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

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. A lot of them have done that with *vanilla investing*."

Shaan Puri

**I think we're going to do basically this:** the first half is *money tips*—meaning personal finance stuff that nobody really teaches you. We get most of our personal finance information from two really bad sources: either our parents, who probably only knew so much—when you're a kid you think your dad knows everything, but when you grow up you realize he's just a person who did the best he could—or TV, books, and salespeople whose incentives are very different from yours. One of my favorite YouTube videos has a picture of Jim Cramer and the caption, "Will this very loud man make me money?" The answer is no—he will not. The blinking lights on his screen and that money guy on TV are not the people to listen to. After that, we'll go over the business ideas you've been brainstorming—your cheat sheet of startup ideas.

Sam Parr

Sean, do you guys know each other well? By the way, I don't even know.

Shaan Puri

We've never hung out in person.

Ankur Nagpal

"We've never hung out. We've exchanged... We've tried to hang out, but haven't. The last episode was the closest we've gotten."

Shaan Puri

"I like you every time we talk."

Ankur Nagpal

Yeah, so... let...

Sam Parr

Let me introduce you, **Sean**. This is my friend **Akar**. **Akar**, this is my friend **Sean**. I've known **Akar** since 2012 or 2013, and we've been buddies since. I've known **Sean** since 2013 or 2014. </FormattedResponse>

Ankur Nagpal

I think I'm one of the only people at this who's met Sam through the internet and has had beers with him. That's how far back we go.

Sam Parr

It was a long way. It was a long time ago.

Shaan Puri

So, give his **background**—his **bio**.

Sam Parr

So when I met **Ankur**, he was doing a **Facebook** app that went viral. He made his first couple million dollars ($2 million) at the age of, like, 26 or 27. </FormattedResponse>

Ankur Nagpal

"No, bro. 20."

Shaan Puri

What was the app?</FormattedResponse>

Ankur Nagpal

All the *silly stuff*: personality quizzes, friend quizzes—like answering seven questions and you find out how good a kisser you are. Crazy stuff like that.

Sam Parr

He started a company called **Teachable**. He was early on the course game. 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 on if I was too low. And now you have a new company called **Carrie**. Was I too low?

Ankur Nagpal

It's **$2.50**, but close enough.

Sam Parr

Oh no, that's not.

Shaan Puri

Even it.

Ankur Nagpal

It's all—it's all around the area, at that.</FormattedResponse>

Sam Parr

"But you made **$100 million** when you were—what, 32 years old?" "Yep. I mean, that's insane, right?" </FormattedResponse>

Shaan Puri

"Did it feel more insane to make $1,000,000 on a silly Facebook app like *How Good of a Kisser Are You*, or was it more insane to make $100,000,000 on this company — you know, this education company?"

Ankur Nagpal

**Zero to something** is always more life-changing, undoubtedly, right? That was also the time when I had just moved to America. I was an international student. I didn't really have... I was so new to everything. But making money in college allowed me to not go to class and to realize that if I can do things on the Internet, why ever get a regular job?

Sam Parr

"How much money did you have in your bank account before you sold **Teachable**? Like one and a half, two, like, basically." </FormattedResponse>

Ankur Nagpal

I was flat. I didn't really spend money or grow money during that entire time. I paid myself, eventually, a salary of *$150*, which in *New York* was roughly my "life breakeven."

Sam Parr

So then, when you got your exit, you just moved the decimal points two places, right? Yeah. I mean, we made... </FormattedResponse>

Ankur Nagpal

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. [Clarification: "40" is unspecified (dollars, percent, units).]

Shaan Puri

I love that you're open with money. I'm almost out of questions—what else can we ask? He's... he's... 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 myself." I assume—could you just talk about this? Why did you do this, and what was the result?

Ankur Nagpal

So, like a lot of founders who first sell a business, most of us know nothing about money. I don't know, Sam, if you knew much or whatever. You get hit up by every single one of the private-wealth people — they're always in your emails — and you read the big brands: **Goldman Sachs**, **Morgan Stanley**. I talked to them, but I couldn't fully tell how legit they were. I had enough money where I was like, "You know what? Let me take a sizable chunk, give them that amount of money, and see what they do." The other half, let me try and learn and figure stuff out myself. I went through sort of the standard post-exit, startup-founder thing: you invest probably in too much, you don't say no enough. You go through a stage where you think you're an investing genius. It was cool to watch that develop over five years, and now to have actual results — and what were they?

Shaan Puri

What are the results?

Ankur Nagpal

The results are, in retrospect: there's nothing particularly special about **private banking**. There's a lot of clout that comes with it, but if you look at the sort of portfolios they do, they're very vanilla. They charge anywhere from 50 basis points to 120 basis points. The best part of my portfolio that they managed was simply indexing the **S&P** [S&P 500]. The S&P returned about 13% in that time. They did a lot of other stupid shit that averaged it down to 6%.

Shaan Puri

What sort of *stupid shit* did they get you into? Was it, like, exotic—random exotic things? Is it real estate? What are they putting you into, and were you saying yes or no on a case-by-case basis, or were they making decisions?

Sam Parr

So... they're clear: they brought your average down to 6% — that... </FormattedResponse>

Ankur Nagpal

It. Yeah.

Sam Parr

Dude, that's the **meme** where a guy puts a stick in his front spoke while riding his bicycle.

Shaan Puri

**Yeah.**

Ankur Nagpal

But again, the *insane* part is: I genuinely think now that, since I know more about this, you can't fully judge performance based on five great years. Theoretically that portfolio should protect your ass in down years of the market, right? We've also had an atypically good time. The things that were rough with them: one, for a lot of products they charged over 100 basis points (more than 1%) to basically do what Vanguard funds could have done. Two, they also put a lot into fixed income (bonds and similar), which for a 31- or 32-year-old with, like, infinite risk tolerance doesn't really make sense. So eventually I got them to stop doing a lot of those things. But the whole process of working with them made you realize: these people—their product has such insanely good margins that they can afford to do whatever, and they really sort of sell a lifestyle. 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...

Sam Parr

Of a... you know, it's... it's a... it's a...

Ankur Nagpal

"Status thing as well, right?"

Sam Parr

Like, what goal were—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—what's...?

Shaan Puri

So, what did you do?

Ankur Nagpal

It didn't make sense for me. For me, I never valued it that much. But yes, they have a concierge team that can get you tickets to the *US Open* and 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. </FormattedResponse>

Shaan Puri

"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.'"

Sam Parr

"It's—wait, so that's a really expensive US Open seat."

Ankur Nagpal

"Correct. I mean, you do the math, right? 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'd be auditing that all the time. But that is what is so *genius* about this business model: 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 $10,000,000 smaller twenty or thirty years from now."

Sam Parr

"But what's the argument against this? They've been around for a hundred years; they're huge. A lot of smart, rich people use it. Surely... I mean, *what's the value?*"

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 a **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 advisers — you pay them $5 a year, $10 a year, $20 a year — I don't care. You can easily get an ROI there. But it's that… whatever, **1%** of your wealth that's the part that gets really silly the better and better you do. </FormattedResponse>

Sam Parr

Alright. A few episodes ago I talked about something, and I got thousands of messages asking me to go deeper and explain. That's what I'm about to do. I told you guys how I use **ChatGPT** as a life coach or a thought partner. What I did was upload all types of information: my personal finances, my net worth, my goals, different books that I like, and issues going on in my personal life and businesses. I uploaded so much information. The output is that I have this GPT that I can ask questions about problems I'm facing in my life, like: "How should I respond to this email?" or "What's the right decision, knowing my goals for the future?" I worked with **HubSpot** to put together a step-by-step process showing the audience the software I used and the information I provided to **ChatGPT**. It's super easy for you to use. Like I said, I use this 10 to 20 times a day. It's literally changed my life. If you want that, it's **free**. There's a link below—just click it, enter your email, and we will send you everything you need to set this up in about twenty minutes. I'll show you how I use it again, 10 to 20 times a day. Alright, so check it out. The link is below in the description. Back to the episode.

Shaan Puri

I want to ask you about **indexing**. Indexing is obviously super popular now, and you had some notes on simple, other ways you can index that are, maybe, things people should consider.

Ankur Nagpal

Yeah. So in general, my overall thesis is: most people are not going to get dramatically differentiated performance from investing. But that's actually okay. It's kind of wild that an average person — again, think about my example — I had all these 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&P 500**, and historically that happened a lot. So most people should not try to find **alpha** on the investment side. However, if you can be smart about saving money on taxes, that is where your alpha comes from. 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. The advantage is you have more positions, so more volatility at any given time. More companies are down, so you can harvest those losing positions. Net-net, you track the same as an index, but you'll get about 40% of your investment as a usable tax loss.

Shaan Puri

Sam, do you do this, by the way?

Sam Parr

No. I think—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. Number two: from my understanding, actually those gains eventually go... they go away. So it can't—unless...

Ankur Nagpal

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.

Sam Parr

But no, Sean, I don't do it. Do you?

Shaan Puri

Yeah, I do. So, I invest in this company called **Freck**, and they do this... So, Uncle, have you seen Freck?</FormattedResponse>

Ankur Nagpal

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 [unclear: "holders on crack"], and I don't want to put, like, five or ten or whatever on them. I'm an investor too, but yes—I use them.

Shaan Puri

The guy's **really smart**. He sort of sat me down and explained it because I was like, "Look, don't assume I don't know anything — I read this and it sounds good, but it's kind of *hand‑wavy* to me. How does this actually work?" He explained it, and I said, "Okay, cool." So I put 250 in as a test. I'm basically doing the exact same thing I otherwise would have been doing.

Ankur Nagpal

Doing *exactly*.

Shaan Puri

Which is indexing the **S&P**, so I got the same performance as the **S&P**. But I—on my 250—I added an extra $16,000 in **tax-loss harvesting** while just holding the exact same asset as before. So... you know, I was like, "Wait—should I give this startup, like, millions of dollars? How do I want to do this?" And then he's like, "Well, we don't know. All fintech is basically built on top of other providers—other pools of money." It's not a startup that holds your money; the custodians are usually somebody else. Same thing with Robinhood and others. So, anyways, I think it's kind of amazing.

Ankur Nagpal

Like an even simpler example: if **direct indexing** is too hard, most people right now keep their cash in a high-yield savings account or something. But if you are a high taxpayer [high-income taxpayer], there's likely better places for it. There are muni funds [municipal bond funds], where you pay no federal taxes; Treasuries, where you don't pay state and local taxes; and muni funds specific to New York and California, where you won't pay federal and state taxes. 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%.

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 totally about..." </FormattedResponse>

Ankur Nagpal

Totally. There's some percentage of people who say, "Oh, my business makes $50 a year — how do I save money on taxes?" It's like, "Bro, you don't have a **tax problem**, right? You need to make—"

Sam Parr

I was at a bike shop the other day, looking at a bike. There was one that cost $2,500 and another that was $5. I asked, "What's the difference?" They said it was only about *two pounds* [weight]. So the price difference is huge, but the weight difference is minimal. There was also a water bottle made out of carbon. I thought, "Well, I'm kind of chubby—why don't I just lose weight?" Couldn't I lose five pounds by not eating for a week? Then I'd save that money and be fitter. How about that? That's kind of the same thing.

Ankur Nagpal

Absolutely. I think—for people like us, it matters at our level when the *compounding* and stuff makes a big difference. But at like $30k, $40k, $50k in revenue, making more money is **far more effective**.

Shaan Puri

**Direct indexing** — I like these because they're *set-it-and-forget-it*. I made a decision; it took me two seconds to roll. I literally pushed a button and it did 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 was a two‑second change that has since yielded, like, you know, $16k–$18k of extra alpha. I don't have to do anything. I would never do that if it was something I had to keep thinking about or keep doing on a regular basis. Same thing with what you're talking about with buying muni bonds versus holding cash in a money‑market fund. If you're just going to put cash in a place and be like, "okay, it's earning 3 or 4%," well, if you can do the same thing with a muni bond and just not pay the state taxes, it's the same one decision — it didn't take any extra time.

Ankur Nagpal

For the average person, though, I would say: for the person doing nothing — **fuck it, do a Vanguard fund**. The most important thing is to do something. But for people who already have an index fund, this is the sort of *alpha*.

Sam Parr

"What else is on the list? Like, alright — 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 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."

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 they should run their companies. At the time, everyone who joined the company did it because they were like, "Oh, you know, this guy will succeed again." So I feel like the pressure I put on myself is... *fully my own construct*, at the end of the day.

Shaan Puri

Can we switch away from emotions and can you tell me how to make a backdoor Roth [backdoor Roth IRA]? *I don't really care how you feel;* I just really want to know about this Roth tax optimization. What?

Sam Parr

"So, this has been—this has been *kind of wild*. I want to know how Peter..."

Shaan Puri

"Thiel made $5,000,000,000 ($5 billion) and didn't pay any tax on it. What was that?"

Sam Parr

*Yeah, talk dirty.*

Shaan Puri

"Tell me how you feel later. I'll dirty, yeah."

Sam Parr

*Whisper softly* and tell me about my "backdoor box." Backdoor, yeah.

Ankur Nagpal

But yeah, Peter Thiel—well, a lot of people read about what he did, which is like **tax magic**. Most people have access to a Roth IRA. He put his PayPal founder shares in a Roth IRA, sold those for about $27,000,000, then used this as a supercharged investment account to where it is today, where he has $5,000,000,000 in his Roth. He retires next year, so he gets all of that but no taxes.

Sam Parr

"But you gotta dumb this down, man. What's a **Roth IRA**? You gotta talk down to me a little bit."

Ankur Nagpal

**Yeah, so a 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. 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 1970s… do you know what the top tax rate was in America?

Shaan Puri

"It was *like* 20%."

Ankur Nagpal

"It was 80% — it was insane. The top marginal bracket was 80%; it was super high. But the advantage of a **Roth IRA** is that once you have dollars in, no matter how high taxes get, you pay nothing on what is in that account."

Sam Parr

And what was the incentivization there for these people? So, it was a...

Ankur Nagpal

A very short-term incentive at the time. 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 upfront.

Sam Parr

"I was saying, 'Why would the government agree to this?'"

Ankur Nagpal

They want to incentivize retirement savings in general. Compared to a **Traditional IRA**, this brings tax revenue forward. It was always designed with a maximum income: once you make more than a certain amount, you are not supposed to have access. Today, those numbers are, I think, $150,000 or so. You don't really have access if you go the normal route, but that's where you have things called a **backdoor Roth IRA**.

Shaan Puri

So, before you explain that... Basically, if you make under a certain amount, you can put away about **$7,000** a year. You've already paid tax on it when 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 sort of paid it upfront. What does that do?

Sam Parr

Be an age limit, like 65. </FormattedResponse>

Ankur Nagpal

You have to. Yeah, you can get your dollars at 59½, but you can withdraw the dollars you contributed at any time, for any reason. It's only the *growth* that is kind of locked up.

Shaan Puri

So what **Peter Thiel** did — which was great — was that he put his **PayPal** shares in there when they were *valued at nothing*.

Ankur Nagpal

So, he was able to buy his founder shares at, like, *0.0001*, or whatever.

Shaan Puri

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.

Ankur Nagpal

**$27,000,000** — oh, at least from this **Roth IRA**. He put in **$1,700** worth of the founder shares, and he made **$27 or $28 million**.

Shaan Puri

Okay, so then he used that money to invest in Facebook within his Roth IRA. So the "Facebook game" is why it became billions of dollars.

Ankur Nagpal

Exactly. But you then read about **Mitt Romney** doing the same thing. Because I'm in this line of work, I've now met so many regular people with 8- and 9-figure **Roth IRAs**, which is insane. You have $10 million 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. So tell me.

Sam Parr

A story of someone who's done this with, so, **eight or nine figures**. So you're saying **10,000,000** or **100,000,000**?

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 in. The whole game becomes: how do I get a lot of money in? Once you get $20,000,000, going from $20 million 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—alright, the names of these... yeah, the naming is not ideal, but...

Sam Parr

What about the "triple mega"?

Shaan Puri

"The triple mega," right? </FormattedResponse>

Ankur Nagpal

It's like the least creative days of all time, but the **mega backdoor Roth** lets you use a 401(k) to get in $70,000 a year into this account. So you can combine the two and 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 a Roth IRA by age 21 and the mega backdoor by around 30. Even if you just index the S&P and use the 100-year average of the S&P, you end up with $30,000,000 in your Roth IRA at retirement. So if you do this consistently enough, the tax benefit here is **massive**.

Sam Parr

Okay, so who came up with this mega? Who's done this?

Ankur Nagpal

**Mega backdoor** — yeah. So, the way people find loopholes is this: the **IRS** never intends for it to be this way. They write the law a certain way, and some smartass accountant says, "Well, actually, if you do this, this, and this, we're still fully in compliance." The IRS challenges it, loses in court, and that's how we have loopholes. Every single loophole comes the same way. The **mega backdoor Roth**, for instance—there has been legislation to outlaw it for the last few years. It comes up every time. But the mere fact that someone wants to make it illegal, by default, deems it a valid loophole for now. It's the sort of thing that gets negotiated down every single time. Every tax bill has it. Typically the **Republicans** fight against it, and it just gets deferred and deferred and deferred.

Sam Parr

Alright. What are examples of people who have done this to **10** or **$100,000,000**?

Shaan Puri

So, what do you want—their name and address? What do you want them to say: "name"?

Sam Parr

And address? No. You can do a little chat of **house rules**. You can kind of anonymize them a little bit.

Ankur Nagpal

So, I will tell you that these are people that you and I have never heard of. There's a lot of anonymous, wealthy, financially savvy people — 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. I think if you can structure your 401(k) in a way that you can put in $70,000 here into your Roth IRA — which I do now — honestly, just the *sport of it* is fun enough. If you do this over a long enough time, you have these results. It's a sort of thing that we don't know how long this loophole will exist, but for now it's, you know, hundreds of millions of dollars with $0 in taxes. It's very good insurance against where tax rates may go in the future.

Shaan Puri

Let's... should we switch to **business ideas**, Sam?

Sam Parr

Yeah, let's do it. Cool.

Shaan Puri

So, **Ankur**, you sent us a list of ideas that you think any founder could go build—or that some founder should go build—in this space. You've started multiple successful companies now, so maybe you have interesting taste and maybe you're looking where other people are not. When I saw this list of ideas, these were not the same five "AI assistant" ideas that you hear from most people. So, hit us with your favorite one, and then let's go in order.

Ankur Nagpal

Sweet. So I'll go in somewhat random order because I have a few different ones. One of the things I think about a lot is that 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. You have all these high-end executive services for concierge health, basically—*superpower functional health*.

Sam Parr

I don't... you guys have to explain this. 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. I think in the course of two or three years it got to $100,000,000 in revenue. I believe they've just raised another round of funding — in the billions [of dollars]. 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.

Ankur Nagpal

And it's commoditized — everyone uses the same blood-testing companies. It's... but I'm telling you, we're just moving to a world of **proactive wellness**. I think everyone has realized the medical system in the U.S. is that you kinda sit back and wait for really bad things to happen. People of our generation have realized that you want to be proactive about this and not just... not just kinda chill.

Shaan Puri

Yeah, I think there are a bunch of factors, right? First, there’s the Bryan Johnsons of the world. Now you have these really big, attention-getting influencers who are bringing attention to your health and wellness and making you realize how much of a knowledge gap there is — how much more you could be doing. You might have thought you were already doing enough, and then somebody shows you that there’s a new level of enough. Underneath that, you have all the infrastructure: lab testing in different places so you can go get your blood drawn. When I went on Superpower, it was like, “Cool — do you want a nurse to come to your house, or do you want to go eight miles away? There are three locations near you.” I was like, “Wow, this is amazingly convenient.” Then the next piece is that I think the HIPAA laws or the medical records stuff changed. I just gave them my ID and they pulled all my health records. I never even had that myself — like, to have my health records in a beautiful website. They pulled all my medical history, which, if I wanted to go look at my own medical history, I couldn’t have even done before. So that was a change that happened. You have all these different things stacking on top of each other that, like Ankur said, create a cultural movement toward *status* — *status* being associated with being healthy rather than being a degenerate. Before, in my circles, the more you partied the cooler you were — the more bad-for-you your lifestyle was, the cooler you were. Now the more good-for-you your lifestyle is, the better you are — the cooler you are. I don’t know if it’s just that I changed or culture changed.

Sam Parr

"Tell me, how were your results?"

Shaan Puri

"Oh, you didn't see my *tweet* about this?"

Sam Parr

Yeah—what did you—what did you say?

Shaan Puri

"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 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…'" </FormattedResponse>

Sam Parr

"Oh, look—I have the body of a 23-year-old, you know, Russian gymnast. Cool. Thanks for... I'm *so* happy..."

Shaan Puri

Used. Why this?

Sam Parr

Were you so?

Shaan Puri

"I'm the only person... I'm the only person I've ever seen with."

Sam Parr

A higher biological — *literally never*. I've never seen anyone. No.

Shaan Puri

"I *think* I broke the record."

Sam Parr

Yeah—what—what was so old about you?

Shaan Puri

It's pretty cool because the next thing that happens is there's a **concierge doctor** who, within a week, gives you an action plan. They do about 30 tests from a single blood draw and then say, for example, that your LDL is high—or something else is wrong. Then they'll start to talk to you. There's a little concierge chat where somebody will work with me to develop an action plan: things I could change—eat slightly differently, walk more, do a cold plunge for six minutes—whatever people do. You come up with an action plan so you know whether this is life-changing or not. They're probably going to suggest simple things. For example, they might say, "Delete DoorDash off your phone"—that'll probably do the trick. There are a few different ways you can help somebody. Again, this is not how normal medicine typically works. Normal medicine is like a car mechanic: you go there when you're broken, they try to fix it, and most of the time they say, "Yeah, it'll never really run the same." We're in maintenance mode from here on out. At least this operates under the assumption of being *proactive rather than reactive* and that there are actual lifestyle steps you can take—not simply medicines you can get on—to improve your health.

Ankur Nagpal

Yeah, I also think—in addition to all of that—I *genuinely* believe a lot of people are sicker than before, particularly in the US, and some of my other ideas have to do with that. But I do think, when you look around—whether it's fertility, gut health, or allergies—shit's kind of falling apart in a lot of places, and people are reacting to that.

Shaan Puri

But, by the way, the upsell in this thing is crazy because the initial deal is super good, right? It's like $500, and you're going to have a ten-times-better version of your annual physical. It's like, "Okay, that's actually a good trade—you don't need to be super wealthy to do it." You can pay $500 and get a better version of your physical. But when you're in there, it's like, "You want to know how your gut's doing on a microbiome test?" I'm like...

Sam Parr

Yeah, yeah. I'd love to, *kind of*...

Ankur Nagpal

Dude, I...

Sam Parr

I had to click "Next" on the upsell page for **Function Health**. I clicked "Next"—I'm not joking—**15 times**.

Shaan Puri

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 blood cancer test, and I just said yes to all of them. So they upsold me a couple thousand dollars' worth of tests. But honestly — great. I wish my doctor had been offering me these. Why doesn't my doctor offer me these either?

Sam Parr

Do they do it the other way around? They're like, "Oh, you want to get your testosterone checked? You look fine." Yeah. Awaken, yeah.

Shaan Puri

"What's your wife say to you?"

Ankur Nagpal

I'm like...

Sam Parr

"What? Why is this so personal? So, what's your idea here?"

Ankur Nagpal

A lot of these services are doing really well. I think what you cut out is the motivation: a lot of times people are driven by the *aesthetic* side. People want to look good. If you had a *functional health* approach for physical appearance, it would completely crush. You come in and it's like, "Wow, Sean—your hairline has receded two inches." You tie in a DEXA scan to it. Basically, it's a **concierge service** to elevate the experience. Two of my college roommates are plastic surgeons, and I've heard a bit about that side of the business. Marrying these two ideas—basically concierge look-ups with improving your aesthetics—I think is a fantastic business.

Shaan Puri

"This is *actually* a great idea."

Sam Parr

We had Justin Mares on the podcast, and his skin was *glowing*... </FormattedResponse>

Shaan Puri

He's telling us about his inner health, and we were just like, "He's **handsome**."

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*.

Shaan Puri

We went out to breakfast — Sam. Literally, everything he ordered, I just said, "Whatever this man eats, I need to eat." So when he ordered this drink, the waiter looked at me. I said, "Did you not understand the instructions? Whatever this man eats, I eat." So I had an identical meal to him.

Ankur Nagpal

But... I think you have to, like, [unclear: "stamina are"] investors in a *testosterone* company, and if the founder was not jacked.

Sam Parr

I would not have invested in the company.

Ankur Nagpal

"Like, I think..."

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.

Ankur Nagpal

Yeah, so you have to look the part in order to do it. I think, yes — businesses that focus around the aesthetic part of it would crush. I mean, you already have concierge medicine in Turkey, stuff like that. Secondly, I think anything that helps us break out of the U.S. food system will do quite well, and again, probably more so in cities like New York. But it's kind of funny... 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*. They literally park on the side of the street and you make this little transaction. I have a lot of people who just want to break out of the U.S. food system, and I think businesses that enable people to do that will go quite, quite a long way.

Shaan Puri

And so, how did you find this Amish farm? What was your process to find this alternative?

Ankur Nagpal

So it's word-of-mouth. A lot of my friends were all talking about it, then someone's like, "Oh, I get my beef from this place." That actually started out with—you know—you buy beef and then you get upsold on all the other products. Now, before you know it, my soap is made out of goat milk and shit. That's probably not even relevant or helping, but, you know, they were pretty, pretty nice business. They go straight from farm to... they drive out to New York City with this little truck. They park the truck on the side of a street corner. You have a **30-minute window** to meet them. 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—sure—I'll add $4 for the raw milk. But I think breaking out of the US food system—at least, you know, we'll see what RFK does—short term, I think there are a lot of people that will pay quite a bit of money for...

Sam Parr

"Do you get all your meat from this Amish fellow?" </FormattedResponse>

Ankur Nagpal

I do. It's *so* good. Dude, I don't like chicken in America. As someone who'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... you know, it's such a big difference if you have the same stuff outside the U.S.

Sam Parr

We all need one of these Amish guys.

Shaan Puri

"Isn't this what a farmer's market is supposed to be, by the way?"

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. </FormattedResponse>

Shaan Puri

Well, the way you describe it, it's more like a *drug deal*, and actually that kind of appeals to me in a way. A farmer's market is a little bit like, "Oh, cute date on a Sunday morning," but I kinda like an *element of danger* with my groceries.

Ankur Nagpal

"This is *contraband.* This is *contraband.*"

Shaan Puri

Exactly.

Ankur Nagpal

Not only that—when you buy something, all the signs on it will very clearly say, "Not for human consumption," but it's like... *wink wink*—for human consumption. Oh man.

Sam Parr

Can we ground it up and inject it in my vase? That's usually what I do when it says *"not for human consumption."* Yeah.

Ankur Nagpal

"For cats and dogs only."

Sam Parr

Does this stuff make you feel better, *by the way*?

Ankur Nagpal

It does. I mean, of course you have to control for the *placebo effect* and stuff, but generally, yes—I do feel better when I'm eating this.

Shaan Puri

Or don't control for placebo. *Placebo is the best.*

Ankur Nagpal

Placebo is a mess, right?

Sam Parr

Yeah, yeah. Whenever I read about these, I'm like, wait—so you have to study it? Like, the way we were talking about placebo: we act 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. All of that—it's all I ever want: the *fake thing*. No, it's... it's, I mean, the only reason...

Ankur Nagpal

I even went down this rabbit hole. 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 and live like a degenerate. And I'm like, "I feel better. My physical body feels better." I don't think it was the addition of the alcohol. I think it was just the *food system*.

Sam Parr

It could have been that. It could have been some of the other stuff you're...</FormattedResponse>

Ankur Nagpal

Doing on there, too. Yeah, could—could have.

Sam Parr

Never been.

Shaan Puri

Alright, here's the next idea.

Ankur Nagpal

Alright — next idea is a travel agent who books travel using *credit card points*. Again, we've already talked about this, right? I'm on the cutting edge of a lot of personal finance shit, but I still find it a pain in the ass sometimes to actually find the right flights. Right now I have 250,000 Amex points and 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.

Shaan Puri

*How, how, how...* How do you want this to work?

Ankur Nagpal

I want this to be a **concierge service**. I want to tell people exactly what I have—like what points or whatever I have—and where I'd like to go. Often I don't even care exactly where I want to go; it can be a warm destination in a certain part of the world, and they just do it for me.

Sam Parr

Jack Smith is a friend of all of ours, I believe. When Jack suggests something, you take it seriously — even though he's one of the strangest people ever. He's thoughtful enough that there's usually a unique reason why he does things. He *only* books his flights via Flightfox.com, and I've used it a couple of times. 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 roughly when you want to travel, and there's a human on the other end who goes and books it for you. They spend about two hours per flight finding the best option for you.

Ankur Nagpal

"Their business doesn't make sense. What's their margin on this?"

Sam Parr

"I have no idea, but I have booked three or four flights on this, and this is **amazing** — it works every time."

Ankur Nagpal

Just—can you enter your **credit card points** and stuff, or is this just dollars? </FormattedResponse>

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 or sold another person's miles?

Ankur Nagpal

No, but that's the kind of stuff that... I think businesses have made that easier. There's **so much value to be unlocked there**.

Sam Parr

Have you ever heard of this Sean?

Shaan Puri

"I've heard of it. I've never done it before. Have you done it?"

Sam Parr

I've done it. I booked a flight where I had a friend who spent roughly $10–$15 million a year on advertising with his Amex card (or some credit card). He said, "If you wire me the money, I'll book the plane ticket for you; I'll take a small fee and you get the discount." I did. I think I saved 30% or 40%—something pretty significant—because I was buying six first-class flights. It was very expensive, and I saved thousands of dollars.

Ankur Nagpal

So who's this friend? Basically, it's what they're doing, but I would like it to work as a true, *professionalized service*. I think you can now automate a lot of the back-end with...

Sam Parr

But there's an issue.

Ankur Nagpal

Smart tech and stuff.

Sam Parr

"This is *highly not illegal*, but it's against the terms of service of all these airlines. If you get caught doing it, I think they take your ticket."

Ankur Nagpal

"I feel like a disproportionate number of my ideas are turning out to be **illegal**." </FormattedResponse>

Sam Parr

But yeah. Yes — so, what were you saying about the **financial services company** that you currently run? Yeah. Alright. Let's... let's... let's... "illegal raw milk"? I don't...

Ankur Nagpal

"I don't want my **Chief Compliance Officer** to message."

Shaan Puri

Me after the FCC.</FormattedResponse>

Ankur Nagpal

"I should add: nothing shared here should..."

Sam Parr

"Be considered as legal advice, investment advice."

Ankur Nagpal

"Or tax advice. Everything is for information or health advice."

Sam Parr

Health advice — that's fine.

Ankur Nagpal

That's *not that regulated* in this country.

Shaan Puri

No, but you're right on the points thing. I use, like, "seats.dot.arrow," I think [site name uncertain], which is basically—you plug in what points you have and it's like a search engine. But it's very slow and it's very hard; I have to do it myself. You're absolutely right. I want either a human or I need **AI** to be able to do this where it just knows. I just say what I'm trying to do... and sometimes it's as fuzzy as what you described. Like, "I just want to go somewhere warm in the summer." It's okay if it's Puerto Vallarta and it's okay if it's Hawaii. I'm not—yep—not dead set on one place. Sometimes I am dead set on a date and a place; sometimes I'm not. Either way, I want to be able to make use of these points because I think I have 7,000,000 **Amex points**.

Ankur Nagpal

Seven. Yeah, exactly. There's so...</FormattedResponse>

Sam Parr

"Much arbitrage. Wait — you have **7 million**?"

Shaan Puri

"Yeah — at least 7 million."

Sam Parr

How does that convert? Is that, like, **$70,000**?

Ankur Nagpal

Once you get good at it, the *value is so much more than the dollar amount*. But finding the "purse" [unclear—word may be "purse"]... The average person is not going to get good at it, so finding the intermediary that's good at it extracts some value off the top.

Sam Parr

"Even though you're *incredibly wealthy*, do you still use airline points like crazy?"

Ankur Nagpal

Dude, **Naval** destroyed me on Twitter. I posted some... pack, and he's like, "I thought you sold a company." **Ray** showed the hell out of me.

Sam Parr

Yeah, do you sell credit card churn?

Ankur Nagpal

I don't do **credit-card churn**. I don't do things that are high effort, but I do the basics: if I'm spending money on shit, I'll use a credit card and get the points. I still struggle. If a flight is over $10,000, I still struggle — even though, mathematically, you're like, "oh, you can afford to spend that." </FormattedResponse>

Sam Parr

Do you still mostly buy items on sale?

Ankur Nagpal

Not on sale items. There'd be a time when, if I went to e‑commerce and you got a 20% new-customer discount, I'd create another account. No—I don't do that now. I'm like, "That's, that's, that's, that's *too much effort*."

Sam Parr

You quit doing that yesterday. Yeah, but...

Ankur Nagpal

**Credit card points.** I think if you spend a bunch of money, it just helps a ton. Also, as a brown kid, it's very helpful because it allows me to buy things for my parents. My parents will not accept me buying a ticket for them, but if I tell them the ticket comes from points, they have no problem accepting it. </FormattedResponse>

Shaan Puri

Yeah, *totally*. I do the same.</FormattedResponse>

Sam Parr

*Weird psychology...* Yeah, exactly.

Ankur Nagpal

*Sometimes, it is.*

Shaan Puri

"It's like, just tell her it's *points*."

Ankur Nagpal

Yeah.

Shaan Puri

"And then don't bother with the points — it's going to be too confusing. Just get her the ticket. Could you tell me: I read somewhere that you've built a few things with AI, like personal software for your own life. What did you build, and what do you see as the opportunity there?"

Ankur Nagpal

So I was—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 ten-plus years. I understand enough, but I just felt like everything kind of went away for me until now with **AI**, where it's again become super fun to play around with stuff and build small apps. I started by building things that solved annoying workflows I have to do. For example, every time we host a webinar we have to download something from one place and re-upload it somewhere else. I started building these internal tools. But now it's reached a point where I have all these annoying—*we're talking about homeownership*—things I need to do for my house. Building a very simple 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.

Sam Parr

What did you make?

Ankur Nagpal

So, *for now*, it's a very simple **task-management app**. There are certain things in my house I have to do at different cadences — property taxes (you pay quarterly), changing the fucking water filters (once every X months), and other similar tasks. You enter all these tasks, and in some cases you attach another person to them. It kind of pulls it all together automatically. It's like: "Oh, it's been... this month here are the things that you should do, and here are the people that can do it." Again, this is something just for my own entertainment/amusement, whatever, but you can extrapolate how any local business could use it for whatever annoying things they have to do.

Sam Parr

**Sean,** whenever I hear "Ankur's single," I think, "Well, you're not—you're unmarried." Whenever I hear "a single guy"... sorry, that sounded like, you know, I'm not your mother. I'm not trying to diss you.</FormattedResponse>

Ankur Nagpal

This already sounds like a condescending, "no—it's..." *Dad-type* statement. Listen: Dad's like, "Well, it's so simple for you."

Sam Parr

You don't understand.

Ankur Nagpal

But go on.

Sam Parr

No. What I'm saying is it's the *opposite*. When I hear you describe this stuff, I think to myself: if I didn't have a wife—or she just walked out on me—I have no idea how I would handle any of this. I don't understand how a lot of our bills are paid; they're just kind of magically paid. When I have a bunch of my single friends—like **Sofia Amoruso**, one of our mutual friends—she tells me all the time about how much she has to spend doing all this, and I'm like, "Dude, I'm used to having two of us." You know, I wash, she dries. I'm used to having two of us. To have one person manage all of this as part of a household, when you own a home and have responsibilities, that sounds so hard. Do you know what I mean, **Sean**? Can you imagine having to do this stuff—everything?

Shaan Puri

"I just wanted to see if you could *land the plane* on that one, and I would say..."

Sam Parr

"Did I land it?"

Ankur Nagpal

Yeah — he did. He did, he did.

Shaan Puri

It was like a Southwest... *you know*, there was a bump. There was a little bump on.

Sam Parr

"The way down, but... you did, you did. What I'm saying is: *it's so much work* — I don't understand how people do it."

Ankur Nagpal

Especially when you add in the dynamic of *homeownership*. Especially as someone who grew up outside the US, I have no actual life skills. I feel like people in America know how to do shit—they don't need a plumber; they've learned it somehow. But growing up outside the country, I'm not handy, so running a house is...

Sam Parr

It's quite a *stereotype* that Americans know how to fix toilets.

Ankur Nagpal

Yeah, I... you don't think it's true?

Sam Parr

Well, I do think that, amongst all of my brown and Asian friends, all of them *hate* Home Depot, yeah.

Ankur Nagpal

Like, *self-reliance* was not a status symbol in the U.S. It is a status symbol—you're higher status if you can actually fix stuff. In India, it's like, "Oh, you have someone to do all this stuff for you." </FormattedResponse>

Shaan Puri

"Sam, it's not true. If you go to Home Depot on the first Saturday of every month, it'll be filled with Indian people. Do you know why?"

Sam Parr

No. What are they doing?

Shaan Puri

Because that's when they host the **free Home Depot class**, where you and your kids can come build things. It's totally free — they give you a kit and you build it. It's amazing; it's like a free educational program. It's only in the store during the **first Saturday of the month**, and, by the way, it's amazing. If you're not using this, you should use it.

Sam Parr

Is that a true stereotype? Ramit has told me he was like, "My Rich Life" — he explains all the stuff and he ends it with, "and also, never step foot into a Home Depot." Yeah, no.

Ankur Nagpal

I mean, it *definitely*—at least when I first moved to America—it struck me as strange how handy everyone was, and how much pride they took in it. Growing up, it was the opposite. It was even weird to change a light bulb—maybe that's an exaggeration. But yeah, I definitely think that being a homeowner here, as someone who didn't grow up here, you're **not prepared** for it.

Sam Parr

That's awesome. That's funny.

Shaan Puri

Alright — tell me about this *pickleball* thing you're writing about.

Ankur Nagpal

Oh, dude... this is so— I was like, in terms of things I spend money on, after food my second-biggest expense in New York right now is a sport called *padel*. It's pretty crazy. Is it "paddle"? "Paddle"? "Padel"? Whatever—same thing.

Sam Parr

Same sport. See, I *wanna*...

Ankur Nagpal

Say it right: it depends — Latin America versus the U.S. 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. In New York it's sort of... there's a place near my office. It's the closest we have to a country club because there's not enough space here. You see a lot of our mutual friends 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 — now in the U.S., where we're super, super early, there are about 2,000 courts here and about 20,000 in Spain. It's on a fantastic upward trajectory: an incredibly fun sport with a demographic that has a high propensity to pay.

Shaan Puri

What's the difference between this and *pickleball*?

Ankur Nagpal

It is — it is *substantially more athletic*. A lot of people who play this are like, "Well, pickleball is a game; padel is a sport." </FormattedResponse>

Shaan Puri

Nice—like that. I do like it a bit.

Ankur Nagpal

Of snobbery, *pickleball is uniquely American* in that... it's like, I don't know — it's so slow compared to anyone who's actually played sports. Like, pickleball has a lot of ex–D1 tennis players, a lot, but you're

Sam Parr

*Not exactly* explaining the attributes of.

Shaan Puri

"The game's... you're more so."

Sam Parr

"Than a bigger club? *Yeah.* Is it a bigger court, or...?"

Shaan Puri

"A cyborg paddle? Like—what's the difference?"

Sam Parr

"The difference is that Paddle Ball is just a bunch of fat, disgusting pigs. They're slow and they're athletic. Patel's the same thing — it's just Division One ex-athletes, yeah."

Ankur Nagpal

So imagine a slightly smaller, yet wider, tennis court with a back wall. It's... I know, depressurized tennis balls, so it's quite fast because you have the back wall. Instead of hitting the ball out, it hits the back wall, bounces back, and you kind of go back and forth. It was really big in Latin America and Europe, and it's finally coming to the U.S. in a way that I think you can go to any *tier-two* city, spin up a location, and probably do quite well for the next few years. 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. Again, New York is probably the most extremely expensive market in the U.S., but it kind of cascades all the way downward, I think.

Sam Parr

You have an app? Well, I was with you one time and you were like, "Oh my God—someone just took my spot as the leader." Oh.

Ankur Nagpal

It's the—it's the worst. It's the *game within a game*. There's a rating every game you play, and it's insane. I'm playing with people who are all in their twenties, thirties, and forties—insanely good at their professional lives—but they have this unmet competitive need. Everyone is so aggressive about their rating, about their ranking. A buddy of mine was texting me after we lost our match. We were 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..." [trails off]

Sam Parr

But is it like a game?

Shaan Puri

We lost.

Sam Parr

Is it a *self-reported* system?

Ankur Nagpal

Well, how's the rating? Yeah, so we all have scores. Let's say I beat you. I entered 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 he actually went down despite beating him.

Shaan Puri

It's like an *Elo* score.

Ankur Nagpal

Exactly. 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.

Shaan Puri

"Is this basically a social network that somebody built?" </FormattedResponse>

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, 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 space — on all these apps.

Shaan Puri

"You said that New York has **1,000** courts and there's **20,000** in Spain. In the U.S.—the U.S. **1,000**? Only in the U.S., and there's **20,000** in Spain, correct? Wow, that's pretty crazy." </FormattedResponse>

Ankur Nagpal

And again, the **Google Trends** for the sport—just look it up, or I can drop a graph. It's like *straight up and to the right*, picking up momentum.

Shaan Puri

So, *dumb question* here: since squash and racquetball are almost identical games to this, what are they — just like, how mad are they that they just sat there? They're pretty... they're pretty.

Ankur Nagpal

Mad at me, but *squash*—squash has been on the fringes for a while in the U.S. It's like either an immigrant sport or it has a rich, white, Ivy League connotation. There's no—there's no in between. *Paddle* has also become...

Shaan Puri

Any different?

Ankur Nagpal

It's become — I mean, globally, it's growing *really, really fast*. I think it's all a case of catching the right timing. It's a sort of sport where you can play the first time and 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. The community that's formed around it has been awesome to see. I think even Andrew Schulz was talking about it on Joe Rogan, and it's starting to become a thing. We're so early; people are like, "I don't think it's anywhere near mainstream consciousness." But I don't know — it's 05/12/2025. Come back to this in two years; I think it's gonna... you're gonna see.

Sam Parr

I saw a lot more last year. I went to—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 know what it was. But when I went there, I think it was the same place, **Ankur**, that you go to. The whole place was all black: black walls, like **Barry's** or **SoulCycle**. It had that vibe. Everyone was hot and cool; it was definitely a scene.

Ankur Nagpal

"Were you good?"

Sam Parr

I didn't even play. I was at an event, but I was watching these people. When I got there, I got the vibe—like, "they want to exclude people from coming here." That's the vibe I got. If I don't wear a collared shirt, they're going to kick me out. That was the vibe. I could *smell the racism*, you know what I mean? No. I try to play real sports. I don't want to play those things. No, I don't.

Shaan Puri

Order, yeah.</FormattedResponse>

Sam Parr

That's a game. No, I don't. I don't really like it. I feel silly playing paddleball, *if I'm being honest*.

Ankur Nagpal

The **one thing** I dislike about New York is it's so hard to have a country-club–like place you can go to and play all the sports. I do think smaller spaces like this are potentially one of the answers. I have a bunch of friends who are dads for the first time. A lot of them don't know how to make friends as an adult. They're like, "Hey, I've moved to a new city," or "I don't like my old friends." How do I actually make friends as a man who is *not dating, not drinking, not going out*? What do you do? I think places like these are the answer quite often, since people come, hang out, chill out, and some community forms around it.

Sam Parr

How do you meet friends, **Sean**?

Shaan Puri

"No new friends, baby. No new friends."

Sam Parr

I'm trying to keep up. I'm trying to do...

Shaan Puri

I do a good job keeping in touch with my existing friends, so I'd rather make new friends now. There's a lot through the school, actually. Once your kids get into school, the priority sort of shifts to, "Well, I'm going to be around these people anyway—let me just find the coolest people in this group." I already have, like, three things a month that I have to do with this set of people, so is there anyone here who I get along with? If I can find that person, I get a double win: I get the playdates for my kids while I get to hang out with somebody cool. That became the focus for me, rather than going out and individually making a friend. I have three little kids under five years old—if I'm going to go do a hangout with friends, that's a pretty hard choice. It only benefits me; it doesn't really integrate with the rest of my life. I do play in a basketball league that I take *uber* seriously. Our friend Ruben runs a basketball league called **SF Hoops**; he's been doing it for like a decade. We play one game a week, and you would think, "Oh, it's just pick-up basketball—who cares?" But no, I take it so seriously. Basically the six other days of the week are just preparation for the one big game night. After the game, I get the footage off the AI camera and start sending clips to the team. I send them partly as commentary—kind of funny—but also like, "Yo, we gotta correct this for next week. We're not going to... we can't do this again." So we take it very, very seriously.

Ankur Nagpal

Seriously — same in our groups. Because it's a *two-on-two* sport, people are sending coaching videos back and forth, and the whole thing, whole thing is pretty insane.

Shaan Puri

"You bought a piece of a cricket team." </FormattedResponse>

Ankur Nagpal

"I bought a piece of a cricket team."

Shaan Puri

What's the story here?

Ankur Nagpal

So, again—flashback. From about **ages 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*. I think we've all felt this: the older you get, the more you want to do what the eight- or nine-year-old version of you thought was "dope." I got in touch with someone who said one of the shareholders in what is the most valuable cricket team in the world—worth roughly $1,000,000,000 in the Indian league—was selling a stake. I was like, this is the whole point of having money, right? To be able to do things like this. So I jumped on it. I put in a bunch of dollars myself and also pooled funds from other investors. We now own a small piece of the team. In time, the idea is we can keep buying a bigger and bigger piece. I joke about this a lot.

Sam Parr

You gotta be like the *non-douchey* Chamath. </FormattedResponse>

Ankur Nagpal

The "douche" part is uncertain for now, obviously. Yeah.

Shaan Puri

So... which team is it? And do you, like, ballpark it? Are we talking six figures, seven figures, eight figures? How much did you put in?

Ankur Nagpal

I put in... the group we represent put in a high seven-figure amount, of which I think 20% was my own money. The valuation of the team was close to $1 billion, so as a percentage it's still tiny. The team is called **Chennai Super Kings**. They've won—I want to say—six championships. The Indian league is about 15 years old, so they've won more titles than any other team and have the highest market cap. It's such a monopoly because India is the biggest country in the world and it's truly a *one-sport* country. The delta between sport number one and sport number two is massive. As far as the league goes, they just have so much room to run since there still aren't 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: 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.

Shaan Puri

You said, "It's the third most valuable league in the world."

Ankur Nagpal

Yeah, it's—by TV rights per game—actually **number two after the NFL**. And, by total revenue, it's *more than any of the European soccer leagues*, for instance, which is crazy for a league that...

Shaan Puri

Is [it] worth more than the **Premier League**? How is this possible? How could the most valuable team be **$1 billion**, but the league be worth more than that? There are players in soccer who can almost make **$1 billion**.

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. My interpretation was that the European leagues are just very bad at monetizing their commercial value. Maybe the value in the league is to the team. So, while **Manchester United** may be worth substantially more, the franchise value of the **EPL** may not be that much. That was my...

Shaan Puri

Gotcha.

Ankur Nagpal

Have you?</FormattedResponse>

Sam Parr

Flown there and, like, participated in any of the [inaudible].

Ankur Nagpal

I haven't had a chance to yet because this deal came together very recently, so I haven't done it yet. *Long term*, that's what I actually want. Everyone's like, "Wouldn't it be cool to earn the upside?" No—I want to draft players. I want to be able to kick people out. To me, *long term*, when I have time, that is the more fun part of this whole thing. Sure—don't lose money—but being an annoying, **overly involved owner**, I think. </FormattedResponse>

Shaan Puri

**Hell, yeah.**

Ankur Nagpal

Sounds awesome.

Shaan Puri

I don't know.

Sam Parr

If you did, did you guys read about... Did you guys read?</FormattedResponse>

Ankur Nagpal

About this **VC [venture capitalist]** dude in Europe who bought a soccer team and then put himself on the team.

Sam Parr

Yes—no, but that's awesome. Yeah, who is that?

Shaan Puri

He's like a *player* on the team.

Ankur Nagpal

And it's so funny, because 90% of the world is like, "Oh, that's pathetic." I also was like, "That's awesome — I would totally do it."

Sam Parr

Did you guys see—did you guys watch the *Netflix* show, or was it on something else? I forget what it was on... the one with **Ryan Reynolds** and **Wrexham**.

Ankur Nagpal

"I didn't watch the show, but yeah—I read a lot about it."

Sam Parr

How has it turned out, Sean? Do you know? That's been like four years — has it?

Shaan Puri

I think it's going well. They got promoted—I think a couple of times, actually. I think they've moved up a couple of times. We had a guy on the podcast, Heralabad, who did the same thing. He's bought a team in—it's like, I don't know, a third-division team or whatever. I don't know which division they're in exactly, but they're, you know, up for basic promotion. He's bringing a *Moneyball* approach. He's basically a kind of data guy; he's a sports bettor—that's his background—so he's bringing a *Moneyball* sort of approach to drafting the right players—or not drafting, but signing the right players—playing the right strategy, and selling at the right times on players.

Ankur Nagpal

Did you see the Celtics sold for **$6,100,000,000**? That basically changed everyone's model, right? People were underwriting sports teams being worth $1 billion, then $2 billion, and maybe $2.5–$3 billion. They sold for $6.1 billion, so it kind of puts into question just how much the rest of these teams can be worth. Who do they sell to? Was it some PE [private equity] group?

Sam Parr

Yeah, it doesn't seem— it just seems that the sports teams are... It seems challenging. It seems like a very challenging thing. I mean, I'm a little nobody, but it seems challenging to have a proper market for it, because it seems like one of those things that, *if you want it, you want it*, you know what I mean? And the only people... it's...

Ankur Nagpal

"Like a domain name — it's very hard to say, 'this domain is worth **$400,000.' There's such a small supply, and demand is very, very limited."

Sam Parr

There's three potential buyers, and whoever wants it will potentially pay. For example, if **Jeff Bezos** wants a sports team he grew up with, he will almost pay an unlimited amount of money. It doesn't have to make sense, and that sets the market price for the...

Shaan Puri

Next — well, **number four**: the number of billionaires keeps going up. The number of teams in the **NBA** stays the same. They're about to launch — they're about to open up two new franchises, and each one of those will get **$6,000,000,000**. Then that revenue goes to the other owners...

Ankur Nagpal

That's... wait.

Sam Parr

Two, two new franchise—*wait, what?*

Shaan Puri

The NBA is going to expand by two more teams. They're going to add a Vegas team and probably a Seattle team. They wanted the Celtics franchise to sell at a very high price so that they could then go to those new franchises and say, "You're also a **$5 to $6 billion** price tag," which is pretty crazy. I mean, 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 **$6,000,000,000** or whatever he bought it originally for.

Sam Parr

I have to look it up, but...

Shaan Puri

It was very low. Basically, he compounded, kind of like, 20% over a twenty-five-year period.

Ankur Nagpal

And... or something like.

Shaan Puri

So, he— you know— did really, really well on that investment: won the championship last year, and then sold to this guy who had previously started, or was a partner at, this big PE shop [private equity shop]. That guy was a lifelong Celtics fan. It's the same thing: this is a **trophy asset** that also has all these other interesting things, like the **media rights** and other things that are...

Ankur Nagpal

There's the title that's in the U.S. You can also get **massive tax write-offs**. There are all kinds of weird tax strategies where some people have taken **player contracts** as a depreciating asset and used that depreciation to offset income. *So crazy.*

Shaan Puri

And there's a **real estate play**. Basically, some teams buy their own stadium — they own the real estate. Then they buy the existing real estate right around the stadium because they're the hub, so they know that that real estate right around is going to be really worthwhile. Some people are trying to open casinos because now **sports betting is legal**, which is a whole other vector for generating revenue. So you have all these. And by the way, your expenses are capped — there's a **salary cap**. In the NBA, for example, you can only pay so much, but you can still earn more, and your franchise can go up in value.

Sam Parr

I went and heard a talk by Marc Lasry. Do you guys know who that is? I think he owned the Bucks. He was telling a story. He's a billionaire and his whole thing now is buying sports teams. He said 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 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 so that it works out." So he's like: you either want to win, and you have to have a lot of extra cash flow to cover that nut, or you're going to lose but you'll be profitable. You pick one or the other.

Ankur Nagpal

I bet it also depends on the sort of sports salary. Again, that was the whole *Moneyball* approach, right? Back in the day—or whatever—where you're spending a lot less but, relatively speaking, you're doing well. I think for a lot of people—at least for me—many who do this had, at some [point], **failed athletic ambitions**. There are 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.

Sam Parr

Well, we talked to a guy.

Shaan Puri

But, by the way, I don't believe that *marketing* is true. Like, the Warriors — when the Warriors win, they generate more revenue than anybody in the NBA. They're worth $9 billion now. They did all of the above, so I don't think that's necessarily true.

Sam Parr

Revenue or profit?

Shaan Puri

They're also profit.</FormattedResponse>

Ankur Nagpal

"Well, it may be true in Milwaukee, yeah."

Shaan Puri

Exactly. I think in small markets that actually might be...

Sam Parr

And we were with... we were with Alexis at the basketball thing, Sean, and he was telling us about how he...

Ankur Nagpal

"Invested soccer team? No."

Sam Parr

He bought the women's soccer team. He's starting a track league—he invested in that. He also told us about how he either did buy, or was trying to buy, a piece of a team in **Tiger Woods**' new golf league — this weird stadium-style golf league, which sounds pretty awesome. He was like, "Well, the numbers sound crazy... I don't remember what he said, but let's say hypothetically it was $20,000,000." He continued, "That sounds ridiculous, but let me explain the math: this sport gets this amount of views and they make this much money; this sport gets this amount of views and they make this much money; therefore..." He backed into it, and what sounded like incredibly high numbers on the surface seemed incredibly reasonable. I heard another guy do the same thing with sailing. This guy, **Mark Lazarus**, was like, "I'm trying to buy a sailing league," and he was explaining the numbers. Basically, the whole business of the sports stuff was finding undervalued media rights and figuring out whose contract is going to end soon so they can purchase them and renegotiate the contracts in such a way that they get value.

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 on how well they monetize eyeballs, it's terrible. In the US, you have very small leagues that are so good at squeezing out every last dollar. The **NFL**, obviously, is a world-class case study—they've monetized so well that they're literally hitting a [saturation point]. They're like, "We need to go outside the US to meaningfully still grow from this." That's insane.

Sam Parr

"Ankur, awesome—hanging out with you, dude." </FormattedResponse>

Ankur Nagpal

"Yeah. It's great. Great — thanks for having."

Sam Parr

Me too, thanks. Do people find you?

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**. It's called the **OO Summit**, and 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 [unclear in transcript]. For any tax optimization stuff: kerry.com

Sam Parr

Alright. *We appreciate you.* That's it — that's the pod.