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

i've now met so many regular people with eight to nine figure roth ira on which you won't owe any taxes at all and a lot of them have done that with vanilla investing i feel like i could rule world to know i could be what i want to from at all in it like a days off on a goal less travel never looking i think that we're gonna do basically like first half of this is like money tips meaning like you know sort of like for personal finance stuff that nobody really teaches you you know because we get most of our personal finance information either in from two really bad sources either your parents who probably only knew so much and like when your a little kids you think your dad knows everything but then when he grow up you're like oh he's just a guy and like you know he did the best he could with what he had and the other thing is like you know tv or books or salespeople who's was like their incentive is very different than yours right like one of my favorite youtube videos is like about it has a picture of jim cram and it says will this will this very loud man make me money if it's like no he will not the blinking lights on this guy's screen and that this money guy on tv is not the guy to list too so we'll do that and then you had a bunch of business ideas also like the jeep brainstorming your cheat sheet of startup up ideas so we'll go to that after but sean do you do you guys know each other well by the way don't even know we've never hung out and person hung out we've exchanged we've tried to hang out haven't hung out the last episode was the closest we've gone i like all way every time we talk yeah so let me introduce you sean this is my friend ak this my friend sean i've known ak since two thousand and twelve for two thousand thirteen and we've been buddies since and i've known sean since two thousand thirteen two thousand fourteen i think of i'm one of the only people this one that's met sam of the internet who's had beers with him that's how that's how far back we go it was a long way it was a long time ago so give his was give his background on his bio so when i met on he was doing a facebook app that went viral and he made his first couple million dollars at the age of like twenty six or twenty seven no bro oh twenty what what was the app all this silly stuff personality quizzes friend quizzes how like answers seven questions and you find out how good a kiss where you are crazy stuff like that then he started a company called teachable he was early on the course game he's he nah he didn't quite bootstrap that company but he owned the majority of it and sold it for something like a hundred and fifty million dollars which i'm sure you get correct me if i was too low and then now you have a new company called carrie was like too low it's two fifty but closing off oh no that's not even it's all it's all around here at that point but you made like a hundred million dollars when you were what thirty two years old yep i mean that's insane right did it feel more insane to make a million dollars on a silly facebook app like how good of a kiss are you or was it more insane to make a hundred million dollars on this company that you you know this education company zero to something is always more life changing undoubtedly right like that was also the time where i just moved to america i was an international students i didn't really have i was so new to everything but like making money in college allowed me to like not go to class and like realized that if i can do things on the internet like why why ever get a regular job how much money did you have at your bank account before you sold teachable like one and a half two like basically i was flat i didn't really spend money or grow money during that entire sort of time paid myself eventually a salary of a hundred and fifty grand which in new york was like roughly my life break so then they when you when you got your exit that you just moved the decimal points at place like two points right yeah million basically i mean we made like little bit over forty in cash the rest is equity but the equity is pretty nice it's just this random thing that you know keeps paying you out i love that you're open with money i'm almost out of question what else do we you yee he's dev everything this is amazing well you you sent us this list of topics and you said when i sold my company i ran an ab b test with the money i made i gave half to goldman sachs to invest and i invested the other half yourself i assume could you just talk about this what why'd did you do this and what was the result so like a lot of founders that first sell a business most of us know nothing about money i don't know sam if you knew much or whatever and i you get hit up by every single one of the private world people they're always in your emails and you know you read the big big brand goldman sachs morgan finally so i talked to them i couldn't fully tell how legit they were and i had enough money where i'm like know what let me take a sizable chunk let me give them that amount of money and see what they do the other half let me try and learn and figure stuff out myself and went through sort of the standard start post exit start founder thing where you invest probably in too much you don't say no enough you go through a period where you think you're investing genius but it was cool to sort of see that develop over five years and now to have actual results and what were they what are the results the results are in retrospect there's nothing that special about private banking there's a lot of clout that comes with it but you look at the sort of portfolios they do their very vanilla and they charge you anywhere between fifty basis points to you know a hundred and twenty basis points the best part of my portfolio that they did was simply indexing the s and p the s and p has returned about thirteen percent at that time they did a lot of other stupid ship at average it down to six percent what sort of stupid that they gets you into was it like exotic you know is it random exotic things was it real what what are they putting you into and were you saying yes or no on a case by case basis or they were making decisions so in the sense of the clear they brought your average down to six percent than it yeah dude that's like a the meme where there's like a guy like putting a stick in his own front spoke as he's running his bicycle yeah but again the insane part is i i genuinely think now that i know more about this like you can't fully judge the performance based on like five great tiers like theoretically that portfolio should protect your ass in down years of the market right we've also had an a atypical good time but the things that we're rough with them is one for a lot of products they charged over a hundred basis points to basically do what vanguard funds could have done they also put a lot of fixed income which is bonds and stuff that so thirty one thirty two year old with like infinite risk tolerance it doesn't really make sense right so eventually i got them out of doing a lot of those things but the whole process of kind of working with them you realize all these people their product has such insanely good margins that they can afford to do whatever and they really sort of sell a lifestyle that now that i know more it doesn't make sense for me but for a lot of people who newt the idea of having money it's kind of a you know it's it's a it's a status thing as well right like what did you what were the what are the perks of the status i mean you're a single guy surely not walking around sure that says i work with goldman like what whoa like what's or what what did you do it it didn't it didn't make sense for me like for me and i never valued it that much but yes they have a you know concierge team that can you know get your tickets to the us open and like take you out for nice dinners whenever you want i was the wrong target demographic because when they wanted to get dinner i'm like fuck it's another person to hang out with but there's a lot of people who really enjoyed that side of it they're like these tech guys are the best they're introverts they don't even take us on any appreciate we just get to charge of the fees it's wait so that's a really expensive us open seat correct i mean you do the math right and because you get charged the percentage of your assets you never feel the pain but you're paying them six figures a year if you have to cut them a check for ten thousand dollars a month you're like auditing that all the time but that is what is so genius about this business model where you basically just keep running through this and over the course of your lifetime you end up with many many millions of dollars in fees and it's not just a fees those dollars would otherwise be invested whenever you run the math you realize your ending portfolio is probably ten million dollars smaller twenty or thirty years from now but what's the argument against this because they've been around for a hundred years they're huge a lot of aren't rich people use it surely they're i mean what's the value i think the sweet spot and in fact i think our friend ram talks about this a lot is i think financial advice is incredibly valuable i think they serve a really good purpose but at a certain point the math on going flat fee is just substantially better for you right like if you have five million dollars fifty million dollars five hundred million dollars they don't do dramatically more things yet every step you pay an order of magnitude more in fees i think there's a lot of fantastic financial advisers you pay them five grand a year ten grand a year twenty grand year i don't care you can easily get an roi there but it's the whatever one percent of your wealth that's the part that gets really silly the better and better you do i wanna ask you about indexing so indexing obviously super popular now and you had some note on like simple other other ways you can index that are you know maybe things that people should consider yeah so in general like my overall thesis is more most people you're not going to get crazy differentiated performance from investing but that's actually okay it's kind of wild that an average person like again think about my example i had all these financial financial advisers i had so much differentiated access we know so many entrepreneurs founders whatever the best part of my portfolio was indexing the s and p five hundred and historically that happened a lot so most people should not try and find alpha on the investment side however if you can be smart about saving money and taxes that is where your alpha comes from so one example i think sam and i talked about this on twitter i've started to do something called direct indexing thing where instead of buying a vanguard fund it buys each and every one of the five hundred companies individually and the advantage with that is you have more positions so more volatility at any given point more companies are down so you harvest those losing positions so net net you track the same as an index but you'll get thirty forty percent of your investment has a usable tax loss say sam do you do this by the way no because i think my i'm not entirely well versed on it but i don't do it because what i'm doing is working just indexing and i sleep better at night and number two from my understanding ak those those gains eventually go go they go away so if you lost you're investing on an ongoing basis so if you do a lump sum investment after three years you'll harvest most of your losses but if you're investing x amount per year that kind of infinitely goes long but no sean i don't do it do yeah i do so i i vest in this company called f and they do this so okay you receive f i i'm i'm actually a little bit nervous because i use them as well but i don't wanna be their biggest customer i have a couple million holders on record and i don't wanna put like i was little nervous about putting like five or ten or whatever on them i'm an investor to but yes i i use i use them guys are really far behind he sort of sap down explain it because i was like look don't assume i don't know anything because i read this and it sounds good but it's kinda hand waving to like how does this actually work so he he explained it and i said okay cool i put two fifty k in as a test so i've basically doing the exact same thing i otherwise would have been doing it exactly which is indexing the s and p so i got the same performance as the s and p but i i on my two hundred fifty k i added an extra sixteen thousand in tax loss harvesting just holding the same exact asset as it wood before and so and you know you like you i was like wait should i give the startup up like millions of dollars or or you how do i wanna do this and like you know then he's like well we don't you know all fintech is basically built on top of other like providers you know other pools other other pools of money so you know they're it's not a startup up that holds your money it's like you know the custodian is usually somebody else same thing with robinhood hood and others like so anyways i think it's kind of amazing like an even simpler example if direct indexing thing is too hard is most people right now keep their cash in like a high yield savings counter or something but if you are a high taxpayer payer there's likely better places for it you there's either mu funds or you pay no federal taxes there's treasuries where you don't pay state and local taxes there's new funds specific to new york and california where you won't pay federal and state taxes like we built a very simple product that will just take your cash calculate your tax rate and find the best money market fund for you that itself will take your tax equivalent yield from like three four percent to like six seven percent when i hear you say all the this for most people when they talk about this i see a lot of people talk about this and i think it's to myself you guys should just focus on earning more money you should increase your revenue first increase the revenue and then worry about totally totally like there's some percentage of people where they're like oh my business makes fifty grand a year how do i save money and taxes it's like bro you don't have a tax problem right you you need to make more money like i was at the i was at a bike shop the other day and i was looking at a bike and there was a bike that was twenty five hundred dollars and then there was a bike that was like five grand i was what's the difference and they're like like two pounds so it's a lot and then like this water bottle was made out of carbon in this and i was like well i'm kinda chu so why don't i just lose weight you know like when i is like i could like lose five pounds just by not eating for like you know a week and and and i'll save myself that money and i'll be fitter how about that and that's kind of the same thing absolutely i think i think for people like like i i'd it matters at our level when the compounding and stuff makes a big difference but at like thirty forty fifty k in revenue making more money is is far more effective i'll you say two these things one this like direct the direct direct indexing i like these because these are set it and forget i've made a decision it took me two seconds to just roll i literally push a button and it it roll does the aca cat rollover over of my s and p whole etf holding my vanguard d diff holding from one brokerage to theirs i never had to do anything so it's like it was a two second change that has since yielded like you know eighteen k sixteen k of extra fax losses that i have yeah exactly like so i don't have to do anything is i would never do that if it was like something i have to keep thinking about or keep doing something on a regular basis same thing what you're talking about with the buying mu bonds mh versus holding cash in i'm in a money market right if you just get put cash in a place but like okay it's earning like three or four percent well if you could just do the same thing with the medi bond just not pay the state taxes like it's a it's the same one decision didn't take you any extra time for the average person though i would say for the person doing nothing fuck do a vanguard fund that the most important thing is to do something but for the people that already have an index fund this is the sort of alpha what else what is on the list of like alright your wired tens of millions of dollars you're worth nine figures i expected this to happen in terms of financial investments someone was gonna present like this amazing deal to me someone gonna offer this amazing service and it just was not what i thought and everyone could have access to this for the first time i felt like it didn't matter if i failed even though arguably i needed the dollars more now it we would feel so stupid to fail i've been on panel telling other people you should run your company and you know they you have like this time everyone who joined the company did because they're were like oh you know this guy will succeed again so i feel like my pressure on myself and it's fully my own construct at the end of the day can we switch away from emotions and you tell you how to mega backdoor roth i don't really care how you feel i just really wanna know about this roth tax optimization what is this this is been this has been quite a while i wanna know how deal made five billion dollars and didn't pay any tax audit it what what was that yeah talk to her later she whisper softly tell me about my backdoor back door yeah but yeah peter every well a lot of people write about peter t what he did which is like tax magic is most people have access to roth ira he put his paypal founder shares in a roth ira sold those for about twenty seven million dollars then use this as a supercharged investment account to where it is today where he has five billion dollars in his roth he turns he retire next year so he gets all the fab and no taxes but it's you gotta done this down man what's a roth ira like you gotta like talk down me a little bit yeah so roth ira is an account that the government basically has gifted to taxpayers there's a guy named william roth who i think you know fifteen twenty years ago or whatever created this account ideally for the middle class it was never meant to be for the richest people where you put in after tax money but then all further growth in that account is tax free including no matter how high tax rates go in the future right so if you look back in the nineteen seventies do you know what the top tax rate was in america this is like twenty percent there's like eighty percent it was insane like the top marginal bracket was like eighty or was super high but the advantage for roth ira is once you have dollars in no matter how high taxes get you pay nothing on what is in that account and what was the inc centralization there for these people so the it was a very short term incentive at the time because the advantage is the government gets the tax revenue today because you're putting in after tax dollars today you're giving away in the future is future revenue but you're actually collecting more money up upfront say why would the government agree to this they want incentivized retirement savings in general and compared to traditional ira this brings this brings tax revenue forward but it was always designed in a way that there was a maximum income once you make more than a certain amount you were not supposed to have access today those numbers are i think a hundred and fifty thousand dollars or something you're not you don't really have access if you go the normal route but that's where you have things called the backdoor door raw rate but before before you explain that so basically it was if you make under a certain amount you can put away some seven thousand dollars or whatever a year and you so you've already paid tax on it you put it there now it's gonna compound tax free when you take it out after all those investments of compound compounded you don't pay any taxes on that money because you you sort of paid it up upfront when does it get be an age limit like sixty five you have to see yeah you get your dollars at fifty nine and a half but you can take out the dollars you contribute at any point for any reason it's only the growth that is kind of locked up so what peter till did which was great was he put his paypal shares in there when they were valued at nothing so it was like exactly he bought his founders shares at like zero point zero zero zero one dollars or whatever and he probably knew hey this is a good chance that the thing can become valuable it's crazy by the way he only made twenty seven million dollars on paypal health twenty seven million dollars at least from this roth diary but in seventeen hundred dollars worth the founder shares and he made twenty seven or twenty eight million dollars okay so then and then he used that money to invest in facebook within his roth ira so then the facebook game is why it could became billions of dollars exactly but you then read about mitt romney doing the same thing but because i in this line of work i've now met so many regular people with eight to nine figure roth ira which is insane because you have you know ten to a hundred million dollars on which you won't owe any taxes at all and a lot of them have done that would somewhat vanilla investing like so tell me a story of someone who's done this with so eight or nine figures so you're saying ten million or a hundred million yes exactly so roth ira limits are normally seven thousand dollars a year the challenge with that is it's tough to get a lot of money in the whole game becomes how do i get a lot of money and once you get twenty million going from twenty to much more is actually easier it's how do you get the first amount of dollars in so in addition to the backdoor roth ira there's something called the mega backdoor roth ira which i these yeah the naming of this is not is not ideal but what about the triple vega right it's like the least the least creative days of all time but the mega ba roth ira lets you use a four zero one k to get in seventy thousand dollars a year into this account so you can combine the to get in seventy seven thousand dollars a year i actually sanity tested this i built a very simple model that makes the assumption that you start contributing to roth ira area by twenty one the mega backdoor by like thirty even if you just index the s and p and you'd look to the hundred year average of the s and p you end up with thirty million dollars in your roth by and retirement so it's if you do this consistently enough the tax benefit here is massive okay so who came up this making instead make i go back yeah all so the way people find the loopholes is the irs never intends for it to be this way they write the law a certain way some smart ass accountant is like well actually if you do this this and this we're still fully in compliance the irs challenges this loses in court and that's how we have loopholes like every single loophole comes the same way the mega backdoor roth for instance and there's been legislation to for the last few years it comes up every time but the existence of the fact that someone wants to make make it illegal by default deem dis it's a valid loophole for now so it's the sort of thing that like this gets negotiated down every single time every single tax bill has it typically the republicans fight against it and it just gets deferred and deferred and deferred and what are examples of people who have done this to ten or a hundred million dollars so you what their name address what do you want him them to say neil no you could do a little chat of house rules you could kinda of like an them a little bit so i will tell you that these are people that you and i have never heard of there there's a lot of like anonymous wealthy financially savvy people where it's a coalition of families and they have a family office that specializes in this sort of tax alpha as a service but it's just a case of doing all the fundamentals together and then having very very good investments but i think if you can structure your four zero one k a wave that you can put in seventy thousand dollars year into roth ira which i do now honestly just the sport of the sport if it is is is fun enough and you do this over a long enough period of time you have these results it's the sort of thing that we don't know how long this loophole will exist but for now it's like you know hundreds of millions of dollars with zero dollars in taxes it's very good insurance from where tax rates may go in the future let's truly we switch to business ideas sam yeah let's do cool so ak you sent us a list of ideas that you think any founder could go build or you think that some founders should go build in this space and you've started multiple successful companies now so maybe you have interesting taste and maybe you're looking where other people are not because when i saw this list of ideas these were not the like same five ai you know assistant ideas that you hear for most people so hit us with your favorite one and let's go let's go and let's go in order sweet so i'll i'll go in and i'll go in someone random order because have a few different ones but one of the things i think about a lot is right now there's such a focus on proactive health and wellness i don't know new york city for instance people are spending all their time not at bars and clubs but at you know sauna and cold plunge or whatever and you have all these high end executive services for like concierge health basically you know power function health function health i don't you guys have to explain this basically what they do is you do a blood test and tell you all about your body and and everything but this has existed for decades i've been using it i started using these years and years and years ago this company function health has skyrocketed and i think in the course of like two or three years it got to a hundred million in revenue i believe they've just raised another round of funding in the billions i have no idea why this category is booming like it is because it doesn't i i didn't know this i don't know how this makes it any different from the decades of other companies doing this before and it's comm commodities everyone uses the same blood testing companies it's it's but i'm telling you we're just moving to a world of proactive wellness like i think everyone has realized like the medical system in the us is you kinda sit back and wait for really bad things to happen and people of our generation have realized that you wanna be proactive about this and not just not just kinda chill yeah i think i think there's a bunch of factors right like there's there's the brian johnson's of the world so now you have these really big attention getting influencers who are bringing attention to you know your health and wellness and making you realize like how much of a knowledge gap there is how much of how much more you could be doing you might have thought you were already doing enough and you somebody shows to you that there's a new level to right so you have the the influencer side underneath you have all the infrastructure so you have lab testing in all these different places so you can go get your blood drawn you know when i went on supermarkets it's like cool go you know do you want some a nurse to come to your house or do you wanna go point eight miles away and there's three locations near you and i was like wow this is like amazingly convenient then the next piece is that i think the hipaa laws change or the medical records stuff changed so i just gave them my id and they pulled all my health records i never even had that myself like 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 saying 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 party the cooler you were right the more to more sort of bad for you your lifestyle was the coolest you were now the more good for you the lifestyle you have the better you the cooler you are and i don't know if it's just i changed or culture changed tell me how are your results oh you didn't see my tweet about this yeah what did you what did you say i said oh i just found out that my chronological age thirty seven is different than my biological age forty but long term i'm not concerned because i'm just gonna 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 twenty three year old you know russian gym cool thanks for i i'm so have to use this app why were you so i'm the only person i'm the only reason i've ever seen with a higher balance never i've never seen anyone i i think i broke the record yeah what what was so old about you well so it's pretty cool because actually the next thing that happens as they go there's a concierge doctor who basically is gonna in a week give you kind of an action plan so it's says okay look we did these thirty tests in one and a single blood draw to do these like thirty tests right and they say look right now let's say i don't know let's just pretend it's like you're 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 level little chat here where somebody's want you 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 p people do go to cold plunge for six minutes like all those things and you come up with a an action plan so you know whether this is like life changing or not they're probably just could be like y like delete door dash off your phone like you know that that'll that'll probably do the trick like there's you know there's a few different ways that you could 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 times they're like yeah it'll never really run the same right like we're we're in maintenance mode from here on out whereas at least this operates under the assumption of being proactive rather than reactive and that there's actually something you could do there's there's actual lifestyle steps you can take and not simply like medicines you can get on to improve your health yeah i 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 held allergies like shit's kind of falling apart in a lot of places and people are reacting to that but by the way the the upsell in this thing is crazy because the the initial deal is super right so it's like five hundred bucks and you're gonna have like a ten times better version of your annual physical so 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 five hundred bucks and get a better version of physical but when you're in there it's like you wanna know how that gut doing on a microbiome test i'm like yeah i'd love to i kind of a dude die i had click next the upsell page on function health i did function health i clicked to next i'm not joking fifteen times i didn't even click i clicked yes i was like yep give me an allergy test give me i'm 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 ups sold me like a couple thousand dollars worth of test but honestly like great i wish my doctor had been offering me these like why doesn't my doctor like offering me these either these they do it they do it the other way around they're like oh you wanna get your testosterone checked feel like fine there's oh can help them yeah what's your wife's gave you i'm like what why so personal so 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 if 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 rec recite two inches and you you get you you tie an alexa 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 look ups with improving your aesthetics i think is a fantastic business this is actually a great idea we we had justin mayors on the podcast and his skin was glowing like it would he's glowing us about like his inner health and we were just like handsome yeah how's was the dude your hair is full your skin has a glow your teeth nice can you just tell me about that and so yeah i'm on board we went out to breakfast sam and he what literally everything he ordered i just said whatever this man i need to eat so he ordered this drink i said the way to looked me said did you not understand the instructions whatever this man eats i eat and so i had a identical realtor but but i would you have to like stamina our investors in a testosterone company and if the founder was not jacked i would not have invested in the company like i think i think that's true 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 if it would crush we already have concierge medicine in turkey stuff like that secondly i think anything that helps us break out of the us food system will will do quite well and again probably more so in cities like new york but it's kind of funny like 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 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 us food system and i think businesses and enable people to do that will go quite quite a long way and so how did you find this amish farm like what what was your process to find this this alternative though were so it's word mouth a lot of my friends were all talking about it and then someone's like i get my beef from this place and i'd actually started out with like you know you buy beef and then you get ups uphold them 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 not even relevant or helping but you know they they were they were pretty 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 if you have a thirty minute window to meet them and as much as the joke about it it's actually pretty cool it does improve the quality of my life i do think the products taste well raw dairy is more of an novelty you know that's something that like sure and i'll add four dollars for the for the raw milk but i think breaking out of the us food system at least you know we'll see what rf does but in the short term i think that there are a lot of people that will pay quite a bit of money for duke get all your meat from this this amish fellow i do it's so good like like dude i don't like chicken in america like if someone has 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 us but we all need one of these amish guys isn't this 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 it's more like a drug deal and i actually that's kind of appeals to me in a way like farmers market it's a little bit like oh cute date on a sunday morning but like i kinda like an element of danger with my groceries this is i think this is this is contra band this contra sex 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 humans since i shit marriage can we ground it up and rejecting in my face and that's usually i do what it says not for cubic it's like 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 meeting this or or don't control for placebo placebo is the past placebo was a mess right yeah yeah whatever i read about these i'm like wait so you have like study like the way when we were talking about placebo but we act like it's like it's an issue and i'm like wait a minute you're telling me i could take a fake thing and she asked me the real results give me all of the fake things almost that's all i ever want is 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 i don't think it was the addition of the alcohol i think it was it was just just a food system it could've have been that it could've have been some of the other stuff here chatting on there too yeah could could've have been never just alright next idea is a travel agent but for credit card points like again i have i'm 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 two hundred and fifty thousand mx points a hundred thousand chase points i'd pay a good amount of money for someone to go find me two first class tickets to someplace place warm in the summer how how how do you how do you want this to work i want this to be a concierge service i wanna 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 they just do it for me jack smith is a friend of all of ours i believe jack smith very when he suggests something you you take it seriously even though he's 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 flight fox dot com and i've used it a couple times but basically you sign up and at the time i think it was free now it looks like it's twenty dollars per ticket you tell them like roughly when you wanna do something and there's just 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 this is amazing it works every time it just like your credit card points and stuff or is this just dollars yes 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 dot dot com and book it let me tell you another the crazy thing have you guys ever heard have you ever bought another bought or sold another person's smiles 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 have you ever heard of this sean i've heard it i never done it before have you done it i've done it so i booked a flight where i i had a friend who spent roughly ten or fifteen million dollars a year on advertising with his am card or some some credit card and he's like i have all of these points if you wired 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 that the flights i think i saved forty percent or thirty percent something like pretty significant because i was buying like six six first class fights it was very expensive and it was like thousands of dollars that i saved so who's who's this friend basically what they're doing but as a true sort of professional service is how i would like it to work and i think you can now automate a lot of the back end with but there's an 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 were they take your if feel like a disproportionate number of my ideas are turning out to be illegal but yeah yes so one say about the financial services company that you currently run alright illegal wall milk i don't i don't i don't i don't want my chief compliance officer dude that's i i should add nothing shared here should be considered as legal advice investment advice or tax advice everything for information either or advice all that's fine that's not that regulated in this country but but you're right on the points thing so like i use like seats dot arrow i think which is basically you plug in what point you have and it's like a search engine but it's like very slow it's very hard and i have to do it myself you're absolutely right like i want either a human or i i need like 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 like just want to go somewhere warm in the summer like it's okay if it's puerto of it's okay if it's hawaii right like i'm i'm not yep as dead said 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 seven million am mx point seven yeah exactly there's so much arbitrage but you have seven million yeah at least seven million how does that convert is that like seventy thousand dollars once you're get good at it the value is so much more than the dollar amount but finding the purse 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 so you still use airline points like crazy still neville destroyed me on twitter like i like posted some like point hack and he's like i thought you sold a company showed the hell out of me yeah do you sell credit card churn i i don't credit a card churn i don't do things that are like high effort but like the basics like oh i'm spending money on shit like yes i'll use a credit card yes i'll get points and i still struggle like if a flight is over ten thousand dollars i 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 item like now like like there'd be a time where if i'd go to e commerce and you know you'd get a twenty percent new customer discount i create another account now i don't do that now i'm like that's that's that's that that's too much you quit doing that yesterday yeah but my credit card points i think if you spend a bunch of money it 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 point they have no problem mix except yeah totally slower so it's like i've been the weird psychology like yeah exactly it's all 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 it's i read somewhere that you've built a few things with ai to like personal software software for your own life what did you build and also like what do you see as the opportunity there so i was someone again for context i had a computer science degree i wrote enough code to launch the first version of teachable and i have not written line of code in like ten plus years so i understand enough but i just felt like everything kind of went away from me until now with the eye where it's again becomes 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 like every time we host a webinar we you're download something from some place re uploaded it somewhere else started building these sort of internal tools but now it's reached a point where i have all these annoying we're talking about homeowners ownership so 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 have to do it it's different cadence property taxes you pay quarterly to change the fucking water filter as 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 and 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 anchor single i think well you're not you're married whenever i hear a a single guy sorry that sounded like you i'm not your mother i'm gonna try to this is just already sounds like condescending no it's not the type statement listen listen let's dad's like well it's so simple for you understand 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 kinda magically paid and so when i have a bunch of my single friend so like sophia i'm marissa 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 drives like i'm used to having two of us to hear it 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 do you know what i mean sean you imagine like having to do this stuff like everything i just wanted to see if you could land the plane on that one and i was i landed yeah he 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 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 homeowners ownership especially as someone that grew up outside the us 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 so running a house is is is is that a stereotype that americans are not a fixed toilets yeah i you don't think it's true well i do think that amongst all of my brown friends my eight my brown asian friends all of them hey home depot yeah like self self alliance was not a was not a status symbol in the us it is a status symbol like you were higher status if you can actually fix stuff in india it's like oh you have someone to do all this stuff for you say 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 you know why no what do they do 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 took a free educational thing only indians in the store during first saturday the month and it's by way it's amazing if you're ever if not using this you should use this is that a true stereotype type roommate has told me he was like my my rich life he like explains all the stuff and the hands it with like and also to never step foot into a home depot pip yeah no i mean it it definitely if at least when i first moved to america 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 a weird to like you know even change a light bulb maybe an exaggeration but but yeah i definitely think being a homeowner here as someone didn't grow up here you're not prepared for it awesome that's funny i what tell me about a tell me about this like pickle thing that you're you you're writing about oh dude this is so i've so i was like in terms of things i spend money after food my second biggest expense in new york right now is a sport called it's pretty crazy it's like is it not ten not paddle paddle whatever same thing same store i wanna say it right it depends like latin america versus us either one is fine it's spelled p a d e l not p a d d l e so 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 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 to point now in the us where we're super super early there's like two thousand courts here and there's like twenty thousand in spain it's on a fantastic trajectory upward incredibly fun sport demographic with a high propensity difference what's the what is the difference between this in pickle it is it is substantially more athletic so a lot of people who play this are like well pickle ball it's a game a sport that is like that i do like a lot of sn the pickle ball is uniquely american in that like it's like it's like i don't know it's it's so slow compared to anyone who's actually played sports like has a lot of like x d one tennis players like like you're not exactly explaining the attributes of the game you're more for yeah they're core like paddle like what's the the difference is is that compatible and just a bunch of fat discussing pigs and there's slow either athletic and patel is the same thing it's just division one exactly yeah so imagine imagine a slightly smaller yet wider tennis court with the back wall it's a i know depress tennis ball so it's quite fast because you have the back wall instead of hitting the ball out to hits the back wall bounces back and you kinda go back and forth 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 cities spin up a spin up a location and probably do quite well for the next few years i think we're in this a unique sort of arbitrage opportunity in new york courts are about three hundred dollars an hour and booked out over weekends and again new york is probably the most extremely expensive market in in the us but it kind of cascade all the way downward and i don't you have like a app well i was with you one time and you're like oh my god someone just took my spot as the leader it's dude it's it's the worst that it's the game within the game there's a rating every game you play and it's insane because i'm playing with people that are all in their thirties sometimes twenties and forties 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 body 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 it like a is it a self reported system well how's the rate this itself 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 three point nine sam is a two point six but you only beat him by little who've actually went down despite beating him it's like a el 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 like is this a social network basically is that somebody's built so there's a company called play atomic that's built this in europe and they've white labeled it and i bet that that's also by we a fantastic business it's just i don't know how big a market it is but this one company has monopoly on this little paddle tennis h these apps you said that new york has a thousand courts and there's twenty thousand in spain in the us there's us one thousand only in the us there's twenty thousand in spain correct wow that's all 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 ra almost an identical game to this what are they just like how mad are they that they just like sat pretty i mean but squash squash has been on the fringes for a while in the us it's like either an immigrant support or like rich white ivy league like connotation there's no there's no in between paddle is also any different it's pete it's it's become 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 and 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 you're pretty terrible it'll take you months to you know 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 i think even andrew schultz was talking about it on joe rogan and like it's it's starting to become a thing that we're so early like people are like i don't think it's anywhere hit mainstream consciousness but like i don't know it's may twelfth twenty twenty five come back to this in two years i think it's gonna be gonna see a lot sean last year i went to a my friend held an event at the court and i wasn't sure 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 soccer 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 what are you good i didn't even play i was like i 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 there like this is like the like you know they wanna exclude people from coming here like that's like the vibe that i got like if i don't wear a collar shirt they're gonna kick me out like that's like that was the vibe that i got like i just smelled the racism system you know what medical ball or don't i no i try to play like real sports i don't wanna play those all there no order yeah that's a game no i don't i don't really like i i feel silly playing pat i'm being honest the the one thing the one thing i dislike about new york is it's so hard to have a like a country club 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've 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 and how do 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 it's community forms around it and all that how do you meet friends sean no new friends baby no new friends i've tried to keep i'm trying to do a good job keeping in touch with my existing friends rather big difference 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 gonna i already have like three things a month that i have to do with you know this this set of people so 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 plate dates for my kids while i get to hang with somebody cool that that became like the focus for me rather than like you know going and individually making a friend and then yeah i got three little kids under five years old like if i'm gonna go do a hangout with my friends that's pretty that's a pretty hard like that's just like a a choice that's only benefiting me it doesn't really benefit like the whole that doesn't integrate with the rest of my life but i do i do play a basketball league that i treat like uber seriously like this our friend ruben runs a basketball league called s f 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 joe we gotta correct this for next week we're not gonna we we can't do this again ed so we take it very very very it's seriously exactly the same in our in our groups because the two and two sport people are sending coaching videos back and forth and the whole thing whole thing is pretty insane you bought a piece of a crooked team i bought a piece of a cricket team what's the story here so again flashback i don't know age eight to fourteen 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 wanna do with like the eight or nine year old version of me thought was was dope and then i got in touch with someone who said one of the shareholders and 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 gotta be like the non douche sham off i the dude the douche part is uncertain for an now yeah so so the which team is it and you like ballpark is that we're talking like six figures seven figures eight figures how much did you put in i put yeah so i put in seven seven the the group we represent put in i seven figures of which i think i was twenty percent was my my my own dollars the comp the valuation of the team was close to a billion dollars so as a percentage it's still still tiny the team is called chen super kings they're vi one like wanna say six championships the indian league is about fifteen years old so they have 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 on in 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 there's i think it's also a fantastic investment where like it's not gonna generate pe 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 yeah 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 leaks for instance which is crazy for a league that is 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 well i'll i'll quote my source after this but it is and 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 maybe worth substantially more the franchise value on the ep p 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 it chance too 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 to be cool to like earn the upside no i wanna i wanna draft players i wanna 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 awesome i don't know if you did you did you guys read about do you guys read this vc dude in europe who like bought a soccer team and then he put himself in the team yes no but that's awesome yeah who was that he's like a player on the team i and it's so funny because eighty ninety percent of the world are like oh that's headache i also was like that's awesome i would wanna wait to it did you guys see did you guys watch the the netflix show or or some i forget forgot what it was on where ryan reynolds and rex yeah i didn't watch the show but yeah i i read a lot about it how how has it turned out sean do you know that's been like four years has it i 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 bob who did the same thing he's bought a team in the that's like a i don't know third division team or whatever i don't know which division they're in exactly but they're you know up for basically promotion and he's like bringing like money ball like there's he's he's basically like a kind of data guide he's a sports better that's his background and so he's bringing like a money ball sort of approach to like drafting the right players and or not drafting people like you know signing the right players playing the right strategy and selling at the right times on on players did did you see the celtic sold for six point one billion yeah so that basically changed everyone's model right because people were underwriting sports teams being worth worthwhile and then two and then maybe two and a half three they sold for six it's kind of put into question at just how much the rest of these teams can be worth so well who do they sell to can i some pe group yeah it doesn't seem it just seems that the sports teams are just it it seems challenging it seems like a very challenging thing as a i mean i'm i'm little plea nobody but it seems like a challenging to have a proper market for it because it seems like one of those things that if you want it you want it do you know what mean and the it's like a domain name like it's very hard to be like this domain is worth four hundred thousand dollars there's such few supply and demand is both they're 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 yeah 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 billionaires keeps going up the number of teams in the nba far fine yeah they're about to have launched they're about to open up two new franchises each one of those will get six billion and then that revenue goes to the other owners and that's like two two new franchise wait what like the nba is gonna expand two more teams they're gonna do like a vegas team and they're gonna do probably a seattle team and they wanted the celtic franchise to sell at a very high price went so that they could then go to those new franchises and say you're also a five to six billion dollar price tag which is pretty crazy i mean like you know when mark cuban bought the math i think he bought them for like two hundred something million right like the original celtic jersey just sold for six billion or whatever he bought it originally for i gotta have to look it up but it was like very low it it's basically like he compounded kinda like twenty percent over you know a twenty five year or something like that and so he you know it 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 celtic 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 other things that are there's the tile the in the us you can also get massive tax write offs like there's all kinds of weird tax stuff where like some people have taken player contracts as a depreciate asset and use that depreciation to offset income so crazy and 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 exist the real estate right around the stadium because they're the hub and so they know that that real estate right around it's gonna 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 so you have all these in then by the way your expenses are capped does a salary cap so like give be a be for example so like you can only pay so much but you can still earn you know you can still earn more into your franchise and go value we i went and heard to talk by mark la because who that is he yeah i think he what he don't the box and he was telling a story he was like he his whole i 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 profit and if you want run it profit you will lose your your team will lose or you run it in such a way where you lose two hundred million dollars a year and you win championships and then you hope that you can sell it for enough money that it it it works out so he's like you either wanna win and you gotta have a lot of extra cash flow to cover this nut or you're gonna lose but you'll be profitable you pick one or two i bet it also depends on this sort of sports salary i getting that was a 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 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 talk to a guy what my i don't believe marketing is true like the warriors win the warriors generate more revenue than anybody in the nba they're worth nine billion dollars now like they did all of the so i i don't think that's necessarily true revenue of profit they're also profitable well and maybe true in milwaukee yeah exactly yeah i to it small markets that that actually might be turn maybe and we were with we were with alexis the basketball thing sean and he was telling us about how he the women's soccer team no he bought the women's soccer team he's starting a track league he or invested in that he also told us about how he was either he either did buy or he was trying to buy a piece or a team in tiger woods new golf league or you know the it this weird like stadium golf leak which sounds pretty awesome and he was and he was like well the number sound crazy i i don't remember what he said but let's say hypothetically it was twenty million dollars 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 use they make this much money therefore and it he backed into it and it sounded it made incredibly high numbers in the surface seem incredibly reasonable i heard another guy do the same thing with sailing this guy mark las he was like i'm trying to buy a sailing league and he was like 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 per just them and renegotiate the contracts in such a way where i get value yep and the us 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 at how well they monetize eyeballs it's terrible like you in the us you have very small leagues that are so good it's 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 us to like meaningfully still grow from this point that that's insane hon awesome hanging hang out what you dude yeah it's great great thanks for having me where is have find you so we're hosting a big conference for people who are seeing this sponsored by a lot of people at top hubspot and the hustle called the o o summit it's this friday so we'll be seeing a bunch of people there otherwise i'm active on social media my twitter's is my name and our for any tax optimization stuff carrie dot com alright we appreciate you that's it that's about i feel like i could rule the world and know i could be what i want to from my all in it like the days all on a go travel never looking back