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- [00:00]
Ankur Nagpal
I've now met so many regular people with 8 and 9 figure Roth IRAs 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 can rule the world. I know I could be what I want to.
- [00:15]
Sam Parr
I put my all in it.
- [00:16]
Ankur Nagpal
Like days off on a road, less travel, never looking.
- [00:19]
Sean P. O'Connor
I think that we're going to do basically, like, first half of this is like money tips, meaning like, you know, sort of like 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 you're a little kid, you think your dad knows everything, but then when you 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 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 Cramer, and it says, will this. Will this very loud man make me money? And 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 listen to. So we'll do that. And then you had a bunch of business ideas also like that you've been brainstorming your cheat sheet of startup ideas. So we'll go to that after.
- [01:09]
Sam Parr
But, Sean, do you. Do you guys know each other well, by the way? I don't even know.
- [01:12]
Sean P. O'Connor
We've never, like, hung out in person.
- [01:14]
Ankur Nagpal
We've never hung out. We've exchanged. We've tried to hang out, haven't hung out. The last episode was the closest we've gotten.
- [01:20]
Sean P. O'Connor
I like you every time we talk.
- [01:22]
Ankur Nagpal
Yeah.
- [01:22]
Sam Parr
So let me introduce you. Sean, this is my friend, Ankur. Ankur. This is my friend Sean. I've known Ankur since 2012 or 2013, and we've been buddies since. And I've known Sean since 2013, 2014.
- [01:35]
Ankur Nagpal
I think I'm one of the only people at this point that's met Sam through the Internet, who's had beers with him. That's how. That's how far back we go.
- [01:41]
Sam Parr
It was a long way. It was a long time ago.
- [01:44]
Sean P. O'Connor
So give his. Give his background, his bio.
- [01:47]
Sam Parr
So when I met Ankur, he was doing a Facebook app that went viral, and he made his first couple million dollars at the age of like 26 or 27?
- [01:55]
Ankur Nagpal
No, bro, 20.
- [01:57]
Sean P. O'Connor
What was the app?
- [01:59]
Ankur Nagpal
All the silly stuff. Personality quizzes, friend quizzes. How, like, answer seven questions and you find out how good a kisser you are. Crazy stuff like that.
- [02:07]
Sam Parr
Then he started a company called Teachable. He was early on the course game. He. No, he didn't quite bootstrap that company, but he owned the majority of it and sold it for something like $150 million. Which I'm sure you're going to correct me if I was too low. And then now you have a new company called Carry. Was I too low?
- [02:24]
Ankur Nagpal
It's 250, but close enough.
- [02:26]
Sam Parr
Oh, no, that's not even it.
- [02:27]
Ankur Nagpal
It's all. It's all around the error at that point.
- [02:29]
Sam Parr
But you made like $100 million when you were what, 32 years old?
- [02:33]
Ankur Nagpal
Yep.
- [02:34]
Sam Parr
I mean, that's insane, right?
- [02:36]
Sean P. O'Connor
Did it feel more insane to make a million dollars on a silly Facebook app? Like, how good of a kisser are you? Or was it more insane to make 100 million dol that you. You know, this education company, zero to.
- [02:47]
Ankur Nagpal
Something is always more life changing, undoubtedly. Right? Like, that was also the time where I just moved to America. I was an international student. 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, realize that if I can do things on the Internet, like, why. Why ever get a regular job?
- [03:07]
Sam Parr
How much money did you have in your bank account before you sold Teachable?
- [03:11]
Ankur Nagpal
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 150 grand, which in New York was like, roughly my life break even.
- [03:23]
Sam Parr
So then when you got your exit, you just moved the decimal points place like two points, right?
- [03:30]
Ankur Nagpal
Basically. I mean, we made like a little bit over 40 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.
- [03:40]
Sean P. O'Connor
I love that you're open with money. I'm almost out of question. What else can we ask? He's divulging everything. This is amazing. Well, you sent us this list of topics and you said, when I sold my company, I ran an A 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? Why'd you do this? And what was the result?
- [04:00]
Ankur Nagpal
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 wealth people. They're always in your emails and you know, you read the big brand, Goldman Sachs, Morgan Stanley. So I talked to them, I couldn't fully tell how legit they were. And I had enough money where I'm like, you 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 startup, post exit, startup founder thing where you invest probably in too much. You, you don't say no enough. You go through a period where you think you're an investing genius. But it was cool to sort of see that develop over five years and now to have actual results.
- [04:46]
Sam Parr
And what were they?
- [04:47]
Sean P. O'Connor
What are the results?
- [04:49]
Ankur Nagpal
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, they're very vanilla and they charge you anywhere between 50 basis points to 120 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 13% at that time. They did a lot of other stupid shit that averaged it down to 6%.
- [05:15]
Sean P. O'Connor
What sort of stupid shit did they get you into? Was it like exotic, you know, was it random exotic things? Was it real estate? What are they putting you into? And were you saying yes or no on a case by case basis or. They were making decisions.
- [05:27]
Sam Parr
So they're clear. They brought your average down to 6%.
- [05:31]
Ankur Nagpal
They did, yeah.
- [05:32]
Sam Parr
Dude, that's like the meme where there's like a guy like putting a stick in his own front spoke as he's riding his bicycle.
- [05:37]
Ankur Nagpal
Yeah, but again, the insane part is I genuinely think now that I know more about this, like you can't fully judge the performance based on like five great years. Like theoretically that portfolio should protect your ass in down years of the market. Right. We've also had an atypically good time. But the things that were rough with them is one, for a lot of products, they charged over 100 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 31, 32 year old with infinite risk tolerance 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 are new to 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?
- [06:37]
Sam Parr
Like, but did you, what were the, what are the perks of the status? I mean, you're a single guy. Surely you're not walking around with a T shirt that says I work with Goldman. Like, what, like what did you do?
- [06:47]
Ankur Nagpal
It didn't, it didn't make sense for me. Like, for me, I never valued it that much. But yes, they have a, you know, a concierge team that can, you know, get you 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, oh fuck, it's another person to hang out with. But there's a lot of people who really enjoyed that side of it.
- [07:09]
Sean P. O'Connor
They're like, these tech guys are the best. They're introverts. They don't even take us on any of the free shit. We just get to charge up the fees.
- [07:16]
Sam Parr
Wait, so that's a really expensive U.S. open seat.
- [07:20]
Ankur Nagpal
Correct. I mean, you do the math, right? And because you get charged a percentage of your assets, you never feel the pain. But you're paying them six figures a year. If you had to cut them a check for $10,000 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 the fees. Those dollars would otherwise be invested. So whenever you run the math, you realize your ending portfolio is probably $10 million smaller. 20 or 30 years from now.
- [07:57]
Sam Parr
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- [08:38]
Ankur Nagpal
I think the sweet spot, and in fact I think our friend Ramit 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 $5 million, $50 million, $500 million, they don't do dramatically more things, yet at every step, you pay an order of magnitude more in fees. I think there's a lot of fantastic financial advisors. You pay them five grand a year, ten grand a year, twenty grand a year, I don't care. You can easily get an ROI there, but it's the whatever 1% of your wealth, that's the part that gets really silly. The better and better you do.
- [09:20]
Sean P. O'Connor
I want to ask you about indexing. So indexing is 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.
- [09:33]
Ankur Nagpal
Yeah. So in general, like my overall thesis is more most people, you're not going to get crazy differentiated performance from investing.
- [09:41]
Sam Parr
But.
- [09:42]
Ankur Nagpal
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 advisors. I had so much differentiated access. We know so many entrepreneurs, founders, whatever. The best part of my portfolio was indexing the s and P500. 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 on 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, where instead of buying a Vanguard fund, it buys each and every one of the 500 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 30, 40% of your investment as a usable tax loss.
- [10:39]
Sean P. O'Connor
Sam, do you do this, by the way?
- [10:41]
Sam Parr
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, Ankur, those, those gains eventually go, go. They go away.
- [10:54]
Ankur Nagpal
So unless 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.
- [11:07]
Sam Parr
But no, Sean, I don't do it. Do you?
- [11:09]
Sean P. O'Connor
Yeah, I do. So I, I invest in this company called Freck, and they do this. So, Ankur, have you seen Freck?
- [11:15]
Ankur Nagpal
I'm actually, I'm actually a little bit nervous because I use them as well, but I don't want to be their biggest customer. I have a couple million dollars on Freck and I don't want to put like, I'm a little nervous about putting like 5 or 10 or whatever on them. I'm an investor too, but yes, I use them.
- [11:30]
Sean P. O'Connor
The guy's really smart behind it. He sort of sat me down, explained 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 kind of hand wavy to me. Like, how does this actually work? So he explained it and I said, okay, cool. So I put 250k in as a test. So I'm basically doing the exact same thing I otherwise would have been doing exactly, which is indexing the S and P. So I got the same performance as the S and P, but on my 250k, I added an extra 16,000 in tax loss, harvesting, just holding the same exact asset as it would before. And so, and you know, like you, I was like, wait, should I give this startup like millions of dollars or, you know, how do I want to 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, other pools, other. Other pools of money. So, you know, they're. It's not a startup that holds your money. It's like, you know, the custodian's usually somebody else. Same thing with Robinhood and others. Like, so anyways, I think it's kind.
- [12:23]
Ankur Nagpal
Of amazing, like an even simpler example, if direct indexing is too hard, is most people right now keep their cash in like a high yield savings account or something. But if you are a high taxpayer, there's likely better places for it. There's either muni funds where you pay no federal taxes, there's Treasuries where you don't pay state and local taxes. There's muni 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 3, 4% to like 6, 7%.
- [12:58]
Sam Parr
When I hear you say all this for most people when they talk about this, I see a lot of people talk about this and I think 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.
- [13:15]
Ankur Nagpal
Like there's some percentage of people where they're like, oh, my business makes 50 grand a year. How do I save money on taxes? It's like, bro, you don't have a tax problem, right? You, you need to make more money.
- [13:25]
Sam Parr
Like I was at the, I was at a bike shop the other day and I was like 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. And I was like, 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 and this and I was like, well, I'm kind of chubby, so what if I just lose weight? You know, like, why don't I just like, I could like lose five pounds just by not eating for like, you know, a week. And I'll save myself that money and I'll be fitter. How about that? And that's kind of the same thing.
- [13:52]
Ankur Nagpal
Absolutely. I think, I think for people like, like it matters at our level when the compounding and stuff makes a big difference. But at like 30, 40, 50k in revenue, making more money is, is far more effective.
- [14:06]
Sean P. O'Connor
Well, I was going to say two things. One, this, like direct, the direct direct indexing. I like these because these are. Set it and forget it. I made a decision. It took me two seconds to just roll. I literally push a button and it, it roll does an acat rollover of my s&P ETF holding, my Vanguard ETF holding from one brokerage to theirs. I never had to do anything. So it's like it was a 2 second change that has since yielded like you know, 18k, 16k of extra.
- [14:35]
Ankur Nagpal
Tax.
- [14:35]
Sean P. O'Connor
Losses that I. Harvard. Yeah, exactly. Like, so I don't have to do anything. 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 muni bonds versus holding cash in a money market fund, right? If you're just gonna put cash in a place and be like, okay, it's earning like 3 or 4%. Well, if you could just do the same thing with a muni bond and just not pay the state taxes, like, it's a. It's the same. One decision. Didn't take you any extra time.
- [14:59]
Ankur Nagpal
For the average person, though, I would say for the person doing nothing, fuck it. 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.
- [15:11]
Sam Parr
What else is on the list of, like, all right, you're wired tens of millions of dollars. You're worth nine figures. I expected this to happen in terms of financial investments. Someone was going to present, like, this amazing deal to me. Someone was going to offer this amazing service. And it just was not what I thought. And everyone could have access to this.
- [15:30]
Ankur Nagpal
For the first time, I felt like it didn't matter if I failed, even though arguably I needed the dollars more now. It would feel so stupid to fail. I've been on panels telling other people how you should run your company. And, you know, you have, like, this time, everyone who joined the company did it because they're like, oh, you know, this guy will succeed again. So I feel, like, my pressure on myself and it's fully my own construction. At the end of the day, can.
- [15:54]
Sean P. O'Connor
We switch away from emotions? And you tell me about a mega backdoor Roth. I don't really care how you feel. I just really want to know about this Roth tax optimization. What is it? This is so.
- [16:04]
Ankur Nagpal
So this has been. This has been kind of wild.
- [16:08]
Sean P. O'Connor
I want to know how Peter Thiel made $5 billion and didn't pay any tax on it. What? What was that?
- [16:12]
Sam Parr
Yeah, talk dirty.
- [16:13]
Sean P. O'Connor
Tell me how you feel later.
- [16:15]
Sam Parr
Yeah, whisper softly. Tell me about my back door.
- [16:22]
Ankur Nagpal
But yeah, Peter, everyone. Well, a lot of people read about Peter Thiel, what he did, which is like tax magic, is most people have access to a Roth IRA. He put his PayPal founder shares in a Roth IRA, sold those for about $27 million, then used this as a supercharged investment account to where it is today, where he has $5 billion in his Roth. He turns. He retires next year. So he gets all of that, but no taxes.
- [16:45]
Sam Parr
But you gotta dumb this down, man. What's a Roth ira? Like, you gotta, like, talk down to me a little bit.
- [16:51]
Ankur Nagpal
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, 15, 20 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, is tax free, including no matter how high tax rates go in the future. Right. So if you look back in the 1970s, do you know what the top tax rate was in America?
- [17:26]
Sean P. O'Connor
It was like 20%.
- [17:28]
Ankur Nagpal
It was like 80%. It was insane. Like the top marginal bracket was like 80 or. Yeah, it was super high. But the advantage of a Roth IRA is once you have dollars in, no matter how high taxes get, you pay nothing on what is in that account.
- [17:43]
Sam Parr
And what was the incentivization there for these people?
- [17:46]
Ankur Nagpal
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. What you're giving away in the future is future revenue, but you're actually collecting more money up front.
- [18:00]
Sam Parr
I'm saying, why would the government agree to this?
- [18:03]
Ankur Nagpal
They want to incentivize 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 $150,000 or something. You don't really have access if you go the normal route. But that's where you have things called the backdoor Roth ira.
- [18:31]
Sean P. O'Connor
So before you explain that. So basically it was if you make under a certain amount, you can put away some $7,000 or whatever a year. And you, so you've already paid tax on it, you put it there. Now it's going to compound tax free. When you take it out after all those investments have compounded, you don't pay any taxes on that money because you, you sort of paid it up front.
- [18:50]
Sam Parr
Does it have to be an age limit, like 65?
- [18:52]
Ankur Nagpal
You have to. Yeah, you get your dollars at 59 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.
- [19:04]
Sean P. O'Connor
So what Peter Thiel did, which was great, was he put his PayPal shares in there when they were valued at nothing.
- [19:10]
Ankur Nagpal
So it was like he bought his founder shares at like $0.0001 or whatever.
- [19:15]
Sean P. O'Connor
And he probably knew, hey, this is a good chance that this thing can become valuable. It's crazy. By the way, he only made $27 million on PayPal.
- [19:22]
Ankur Nagpal
$27 million? Oh, at least from this Roth IRA, he put in $1,700 worth of founder shares and he made 27 or $28 million.
- [19:30]
Sean P. O'Connor
Okay, so then, and then he used that money to invest in Facebook within his Roth ira. So then the Facebook gain is why it became billions of dollars.
- [19:39]
Ankur Nagpal
Exactly. But you then read about Mitt Romney doing the same thing. But because I am in this line of work, I've now met so many regular people with eight and nine figure Roth IRAs, which is insane because you have, you know, 10 to $100 million on which you won't owe any taxes at all. And a lot of them have done that with somewhat vanilla investing.
- [20:00]
Sam Parr
Like, so tell me a story of someone who's done this with so eight or nine figures. So you're saying 10 million or 100 million?
- [20:06]
Ankur Nagpal
Yes, exactly. So Roth IRA limits are normally $7,000 a year. The challenge with that is it's tough to get a lot of money and the whole game becomes how do I get a lot of money? And once you get 20 million, going from 20 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 the naming on this is not ideal.
- [20:36]
Sam Parr
But what about the triple mega?
- [20:38]
Ankur Nagpal
Triple mega, right. It's like the least creative days of all time. But the mega backdoor Roth IRA lets you use a 401k to get in $70,000 a year into this account. You can combine the two, get in $77,000 a year. I actually sanity tested this. I built a very simple model that makes the assumption that you start contributing to your Roth IRA by 21, the mega backdoor by like 30. Even if you just indexed the S and P and you looked at the 100 year average of the S and P, you end up with $30 million in your Roth IRA at retirement. So if you do this consistently enough, the tax benefit here is massive.
- [21:20]
Sam Parr
Okay, so who came up with this mega mega backdoor?
- [21:27]
Ankur Nagpal
So the way people find 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. There's been legislation to outlaw it for the last few years. It comes up every time. But the existence of the fact that someone wants to make it illegal by default deems this is a valid loophole for now. So it's the sort of thing that 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.
- [22:12]
Sam Parr
Okay, and what are examples of people who have done this to 10 or $100 million?
- [22:17]
Sean P. O'Connor
So what do you want their name and address? What do you want them to say?
- [22:21]
Sam Parr
No, you could do little Chatham House rules. You could kind of like anonymize them a little bit.
- [22:25]
Ankur Nagpal
So I will tell you that these are people that you and I have never heard of. There's just 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 401 in a way that you can put in $70,000 year into your Roth IRA, which I do now, honestly, just the sport of it 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 $0 in taxes. It's very good insurance from where tax rates may go in the future.
- [23:16]
Sean P. O'Connor
Let's. Should we switch to business ideas, Sam?
- [23:19]
Sam Parr
Yeah, let's do it.
- [23:20]
Sean P. O'Connor
Cool. So, Ankur, you sent us a list of ideas that you think any founder could go build or you think that some founder should go build in this space. And you've started multiple successful companies now, so maybe you have interesting tastes 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 from most people. So hit us with your favorite one and let's go, let's go, let's go in order.
- [23:49]
Ankur Nagpal
Sweet. So I'll go in somewhat random order because I 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 saunas and cold plunges or whatever. And you have all these high end executive services for like concierge Health, basically, you know, Superpower Function Health.
- [24:13]
Sam Parr
Function Health. I don't you guys have to explain this. So basically what they do is you do a blood test and they tell you all about your body 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 of. I have no idea why this category is booming like it is, because it doesn't, I didn't know this. I don't know how this makes it any different from the decades of other companies doing this before.
- [24:47]
Ankur Nagpal
And it's commoditized. 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 kind of sit back and wait for really bad things to happen. And people of our generation have realized that you want to be proactive about this and not just, not just kind of chill.
- [25:07]
Sean P. O'Connor
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 then you, somebody shows you that there's a new level to enough, 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 Superpower, it's like, cool, go. You know, do you want some, a nurse to come to your house or do you want to go 0.8 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 changed or the medical record 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 anor 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 partied, the cooler you were. Right? The more, the more sort of bad for you. Your lifestyle was, the cooler you were. Now 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.
- [26:37]
Sam Parr
Tell me, how are your results?
- [26:39]
Sean P. O'Connor
Oh, you didn't see my tweet about this?
- [26:40]
Ankur Nagpal
Yeah.
- [26:41]
Sam Parr
What did you say?
- [26:43]
Sean P. O'Connor
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. Cool. Thanks for. I'm so happy I use this app.
- [27:09]
Ankur Nagpal
Why were you so.
- [27:10]
Sean P. O'Connor
I'm the only person, I'm the only person I've ever seen with a higher.
- [27:13]
Ankur Nagpal
Literally never. I've never seen anyone.
- [27:15]
Sean P. O'Connor
Anyone. I think I broke a record.
- [27:17]
Sam Parr
Yeah. What. What was so old about you?
- [27:20]
Sean P. O'Connor
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. So 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, little chat here where somebody's 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, and you come up with an action plan. So whether this is life changing or not, they're probably just gonna be like, yo, like delete doordash off your phone, that'll probably do the trick. There's a few different ways that you can help somebody, but again, this is not how normal medicine works. Normal medicine is a car 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 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.
- [28:41]
Sam Parr
Yeah. All right, folks, this is a quick plug for a podcast called I Digress. If you're trying to grow your business but feel like you're drowning in buzzwords. And B, then check out the I Digress podcast. It's hosted by this guy named Troy Sandage. He's helped launch over 35 brands that drive $175 million in revenue. So if you want to get smarter about scaling your business, listen to I Digress, wherever you get your podcasts. All right, back to the pod.
- [29:08]
Ankur Nagpal
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.
- [29:30]
Sean P. O'Connor
By the way, the upsell in this thing is crazy because the initial deal is super good, right? So 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, kind of.
- [29:53]
Ankur Nagpal
Dude.
- [29:53]
Sam Parr
I had to click next the upsell page on function health. I did function health. I clicked next. I'm not joking. 15 times.
- [30:01]
Sean P. O'Connor
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?
- [30:22]
Sam Parr
These two, they do it the other way around. They're like, oh, you want to get your testosterone checked? You're like, fine, you're awake. And help them. Yeah.
- [30:30]
Sean P. O'Connor
What's your wife say to you?
- [30:31]
Sam Parr
I'm like, what? Why is it so personal? So what's your idea here?
- [30:39]
Ankur Nagpal
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 2 inches, and you tie in a DEXA scan to it. But basically, a concierge service to elevate your experience. Two of my college roommates are plastic surgeons, 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.
- [31:26]
Sean P. O'Connor
This is actually a great idea.
- [31:28]
Sam Parr
We had Justin Mares on the podcast, and his skin was glowing like, it.
- [31:33]
Sean P. O'Connor
Was just telling us about, like, his inner health. And we were just like, he's handsome.
- [31:38]
Sam Parr
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.
- [31:46]
Sean P. O'Connor
We went out to breakfast, Sam. And he.
- [31:48]
Sam Parr
What?
- [31:48]
Sean P. O'Connor
Literally everything he ordered, I just said, whatever this man eats, I need to eat. So he ordered this drink. I said, the waiter looked at me, I said, did you not understand the instructions? Whatever this man eats, I eat. And so I had a identical meal to him.
- [32:01]
Ankur Nagpal
But I think you have to, like, stamina are investors in a testosterone company, and if the founder was not jacked, I would not have invested in the company.
- [32:09]
Sam Parr
That's true. Sean's in on that too, by the way. It seems like we've all invested in the same stuff.
- [32:14]
Ankur Nagpal
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. With Crush, I mean, you already have concierge medicine in Turkey, stuff like that. Secondly, I think anything that helps us break out of the US Food system 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 raw milk dealer, which is super sketchy. It's this Amish farm that drives in. It's illegal, so 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 that enable people to do that will go quite a long way.
- [33:01]
Sean P. O'Connor
And so how did you find this Amish farm? Like, what was your process to find this alternative?
- [33:08]
Ankur Nagpal
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. And 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 were 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, raw dairy is more of a novelty. That's something that like, sure, I'll add $4 for the raw milk, but I think breaking out of the US Food system, at least, you know, 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.
- [34:00]
Sam Parr
Do you get all your meat from this Amish fellow?
- [34:04]
Ankur Nagpal
I do. It's so good. Dude, I don't like chicken in America. As someone that's traveled a lot, most chicken here at a grocery store tastes like nothing to me. You can't really taste anything. But here it actually, again, such a big difference if you have the same stuff outside the U.S. we all need.
- [34:22]
Sam Parr
One of these Amish guys.
- [34:23]
Sean P. O'Connor
Isn't this what a farmer's market is supposed to be, by the way?
- [34:26]
Ankur Nagpal
It is. It is what a farmer's market is supposed to be. This feels more authentic, right? This feels. This feels more real.
- [34:32]
Sean P. O'Connor
Well, the way you described it, 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 cute date on a Sunday morning, but like, I kind of like an element of danger with my groceries.
- [34:43]
Ankur Nagpal
And I think this is contraband. This Is contraband. This is contraband.
- [34:46]
Sean P. O'Connor
Exactly.
- [34:47]
Ankur Nagpal
Not only that, when you, like, you buy something and all the signs on it will very clearly say, not for human consumption, but it's like, wink, wink, not for human consumption.
- [34:57]
Sam Parr
Can we ground it up and inject it in my veins? That's usually what I do when it says not for human consumption.
- [35:02]
Ankur Nagpal
Yeah. For cats and dogs only.
- [35:05]
Sam Parr
Does it make you feel better, by the way, this stuff?
- [35:08]
Ankur Nagpal
It does. I mean, of course you have to control for placebo effect and stuff, but generally, yes, I do feel better when I'm. When I'm eating this and.
- [35:15]
Sam Parr
Or.
- [35:16]
Sean P. O'Connor
Or don't control for placebo. Placebos, yeah.
- [35:18]
Ankur Nagpal
Placebo is a mess, right?
- [35:19]
Sam Parr
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. Like it's an issue. And I'm like, wait a minute, you're telling me I could take a fake thing and it gives me the real results, Give me all of the fake things? That's all I ever want is the fake thing.
- [35:36]
Ankur Nagpal
No, it's.
- [35:37]
Sam Parr
It's.
- [35:37]
Ankur Nagpal
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 live a very healthy New York life, cook my own food or whatever, and then I'd go to Argentina for a month, live like a degenerate, and I'm like, I feel better. My physical body feels better. And I don't think it was the addition of the alcohol. I think it was just the food system.
- [36:00]
Sam Parr
It could have been that. It could have been some of the other stuff you were doing on there too.
- [36:03]
Ankur Nagpal
Yeah. Could have been.
- [36:04]
Sam Parr
Never.
- [36:08]
Ankur Nagpal
All right, 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 250,000Amex 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.
- [36:38]
Sean P. O'Connor
How do. How do you want this to work?
- [36:40]
Ankur Nagpal
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 they just do it for me.
- [36:59]
Sam Parr
Jack Smith is a friend of all of ours. I believe Jack Smith very. When he suggests something, 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 flightfox.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 $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.
- [37:38]
Ankur Nagpal
Their business doesn't make sense. Like what's their margin in on this?
- [37:41]
Sam Parr
I have no idea. But I have booked three or four flights on this and it is amazing. It works every time. It just works.
- [37:49]
Ankur Nagpal
Can you enter like your credit card points and stuff or is this just dollars?
- [37:53]
Sam Parr
Yes. So 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?
- [38:09]
Ankur Nagpal
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.
- [38:16]
Sam Parr
Have you heard of this, Sean?
- [38:18]
Sean P. O'Connor
I've heard of it. I've never done it before. Have you done it?
- [38:21]
Sam Parr
I've done it. So I booked a flight where I, I had a friend who spent roughly 10 or $15 million a year on advertising with his Amex card or some, some credit card. And he is 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 the, the flights, I think I saved 40% or 30%. Something like pretty significant because I was buying like six, six first class flights. It was very expensive and it was like thousands of dollars that I saved.
- [38:57]
Ankur Nagpal
So who's, 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 back end with.
- [39:08]
Sam Parr
But there's an issue. 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.
- [39:18]
Ankur Nagpal
I feel like a disproportionate number of my ideas are turning out to be illegal, but yeah.
- [39:24]
Sam Parr
Yes. So what were you saying about the financial services company that you currently run?
- [39:32]
Ankur Nagpal
All right.
- [39:33]
Sam Parr
Illegal raw milk.
- [39:36]
Ankur Nagpal
I don't want my chief compliance officer to message me after this. I should add, nothing shared here should be considered as legal advice, investment advice or tax advice. Everything is for information. Health advice or health advice or health advice. That's fine. That's not that regulated and this country.
- [39:52]
Sean P. O'Connor
No, but. But you're right on the points thing. So, like, I use like, seats arrow, I think, which is basically like you plug in what points 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 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, 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.
- [40:29]
Ankur Nagpal
Seven. Yeah, exactly. There's so much arbitrage.
- [40:32]
Sam Parr
Wait, you have 7 million?
- [40:34]
Sean P. O'Connor
Yeah, at least 7 million.
- [40:36]
Sam Parr
How does that convert? Is that like $70,000?
- [40:39]
Ankur Nagpal
Once you 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.
- [40:53]
Sam Parr
Even though you're incredibly wealthy, do you still. So you still use airline points?
- [40:58]
Ankur Nagpal
Like, crazy naval destroyed me on Twitter. Like, I like, posted some like, point hack. And he's like, I thought you sold a company. Ratioed the hell out of me.
- [41:09]
Sam Parr
Yeah. Do you sell credit card churn?
- [41:11]
Ankur Nagpal
I don't credit card churn. 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. And I still struggle. Like, if a flight is over $10,000. I still struggle. Even though mathematically you're like, oh, you can afford to spend that.
- [41:29]
Sam Parr
Do you still mostly buy on sale items?
- [41:33]
Ankur Nagpal
Not on sale item. Now there'd be a time where if I'd go to E Commerce and 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 too much effort.
- [41:44]
Sam Parr
You quit doing that yesterday.
- [41:46]
Ankur Nagpal
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 from 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.
- [42:07]
Sam Parr
Yeah, totally.
- [42:08]
Sean P. O'Connor
So it's like I do the same thing.
- [42:10]
Ankur Nagpal
Weird psychology, like, yeah, exactly.
- [42:11]
Sean P. O'Connor
I told my sister and I was like, just tell her it's points.
- [42:14]
Ankur Nagpal
Yeah.
- [42:14]
Sean P. O'Connor
And then don't bother with the points. It's going to be too confusing. Just get her the ticket. Can you tell me 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?
- [42:33]
Ankur Nagpal
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 a line of code in like 10 plus years. So I understand enough. But I just felt like everything kind of went away from 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 have to download something from someplace, re upload 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 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.
- [43:28]
Sam Parr
What did you make?
- [43:30]
Ankur Nagpal
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. 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.
- [44:09]
Sam Parr
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 disable you.
- [44:20]
Ankur Nagpal
This is. This already sounds like condescending.
- [44:22]
Sam Parr
No, it's not.
- [44:23]
Ankur Nagpal
Type statement.
- [44:24]
Sam Parr
Listen, listen, listen.
- [44:25]
Ankur Nagpal
That's like. Well, that's so simple for you.
- [44:27]
Sam Parr
No, I.
- [44:28]
Ankur Nagpal
Go on.
- [44:29]
Sam Parr
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. And so when I have a bunch of my single friends, so, like, Sophia Amoruso, one of our mutual friends, she tells me about, like, all the time she has to spend been 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 sounds so hard. You know what I mean? Sean, can you imagine, like, having to do this stuff, like, everything?
- [45:11]
Sean P. O'Connor
I just wanted to see if you could land the plane on that one. And I was.
- [45:14]
Sam Parr
Did I land it? Yeah, he did.
- [45:15]
Ankur Nagpal
He did. He did.
- [45:15]
Sean P. O'Connor
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.
- [45:21]
Sam Parr
What I'm saying is, it's so much work, I don't understand how people do.
- [45:25]
Ankur Nagpal
It, especially when you add in the dynamic of homeownership, 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 Wait, is.
- [45:46]
Sam Parr
That a stereotype that Americans know how to fix toilets?
- [45:48]
Ankur Nagpal
Yeah. I. You don't think it's true?
- [45:51]
Sam Parr
Well, I do think that amongst all of my brown friends, my eight, my brown Asian friends, all of them hate Home Depot.
- [45:57]
Ankur Nagpal
Yeah. Like, self. Self reliance was not a. 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.
- [46:11]
Sean P. O'Connor
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?
- [46:18]
Sam Parr
No. What are they doing?
- [46:19]
Sean P. O'Connor
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 first Saturday of the month. And it's. By the way, it's amazing. If you're. If not using this, you should use this.
- [46:36]
Sam Parr
Is that a true stereotype? Ramit has told me. He was like, my. My rich life. He, like, explains all the stuff, and he ends it with like. And also to never step foot into a Home Depot. Yeah.
- [46:46]
Ankur Nagpal
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.
- [47:09]
Sam Parr
That's awesome. That's funny.
- [47:11]
Sean P. O'Connor
All right, what. Tell me about. Tell me about this, like, pickleball thing that you're.
- [47:15]
Ankur Nagpal
You.
- [47:15]
Sean P. O'Connor
You're writing about.
- [47:16]
Ankur Nagpal
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. It's pretty crazy. It's like, is it not tennis?
- [47:30]
Sam Parr
Not paddle.
- [47:31]
Ankur Nagpal
Paddle, Padel. Whatever. Same thing, same sport.
- [47:33]
Sam Parr
I want to say it, right?
- [47:35]
Ankur Nagpal
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 Padel. Padel, 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 US where we're super, super early. There's like 2,000 courts 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.
- [48:18]
Sean P. O'Connor
What is the difference between this and pickleball?
- [48:21]
Ankur Nagpal
It is substantially more athletic. So a lot of people who play this are like, well, pickleball is a game. Pedal is a sport.
- [48:29]
Sean P. O'Connor
It is like that. I do like a little bit of snobbery.
- [48:32]
Ankur Nagpal
Pickleball 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, Padel has a lot of like X D1 tennis players.
- [48:44]
Sam Parr
Like, you're not exactly explaining the attributes of the game. You're more so, yeah.
- [48:50]
Sean P. O'Connor
Paddle, like, what's the difference?
- [48:52]
Sam Parr
The difference is, is that paddleball is just a bunch of fat, disgusting pigs. And they're slow, they're athletic, and Padel's the same thing. It's just Division one ex athletes.
- [49:03]
Ankur Nagpal
Yeah. So imagine, imagine a slightly smaller yet wider tennis court with a back wall. It's a. And 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. 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 2 city, spin up a location and probably do quite well for the next few years. I 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.
- [49:48]
Sam Parr
Don't you have like a app? I was with you one time and you're like, oh my God, someone just took my spot as the leader.
- [49:54]
Ankur Nagpal
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 unmet competitive need. So everyone is so aggressive about their rating, about their ranking. 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, 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 so angry about.
- [50:31]
Sam Parr
Is it a self reported system? How's the rating?
- [50:34]
Ankur Nagpal
Yeah, so we all have scores. Let's say I beat you, I enter that in the system and the algorithm is like, oh, I'm a 3.9, Sam is a 2.6, but you only beat him by a little. So you actually went down despite beating him.
- [50:47]
Sean P. O'Connor
It's like an ELO score.
- [50:49]
Ankur Nagpal
Exactly. And it's the most insane thing because you have all these people taking this way too seriously. Right. Everyone has real life jobs and responsibilities, but people get so cranky about this.
- [50:59]
Sean P. O'Connor
Is this a social network basically that somebody's built?
- [51:02]
Ankur Nagpal
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.
- [51:19]
Sam Parr
New York City founders. If you've listened to my first million before, you know I've got this company called Hampton. And Hampton is a community for founders and CEOs. A lot of the stories and ideas that I get for this podcast, I actually got it from people who I met in Hampton. We have this big community of a thousand plus people and it's amazing. But the main part is this eight person core group that becomes your board of advisors for your life and for your business. And it's life changing. Now to the folks in New York City, I'm building a in real life core group in New York City. And so if you meet one of the following criteria, your business either does 3 million in revenue or you've raised 3 million in funding, or you've started and sold a company for at least $10 million, then you are eligible to apply. So go to joinhampton.com and apply. I'm going to be reviewing all of the applications myself. So put that you heard about this on mfm, so I know to give you a little extra love. Now back to the show.
- [52:12]
Sean P. O'Connor
You said that New York has a thousand courts and there's 20,000 in Spain in the US. The US there's 1,000 only in the US and there's 20,000 in spain.
- [52:22]
Ankur Nagpal
Correct.
- [52:22]
Sean P. O'Connor
Wow, that's crazy.
- [52:24]
Ankur Nagpal
And again, the Google trend for the sport, like, just look it up or I can drop a graph. It's like straight up and to the right and picking up momentum.
- [52:32]
Sean P. O'Connor
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?
- [52:41]
Ankur Nagpal
They're pretty mad. I mean, but squash. Squash has been on the fringes for a while in the US 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.
- [52:53]
Sean P. O'Connor
Is also any different.
- [52:56]
Sam Parr
It's, It's.
- [52:58]
Ankur Nagpal
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 catching the right timing. And it's the 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 people. Like, 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. You're going to see a lot, Sean.
- [53:38]
Sam Parr
Last year I went to a. My friend held an event at the Padel Court, and I wasn't sure if 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, Ankara, 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.
- [54:03]
Ankur Nagpal
Were you good?
- [54:04]
Sam Parr
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. The, 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 know what I mean?
- [54:26]
Sean P. O'Connor
Pickleball or Padel.
- [54:28]
Sam Parr
I. No, I try to play, like, real sports. I don't want to play those things. Yeah, that's a game. No, I don't. I don't really like. I feel silly playing paddleball, if I'm being honest.
- [54:46]
Ankur Nagpal
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. 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 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.
- [55:28]
Sam Parr
How do you meet friends, Sean?
- [55:31]
Sean P. O'Connor
No new friends, baby. No new friends. I try to keep up. 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 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 play dates for my kids while I get to hang with somebody cool.
- [56:05]
Ankur Nagpal
So that.
- [56:05]
Sean P. O'Connor
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 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, our 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 rec ball, who cares? Pick up basketball basically. But no, I take it so seriously. Basically the six other days of the week are just preparation for the one big game night. And then after that 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 partially funny, you know, just commentary, but also like, yo, we gotta correct this for next week. We're not gonna, we can't do this again. And so we take it very, very, very seriously.
- [57:10]
Ankur Nagpal
It's exactly the same in our groups. Cause it's a two on two sport. People are sending coaching videos back and forth and the whole thing, whole thing is pretty insane.
- [57:18]
Sean P. O'Connor
You bought a piece of a cricket team?
- [57:19]
Ankur Nagpal
I bought a piece of a cricket team.
- [57:21]
Sean P. O'Connor
What's the story here?
- [57:23]
Ankur Nagpal
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, 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 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 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 steak 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.
- [58:17]
Sam Parr
But you got to be like the non douchey chamath.
- [58:21]
Ankur Nagpal
The douche part is uncertain for now. Yeah.
- [58:27]
Sean P. O'Connor
So which team is it? And you like ballpark? Are we talking like six figures? Seven figures, Eight figures? How much did you put in?
- [58:35]
Ankur Nagpal
I put, yeah, so I put in seven. Seven. The group we represent put in high seven figures of which I think I was 20% 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 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 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. I think it's also a fantastic investment where it's not going to generate tech startup returns, but it's unlikely to lose money. There's such a long way the sport has to run.
- [59:38]
Sean P. O'Connor
You said it's the third most valuable league in the world.
- [59:41]
Ankur Nagpal
Yeah. By TV rights per game, it's actually number two after NFL. And by total revenue, it's more than any of the European soccer leagues, for instance, which is crazy for a league.
- [59:54]
Sean P. O'Connor
That is worth more than the Premier League.
- [59:56]
Ankur Nagpal
How is this possible?
- [59:56]
Sean P. O'Connor
How could the most valuable team be a billion, but the league be worth more than there's players in soccer that can almost make a billion dollars.
- [60:05]
Ankur Nagpal
Well, I'll quote my source after this, but it is 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.
- [60:29]
Sam Parr
Have you flown there and participated in any of the.
- [60:33]
Ankur Nagpal
I haven't had a chance to because this deal came together very recently. So 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 earn the upside? No, I want to draft players. I want to be able to. 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 sounds awesome.
- [60:59]
Sam Parr
I don't know if you.
- [61:00]
Ankur Nagpal
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?
- [61:06]
Sean P. O'Connor
Yeah.
- [61:07]
Sam Parr
No, but that's awesome. Who is that?
- [61:10]
Sean P. O'Connor
He's like a player on the team.
- [61:12]
Ankur Nagpal
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.
- [61:19]
Sam Parr
Did you guys see. Did you guys watch the. The Netflix show or something? I forget what it was on where Ryan Reynolds and.
- [61:27]
Ankur Nagpal
I didn't watch the show, but yeah, I read a lot about it.
- [61:31]
Sam Parr
How. How has it turned out, Sean? Do you know that's been like four years. Has it?
- [61:34]
Sean P. O'Connor
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, you know, up for basically promotion. And he's like bringing like, Moneyball, which is. He's. He's basically like a kind of data guy, and he's a sports bettor. That'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.
- [62:10]
Ankur Nagpal
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.
- [62:29]
Sam Parr
Well, who do they sell to?
- [62:32]
Ankur Nagpal
Some PE group?
- [62:33]
Sam Parr
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 of. I mean, I'm an. I'm a little plea 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. Do you know what I mean?
- [62:51]
Ankur Nagpal
And the only thing, 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.
- [63:00]
Sam Parr
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.
- [63:14]
Sean P. O'Connor
Well, the number of billionaires keeps going up. The number of teams in the NBA is 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 and then that revenue goes to the other owners and that's.
- [63:27]
Sam Parr
Wait, two, two new franchise, wait what?
- [63:30]
Sean P. O'Connor
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 dollar 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 just sold for 6 billion or whatever he 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. 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, this is, 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.
- [64:27]
Ankur Nagpal
There's the T. In the US you 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 depreciating asset and use that depreciation to offset income. So crazy.
- [64:41]
Sean P. O'Connor
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 existing, the real estate right around the stadium because they're the hub and so they know that that real estate right around it's going to be really worthwhile. Some people are trying to do 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 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.
- [65:14]
Sam Parr
We, I went and heard a talk by Mark Lazary. Do you guys know who that is? He. Yeah, I think he owns the Bucks. 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. Your. Your 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.
- [66:01]
Ankur Nagpal
I bet it also depends on the sort of sport salary. Again, that was the whole Moneyball 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 kid play a bunch of sports, or you can buy a sports team and still feel like you're doing the same thing.
- [66:27]
Sam Parr
Well, we talked to a guy, by the way.
- [66:29]
Sean P. O'Connor
I don't believe that thing is true. Like, the warriors win. The warriors generate more revenue than anybody in the NBA. They're worth $9 billion now, like they did all of the above. So I don't think that's necessarily true revenue or profit. They're also profit.
- [66:44]
Ankur Nagpal
Well, it may be true in Milwaukee.
- [66:46]
Sean P. O'Connor
Yeah, exactly. I think in small markets that actually.
- [66:49]
Ankur Nagpal
Might be true, maybe.
- [66:50]
Sam Parr
And we were with Alexis at the basketball thing, Sean, and he was telling us about.
- [66:59]
Ankur Nagpal
He bought the women's soccer team.
- [67:00]
Sam Parr
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 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. And he was. And 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 sounded. 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 like, explaining the numbers. And basically the whole business of the sports league 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.
- [68:01]
Ankur Nagpal
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, in the US 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 US to, like, meaningfully still grow from this point.
- [68:30]
Sam Parr
That's insane. Ankur, awesome hanging out with you, dude.
- [68:35]
Ankur Nagpal
Yeah, great, great. Thanks for having me.
- [68:37]
Sam Parr
Where do people find you?
- [68:40]
Ankur Nagpal
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 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 is my name, and our for any tax optimization stuff. Carrie.com.
- [69:00]
Sam Parr
All right, we appreciate you. That's it. That's the pod.
- [69:03]
Ankur Nagpal
I feel like I can rule the world. I know I could be what I want to.
- [69:07]
Sam Parr
I put my all in it.
- [69:09]
Ankur Nagpal
Like my days off on a road.
- [69:11]
Sam Parr
Lesson travel, never looking back. Hey, everyone, a quick break. My favorite podcast guest on my first million is Dharmesh. Dharmesh founded HubSpot. He's a billionaire. He's one of my favorite entrepreneurs on earth. And on one of our podcasts recently, he said the most valuable skill that anyone could have when it comes to making money in business is copywriting. And when I say copywriting, what I mean is writing words that get people to take action. And I agree. By the way, I learned how to be a copywriter in my 20s. It completely changed my life. I ended up starting and selling a company for tens of millions of dollars. And copywriting was the skill that made all of that happen. And the way that I learned how to copyright is by using a technique called copy work, which is basically taking the best sales letters and I would write it word for word and would make notes as to why each phrase was impactful and effective. And a lot of people have been asking me about copy work. So I decided to make a whole program for it. It's called Copy that, Copy that. It's only like 120 bucks, and it's a simple, fast, easy way to improve your copywriting. And so if you're interested, you need to check it out. It's called Copy that. You can check it out@copy that.com.