Sam and Shaan bring on Aner Ben-Ami, founder of Teachable (sold for ~$250M) and CEO of Carry, to share what founders actually learn about money after an exit. Aner’s AB test — giving half his exit to Goldman Sachs, investing the other half himself — revealed private banking is mostly status theater. The conversation covers Roth IRA mechanics, mega backdoor Roth, direct indexing via FE, and tax-equivalent yield on cash. The second half pivots to Aner’s startup ideas: concierge aesthetics health, breaking out of the US food system, a credit card points travel agent, Padel courts as investment, and AI personal software. Ends with Aner’s purchase of a stake in the Chennai Super Kings cricket team and the sports investing meta-trend.
Speakers: Sam Parr (host), Shaan Puri (host), Aner Ben-Ami (guest, founder of Teachable, CEO of Carry)
Introductions [00:00:00]
Sam: Let me introduce you. Shaan, this is my friend Aner. I’ve known Aner since 2012 or 2013. We’ve been buddies since. And I’ve known Shaan since 2013 or 2014.
Aner: I think I’m one of the only people who met Sam through the internet and then actually had beers with him. That’s how far back we go.
Sam: Give his background. When I met Aner, he was doing a Facebook app that went viral — he made his first couple million at around age 26 or 27.
Aner: Twenty.
Sam: Twenty? What was the app?
Aner: All the silly stuff. Personality quizzes, friend quizzes, “answer seven questions and find out how good a kisser you are.” Crazy stuff. Then he started a company called Teachable — early on the online course game, not quite bootstrapped but he owned the majority — and sold it for something like $150 million.
Aner: $250 million. But close enough.
Sam: And you made around a hundred million when you were 32. Did it feel more insane to make your first million on a silly Facebook app, or to make a hundred million on an education company?
Aner: Zero to something is always more life-changing. That was also when I’d just moved to America as an international student. Making money in college allowed me to skip class and realize that if I can do things on the internet, why ever get a regular job?
Sam: How much money did you have before you sold Teachable?
Aner: About a million and a half, two million. I paid myself a salary of $150K in New York, which was roughly my life break-even. Then the exit basically moved the decimal two places — from about a million to a hundred million in liquid cash. The rest is equity that keeps paying out.
The Goldman Sachs AB Test [00:06:00]
Sam: You sent us a note saying that after you sold your company, you ran an AB test. You gave half to Goldman Sachs to invest and invested the other half yourself. What happened?
Aner: Like a lot of first-time founders who sell a business, I knew nothing about money. You immediately get hit up by every private wealth manager. You see Goldman Sachs, Morgan Stanley. I couldn’t fully tell how legit they were, so I thought: let me take a sizable chunk, give it to them, and see what they do. The other half I’ll learn with myself.
I went through the standard post-exit founder experience — invest in too much, don’t say no enough, go through a phase where you think you’re an investing genius. Then five years later, you have actual results to look at.
The results: there’s nothing special about private banking. They charge 50 to 120 basis points. The best-performing portion of my Goldman portfolio was simply indexing the S&P, which returned about 13% over that period. They did a lot of other things that averaged that down to 6%.
Shaan: What sort of “other things”?
Aner: A lot of fixed income — bonds — for a 31-year-old with infinite risk tolerance. Doesn’t make sense. They also charged over 100 basis points for products Vanguard could have done for almost nothing. Eventually I got them out of the bond positions, but the whole experience showed me that their product has such insanely good margins that they can afford whatever, and they really sell a lifestyle.
Sam: What were the perks?
Aner: A concierge team. They’ll get you tickets to the US Open, take you out for nice dinners. I was the wrong demographic — when they wanted to get dinner, I was like, “Ugh, another person to hang out with.” But a lot of people genuinely enjoy it. And there’s genius in the fee structure: because you pay a percentage of assets, you never feel the pain. But you’re paying them six figures a year. If you had to cut a $10,000 check every month, you’d audit it constantly. That fee — plus the compounding those dollars would have done — means your ending portfolio is probably $10 million smaller 30 years from now.
Sam: What’s the argument for them?
Aner: Financial advice is genuinely valuable at a flat rate — $5K, $10K, $20K a year, I don’t care. You can get ROI on that. It’s the “1% of your total wealth” model that gets silly. The better you do, the less sense it makes.
Indexing, Direct Indexing, and Tax Alpha [00:18:00]
Sam: Talk about indexing. You had a note on ways to index that are smarter than the default.
Aner: My overall thesis is: most people are not going to get differentiated performance from investing, and that’s actually okay. Historically, even with all my access — financial advisors, founder networks, whatever — the best part of my portfolio was indexing the S&P. So most people should not try to find alpha on the investment side.
Where your alpha comes from is saving money on taxes. One example: direct indexing. Instead of buying a Vanguard fund, a service like FE buys each of the 500 companies individually. You have more positions, so more volatility, and at any given time more companies are down. You harvest those losing positions. Net-net, you track the same as an index, but you’ll capture 30-40% of your investment as a usable tax loss.
Sam: Do you do this, Shaan?
Shaan: I do. I put in $250K as a test. I got the same performance as the S&P, but I captured an extra $16K in tax loss harvesting on the same underlying assets. It was a two-second decision — literally pushed a button, it did an automatic rollover of my Vanguard ETF holding. I never had to do anything.
Aner: Exactly. An even simpler example for people holding cash: most people use a high-yield savings account, but if you’re a high taxpayer, there are better places. Muni funds — you pay no federal taxes. Treasuries — no state or local taxes. State-specific munis for New York or California — no federal and state taxes. At Carry, we built a product that takes your cash, calculates your tax rate, and finds the optimal money market fund for you. That can take your tax-equivalent yield from 3-4% to 6-7%.
Sam: When I hear all this, I always think: for most people, just focus on earning more money first. Increase revenue, then worry about taxes.
Aner: Completely agree. If your business makes $50K a year, you don’t have a tax problem. You need to make more money. It’s like being at a bike shop and agonizing over a $5K ultralight frame when you’re a little overweight. Just lose the weight. The tax stuff matters at our level where compounding makes a real difference, but at $30-50K in revenue, earning more is far more effective.
The Roth IRA and Mega Backdoor Roth [00:28:00]
Aner: I want to tell you how Peter Thiel made $5 billion and paid no taxes on it.
Sam: Talk dirty to me. Whisper softly about my backdoor Roth.
Aner: A Roth IRA is an account where you put in after-tax money, and then all further growth is tax-free — including if tax rates go way up in the future. In the 1970s, the top marginal rate was about 80%. The Roth protects you from whatever rates are in the future. William Roth created it about 20-25 years ago, ideally for the middle class — it was never supposed to be for the wealthy.
What Peter Thiel did: he put his PayPal founder shares into a Roth IRA when they were valued at essentially nothing — maybe $1,700 worth. He sold those for $27-28 million. Then he reinvested those gains within the Roth into Facebook. That’s how the $5 billion got there. Every dollar of that $5 billion: zero taxes.
Sam: But there’s an income limit on the Roth, right?
Aner: Yes — around $150K, you lose access to direct Roth IRA contributions. But that’s where the backdoor Roth IRA comes in. And on top of that, there’s the mega backdoor Roth, which uses a 401k to get $70,000 a year into the account. Combined with the standard Roth IRA limit, that’s $77,000 a year going in tax-sheltered.
I modeled this: if you start contributing to a Roth at 21 and the mega backdoor at 30, and you just index the S&P at the 100-year average return, you end up with $30 million in your Roth IRA at retirement. No taxes on any of it.
Shaan: Who came up with this?
Aner: The IRS never intends these loopholes. A smartass accountant finds a way to stay fully in compliance. The IRS challenges it, loses in court, and that’s how you get loopholes. The mega backdoor Roth has had legislation to outlaw it for years — it comes up in every tax bill. Republicans fight it, it gets deferred. It keeps surviving.
I’ve met people — families with family offices — who’ve used this to accumulate eight and nine-figure Roth IRA balances. Ten to a hundred million dollars with zero taxes owed. It’s insane.
Business Ideas: Health, Food, and Software [00:45:00]
Sam: You sent us a list of startup ideas. Hit us with them.
Aner: First: there’s so much focus right now on proactive health and wellness. Services like Function Health — you do a blood test, they tell you everything about your body. That category has exploded. Function Health hit $100 million in revenue in two or three years. But all of this is commoditized — everyone uses the same blood testing companies.
What I think will crush: Function Health but for your physical appearance. A concierge service where you come in, get a full aesthetic audit — hairline, skin, body composition, a DEXA scan — and then build an action plan around it. I have two college roommates who are plastic surgeons. Marrying that kind of expertise with the concierge proactive-health model is a fantastic business.
Shaan: We had Justin Mars on the podcast and his skin was literally glowing. We all immediately asked what he was doing.
Sam: I went to breakfast with him and I just said: “Whatever this man orders, I eat.”
Aner: Second idea: anything that helps people break out of the US food system. Every Friday evening I go meet my raw milk dealer. It’s an Amish farm that drives into New York City, parks on a corner, and you have a 30-minute window. The product says “not for human consumption” — wink wink. But it actually tastes like food.
I got into this because I’d spend a month in Argentina living like a degenerate and my physical body felt better — and I don’t think it was the alcohol. I think it was just the food. Businesses that enable people to get clean, traceable food will go quite far.
Shaan: It’s like a farmers market except it feels more like a drug deal, which somehow makes it more appealing.
Aner: Third: a travel agent but for credit card points. I have 250,000 Amex points, 100,000 Chase points. I would pay a meaningful amount of money for someone to just go find me two first-class tickets somewhere warm this summer. There’s a company called Flightfox — a human books flights for you, spends like two hours per flight — but the business model barely makes sense at $20 per ticket.
I’ve also personally sold points. A friend who spends $10-15 million a year on Amex was like: wire me the money, I’ll book the ticket, I’ll take a small fee, you get the discount. I saved 30-40% on six first-class flights. Highly not illegal, but against terms of service. What I want is that as a professional service, with AI doing the back-end searching.
Aner: Fourth: I built a simple personal software app using AI. I haven’t written code in 10 years, but now it’s fun again. I started with annoying workflow automations — every time we host a webinar, you have to download something from one place and re-upload it somewhere else. Now I’ve built a simple home task management app: property taxes quarterly, water filters every X months, who’s responsible for what. It pulls the schedule automatically.
Any local business could do something similar for their recurring annoying tasks. I think more people will start building personal software for their own life.
Padel, Cricket, and Sports Investing [01:05:00]
Aner: Last idea: Padel. After food, my second biggest expense in New York right now is Padel courts. It’s spelled P-A-D-E-L. Imagine a slightly smaller but wider tennis court with a back wall, played with a depressurized tennis ball. Because of the back wall, instead of hitting the ball out, it rebounds and play continues. Very big in Latin America and Europe.
In the US, there are about 10,000 courts. In Spain, there are 20,000. The Google trend is straight up. In New York, courts are $300 an hour on weekends — booked out. I think you can go to any tier-2 city right now, build a Padel location, and do quite well for the next few years. The window is open but won’t be forever.
Shaan: It has a scene quality to it. The place I went was all black walls — like Barry’s Bootcamp or SoulCycle. Everyone looked hot and cool. There’s an element of exclusivity.
Aner: Exactly. And there’s a social layer on top — there’s a company called Playtomic that’s built the rating system. Every game you play, your ELO score updates. I have friends — successful adults with families — texting after a loss like, “I can’t stop thinking about this. Why am I so upset?” They have 14 unmet competitive needs that this sport absorbs. That community formation is a real business in itself.
Sam: What’s the difference between Padel and pickleball?
Aner: Padel is substantially more athletic. A lot of players are ex-D1 tennis players. I’ll be diplomatic and say: pickleball is a game, Padel is a sport.
Sam: You bought a piece of a cricket team?
Aner: I did. Flashback to age 8 through 14 — cricket was the only thing I cared about. I played internationally for my home country. Someone told me a shareholder in one of the most valuable teams in the Indian Premier League was selling a stake. The team is the Chennai Super Kings — six championships, highest market cap in the IPL. The league is about 15 years old and the team’s valuation is close to a billion dollars.
Our group put in high seven figures total. I was about 20% of that. It’s a small percentage, but the investment thesis is solid. The IPL is already the third most valuable sports league in the world by some measures — after the NFL by TV rights per game. The total market still has a massive runway: India is a one-sport country, and the delta between cricket and the number-two sport is enormous.
Shaan: How does that compare to the Boston Celtics selling for $6 billion?
Aner: The Celtics sale basically reset everyone’s model. People were underwriting sports teams at one or two billion — then one sells for six. The number of billionaires keeps going up. The number of teams stays the same. Two new NBA franchises are coming — Vegas and probably Seattle — and the league wanted the Celtics to sell high specifically so they could price those expansion slots at $5-6 billion each.
Sam: Mark Cuban bought the Mavs for something like $200 million, right?
Aner: Something like that. The compounding on sports assets over 20-25 years has been exceptional. And the US is uniquely good at monetizing eyeballs — the NFL is hitting the point where they have to go international to meaningfully grow. That’s insane. The European leagues have massive teams but terrible commercial monetization by comparison.
Sam: What do you actually want out of owning part of Chennai Super Kings?
Aner: Long term I want to draft players. I want to be able to kick people out. Being an annoying, overly-involved owner — that’s the fun part. The financial returns are nice, but that’s the whole point of having money. Do things the eight-year-old version of you thought was cool.
Sam: Aner, where do people find you?
Aner: On Twitter, it’s my name. And for tax optimization: carry.com.