$250M Founder Reveals How The Rich Avoid Taxes (Legally)

Today we are talking taxes and we're talking taxes because taxes are my favorite subject. They became my favorite subject when I paid way too much in tax when I sold my company and I was so happy and so sad at the same time. Today's guest had the same problem. He sold Teachable for over $200 million and then decided, you know what, he's gonna go on a renegade to make sure that no entrepreneur pays more taxes than they need to. Um, we basically invited him here and he was like, you know, I could talk about my story. I could talk about my life. We were like, nah, dude, talk about taxes.

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off.

On the road, let's travel. Ankur, welcome to the show, man. Uh, and it's a long time coming.

Yeah, I'm excited to be here. It's weird how I've now accumulated a lot of specific knowledge in this one kind of very narrow topic, and I'm excited to share it.

And the summary of your story, and we'll talk about it a little bit later in the episode, but we want to talk about taxes. Summary of your story is prodigy entrepreneur, had a bunch of stuff started in college. You started a company called Teachable, sold it for $250 million when you were 31. That was like a courses business. Now you've got a new thing, was called Carry now, or no, was called Ocho, now called Carry. And it's like a 401k, like a self-directed 401k thing.

Yeah, absolutely. It's basically the bigger vision is how do we help people build wealth? By saving money on taxes and the solo 401k is our first product. But yeah, that's the story. The quick sort of other bit is I did not grow up in America, so I knew nothing about the US financial system. The country I grew up in never had taxes. Taxes were just not a thing that existed in Oman where I grew up. So the first time I heard about taxes was when I was 21 years old and I was like, wow, you actually have to give money that you earn. This is crazy. Uh, but yeah, you got most of the story.

By the way, before we talk taxes, I know we're supposed to just start with the taxes thing.

Yeah.

You, you, you have earned your seat on My First Million. You made your first million bucks when you were like 20 years old, right? With something pretty funny. Well, can you tell that story? Can you tell the fast version of that story?

Yeah, absolutely. I was in, I was in college at Berkeley and at the time Facebook released the Facebook platform. So you could, you know, send gifts to people, answer quizzes and all of that. And I built these viral Facebook applications starting from when I was 18 all the way to 20. And it was really fun. I mean, you know, we created personality quizzes, like you could answer a few questions and find out how good a kisser you are or which Friends character you're most like.

If you have to take a Facebook quiz to figure out if you're a good kisser, you're probably a bad kisser, right?

Well, the funny thing is I'm not gonna name names. One of the Facebook founders actually took that quiz multiple times, and I know that because you get their Facebook user ID in the database. So user ID number, I'm not gonna tell you which number it is, is, was in our database and we're like, wow, this person really wanted to know. But anyways, yeah, so we created these personality quizzes and then friend quizzes and stuff. And yeah, I, you know, Millions of daily users, uh, was able to make $1 million before S21, which was pretty cool.

Yeah, that's amazing. Um, so you've, you've earned your, your street cred here for us, uh, on My First Million. All right, so let's talk, let's talk taxes. If I'm an entrepreneur, what are the biggest things that I need to know about taxes? What are the things I should be knowledgeable of and doing in order to save money?

So it's rigged in favor of business owners and real estate. And most people kind of ignore this. I would say like the advice I got growing up was, you know, go to a good school so you can get a good job. That's what winning was. And even the advice around money, which was kind of like, You know, hope, you know, try, try to get like a, a raise, maybe 10%, you know, try to save. But the hard part about saving is that your biggest expense is taxes, right? Your, your, your taxes might be 30 to 50% depending on where you live and, and how, what bracket you're in. That's your biggest expense and that's every single year off every dollar you make unless you're able to shield it with some of these, these things you're going to talk about.

I think, I don't know if you remember, but Warren Buffett back in the day had a famous quote where he's like, My secretary pays a higher tax rate than, than, than I do, right?

Yeah. What an asshole.

Well, I think, I think the issue though, it's not an issue. It's just, it is what it is. If you have W-2 income, I'm almost positive there's close to no way that you can reduce that, your tax liability, other than maybe, um, like minor percentage points.

You can do crazy stuff by using your spouse. You can have your spouse become a real estate professional. So then you as a couple can write it right off real estate depreciation, but you have to get pretty fancy to do things with W-2s. You're right, there is a universe of things, it's just much smaller.

And then like, let's say I make $1 million a year as a business owner. Like, I actually don't know what the savings can be. I know with QSBS I saved a huge sum, but I don't know what I could reduce my taxable income by as a business owner, but I know it's a lot. Whereas the W-2, it ain't.

Well, let's tell the W-2 story real quick, because I know people in San Francisco that have high-paying jobs at like, you know, a Facebook or a Google. And, you know, they're marrying somebody and they're like, hey, guess what, honey? You're a real estate broker now. They're like, what? I don't want to do real estate. You want— you're a real estate professional now. It's like they have to get the status and then they're buying Airbnbs in order to offset their W-2 income.

Yeah. And before it even comes to you, it's just taken out of your paycheck before you even get it. Um, all right. So let's say we are an entrepreneur. Sam mentioned QSBS. I'm guessing that's going to be number 1 on your list because it's such a huge advantage. Explain what it is and then explain the kind of beginner level and then the advanced level version of doing it.

You're forgetting the up to $10 million or 10 times your basis, whichever is greater. Great point.

It's a great point. It's either $10 million or 10 times what you pay for the shares. As a founder, it's most likely going to be $10 million since you buy your shares for almost nothing. But this is, this is massive. Like when I sold my company, I live in New York State and in New York State, even New York State doesn't charge you taxes. So I only had to pay New York City taxes on the first $10 million in gains. And this is just by size of benefit. It's absurd, right? Because you think about. W-2 employees getting taxed so heavily, and here you have startup founders, employees, investors paying nothing on $10 million when they sell their company.

Sean, I think California is the only state that doesn't recognize QSBS.

There's actually 6 or 7 states. There's a couple that partially don't recognize it. 43 don't. 43, uh, you'd pay no state taxes as well.

If you're not paying any taxes on $10 million in gains, you would normally otherwise pay long-term capital gains, which would be roughly 20% plus there's like a 3.6% something extra fee. So it's like, you know, basically $2.3 million is what you get net extra, correct? That's, that's the actual in your pocket.

In New York, substantially more. Don't forget there's another million plus in New York taxes that I'm not paying.

Okay, cool. So, and then, yeah, so for California, you'll pay another 13% on top. If New York, if you're in one of the QSBs, uh, you know, free states, then you're saving another, let's say, million to million, $1.3 million. In additional state taxes. So about $2.5 to $3.5 million in your pocket.

Yep. Or I've got a friend who had a company who was, I won't say publicly, but Ankur, you and I are very close friends, who had a company that was, I think, an S corp. He converted to a C corp at a $30 million valuation. And so eventually when he sells, it will be 10 times $30, so $300 million. So that, that difference, which is, uh, I can't do the math, but $270 million gain, that will be the tax-free portion.

Personally, for me— wait, so what happens if you, what if you set up for 3 future kids and you only have 1 future kid?

You can basically set up like the, so what I did for instance, right? I have no kids is you can set it up for future beneficiaries as well. So it's any of my future children are entitled to have the trust. What's important is it's an irrevocable gift. You can't take it back yourself.

Okay. But what happens if you don't have kids now?

Um, it has to go to either my parents, my brother. I've named a bunch of different beneficiaries.

So there's like a line. There's like a, there's like an order, order of operations.

Yeah.

Yeah. You're like the only brown parents who are like, oh, Ankur, it's okay if you don't have children. It's okay. As long as you're happy, as long as you're happy, it's okay.

I wish, I wish honestly that would be, it would be worth the $10 million to not be harassed by my parents.

So this is called like stackable trust, right?

The way that companies get around this, right, is you do the 83 election, right? And you basically buy your shares at the super low price.

We should explain how archaic the IRS is. So there's this thing called the 83B, which I don't exactly know what it means, but it's basically you may, whenever I start a company, I've got to write a check to myself for $100, or I write from Sam Parr to the name of the company, Inc. And I have to mail it to the IRS and I like handwrite on it and I write a letter to them and I say, this is Sam Parr. I'm writing you one check for $100. And I'm literally writing this out by hand. Will you please send this stamped envelope back to me that has proof that you received this?

It's literally like the tooth fairy, dude.

Yeah, it's like the tooth fairy. And you write the address and you just write like IRS, like, uh, I forget where it is in California. And by the way, you have to do this 3 weeks, I think, or 90 days, 30 days, 30 days, 30 days after you do this, they have to get it. And so right when you file the company, you've got to run to the convenience store and get your stamp and envelope and hurry up and do this thing. And then you write this out and somehow this works. And what's even crazier is the IRS won't check in on you to make sure that you did this right unless you get in trouble and you have to like save this like envelope. Like, gotcha, bitch. I got the envelope. I filed it away. Like, it's crazy how this works.

And if you don't do it, you have to pay millions of dollars in taxes. Like, it's a very, very high—

or hundreds of millions.

Yeah. It's a very high stakes document. Yeah.

It's a high stakes document and you like have to write it. I remember like thinking like, I gotta make sure my 7 is perfectly clear. So that's not a T or like, it's like a very stressful thing and you have to write it up by hand. It's crazy how like archaic it is.

I didn't understand this rule. Um, but our CFO was like, hey, did you do your 83B? And I'm like, nah, nah, it's pretty fine. She's like, no, no, you have to do it within 30 days. And I was like, okay, well, can you just like, you know, where's the form? Can you send me the link? She's like, no, no, you have to print this out. You got to go take it to the post office. And I was like, oh man. And she looked at me. She's like, you don't do those types of things, do you? I was like, no, I don't run errands like that. I just simply don't. I'm out of the postal system. Like, I don't mail things. I don't check my mail. Like, I'm out of that whole system in general. Yeah.

You're like, how many stamps do I need? Like 50, 40?

Yeah.

I was like, what part do I lick? And so I'm like licking the form and I'm like, then I finally have it and I realize I'm on day 37. And so for the next 5 years, it just haunted me. I was like, I didn't do that goddamn form. And then when my company finally basically failed, I was like, didn't matter. I was like, it didn't come back to bite me. Cause I was for 5 years had been dreading that my lack of, uh, you know, belief in doing shit, like doing annoying paperwork things was going to bite me. And I was so happy when that one entity failed and that the other entity was the one that sold. I was like, this is, this is amazing.

Here's the crazy part is you can claim you did it in time, right?

So very technically what the document means is it says, I am like, tax me on what the value is today. I'm choosing to be taxed upfront. But if not for signing this, anytime your company grows in valuation, you could theoretically be liable for taxes. Can you imagine what a nightmare that is? Like, let's say you raise a Series A, a Series B, a Series C.

Yeah, you would not, you wouldn't have money.

You wouldn't have money, but you'd have a tax bill. It's like really, really bad.

So there's a dark side to this, which is that sometimes if you join a company later, like I think Bolt got pretty popular. This happened at Bolt. So Bolt was like, hey, we are lending our employees money to buy their shares. That was such a shit show at a like $5 billion or $10 billion valuation. And they were like, see, this is great because now they're going to start their clock of owning the shares. But people were like, okay, so what happens if the valuation goes down? And they're like, now not only do my shares become worthless, I owe the money for those shares at that premium valuation and people were like, this is not going to end well. The full story hasn't played out. You know, Bolt is, uh, is still going. So it's unclear exactly what's going to happen with that.

It's trending in the direction like that was a bad idea.

I think it's undoubtedly a bad idea. It was a 2021 valuation, like tens of billions of dollars. Like it's, it's not good. And people saw it coming and it's, it's really bad when you now, like, I'm, I'm hoping they forgive those loans because otherwise you have not only are you making nothing in equity, you have, you owe $80,000, $100,000 just for working there.

At our company, our investor was like, here's the promissory note. You don't have to come up with the cash and we'll forgive this if this ever happens. And I was like, can you write that? They're like, no, we can't write that down. It was like, you know, just have to trust us. I was like, okay, I do trust you. And they did.

If they, if they were to write it down, it's taxed to you as income. So that's why they can't write it down. Right.

Yeah.

Yeah.

All right. I want to go to the counter opinion. So we got friends who You know, they're like, oh, the number one thing, get out of California, you schmuck. Come to, come to Texas. No, no, no. Forget Texas. You're still in federal paying federal tax. Come to Puerto Rico. What do you think about that? Should you, should I move to Puerto Rico to save money in taxes according to Ankit?

So to me, this gets to the meta level, right? Like, why do we have money? What is the point of money? And I think there's two camps of people. Camp one is like, they look at their life as, as this vessel to make as much money as possible. And other people look at money as a tool to live the life you want. So I very firmly fit into the latter camp where money enables me to live the life I want. Yes, I don't want to pay more in taxes than I have to. And, you know, gamifying the tax system is also fun just because like I'm a hustler and it's kind of fun to do, but I want to live the life I want. And to me, that means living where you want. So I, I wouldn't, I would personally never ever move somewhere just to save on taxes.

Well, you've done the exact opposite. You, you, you live currently in, you live in the highest tax place in America, I believe.

Correct. And, um, I'm totally fine with that because again, like money enables me to live the life I want. I just tend to think, and it's ironic because, you know, I'm running a company that helps people save money on taxes. The kinds of people who spend all their life worrying about taxes are some of the unhappiest people I know. So I don't ever want to get to that point. And sometimes when you move to like, you know, a utopia with zero taxes, you're surrounded with everyone else that moved there for that reason. That's your group. Your friends are other people who hate taxes. And I don't know if, you know, that's the social circle I want.

Dude, we had John Lee Dumas on the pod. Do you remember this, Sean? And we were talking about taxes and he was like bragging about how he moved to Puerto Rico or something like that.

Dude, he was glowing. I thought he was pregnant. I was like, wow, this guy's so happy he moved to Puerto Rico.

And he was so happy about it. And he, and then he started making fun of me. That I didn't live in Puerto Rico. Do you remember that? He was like insulting me and I was like, John, we're not close enough that you can make fun of me that hard.

It's a podcast, sir. You know, I think that the thing, you know, a lot of people who listen to this podcast, we all share one goal probably. We have many different goals, but one we share is we all want financial freedom. And most people think financial freedom is Oh, I'm free to buy what I want, do what I want. It's the financial leather jacket. You're a financial badass now. All right, cool. But I think the real financial freedom is when money doesn't have a hold on you. So it's not about you being able to buy and do certain things. It's that money no longer dictates your decisions. Money does not control you or make you do things that you don't want to do. And so it's more of freedom from money, not freedom to spend money. You had a point on this thing I want you to explain, and it's really a direct attack at Sam. You said the point of having money is to not worry about money. If you are wealthy but still stressed about money, which I see all the time, you're missing the point.

All right, Sam, look this man in the eye and uncle, tell him, dude, I don't blame him if it's him or anyone else, because these are beliefs we form very young in life. Like to some degree, they're not even fully conscious beliefs. So if they're not conscious beliefs, you try and sort of program It, but yeah, I have so many like super wealthy friends, friends, you know, with hundreds of millions of dollars who are stressed about the pursuit of more money. They are 100 millionaires who want to be billionaires or something. And again, like you said it really well, right? The whole point of money is to be free from it and do what you want. Like to me, the best thing I bought with money was being able to say no to a job that would have paid me tens of millions of dollars in equity because guess what? I don't need it anymore.

Can I just say, Shawn, so look, I, let me defend myself. I came on here and I expressed my belief on money and how I'm fearful of it and how I want it to make me happy and it doesn't. But you did Camp MFM and you told me about Joe Gebbia. Joe Gebbia is worth $10 billion. And you told me this crazy story that blew my mind about how happy he is and everything like this. And so I radically changed my opinion on money and happiness. And now I realize I just need $10 billion to be happy. That's all I need is $10 billion. So like my opinion has been changed. It's no longer care about scarcity mindset. If I have $10 billion, I will be happy.

There you go. I'm glad, I'm glad you— there we go, you've been enlightened. All right, Anker, um, give me a couple other quick hot takes before we go.

No, you're going to make fun of Sean now, which is there's no true alpha.

Let's frame it. You said there's no true alpha in investing. I realize that's sort of a fool's game. That's why instead I realize I can, I can optimize my tax setup and make more money that way than try to beat the market. As a guy who has been attempting to beat the market for quite some time now, unsuccessfully.

How's that been going?

Wait, answer the question. What are the wins and what are the losses? And we're not talking about private. We're talking about, have you been trying, have you, did you try to beat the market in terms of public too?

He looks kind of sheepish. He looks kind of sheepish.

He's like, yeah, are we trying to make me cry? What's happening here?

No, no, no. I don't know. I actually don't know if you pick and choose stocks. I know you pick and choose private companies, but that was like your job.

I agree that most people cannot beat the market. I do not agree that nobody can beat the market over a period of time. I know that that's an unpopular opinion and I know that, you know, the famous Warren Buffett bet. I know all those things. I just refuse to believe that it's a, it's not a bell curve.

So, um, I think the people that beat the market spend all their lives doing that with their own capital, right? Like think about Jim Simons, right? His hedge fund has returned like 40% on average. They're not taking outside capital. What I think is a little bit of a scam is a lot of the financial services industry that tries to promise you outsized returns.

Who promises that? Like, what's that stereotype? Hedge funds? Because I've never met like a financial advisor that would be dumb enough to promise that.

Any actively managed fund, right? So yes, hedge funds are a big, big sort of thing. Any active stock picking fund. I mean, there's a lot of stock picking funds that charge you 1% to 2%, 1% a year and their portfolio they say will outperform or whatever. So does every real estate fund, venture fund, basically like anything that charges outsized fees, anything that charges more than a Vanguard fund.

That's crazy that people like buy into that though.

Correct. So our thesis is always like, okay, fine. I do think better tax strategy can actually create alpha. Alpha is a finance term for like you will outperform. And using that tax alpha to just put more dollars in the market, I think is a smarter approach and the approach I like and, you know, I'm taking with my money as well.

Out of 100% of your net worth, is 100% of it in the S&P index?

No, absolutely not. Like I have, I have a lot of it not in the S&P index, but that's my fund money. I think there's a good chance I don't outperform. And a lot of it is in private, private investing, which are funds that I own. But I think I'm the only person I know who has a fund as big as mine and charges no management fees. The average venture fund charges 20 to 25% just in management fees, and the average person does not realize that. We charge 0%.

Sean, do you know how I tell you that I don't buy individual stocks? Yeah, I real— I looked at my portfolio the other day. It was the first time in a year that I looked at it, and I realized I was wrong. I've done it twice or three times. The company that I did it on was Playboy. Uh, I had read— I read their annual report.

Yeah, you can't just call their magazine their annual report, dude.

That's called their monthly Yeah, but yeah, actually their annual report, they have a lot of photos. Yeah. And oh, Jenny, old Jenny McCarthy picture holding up the balance sheet. That's nice. I did that because I was like, oh, well, like their prop, their real estate asset is worth more than what they're trying to sell the company for. And I was like, that's smart. I'll do that. Did not win on that one. So lost on that one. Also did Coinbase at the IPO.

Oh God.

And then I sold it 2 weeks before it popped, like 3 months ago or whatever, whenever it was.

Like 400%.

So I've, I've done, I've done 2.

No, you've also done it with HubSpot. You got HubSpot stock. You could have sold it and diversified. You decided to hold. That is a decision to buy.

That's correct. And with Airbnb. Yeah, correct.

The 2 biggest holdings in your portfolio. Correct. So you do it too.

We all do it. No, those aren't my, those aren't my 2 biggest holdings. The, my index funds are significantly larger. But yeah, I have done it, so I've done it as well.

So I'm like you, Ankur. I have my fun money thing. It's just that I happen to have a fun money stash that's 80% instead of 20%. Yeah.

I mean, look, at the end of the day, as long as we realize what we're doing, it's fine, right? Like I think we all have to learn this lesson ourselves. In 2021, I thought I was a damn genius. I was like, these index funds are stupid. My portfolio is up like 300%. I should just be a stock picker for life. And yeah, then you come back to reality and Didn't realize.

What was the, was there a day where you're like, uh, huh, that's not the way.

It was many. See, because again, if you remember, there's such an insane run-up for a while. You couldn't lose. Every company was up 100% day on day. It was when investing was the most fun. It should not be that fun. And then yeah, there were numerous days of like, cool, I've lost $300,000 today. Cool. Down half a million dollars today. Cool. And just that happening repeatedly while the S&P 500 kind of just kept chipping away and growing. And, you know, Nvidia comes out of nowhere and all these stocks that I only held because I had an index fund, otherwise I had no exposure.

Sean, let me— and Ankur, let me tell you this crazy story about tax stuff that I learned. This is like one of those tax hacks. I'm not the biggest fan of tax hacks. This is actually a good one. I met this lady, she was speaking at one of our events, and I don't want to say her name of her company, but she was on the commercial for this credit card company because she loved the credit card so much. And her business was doing, let's say, 50 million a year, and she was putting a lot of it on a credit card and it was giving her $300,000 a year of either points or cash back. And according to the IRS, a cash, cash back from a credit card is considered a rebate. And I believe you get up to, I don't remember what it is. I don't know what it is now, but 3 years ago when she told me this, she said it's, uh, $300,000 a year of rebates. Is that, you know what it is nowadays? Is it the same?

Something like that. Depends on the card itself, but yeah.

Oh, I thought it was by the government. I thought it was limited to the government. It must've been limited to the credit card. She was getting $300,000 a year of cash back, of which she was like, that's my salary. I don't take a salary, or I take a very unmeaningful salary for my company, and I'm living off my credit card points. And that was pretty wild.

Did you know you could actually pay your taxes on a credit card? And it's for some people, you could actually like arbitrage that where, again, this is insane. I would never do it, but it's just, I just found it interesting. You can pay your taxes on a credit card. There's not a very high extra fee. And then a lot of cases you can actually end up slightly better. It's a very painful thing to do.

That's hilarious.

That's insane. That's the other thing with credit card points is once you learn how to use them for travel, the cashback feels less good. Like, yes, the cashback has a theoretical value, but there's so much more valuable applied to travel once you kind of learn how the game works.

What's the smart way to do it?

Okay. So the thing you always want to avoid is never spend the points on your credit card website. That is the thing almost everyone does and you lose a ton of value there.

I do that.

No way. 70%.

Yeah.

I've, I've tested this a lot because what these airlines do, it says transfer, like there's a tiny link that says transfer partners. And you have to, that's where you send your points. You never spend it in the thing.

That's going to save you so many points.

I've spent hundreds of thousands of dollars on flights over the past 10 years through Chase, my Chase Preferred card.

I found this out 2 years ago and it's life-changing. Yeah, absolutely.

What? You got hosed, bro. That, it's so bad to do it the other way.

Wait, you knew that, Sean?

Yeah. I paid for this guy Mo Points. He's like this guy who'll call you, he'll teach you about credit card points. Uh, or like, he'll, he'll just be like, what's your situation? Here's what your credit card setup should be and here's how to use it. And so he showed it to me and I was like, wow, that was like the best $300 I've ever spent because that one session, which I thought, oh, $300 to do this call. That's kind of a lot. Of course. I mean, the savings in just understanding how to book the flights better. Cause he's like, this is luxury travel. You want to travel first class all around the world. Here's what you need to do. And for me, I have an e-com business. So we're spending millions a year in ads. So he's like, you need this Amex Gold because it gives you 4x on every Facebook point that you, uh, every dollar you spend on Facebook or Google. And so you're getting 4x multipliers. He's like, but then you got to transfer it out and then you got to use this website, a website like Points.me or whatever to, um, be able to search for points across all the airlines.

Yeah. I think just transferring out is the 80/20. If you want to tell someone in one sentence how to do better. Transfer your points out.

Do you have any more of those little tricks? What else you got in your hat? Come on, magician, pull something else up. That's pretty awesome.

Solo 401. So that's the one that you have on here that I don't know anything about. What is a Solo 401?

Can you tell the Peter Thiel story real quick? How did he use a Roth IRA to make billions?

The wildest part about that, what you just said is that Peter Thiel only made $27 million selling PayPal.

Yeah. Yeah.

I didn't realize that me and Peter Thiel are sort of, uh, we're sort of, you know, apples and apples, I guess. Uh, right, Sam, like the, The hustle and PayPal netted the founders very similar amounts of money. That's kind of amazing.

Well, what we don't know is if Peter Thiel had other shares not in his Roth IRA, which is quite possible actually.

Ah, damn. Uh, news too good to be true.

Let's just take it. Yeah.

Probably not.

He's going to have to show that to me for me to change my opinion.

Yeah. Yeah.

Yeah.

I'm not going to let facts get in the way of me beating Peter Thiel. What about, uh, can a person have more than one 401?

Yeah, so that's what's cool is if you have a full-time job and a side hustle, you can have a solo 401 for your business while still contributing to your employer 401. But because it's your own 401, you can invest it in anything, right? Your employer 401 has like a list of very specific assets. With a solo 401, you can invest it however you want. If you need liquidity, you could borrow up to $50,000 from it. It's simply the most powerful retirement account in America, but it's not available Unless you have your own business.

Isn't the normal 401k kind of a racket? Like the thing where they're like, you can only buy these funds using our 401k. Is that because they get a kickback?

A lot of them have fees. No, it comes from the 401k provider. The long answer is corporate 401k plans are subject to ERISA laws, like Employment Retirement Investment Something Act. And those acts are just there to protect employees. But as a result, employers can't do things that help them. Like there are limits on how much you can contribute to yourself if your employees are part of the same plan, limit to investments. But if there's no employees, go crazy.

So the solo 401k, you could put that in, could you like put it in real estate? Could you put it in anything?

Is it like, absolutely. If, yeah, the only thing you can't do, which is where the whole Peter Thiel thing may be slightly illegal, is you can't have a self-dealing transaction. So I can't invest in my startup. I can invest in Sam's startup. That's totally fine. But I can't invest in my own company. I can't invest in my house, but I can do commercial real estate.

Gotcha.

Okay.

Well, that's not self-dealing for him, is it? If you, that's just a major angel investment.

He was the founder too, which is why it's sketch. He was the founder of PayPal, remember? If he was just an angel investor, it's fine.

But he was the founder of PayPal.

You shouldn't say too much. He, you know, we might, it might be an accident for Ankur if you keep talking like this out loud. He's got $5 billion riding on nobody paying too much attention to this.

So, um, yeah, I mean, look, so people, cause no, people ask us all the time, can I do what Peter Thiel did? And I was like, look, it may be fine. If you don't own over 50%, I wouldn't, because again, like the thing with the IRS is a lot of these things are not clear rules. There are rules written a certain way. Someone interprets them somehow. The IRS challenges it. Sometimes the IRS loses in court and that's how loopholes are established. Right.

So, so like the problem that I have with my, my personal bookkeepers or accountants, my CPA, like they're pretty reactionary. So it's like at the end of the year, like we are dealing with the problems and then everyone makes the same thing where they say next year I'm doing this right. But I'll worry about it in like 2 or 3 months. And then 2 or 3 months becomes like way later.

That's the real New Year's resolution, to be honest, is the 3 weeks after tax, after you file your taxes is the real New Year's resolution.

To be honest, candidly, that's the problem we're having. Cause right now we're realizing we have to educate the CPAs a lot. And almost everyone that comes to us, and it's a biased sample, they do not like their CPA. Um, and we don't do that yet, right? Like maybe there's a world we'll do it.

But who do you have? Like, do you hire like a tax strategist who is like more offensive? And do they, would they work in tandem with your CPA? What do you do?

So for me personally, once I've, you know, gone down this rabbit hole, um, we're doing this internally. We have a program where we help people with the tax strategy part. We don't do tax filing. So I'm basically using our, our own services. But yeah, there's a big part that's tax strategy that is not the person signing off your tax return.

Should they be separate?

The way the world is written today, the like just laws and stuff, it is because the person filing your taxes typically doesn't do that much strategy. Um, it's sort of just why, like, Even if, let's say you want to set up a trust, you need an estate attorney who's different from your financial advisor, who's different from your accountant. And to the average person, you're like, why? Why can't one person do this? And those are the kinds of things worth thinking a lot about. Like, how do we productize this in some way, shape, or form while still being compliant? Because compliance is a big, big, big part anytime you try and build these kinds of businesses.

I'm like, whoa, whoa, whoa.

No, no, I'm paying you. Hold on. Wait, this is backwards. You work for me. I forgot. Why am I pretending like I have to tiptoe around even asking you for what I want? And so I go in and I'm like, I felt this way. I never want to feel this way again. I want somebody who's going to take care of everything. I, you know, everything from, I want you to literally, I want you to be able to pay bills if I need you to, up to filing my returns for all of these, you know, I got 12 entities, all 12 entities. Um, and I need you to do strategy and I need you to be coming to me every, you know, every quarter with proactive suggestions about what I should be doing. That's what I want. Who can provide me that? And I went on tour basically, and it's such a better way than I was doing before. I highly recommend this for anybody who's like, has enough income and kind of business value where that makes sense to do, which I don't know what that number is, probably different for a lot of people. It wouldn't have made sense for me 3 years ago to do that. It's like, ah, whatever, you're paying, you know, a couple hundred K in taxes or, you know, even a million dollars in taxes, probably not worth that much effort to go do. But as you scale, I think it's important to do that. I'm realizing now. Yep.

And I also think it has to be a collaboration. It's very hard. A lot of people are like, oh, if I had a tax guy, that would solve all my issues. But a lot of the best strategies, they're like long-term, right? Let's say you want to start a business to get acquired 5 years later. That's the kind of stuff that you like need a partnership to be discussing and have someone you're working with somewhat. At least quarterly, right? Because there's a lot of this stuff that, like, the more you know, the more you'll push them and the better the things you'll achieve.

I'm actually going to do that Dataroom thing. That's the second thing that you've said in the last few months that it's like going to have a change in my life. That's really smart.

The first thing, bro, we talk twice a week on this podcast. That's the second thing in months that was good. Yeah.

Yeah. Well, the, well, like a lot of the stuff you say, I'm like, I'm either already doing that or I don't want to do that. Or, uh, like, I'm not sure if you're right or that's only okay. But the, you said that data room thing is actually a really wise, wise way to look at it. The other thing that you said, it was, it hit me. I was like, that's brilliant. And it was when you were selling one of your, your house in San Francisco, you, so like, I forget what real estate agents make, 6%, but you're like, but 6% is not that, that the difference between $2 million and $2.2 million is like 6% isn't that meaningful for the realtor, but it's really meaningful for me as the owner. That's a 6-figure difference. So I'll just give you, my real estate agent, I'll tell you, hey, if you get anything above my asking price of like 2.1, which is my happy number, but if you get anything above that, like 2.2, I'll actually give you like 30% of the fee. So I'm selling a piece of property now and that's what I told my— I went, I just right after the, the pod, I went and called her right away. I go, hey, how about this?

Yeah, I didn't do 30%. That's crazy. But I did more. I did more than the 6%. So you messed that one up a little bit, but that's okay.

Well, but, but, but the thing is, is like, even, I don't remember what you said, like, it's no dollar, right?

Each additional dollar past that is like, yeah, you said like 10%.

I think you even said like you would buy this person a burqa bag. You said something like crazy.

The reason why it broke my frame was because these are like, a realtor is like, uh, you, you think like, well, for some reason you think this is just the law or like there is no negotiating. Like this is how it's always been done and I must do it this way. I'm just going to, and, and when I was thinking about it, I was like, no, that the way that he actually said is 100% better. I didn't realize that I could like question them. Right. Do you know what I mean? And there's actually like, what's crazy is there's people who do that with the IRS as well. So for example, Sean Parker, I believe, is the guy who created— he either created or he was important with helping create it— with opportunity zones in real estate. And like, I remember like reading about opportunity zones and I'd be like, oh, Sean Parker created it. I'm like, wait, what? And I guess like the story is, is he was young, he was still in his 20s, and he convinced the government that it's wise to invest into opportunity zones, which is real estate that's in areas that are impoverished or We want them to be better. And I'm like, how ballsy of that kid to go and convince the IRS or the government that this is the right move. And I love like stories like that. And that was, it was a wild story.

Let's do a couple more before we finish. So you said owning real estate with your business. What's this one?

That's like the classic like immigrant story, which is like a mom and pop like came here from Vietnam and then they bought, they just, they eventually bought their corner store building and then they, the building becomes worth significantly more than the corner store.

And then they bought their G-Wagon.

And the G-Wagon. Yeah.

Like, again, like business owners were already very favored, as were real estate developers. But when Trump was in office, he actually took it to the next level with the Tax Cuts and Jobs Act that basically doubled those benefits. It gave an extra benefit to business owners where they get to deduct 20% of their income called Qualified Business Income Deduction. And it allowed real estate developers, um, and your boy Nick Huber talks about all the time, to do what's called bonus depreciation and depreciate 20 to 30% of the purchase price upfront. Um, so even though the code is already written this way, there's always new incentives to further make it even better for business owners and real estate developers.

Let's do some of these, uh, other things. You, you, you had a good thing on happiness. I want to read it to you. Basically, you were like, happiness It's not that complicated. Uh, what is the kind of, what are the 4 things that, that actually matter when it comes to happiness?

Yeah, I mean, look, after I sold my company, I spent 2 years traveling, chilling, you know, I was like, wow, you know, we spent all our lives waiting to like retire. What if I just lived a retired life now? Um, and a lot of it was like, okay, fine. What are my happiness triggers? And I found for me was very, very simple. Um, the 2, 2 like critical things for like my environment were plenty of time outdoors, ideally with sunlight, like constant movement. Like Sam didn't believe me when I told him I walked 20,000 steps a day. I had to produce receipts. Um, doing work.

That's an insane amount.

That is an insane amount. 3 and a half years. It's just, it's just what keeps me, keeps me going.

My, my trailing 90 days, cause we had the baby, it was, uh, 3,100 steps a day.

Yeah. That to me, that's misery. Like I just need to, I need to be in motion.

What do you, what do you do to get those 20,000 steps? Like, do you have, did you like replace meetings with walking meetings or something? What, what did you do in your habits?

Are you dating anyone?

Uh, not right now.

You'd probably crush it though in that department, right?

Yeah. Look, I mean, again, I enjoy, I enjoy being single. Uh, but at the same time, look, I'm 34 years old and the parental pressure is ramping up. We'll see how it goes.

You're like, I can defeat the IRS, but not the parental pressure.

Yeah.

How old were you, Sam, when you, when you and Sarah got together?

She was 22 and I was 25.

Oh damn, you were young.

It didn't feel that way because I went pretty crazy between like 19 and 24. Like I, I, I did some fun things.

Yeah. I've actually, I've actually drank a beer with you. There's not a lot of people at this chapter of your life that have done that, but yeah.

Yeah, that's true. That's true. And I had a lot of fun. I did this cross-country motorcycle trip and after I just sold the company and I didn't sell it for a lot of money, I had like $50,000 in my bank account. But I was like 23 riding my motorcycle cross country, telling people I just sold my company on Tinder.

Was this apartment list or whatever?

Yeah. Yeah. Yeah. Yeah. It was two apartment lists. Uh, and, and I, and, and I just hosted a conference, so I had money and like, it was, I was the coolest guy ever for like 8 weeks. And then I met my wife, like right when I got home. Um, but, uh, yeah, we've been together for a while. Uh, it's honestly awesome. I like, I, I don't even like talking about this because I remember when we got married, we had to go to like and talk to a priest because we got married in Catholic church. And I was like telling her, I was like telling the priest, I was like, yeah, we, uh, you know, we're a good partnership. We talk about like business and stuff all the time. He's like, well, what about love? And so like, I don't even like mentioning this, but like basically dating someone who is smart and you eventually want to marry, it actually makes you more money. That's not the most important thing, but I think like what I've learned is having a good relationship, I think Actually was the greatest financial decision I made.

I mean, you're not, you're probably less distracted, right? Like people in, people in relationships are like eventually like once are kind of more stable. I think I remember when I was, when I was selling my business, I was negotiating with the dude who like runs General Atlantic, big, big private equity fund. And he's like an old school guy. He's like, are you married? I was like, no. Kids? No. It's like, I don't like that. I can't trust single people. You have nothing to lose. I don't like it. I would feel much better about this deal if you were married and had a family because you're scared or you'd be more nervous, more scared of stuff.

You're like, for $250 million, I can get a 30 Day Fiancé right now, sir. What do you need?

Yeah. Yeah. So Sean, when your wife goes out of town, are you like me where you're like, uh, what the hell am I supposed to do? Like, what do I do? What do I do?

It's 3 hours of heaven, but anything beyond 3 hours, I'm like, oh, this is boring. Like, this sucks. Like, it's so quiet in here. Like, I just started walking around in circles like my dog or something. I don't know what to do.

I want to talk about one more thing. We have a large Indian listenership. You're welcome. Yeah. Thank you, Sean. Uh, I feel like everyone in my life is, is like all my best friends are Indian. You're like going on a tear on social media saying, uh, like particularly you're like, you know, East Asian people, we've got the stereotype of, of us not having a lot of muscle. In reality, it's just because we eat like shit. Or what did you say?

Yeah, I use MyFitnessPal every day for like the past 4 years.

Okay, cool. So there's not one person who's ever counted macros who will fight the Indian diet is healthy. Like not one. It's impossible. It is actually impossible if you track it to see it. Yet it produces this passionate response. I mean, I ended up commenting on an Indian cricketer's physique and an Indian newspaper, the Hindustan Times, ran this like article about me saying, Indian American entrepreneur fat shames like cricketer. And I had to like turn off my Instagram because I got hundreds, thousands of comments, like just attacking me, my family and everything I stood for because I'm not being like, you know, a proud Indian or whatever.

So that's hilarious, man. The, uh, the, I went to an Indian grocer, Sam, you probably don't know this. There's actually just like Indian grocery shops. We have our own separate secret.

Yeah, I go to them.

Okay. So most people don't really realize this, but if you walk in Every single aisle literally is the shittiest food that you could possibly eat. And I went in there and I was like, you know, Jim Carrey in The Truman Show when he's like, wait, the sky is actually like a wall. Like, what is this? What's happening in here? And I was literally like running down the aisle like, what's happening in here? This is fried.

It's all fried.

Why is everything fried? Literally not one thing.

And no protein, right? It's like fried and there's no protein.

It's zero protein.

Why? They just don't care? Is it not part of the tradition? It's just not part of the culture?

Protein is just not really deeply embedded in Indian food. And it is, it is in small parts, but it's just not really a big deal. And it's compounded when you live in America. But I think about it this way, right? I joked about this, but like. I think the spelling bee is the only time I see Indian people on ESPN. Obviously an exaggeration.

That's the ultimate burn, dude. That's so good.

Yeah.

I mean, look, as a native person, I can say it. I don't think you can say it, Sam. You'd get canceled. But yeah, it's really not good. What I think is optimistically, my generation, we're seeing people being aware of this. We're seeing this changing. A lot of South Asian people, right? They're always like, even like Balaji was on a podcast. He's like, oh yeah, I did like as well as I could for my South Asian genetics. I actually think that's kind of bullshit. I think South Asian genetics are honestly not bad at all for people who work out and kind of eat clean and whatever. I mean, all the Indian friends I have that have put in the effort have seen results, but the whole stereotype I think starts because of the diet.

Yeah, I've been on an Indian food kick lately and it's been all like coconut milk. And so I've just not been using that or coconut cream. It's just all creamy shit. And, and, and it tastes so good going in., but it does not feel wonderful.

And Indian parents, when they feed you, and because I'll be like, Mom, why did you give us this? And she's like, this is good for you. I'm like, how is this good for you? And she'd be like, gives you energy. And I think they literally took the idea of calories as like, you know, calories like a measure of energy. It's like, yeah, they were like, gives you energy, this carbohydrate, you're gonna have so much energy. And I'm like, not— that's not how it works. And then even they're like, oh, Dal, dal has tons of protein. It's like lentils basically. It's like, yeah, but has like, you know, the macros on dal are like 20 grams of protein, 35 grams of carbs. And then you add butter, ghee, and like oil to the thing to make it taste good. It's like, well, that's not really going to help then. Right? Like that.

And dal is your protein in the rest of your meal, right? So you have all this other stuff and you're like, oh, for protein, I'll have dal. That's a great example. And yeah, like Indian people will, like the Indian Express actually ran an article being like, yep, we thought dal had a lot of protein too. Like the awareness is increasing now. But it's, it's pretty slow.

I went to a, uh, what's it called? Is it a Holi or Holi? A Holi celebration. And it was, uh, naan with ghee. Is it ghee? So like that, uh, clear butter and then, uh, tons of, uh, buttered, buttered chicken, but instead of chicken, it was cheese. And then it was like, and then it was like the dessert was fried dough and maple syrup. What do you guys call that?

Glob Jamun. It's delicious, by the way. It's delicious. So like, don't—

yeah, it's good for you because it made me smile and smiling is good for you. But, uh, it didn't feel great, uh, 2 hours later.

Yeah. And here's what's changing though, is now Indian people are really wealthy. There's 4 million Indian people. They have an average income of $100,000, the wealthiest ethnic group. So I do think things will change. Like it used to not be a very viable market, but now there's a lot of us and it's a very big market. So I think all of these businesses also make Good commercial sense.

If you read in our comments section on YouTube, um, the most recurring comment is, Sean, you look great. Sean, are you losing weight? Sean, that beard looks wonderful. So Sean's gonna be a sex icon.

$10 on Fiverr, you can get that. Uh, anybody can get that for you. You just go pay $5, go pay on Fiverr. You can get people saying how good you look on YouTube.

I get it.

Everyone's commenting on Sean's looks, uh, except for like, they'll either, they'll make fun of his outfit cuz he wears like a Mickey Mouse t-shirt. Or they'll be like, Sean, your workout program, it's working so well. Like people are just sucking up to them so much.

Well, yep. Thank you. And, uh, Ankur, where should people find you? Where, how do they go and use your product that helps them with taxes?

Yeah, absolutely. We're called Carry. We're at carrymoney.com. And if anyone wants to set up a solo 401 or just get better at what they pay in taxes, check us out.

Appreciate you.

Thank you. Thanks for coming, man.

Sweet, man. This was fun. I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off.

On the road, let's travel, never looking back. Life.