.

57:53The valuation of the team was close to a billion dollars. So as a percentage, it's still tiny. The team is called Chennai Super Kings. They've won like, I want to say six championships. The Indian League is about 15 years old. So they've won more titles than any other team, highest market cap. And dude, it's such a monopoly because India is the biggest country in the world. And it's truly a one sport country like the delta between sport number one and sport number two is a massive and as far as the league goes they just have so much room to run since it's still not that many teams the market is maturing really fast it already is the third richest league in the world um there's i think it's also a fantastic investment where like it's not going to generate tech startup returns but it's not it's unlikely to lose money like there's such a long way the sport has to run You said it's the third most valuable league in the world?

58:47Yeah. It's after, it's by TV rights per game, it's actually number two after NFL. And like by total revenue, it's more than any of the European soccer leagues, for instance, which is crazy for a league that is. It's like worth more than the Premier League? How is this possible? How could the most valuable team be a billion, but the league be worth more than, like, there's like players in soccer that can almost make a billion dollars. um well i'll i'll quote my source after this but it is the whatever source had it the league being worth more than the european leagues which i found crazy and my interpretation was the european leagues are just very bad at monetizing their commercial value like maybe the value in the league is to the team so while manchester united may be worth substantially more the franchise value on the epl may not be that much that was my gotcha have you flown there and and like participated in any of the i haven't had a chance to because this this deal came together very recently so i haven't i haven't done it yet and long term that's what i actually want like everyone's like oh wouldn't it be cool to like earn the upside no i want to i want to draft players i want to be able to kick people out like like to me long term when i have time that is the more fun part of this whole thing like sure don't lose money but being an annoying overly involved owner i think hell yeah sounds awesome i don't know if you did you did you guys read about do you guys read about this vc dude in europe who like bought a soccer team and then he put himself in the team yeah no but that's awesome yeah who is that he's like a player on the team i and it's so funny because 80 90 of the world are like oh that's pathetic i also was like that's awesome i would totally do it did you guys see did you guys watch the the netflix show or something i I forget what it was on, where Ryan Reynolds and – Rexha.

1:00:33I didn't watch the show, but, yeah, I read a lot about it. How has it turned out, Sean? Do you know? That's been like four years. I think it's going well. They got promoted I think a couple times, actually. I think they've moved up a couple times. We had a guy on the podcast, Haralabob, who did the same thing. He's bought a team in the – that's like, I don't know, third division team or whatever. I don't know which division they're in exactly, but they're up for basically promotion, and he's like bringing like Moneyball, which is he's basically like a kind of data guy and he's a sports better.

1:01:03That's his background. And so he's bringing like a Moneyball sort of approach to like drafting the right players and not drafting, but like, you know, signing the right players, playing the right strategy and selling at the right times on players. Did you see the Celtics sold for 6.1 billion? So that basically changed everyone's model, right? Because people were underwriting sports teams being worth one and then two and then maybe two and a half three they sold for six it's kind of put into question just how much the rest of these teams can be worth so who do they sell to can i was some p group yeah it doesn't seem it just seems that the sports teams are just uh it it seems challenging it seems like a very challenging thing as a i mean i'm a little plebe nobody but it seems like challenging to have a proper market for it because it seems like one of those things that if you want it, you want it.

1:01:56Do you know what I mean? It's like a domain name. Like, it's very hard to be like this domain is worth$400 ,000. There's such few supply and demand is both very, very limited. There's three potential buyers and whoever wants it, it will potentially pay. Like if Jeff Bezos wants a sports team that he grew up with, he will almost pay an unlimited amount of money and it doesn't have to make sense. And that sets the market price for the next four years. Well, the number of billionaires keeps going up. The number of teams in the NBA is basically the same. They're about to launch, they're about to open up two new franchises and each one of those will get$6 billion.

1:02:30And then that revenue goes to the other owners. And that's like - Wait, two new franchises, wait, what? Like the NBA is going to expand two more teams. They're going to do like a Vegas team and they're going to do probably a Seattle team. And they wanted the Celtics franchise to sell at a very high price point so that they could then go to those new franchises and say, you're also a$5 to$6 billion price tag. which is pretty crazy. I mean, like, you know, when Mark Cuban bought the Mavs, I think he bought them for like 200-something million, right? Like the original Celtics owner just sold for$6 billion or whatever.

1:03:01He bought it originally for, I'd have to look it up, but it was like very low. It was basically like he compounded kind of like 20 % over, you know, a 25-year period or something like that. And so he, you know, he did really, really well on that investment, won the championship last year and then sold to this guy who had previously started a, or was a partner at this big PE shop. And that guy was a lifelong Celtics fan. And same thing, like, you know, it's a trophy asset that also has like all these other interesting things, which is like the media rights and other things that are - There's the time that's in the US, you can also get massive tax write-offs.

1:03:37Like there's all kinds of weird tax stuff where like some people have taken player contracts as a depreciating asset and use that depreciation to offset income. So crazy stuff. Right, and there's like a real estate play. So like basically some of the teams buy their own state, they own their own stadium. So they actually own the real estate and then they buy the real estate right around the stadium because they're the hub. And so they know that that real estate right around it is going to be really worthwhile. Some people are trying to open up casinos because now sports betting is legal, which is like this whole other vector of like how to generate revenue.

1:04:08So you have all these. And then, by the way, your expenses are capped. There's a salary cap, like in the NBA, for example. So like you can only pay so much, but you can still earn, you know, you can still earn more and your franchise can go up in value. We I went and heard a talk by Mark Lazzari. Do you guys know who that is? He I think he owned the box and he was telling a story. He was like he his whole he's a billionaire and his whole thing is buying sports teams now. And he's like, there's basically two ways to run a sports league or a sports team. The first way is you run it profitably. And if you run it profitably, you will lose.

1:04:45Your team will lose. Or you run it in such a way where you lose$200 million a year and you win championships. And then you hope that you can sell it for enough money that it works out. So he's like, you either want to win and you got to have a lot of extra cash flow to cover this nut or you're going to lose, but you'll be profitable. You pick one or two. I bet it also depends on the sort of sports. salary again that was the whole money ball approach right back in the day or whatever where like you're spending a lot less but relatively speaking you're doing well um i think for a lot of people it's at least for me all of a lot of people who do this had at some point failed athletic ambitions and there's a few ways those can manifest either you can make your your kid play a bunch of sports or or you can buy a sports team and still feel like you're doing the same thing well we talked to a guy uh i don't believe that that thing is true like the warriors win The Warriors generate more revenue than anybody in the NBA.

1:05:42They're worth$9 billion now. They did all of the above. So I don't think that's necessarily true. Revenue or profit? They're also profit. Well, it may be true in Milwaukee. Yeah, exactly. I think in small markets, that actually might be true. Maybe. And we were with Alexis at the basketball thing, Sean, and he was telling us about how he invested. He bought the women's soccer team, no? He bought the women's soccer team. He's starting a track league. He invested in that. He also told us about how he either did buy it or he was trying to buy a piece or a team in Tiger Woods' new golf league. Or, you know, this weird like stadium golf league, which sounds pretty awesome.

1:06:24And he was like, well, the numbers sound crazy. I don't remember what he said, but let's say hypothetically it was$20 million. He's like, that sounds ridiculous, but let me explain the math. Like this sport gets this amount of views and they make this much money. this sport gets this amount of views. They make this much money. Therefore, and he backed into it, and it made incredibly high numbers on the surface seem incredibly reasonable. I heard another guy do the same thing with sailing. This guy, Mark Lazar, he was like, I'm trying to buy a sailing league. And he was explaining the numbers. And basically, the whole business of the sports stuff was basically finding undervalued media rights and figuring out whose contract is going to end soon and I want to purchase them and renegotiate the contracts in such a way where I get value.

1:07:07Yep. And the U.S. is so good at this. Like back to the European leagues. Yes, some of them are massive teams. But I bet if you look at the numbers and how well they monetize eyeballs, it's terrible. Like in the U.S., you have very small leagues that are so good at like squeezing out every last dollar. Like the NFL, obviously, is like a world class case study where they're monetized so well that they're literally hitting a point where they're like, we need to go outside the U.S. to like meaningfully still grow from this point. That's insane. Ankur, awesome hanging out with you, dude. Yeah, it's great.

1:07:42Great. Thanks for having me. Where do people find you? So we're hosting a big conference for people who are seeing this, sponsored by a lot of people at HubSpot and The Hustle called the OOO Summit. It's this Friday. So we'll be seeing a bunch of people there. Otherwise, I'm active on social media. My Twitter is my name. And for any tax optimization stuff, carry.com. All right. We appreciate you. That's it. That's the pod.

1:08:23Hey, let's take a quick break because there's a quote that I love I want to read you. It's that we shape our tools and thereafter they shape us. And, you know, as an entrepreneur, if you're using a bank that was built in the 90s, you're operating like you're in the 90s. And trust me, I've been there. Clunky portals, random holds on your money,$50 wire fees, and then being told, please visit your local branch. Well, that's why I switched to a different type of banking solution, Mercury. It turns your financial chores into a smooth workflow. You can do wires, invoices, cards, reimbursements, two clicks, and I'm done.

1:08:53If you're already using Mercury, respect. If you're still using one of the old big banks, I got questions for you. So go visit mercury.com and give it a test drive. Mercury is a financial technology company, not a bank. Banking services are provided through Choice Financial Group, Column 8, and Evolve Bank & Trust members, FDIC.