Ankur Nagpal, who sold Teachable for $250M at age 31, breaks down the most powerful legal tax strategies available to entrepreneurs — including QSBS stacking, the 83b election, solo 401ks, and real estate depreciation. The conversation also covers money mindset, index funds vs. active investing, and a candid discussion about the Indian diet and health.
Speakers: Sam Parr (host), Shaan Puri (host), Ankur Nagpal (guest, founder of Teachable and Carry)
Introduction and Guest Background [00:00:00]
Sam: Today we’re 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.
Sam: Today’s guest had the same problem. He sold Teachable for over $200 million and then decided he was going to go on a crusade to make sure no entrepreneur pays more taxes than they need to. 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, “No, dude — talk about taxes.”
Sam: Ankur, welcome to the show, man. Long time coming.
Ankur: Yeah, I’m excited to be here. It’s weird how I’ve now accumulated a lot of specific knowledge in this one very narrow topic, and I’m excited to share it.
Sam: So the summary of your story — and we’ll talk about it a little later in the episode, but we want to talk about taxes — summary of story is: prodigy entrepreneur, had a bunch of stuff started in college. You started a company called Teachable, sold it for $250 million, and you were 31. That was like a courses business. Now you’ve got a new thing. What was it called? Carry? Was it called something else first?
Ankur: It was called Oooh, now it’s called Carry.
Sam: And it’s like a 401k — a self-directed 401k thing?
Ankur: Yeah, absolutely. The bigger vision is: how do we help people build wealth by saving money on taxes? The solo 401k is our first product. But yeah, that’s the story.
Ankur: The quick 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 in Oman, where I grew up. So the first time I heard about taxes was when I was 21. I was like, “Wow, you actually have to give money that you earn?” This is crazy.
Ankur’s Origin Story: Facebook Quiz Millionaire [00:02:30]
Sam: Before we talk taxes — you’ve earned your seat on My First Million. You made your first million bucks when you were like 20 years old, with something pretty funny. Can you tell that story? The fast version.
Ankur: Yeah, absolutely. I was in college at Berkeley. At the time, Facebook released the Facebook platform — you could send gifts to people, answer quizzes, all of that. I built these viral Facebook applications starting when I was 18 all the way to 20. It was really fun. We created personality quizzes — you could answer a few questions and find out how good a kisser you are, or which Friends character you’re most like.
Sam: If you have to take a Facebook quiz to figure out if you’re a good kisser, you’re probably a bad kisser, right?
Ankur: Well, the funny thing is — I’m not going to name names — one of the Facebook founders actually took that quiz multiple times. I know that because you get their Facebook user ID in the database. So user ID number — I’m not going to tell you which number — was in our database, and we were like, “Wow, this person really wanted to know.” But anyway, yeah, so we created these personality quizzes, friend quizzes, and stuff like that. Millions of daily users. Was able to make a million dollars before I was 21, which was pretty cool.
Sam: That’s amazing. You’ve earned your street cred here on My First Million.
The US Tax Code Is Rigged for Business Owners [00:05:00]
Sam: All right, so let’s talk taxes. If I’m an entrepreneur, what are the biggest things I need to know? What should I be doing to save money?
Ankur: The first thing I think everyone should know — even people who are not entrepreneurs yet — is the US tax code is rigged in favor of business owners. It’s very intentional. You can look at a country’s tax code and learn a lot about what it stands for, and in America two things stand out: the tax code is rigged in favor of people involved in real estate — it’s the most tax-advantaged asset class — and two, people who start businesses.
Ankur: So the first thing I tell someone is, if you are a full-time W2 employee, if you are not yet a business owner, consider becoming a business owner, because it is the single biggest thing you can do to optimize your taxes. That is just written into the DNA of this country, and it’s something I never realized until I started digging. The playbook for what you can do to pay less in taxes is ten times bigger if you’re a business owner.
Sam: It’s rigged in favor of business owners and real estate, and most people kind of ignore this. The advice I got growing up was go to a good school so you can get a good job — that’s what winning was. And even the advice around money was: try to get a raise, maybe 10%, try to save. But the hard part about saving is that your biggest expense is taxes. Your taxes might be 30 to 50% depending on where you live and 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.
Ankur: I think Warren Buffett had a famous quote where he said his secretary pays a higher tax rate than he does.
Sam: Right. And I think the issue — well, it is what it is — if you have W2 income, I’m almost positive there’s close to no way to reduce your tax liability other than maybe 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 off real estate depreciation. But you have to get pretty fancy to do things with W2.
Sam: And with a business owner making a million dollars a year, I don’t know exactly what the savings can be. I know with QSBS I saved a huge sum, but I know the W2 game ain’t it.
Ankur: Let’s tell the W2 story real quick. I know people in San Francisco with high-paying jobs at Facebook or Google, and they’re marrying somebody and saying, “Hey guess what, honey, you’re a real estate broker now.” And they like, “What? I don’t want to do real estate.” “You’re a real estate professional now.” They have to get the status and then they’re buying Airbnbs to offset their W2 income.
Ankur: We literally say that tongue-in-cheek. We have a presentation on how to lower your tax bill as a W2 professional, and point number three is: marry a real estate professional. It’s tongue-in-cheek, but it’s actually one of the very few things you can do as a W2 professional.
Ankur: I don’t think anyone pays more in taxes than highly paid tech employees. Two people in San Francisco making $400,000 a year together — you’re paying half of it in taxes, and it’s taken out before it even comes to you.
QSBS: The Most Generous Tax Break in America [00:09:00]
Shaan: All right, so let’s say we are an entrepreneur. Sam mentioned QSBS. I’m guessing that’s going to be number one on your list because it’s such a huge advantage. Explain what it is, and then explain the beginner level and the advanced level.
Ankur: Four big letters in the US tax code. This may be the single most generous tax break available today. It’s called QSBS — Qualified Small Business Stock. When you look at all these tech companies being built and sold, the reality is most of them are going to have shareholders that pay very little in taxes, because of QSBS, which roughly says: if you hold shares in a C corporation for five years, you pay no taxes on up to $10 million in gains. It applies to founders, it applies to employees, and it also applies to investors.
Sam: You’re forgetting the “up to $10 million or ten times your basis, whichever is greater.”
Ankur: Great point. It’s either $10 million or ten times what you paid 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 massive. When I sold my company, I live in New York State — and in New York State, even the state doesn’t charge you taxes — so I only had to pay New York City taxes on the first $10 million in gains. And just by size of benefit, it’s absurd. You think about W2 employees getting taxed so heavily, and here you have startup founders, employees, and investors paying nothing on $10 million.
Shaan: I think California is the only state that doesn’t recognize QSBS.
Ankur: There’s actually six or seven states. A couple partially don’t recognize it. Forty-three states — you’d pay no state taxes as well.
Shaan: All right. So if you’re not paying any taxes on $10 million in gains, you would normally pay long-term capital gains, which is roughly 20%, plus there’s a 3.8% surcharge, so it’s basically $2.3 million that stays in your pocket.
Ankur: That’s the actual in-your-pocket in New York. Plus there’s another million-plus in New York state taxes. And if you’re in California, you’d pay another 13% on top, so about $2.5 to $3.5 million in your pocket.
Sam: I’ve got a friend — I won’t say publicly — but Ankur, you and I know this person. He had a company that was an S-corp, converted to a C-corp at a $30 million valuation. So eventually when he sells, it’ll be ten times $30 million — that’s $300 million — and $270 million of that gain will be tax-free.
Ankur: I was saving that for the advanced strategies, but yeah. There’s a lot you can do to truly multiply this benefit. I heard about the $10 million thing and was like wow, this is insane. But then I found out the limit is per shareholder per company. Where this gets interesting: if I give some shares to my mom, my brother, my dad, each of us now has our own $10 million limit. As a family we have a $40 million limit.
Ankur: Or if you go down the estate planning rabbit hole — it’s a little complicated, hire an attorney — you can set up trusts. I set up trusts for my future children, a trust for charity, and each of these trusts gets their own $10 million benefit, which multiplies it theoretically as many times as possible.
Sam: What happens if you set up trusts for three future kids and you only have one kid?
Ankur: You can set it up for future beneficiaries. What I did — I have no kids — you can set it up for “any of my future children are entitled to have the trust.” The important thing is it’s an irrevocable gift, you can’t take it back. But if you don’t have kids, it has to go to either your parents, your siblings — I’ve named a bunch of different beneficiaries, so there’s an order.
Sam: You’re like the only Brown parents who are like, “Ankur, it’s okay if you don’t have children — as long as you’re happy.”
Ankur: I wish. That would be worth the $10 million, to not be harassed by my parents.
QSBS Stacking and Team Strategy [00:15:00]
Sam: So this is called QSBS stacking?
Ankur: Yeah. And a couple of things I didn’t realize the first time around that I’m doing differently now. The first time around, I was the only person to hit the holding threshold because I didn’t understand how it works. This time around, I’ve given all my early team members shares instead of options, so they can start their clock ticking.
Sam: That’s really important. A lot of people don’t realize you have to own the shares for five years — not options.
Ankur: The way companies get around this is the 83b election.
The 83b Election: High-Stakes Handwritten Document [00:16:30]
Sam: We should explain how archaic the IRS is. There’s this thing called the 83b, which — I don’t exactly know what it means, but whenever I start a company I’ve got to write a check to myself for $100. I write from Sam Parr to the name of the company, and I have to mail it to the IRS. I handwrite the letter to them and say, “This is Sam Parr, I’m writing you one check for $100. 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.
Ankur: Yeah, it’s like the Tooth Fairy. And you have to do this within 30 days after you file the company, so you’ve got to run to the convenience store, get your stamp and envelope, hurry up, and send this thing. And somehow this works. What’s even crazier is the IRS won’t check in on you to make sure you did this right unless you get in trouble — and you have to keep this envelope. It’s crazy how this works, and if you don’t do it you have to pay hundreds of millions in taxes. It’s a very high-stakes document.
Sam: I remember thinking, “I’ve got to make sure my ‘7’ is perfectly clear so it’s not mistaken for a ‘1.’” It’s so stressful that you have to write it by hand.
Shaan: I didn’t understand this rule. Our CFO was like, “Hey, did you do your 83b?” And I was like, no, it’ll be fine. She said, “No, no — you have to do it within 30 days.” I said, “Okay, can you just send me the form, send me the link?” She said, “No, you have to print this out, you have to go take it to the post office.” I said, “Oh man.” She looked at me and said, “You don’t do those types of things, do you?” I said, “No, I don’t run errands like that. I don’t mail things. I don’t check my mail. I’m out of that whole system.”
Shaan: I realized I was on day 37. For the next five years it haunted me. I was like, I didn’t do that goddamn form. And then when the company finally failed, I was like — it didn’t matter. I was relieved. For five years I’d been dreading that my lack of doing annoying paperwork was going to bite me.
Ankur: Here’s the crazier part — you can claim you did it in time. What the document technically says is, “I am choosing to be taxed on what the value is today — tax me upfront.” But if not for signing this, anytime your company grows in valuation you could theoretically be liable for taxes. Imagine — you raise a Series A, a Series B, a Series C, and you wouldn’t have the cash, but you’d have a tax bill. Really, really bad.
Ankur: There’s a dark side to this as well. Sometimes if you join a company later — I think Bolt got hit with this — Bolt was like, “Hey, we’re lending our employees money to buy their shares” at a like $5 or $10 billion valuation. “Now they’ll start their clock for owning the shares.” But people were like, “Okay, so what happens if the valuation goes down? Now not only do my shares become worthless, I owe money for those shares at the premium valuation.” People could see it coming, and it’s not good.
Sam: I think it’s undoubtedly a bad idea. It was a 2021 valuation — tens of billions of dollars. People saw it coming.
Ankur: And the issue is not only are you making nothing in equity — you owe $80, $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 the company doesn’t work out.” I said, “Can you write that down?” They said, “No, we can’t write that down.” I said, “Okay, I’ll trust you.” They did honor it. But they can’t write it down because if they do, it’s taxed to you as income — that’s why.
Puerto Rico: Should You Move for Taxes? [00:24:00]
Shaan: I want to go to the counter opinion. We’ve got friends who are like, “Oh, number one thing — get out of California. Come to Texas.” No, forget Texas — you’re still paying federal tax. Come to Puerto Rico. What do you think? Should I move to Puerto Rico to save money on taxes?
Ankur: This gets to the meta level. Why do we have money? What is the point of money? I think there are two camps of people. Camp one looks at their life as a vessel to make as much money as possible. Other people look at money as a tool to live the life they want. I very firmly fit into the latter camp.
Ankur: Yes, I don’t want to pay more in taxes than I have to, and gamifying the tax system is also fun because I’m a hustler. But I want to live the life I want. And to me that means living where you want. I would personally never ever move somewhere just to save on taxes.
Ankur: You’ve done the exact opposite — you live in the highest-tax place in America, and you’re totally fine with that.
Sam: Correct, and I’m totally fine with that. The kinds of people who spend all their life worrying about taxes are some of the unhappiest people I know. And sometimes when you move to a utopia with zero taxes, you’re surrounded by everyone else who moved there for that reason. Your friends are other people who hate taxes — I don’t know if that’s the social circle I want.
Shaan: We had John Lee Dumas on the pod. Do you remember this? He was talking about taxes and he was bragging about how he moved to Puerto Rico. Dude, he was glowing — I thought he was pregnant. He was so happy about it, and then he started making fun of me for not living in Puerto Rico. He was like insulting me, and I was like, “John, we’re not close enough that you can make fun of me that hard on a podcast.”
Ankur: A lot of people who listen to this podcast, we all share the goal of financial freedom. Most people think financial freedom means being free to buy what you want, do what you want — the financial leather jacket, you’re a financial badass. But I think the real financial freedom is when money doesn’t have a hold on you. It’s freedom from money, not freedom to spend money.
Ankur: You had a point I want you to explain — it’s 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.
Sam: All right, Ankur, look this man in the eye and tell him.
Ankur: I don’t blame him or anyone else, because these are beliefs we form very young in life. To some degree they’re not even fully conscious beliefs. But I have so many super-wealthy friends — hundreds of millions of dollars — who are stressed about the pursuit of more money. They’re $100 millionaires who want to be billionaires. And like you said it really well: the whole point of money is to be free from it.
Ankur: 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 I don’t need it anymore.
Sam: Let me defend myself. I came on here and expressed my belief on money — how I’m fearful of it. But Shaan, you told me about Joe Gebbia — worth $1 billion — and told me this crazy story about how happy he is. So I radically changed my opinion. Now I realize I just need $10 billion to be happy. My opinion has been updated — I no longer have a scarcity mindset. If I have $10 billion, I will be happy.
Shaan: I’m glad you’ve been enlightened.
There Is No True Alpha in Investing [00:31:00]
Shaan: All right, Ankur — give me a couple quick hot takes before we finish.
Ankur: No, you’ve got to make fun of Shaan now. There’s no true Alpha.
Shaan: Let’s frame it. You said there’s no true Alpha in investing — that it’s a fool’s game. And that’s why instead you can optimize your tax setup and make more money that way than by trying to beat the market. Shaan, as a guy who has been attempting to beat the market for quite some time now — how’s that been going?
Sam: What are the wins and the losses? And we’re talking about public, not private.
Shaan: He looks a little sheepish right now.
Ankur: I agree that most people cannot beat the market. I do not agree that nobody can beat the market. I know that’s an unpopular opinion. I know the famous Warren Buffett bet. I just refuse to believe it’s not a bell curve.
Ankur: The people who beat the market spend all their lives doing it with their own capital. Think about Jim Simons — his hedge fund has returned like 40% on average, and they’re not taking outside capital. What I think is a bit of a scam is a lot of the financial services industry that tries to promise you outsized returns.
Shaan: Any actively managed fund — hedge funds, active stock-picking funds — charging one to two percent a year. Their portfolio “will outperform.” Does every real estate fund, venture fund — basically anything that charges more than a Vanguard fund charge outsized fees?
Ankur: That’s crazy that people buy into that. Our thesis is: better tax strategy can actually create Alpha. Alpha is a finance term for outperformance. Using that tax Alpha to just put more dollars in the market — I think that’s the smarter approach, and the one I’m taking with my own money.
Sam: Out of 100% of your net worth, is 100% of it in the S&P index?
Ankur: Absolutely not. I have a lot of it not in the S&P index — that’s my fund money. I think there’s a good chance I don’t outperform. A lot of it is in private investing, in funds that I own. And I think I’m the only person I know who has a fund as large as mine that charges zero management fees. The average venture fund charges 20 to 25% just in management fees, and the average person doesn’t realize that.
Shaan: I’ll tell you that I don’t buy individual stocks. Actually, I looked at my portfolio the other day — first time in a year — and I realized I was wrong. I’ve done it twice or three times. The company I did it on was Playboy. I read their annual report—
Sam: You can’t just call their magazine their annual report. That’s their monthly calendar, dude.
Shaan: Well, actually, their annual report does have a lot of photos. I bought because I was like, their real estate asset is worth more than what they’re trying to sell the company for. Did not win on that one. Also did Coinbase at the IPO, and then sold it two weeks before it popped three months ago. So I’ve done it.
Sam: You’ve also done it with HubSpot stock — you could have sold it, diversified, decided to hold. And with my company too.
Shaan: Yeah. But those aren’t my two biggest holdings — my index funds are significantly larger. I have my fun money stash, it’s just that it happens to be 80% instead of 20%.
Ankur: Look, at the end of the day, as long as we realize what we’re doing, it’s fine. In 2021 I thought I was a damn genius. “These index funds are stupid — my portfolio is up 300%, I should just be a stock picker for life.” And then you come back to reality. There were numerous days of, “Cool, I’ve lost $300,000 today. Down half a million today.” Repeatedly. While the S&P 500 just kept chipping away and growing, and Nvidia comes out of nowhere — a stock I only held because I had an index fund.
Credit Card Points Optimization [00:38:30]
Sam: Let me tell you this crazy tax story I learned. I met this lady who was speaking at one of our events — I don’t want to say her name or company — but she was in a commercial for a credit card company because she loved the card so much. Her business was doing about $50 million a year, and she was putting a lot of it on the credit card. It was giving her $300,000 a year in cash back. And according to the IRS, cash back from a credit card is considered a rebate. She was like, “That’s my salary. I don’t take a salary — I’m living off my credit card points.”
Sam: Did you know you can actually pay your taxes on a credit card? For some people you can actually arbitrage that. There’s not a very high extra fee, and in a lot of cases you can end up slightly better.
Ankur: David Hauser did it. He sold his company Grasshopper, I think for $200 million, and he paid his taxes on his Amex. He called Amex and told them what he was going to do. Let’s say it was a $20 or $30 million tax bill — he paid it on his Amex and got like a couple of decades’ worth of flights.
Shaan: That’s the thing with credit card points: once you learn how to use them for travel, cash back feels less good. There’s so much more value when applied to travel.
Sam: What’s the smart way to do it?
Ankur: The thing you always want to avoid: never spend your points on your credit card’s own website. That’s almost what everyone does, and you lose a ton of value. What you want to do instead is create an account with an airline — I do it with Emirates a lot, because I fly international, or with Air France KLM. The international airlines are the best. Look up a flight on their loyalty program, then do the transfer. It takes like 30 seconds, and you’ll probably save 70% of points right there.
Sam: No way — 70%?
Ankur: I’ve tested this a lot. There’s a tiny link that says “Transfer Partners” — that’s where you send your points. Never spend them on the portal. That’s going to save you so much.
Shaan: I’ve spent hundreds of thousands of dollars on flights over the past 10 years through Chase. I found this out two years ago and it was life-changing.
Sam: You knew that, Shaan?
Shaan: Yeah. I paid for this guy “Mo Points” — he calls you, teaches you about credit card points, asks about your situation, tells you what your credit card setup should be and how to use it. I was like, “$300 to do this call?” That’s kind of a lot. But that one session was the best $300 I’ve ever spent. For me with an ecom business spending millions a year in ads, he said, “You need this Amex Gold because it gives you 4x on every dollar you spend on Facebook or Google.” But then you’ve got to transfer the points out, and use a site like PointsYeah or similar to search for award availability across all the airlines.
Ankur: If you want to tell someone in one sentence how to do better: transfer your points out.
Solo 401k: The Most Powerful Retirement Account [00:45:30]
Sam: What about the solo 401k? That’s the one on your list that I don’t know anything about.
Ankur: The solo 401k is the first product we built. I had an LLC for a while, earning some random money, and I found this account called a solo 401k — it’s like your corporate 401k, but it exists exclusively for you. And with it you can do really cool things.
Ankur: One: you can put in up to $69,000 a year. Typically if you max out your corporate account it’s very hard to hit the max because your company match is not enough. With a solo 401k you can put in $69,000 a year and get that as a tax deduction.
Ankur: Two: you can do the whole thing as a Roth contribution. If you’ve read about Peter Thiel and how he grew his billion-dollar Roth IRA — traditionally with a Roth you can only put in $7,000.
Sam: Can you tell the Peter Thiel story real quick? How did he use a Roth IRA to make billions?
Ankur: This was both genius and possibly illegal. What he did is he bought his founder shares at PayPal with his Roth IRA. He spent like $2,000 to buy PayPal shares that became worth $27 million when PayPal sold. Then he had $27 million to make all kinds of investments. He allegedly bought his Facebook shares — 10% of Facebook — through his Roth IRA. So he’s going to turn 59-and-a-half and have roughly $5 billion tax-free.
Sam: The wildest part is that Peter Thiel only made $27 million selling PayPal.
Ankur: I realize Sam and I are sort of — apples to apples, right? The Hustle and PayPal netted the founders very similar amounts of money.
Sam: What we don’t know is if Peter Thiel had other shares outside his Roth, which is quite possible.
Shaan: Too good to be true. Let’s just take it. Probably not — he’s gonna have to show that to me for me to change my opinion. I’m not gonna let facts get in the way of me beating Peter Thiel.
Sam: Can a person have more than one 401k?
Ankur: That’s what’s cool — if you have a full-time job and a side hustle, you can have a solo 401k for your business while still contributing to your employer 401k. And because it’s your own 401k, you can invest in anything. Your employer 401k has a list of very specific assets. With a solo 401k, you can invest however you want. If you need liquidity, you can borrow up to $50,000 from it. It’s simply the most powerful retirement account in America, but it’s only available if you have your own business.
Sam: Isn’t the normal 401k kind of a racket? Where they’re like, “You can only buy these funds using our 401k”?
Ankur: The long answer is corporate 401k plans are subject to ERISA — Employee Retirement Income Security Act — and those laws are there to protect employees. But as a result, employers can’t do things that would benefit themselves. There are limits on how much you can contribute to yourself if your employees are part of the same plan. But if there are no employees — go crazy.
Sam: With the solo 401k, could you put it in real estate? Anything?
Ankur: Absolutely. The only thing you can’t do — and this is where the Peter Thiel thing may be slightly illegal — is self-dealing. 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. Commercial real estate is fine.
Sam: So Peter Thiel investing in PayPal — that was a self-dealing issue because he was the founder?
Ankur: That’s why it’s sketchy. If he was just an angel investor, it’s fine. He was the founder — which is why it might be an issue. And people ask us all the time, “Can I do what Peter Thiel did?” I say, look — it may be fine if you don’t own over 50%. But I wouldn’t, because the thing with the IRS is a lot of these things are not clear rules. Rules are written a certain way, someone interprets them, the IRS challenges it, sometimes the IRS loses in court — and that’s how loopholes are established.
Tax Strategy: Offense vs. Defense [00:54:00]
Shaan: The problem I have with my personal bookkeepers and CPAs is they’re pretty reactionary. At the end of the year we’re dealing with the problems, and then everyone makes the same resolution: “Next year I’m doing this right.” And then two or three months becomes way later.
Ankur: That’s the real New Year’s resolution — the three weeks after you file your taxes.
Shaan: Candidly, that’s the problem we’re having. We’re realizing we have to educate the CPAs a lot. Almost everyone who comes to us is unhappy with their CPA. And we don’t do tax filings — maybe there’s a world where we will — but who do you hire? A tax strategist who’s more offensive? And do they work in tandem with your CPA?
Ankur: For me personally, once I’ve gone down this rabbit hole, we help people with the tax strategy part internally — we don’t do tax filings. But yes, there’s a big part that’s tax strategy that is separate from the person signing off on your tax return.
Ankur: The way the world is written today, they should be separate — the person filing your taxes typically doesn’t do that much strategy. Even if 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. The average person says, “Why can’t one person do this?” And those are the kinds of things we’re thinking a lot about — how do we productize this while still being compliant.
Sam: I was so stressed out last tax season that I treated it like it was its own company. I went on a road show — gave my best pitch to different people. I created a data room: a flowchart, my prior years’ returns, what I paid in taxes, my expectation for next year. A turnkey data room so they didn’t even have to have a phone call without being prepared.
Sam: On the calls, I told them exactly what I wanted. For some reason I would go to these tax people and because I don’t know as much about taxes as they do, I kind of deferred everything — I almost acted like I worked for them. And then I’d splash water on my face and be like, wait, no — I’m paying them. They work for me.
Sam: So I went in and said: I never want to feel this way again. I want somebody who’s going to take care of everything — filing returns for all twelve of my entities, doing strategy, and coming to me every quarter with proactive suggestions. That’s what I want. Who can provide me that? I went on tour. It’s such a better way than I was doing it before.
Ankur: And it has to be a collaboration. A lot of people say, “Oh, if I had a tax guide they’d solve all my issues.” But the best strategies are long-term. If you want to start a business to get acquired five years later, that’s the kind of stuff you need to be discussing with someone at least quarterly. The more you know, the more you’ll push them, and the better things you’ll achieve.
Sam: I’m actually going to do that data room thing. That’s the second thing you’ve said in the last few months that’s actually going to change my life.
Ankur: What was the first thing?
Sam: We talk twice a week on this podcast, and that’s the second thing in months that was good.
Shaan: Yeah, a lot of the stuff you say I’m either already doing or I don’t want to do. But the data room thing is actually a really wise way to look at it.
The Real Estate Agent Incentive Hack [00:59:00]
Sam: The other thing that hit me, Ankur, was when you were selling your house in San Francisco. You said the difference between $2 million and $2.2 million is meaningful for me as the owner, but 6% of that difference isn’t that meaningful for the realtor. So you said, “If you get anything above my asking price of $2.1 million, I’ll give you 30% of the extra.”
Shaan: I’m selling a piece of property now and right after that pod I called my agent. I didn’t do 30% — that’s crazy — but I did more than the standard 6%.
Sam: The thing is, each additional dollar past the base price is meaningful. I had a negative incentive too. I said, “And if you don’t get me the price you promised when you won this listing, there has to be some disincentive.” What real estate agents do is on the way in they woo you — “Oh, this will be great, we can get you that price.” And then two weeks later they’re like, “Oh, you know, the market right now…” and they’re just negging you to reduce your expectations so when an offer comes in you’ll take it, whatever it is, because they just want to turn the deal over.
Sam: So I said, “If you don’t hit the number, you have to buy my wife this bag.” He was laughing, and I let it sit there, and he was like, “Oh, you’re for real?” I said, “Yeah.” He said, “Okay, deal.” And when we were coming to close, he said, “I really don’t want to buy your wife that bag — let me go back to them and see if I can get more.” And he got an extra $30,000 after that.
Shaan: The reason it broke my frame is because these are like established laws — there’s no negotiating. But when I thought about it, the way you framed it is 100% better.
Sam: And what’s crazy is there are people who do that with the IRS too. Sean Parker — I believe he was important in creating opportunity zones in real estate. I remember reading about it and thinking, wait, Sean Parker created this? He was in his 20s and convinced the government it was wise to invest in opportunity zones — real estate in impoverished areas that we want to improve. How ballsy of that kid to go convince the government to make this move.
Owning Real Estate Through Your Business [01:04:00]
Shaan: Let’s do a couple more before we finish. You said owning real estate with your business — what’s this one?
Ankur: If you have a million dollars in business profits, what can you do to lower your tax bill? Buying your office building — or if you have a physical building connected to anything you’re doing, whether it’s your office or a retail location — if you own that real estate, you can use depreciation to offset 20 to 30% of the purchase price as a business loss that year.
Ankur: That’s why you’ll see a lot of old-school businesses actually own their properties instead of renting. You save so much money. People extend this to cars — buy a vehicle attached to your business. There’s the whole Gwagon tax write-off meme — you can actually depreciate more of the purchase price if your car weighs over 6,000 pounds.
Sam: That’s like the classic immigrant story — the mom and pop who came from Vietnam and eventually bought their corner store building. The building becomes worth significantly more than the corner store, and then they bought their G-Wagon.
Ankur: And business owners were already very favored, as were real estate developers. But when Trump was in office, he took it to the next level with the Tax Cuts and Jobs Act, which basically doubled those benefits. It gave an extra benefit to business owners — the 20% Qualified Business Income deduction — and it allowed real estate developers to do what’s called bonus depreciation, depreciating 20 to 30% of the purchase price upfront.
Ankur: So even though the code is already written this way, there are always new incentives to make it even better for business owners and real estate developers.
Happiness After Selling a Company [01:08:30]
Shaan: Let’s do some of these other things. You had a good bit on happiness — basically you were like, happiness isn’t that complicated. What are the four things that actually matter?
Ankur: After I sold my company, I spent two years traveling, chilling — I was like, we spend all our lives waiting to retire, what if I just lived a retired life now? A lot of it was figuring out: what are my happiness triggers? For me it was very simple.
Ankur: The two critical things for my environment: plenty of time outdoors, ideally with sunlight, and constant movement. Sam didn’t believe me when I told him I walk 20,000 steps a day.
Sam: That is an insane amount.
Ankur: Three and a half miles — it’s just what keeps me going.
Shaan: My trailing 90 days, because we had the baby, was 3,100 steps a day.
Ankur: To me that’s misery. I just need to be in motion.
Shaan: What do you do to get 20,000 steps? Did you replace meetings with walking meetings?
Ankur: Meetings, phone calls — a big part is playing sports every day. It’s winter now and that’s why I hate winter, because I’m not getting my outdoor time and my walking has come down a lot.
Ankur: So: happiness triggers — movement, being outdoors, having a higher purpose (for me that’s work with meaning, but for other people it’s religion or something bigger than themselves), and four: relationships that count. I can simplify my life to those four components and that’s all it takes for me to be very happy.
Shaan: Are you dating anyone?
Ankur: Not right now.
Shaan: You probably crush it in that department though, right?
Ankur: Look, I enjoy being single, but at the same time I’m 34 years old and the parental pressure is ramping up. We’ll see how it goes.
Shaan: You’re like, “I can defeat the IRS but not the parental pressure.”
Sam: How old were you when you and Sarah got together?
Shaan: She was 22 and I was 25.
Sam: Damn, you were young.
Shaan: It didn’t feel that way. I went pretty crazy between 19 and 24. I did some fun things.
Sam: I actually drank a beer with you during that chapter of your life. There are not a lot of people here who have done that.
Shaan: Yeah, true. I had a lot of fun. I did a cross-country motorcycle trip after I sold my company — I only had like $50,000 in my bank account, but I was 23 riding my motorcycle cross-country telling people on Tinder I’d just sold my company.
Sam: Was this Apartment List?
Shaan: Yeah, yeah. I had just hosted a conference, so I had money and I was the coolest guy ever for like eight weeks. And then I met my wife right when I got home.
Shaan: We’ve been together for a while. It’s honestly awesome. I remember when we got married we had to talk to a priest — we got married in a Catholic church — and I was telling the priest, “Yeah, we’re a good partnership, we talk about business and stuff all the time.” He said, “Well, what about love?”
Shaan: But basically, dating someone who is smart and you eventually want to marry actually makes you more money. I think having a good relationship was genuinely the greatest financial decision I made.
Ankur: You’re probably less distracted. People in relationships are more stable. I remember when I was selling my business, I was negotiating with the guy who runs General Atlantic — big private equity fund, old-school guy — and he said, “Are you married? Kids?” I said no. He said, “I don’t like that. I can’t trust single people. You have nothing to lose. I would feel much better about this deal if you were married with a family.”
Shaan: For $250 million I could get a 30-day fiancée right now, sir. What do you need?
Sam: When your wife goes out of town, Shaan — are you like me? Three hours of heaven, but anything beyond three hours I’m like, this is boring, it’s so quiet in here. I’m walking around in circles like my dog. I don’t know what to do.
Indian Diet and Health [01:16:00]
Shaan: I want to talk about one more thing. We have a large Indian listenership — you’re welcome.
Ankur: Thank you.
Shaan: I feel like everyone in my life — all my best friends — are Indian. You’re going on a tear on social media lately, saying that East Asian people — or particularly Indian people — you’re like, the Indian diet is just by default not great for building strength or staying in shape. And things are really bad right now for an Indian person living in North America.
Ankur: Statistically, we have the same exact upbringing as anyone, but Indian Americans are anywhere between four to six times more likely to have heart disease, diabetes — it’s real bad. Now that I have more of a voice on social media and people are listening, I feel like it’s something worth talking about. I don’t know if I could have some impact over the next 10 to 20 to 30 years to change that.
Ankur: The hardest part is there’s this cultural deniability where Indian people get really mad when you tell them this. Even now, if you tweet “the Indian diet is traditionally unhealthy” you’ll get all these people getting super angry. But ask anyone who’s ever tracked macros — not one person who has ever counted macros will argue the Indian diet is healthy. Not one. It’s impossible if you track it.
Ankur: I commented on an Indian cricketer’s physique and an Indian newspaper, the Hindustan Times, ran an article: “Indian-American entrepreneur fat-shames cricketer.” I had to turn off my Instagram because I got hundreds of thousands of comments just attacking me, my family, and everything I stood for because I’m not being a proud Indian.
Shaan: That’s hilarious, man.
Ankur: I went to an Indian grocery store, Sam — you probably don’t know this, there are just Indian grocery shops, we have our own separate secret — and I was like Jim Carrey in The Truman Show when he’s like, “Wait, this sky is actually a wall?” I was literally running down the aisles like, what is happening in here? This is all fried. Why is everything fried? Literally not one thing. And no protein — it’s fried carbohydrates with some fat. That’s everything. You just see the moms putting things in their cart for their kids and I’m like, don’t do this.
Ankur: And that’s not even the home cooking. That’s just the grocery store. Garbage in, garbage out.
Shaan: Why don’t they care? Is it just not part of the culture?
Ankur: Protein is just not really deeply embedded in Indian food. It’s in small parts but it’s just not a big deal. And it’s compounded when you live in America. But my generation, we’re seeing people become more aware of this. A lot of South Asian people are changing. Even guys like Baji are on podcasts saying, “Oh yeah, I did as well as I could for my South Asian genetics.” I actually think South Asian genetics are not bad at all for people who work out and eat clean. All the Indian friends I have who’ve put in the effort have seen results. The stereotype starts because of the diet.
Sam: I’ve been on an Indian food kick lately, and it’s all coconut milk — just incredibly creamy. Tastes so good going in but doesn’t feel wonderful.
Ankur: And Indian parents feed you this and you’re like, “Mom, why did you give us this?” And she’s like, “This is good for you.” “How is this good for you?” “Gives you energy.” I think they literally took the idea of calories as energy — “Yeah, calories are energy, this carbohydrate is going to give you so much energy.” And that’s not how it works.
Ankur: And even they’ll say, “Dal has tons of protein.” Dal is basically lentils. It has like 20 grams of protein and 35 grams of carbs. And then you add butter, ghee, and oil to make it taste good. And dal is the “protein” in the rest of the meal. The Indian Express actually ran an article — “Yep, we thought dal had a lot of protein too.” The awareness is increasing, but it’s slow.
Sam: I went to a Holi celebration and it was naan with ghee, tons of butter chicken — but instead of chicken it was cheese. And then the dessert was fried dough and maple syrup.
Shaan: Gulab jamun? It’s delicious, by the way. Don’t come for it. Delicious. Good for you because it made me smile and smiling is good for you. But it didn’t feel great two hours later.
Ankur: What’s changing is now Indian Americans are really wealthy. There are four million Indian Americans with an average income of $100,000 — the wealthiest ethnic group. I think things will change. It used to not be a very viable market, but now there’s a lot of purchasing power and it’s a big market. All of these businesses make good commercial sense.
Wrap-Up [01:25:00]
Sam: If you read our comment section on YouTube, the most recurring comment is “Shaan, you look great. Shaan, are you losing weight? Shaan, that beard looks wonderful.”
Shaan: For $10 on Fiverr you can get anyone to say that.
Sam: Everybody’s commenting on Shaan’s looks — they’ll either make fun of his outfit because he wears a Mickey Mouse t-shirt, or they’ll say “Shaan, your workout program is really working.” People are just sucking up to him.
Shaan: Thank you. Ankur, where should people find you? How do they go use your product?
Ankur: We’re called Carry, we’re at carrymoney.com. If anyone wants to set up a solo 401k or just get better at what they pay in taxes, check us out.
Shaan: Appreciate you. Thanks for coming.
Ankur: Thanks, man. This was fun.