Ankur Nagpal

He A/B tested his exit: half to Goldman, half DIY. Goldman lost.

After selling Teachable, Ankur Nagpal split his money — half to Goldman Sachs private wealth, half invested himself — to see who'd win. Over 5 years the S&P returned ~13%, but Goldman's fees and 'other stupid shit' dragged his managed portfolio down to 6%.

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

Steal thisBefore handing a windfall to private wealth managers, run a real A/B test against a plain S&P index fund.

Private wealth fees can quietly cost you $10M over 30 years

Ankur Nagpal explains the genius of the percentage-of-assets fee model: you never feel the pain because no check is cut, but the foregone compounding means your ending portfolio is roughly $10M smaller decades later.

“If you had to cut them a check for $10,000 a month, you're like auditing that all the time. But that is what is so genius about this business model where you basically just keep running through this and over the course of your lifetime, you end up with many, many millions of dollars in fees. And it's not just the fees, those dollars would otherwise be invested. So whenever you run the math, you realize your ending portfolio is probably $10 million smaller 20 or 30 years from now.”

Pay financial advisors a flat fee, never a % of assets

Ankur Nagpal's rule (echoing Ramit Sethi): advice is valuable, but a 1%-of-assets fee scales absurdly because a $5M, $50M, and $500M client get nearly identical service. Cap your advisor at a flat dollar amount.

“But at a certain point, the math on going flat fee is just substantially better for you, right? Like if you have $5 million, $50 million, $500 million, they don't do dramatically more things. Yet at every step you pay an order of magnitude more in fees. I think there's a lot of fantastic financial advisors. You pay them $5 grand a year, $10 grand a year, $20 grand a year. I don't care. You can easily get an ROI there, but it's the whatever, 1% of your wealth. That's the part that gets really silly.”

Steal thisHire advisors on a flat annual fee, not a percentage of assets under management.

Direct indexing: same S&P return, but harvest 30-40% as tax losses

Instead of buying one S&P index fund, direct indexing buys all 500 companies individually. Because individual names swing, you can harvest the losers — netting the same index return plus 30-40% of your investment as usable tax losses.

“I've started to do something called direct indexing, where instead of buying a Vanguard fund, it buys each and every one of the 500 companies individually. And the advantage with that is you have more positions, so more volatility at any given point. More companies are down, so you harvest those losing positions. So net-net, you track the same as an index, but you'll get 30-40% of your investment as a usable tax loss.”

Steal thisReplace your S&P index fund with a direct-indexing account to harvest tax losses while tracking the same return.

Park idle cash in muni/Treasury money market funds, not high-yield savings

High earners leaving cash in a high-yield savings account are overpaying tax. Muni funds dodge federal tax, Treasuries dodge state/local, and state-specific muni funds dodge both — lifting tax-equivalent yield from ~3-4% to ~6-7%.

“Most people right now keep their cash in like a high-yield savings account or something. But if you are a high taxpayer, there's likely better places for it. There's either muni funds where you pay no federal taxes. There's Treasuries where you don't pay state and local taxes. There's muni funds specific to New York and California where you won't pay federal and state taxes. Like, we built a very simple product that will just take your cash, calculate your tax rate, and find the best money market fund for you. That itself will take your tax equivalent yield from like 3, 4% to like 6, 7%.”

Steal thisIf you're a high earner, move idle cash from high-yield savings into muni or Treasury money market funds for a higher after-tax yield.

How Peter Thiel turned $1,700 into a $5B tax-free Roth

Thiel put his PayPal founder shares into a Roth IRA when they were worth almost nothing, sold for ~$27M tax-free inside the account, then reinvested (into Facebook) until it grew to $5B — all withdrawable tax-free at retirement.

“What he did, which is like tax magic, is most people have access to a Roth IRA. He put his PayPal founder shares in a Roth IRA, sold those for about $27 million, then used this as a supercharged investment account to where it is today, where he has $5 billion in his Roth. He turns he retires next year, so he gets all of that, but no taxes.”

Mega backdoor Roth: stuff $77K/year into a tax-free account

Beyond the $7K Roth limit, the mega backdoor Roth uses a 401(k) to push in $70K/year — combine them for $77K. Ankur Nagpal modeled that starting young and just indexing the S&P leaves you with ~$30M tax-free at retirement.

“But the mega backdoor Roth IRA lets you use a 401 to get in $70,000 a year. Into this account. So you can combine the two, get in $77,000 a year. Um, I actually sanity tested this. I built a very simple model that makes the assumption that you start contributing to Roth IRA by 21, the mega backdoor by like 30. Even if you just index the S&P and you looked at the 100-year average of the S&P, you end up with $30 million in your Roth IRA at retirement.”

Steal thisSet up a mega backdoor Roth through your 401(k) to contribute up to $77K/year into a tax-free account.

Function Health, but for your looks

Ankur Nagpal's idea: a concierge service that marries proactive diagnostics (DEXA scan, blood work) with aesthetics — telling you your hairline receded 2 inches and giving you an action plan to look better, not just be healthier.

“I think if you had a function health, but for your physical appearance, it would completely crush. So it's like you come in, it's like, wow, Sean, your hairline has receded. 2 inches and you know, you get, you tie in a DEXA scan to it, but basically like a concierge service to elevate your experience. Like 2 of my college roommates are plastic surgeons, right? And I've heard a little bit about that side of the business, but marrying these 2 ideas, basically concierge lookups with improving your aesthetics, I think is a fantastic business.”

Steal thisBuild a concierge diagnostics service focused on aesthetics — measure looks, then sell a personalized improvement plan.

AI personal software: build tiny apps for your own annoying workflows

Ankur Nagpal, who hadn't coded in 10+ years, now uses AI to build small internal tools and personal apps for repetitive tasks. The opportunity: every local business can do the same for its own annoying recurring workflows.

“So I started by building things that like, just like annoying workflows I have to do. Like every time we host a webinar, we have to download something from someplace, re-upload it somewhere else. Started building these sort of internal tools, but now it's reached a point where I have all these annoying— we're talking about homeownership— all these annoying things I need to do for my house. Building like a very simple sort of task management app just for myself is super useful. I think you're starting to see more and more people realize this, both for their business and for themselves.”

Steal thisUse AI to build throwaway apps for your own recurring annoyances, then productize the pattern for local businesses.

Padel courts: US arbitrage at $300/hour, 1,000 courts vs 20,000 in Spain

Ankur Nagpal pitches opening padel courts in tier-2 US cities. The sport is exploding (Google Trends straight up), courts run ~$300/hour booked out in NYC, and the US has only ~1,000 courts versus ~20,000 in Spain — a multi-year arbitrage window.

“And it's finally coming to the US in a way that I think you can go to any tier 2 city, spin up a location, and probably do quite well for the next few years. I think we're in this unique sort of arbitrage opportunity. In New York, courts are about $300 an hour and booked out over weekends. And again, New York is probably the most extremely expensive market in the US, but it kind of cascades all the way downward.”

Steal thisOpen padel courts in a tier-2 US city now to ride the supply gap before the sport hits mainstream.

Buying into the Chennai Super Kings, a ~$1B cricket monopoly

Ankur Nagpal pooled high-7-figures (20% his own) of a near-$1B valuation to buy a sliver of the Chennai Super Kings. The thesis: India is a one-sport country, the IPL is the third-richest league in the world, and it has huge room to run.

“The team is called Chennai Super Kings. They're— they've won like, I want to say, 6 championships. The Indian League is about 15 years old, so they've won more titles than any other team. Highest market cap. And dude, it's such a monopoly because India is the biggest country in the world and it's truly a one-sport country. Like the delta between sport number 1 and sport number 2 is massive.”

The US tax code is rigged for business owners and real estate

Ankur Nagpal argues the US tax code is intentionally written to favor business owners and real estate, so the single biggest tax move a W-2 employee can make is to become a business owner.

“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, but 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.”

Steal thisIf you only have W-2 income, start a business — the tax-optimization playbook is roughly 10x bigger for owners.

Marry a real estate professional to shield W-2 income

One of the few ways high-paid W-2 employees can offset income is to have a spouse qualify as a real estate professional, letting the couple write off real estate depreciation against W-2 wages.

“We have a presentation on like, how do you lower your tax bill as a W-2 professional? Point number 3 is marry a real estate professional. Like, it's like tongue in cheek, but it actually, it actually is one of the very few things you can do as a W-2 professional. But I don't think anyone pays more in taxes than highly paid tech employees.”

QSBS: pay zero tax on up to $10M when you sell a C corp

Qualified Small Business Stock (QSBS) lets founders, employees, and investors who hold C-corp shares for 5 years pay no federal tax on up to $10M in gains.

“It's called QSBS, Qualified Small Business Stock. This is insane. So 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. And that's because of what's called QSBS, which roughly says if you hold shares in a C corporation for 5 years, you pay no taxes on up to $10 million in gains. It applies to founders. It applies to employees. It also applies to investors.”

Steal thisHold C-corp shares 5+ years to claim the QSBS exemption on up to $10M (or 10x basis) in gains.

QSBS stacking: multiply the $10M exemption across family and trusts

The QSBS exemption is per shareholder per company, so gifting shares to family members or seeding multiple trusts (for future kids, charity) gives each its own $10M limit — multiplying the tax-free amount.

“But then I found out that the limit is per shareholder per company. So where this gets interesting is if I give some shares to my mom, my brother, my dad, each of us now have our own $10 million limit. So as a family, we have a $40 million limit. Or if you go down the estate planning rabbit hole, which it's a little complicated, but at a certain point, you know, hire an attorney, figure it out. You can set up trusts. I set up trusts for my future children, trust for charity, and each of these trusts get their own $10 million benefit.”

Steal thisGift founder shares to family and irrevocable trusts before a sale so each gets its own $10M QSBS exemption.

Give early team members shares, not options, to start the QSBS clock

QSBS requires owning shares for 5 years — options do not count. Ankur now grants early team members actual shares so their 5-year holding clock starts ticking immediately.

“But this time around, I've given all my early team members shares instead of options so they can start their clock ticking. That's a really important thing that a lot of people don't realize is you have to own the shares for 5 years, not options.”

Steal thisIssue shares (not options) to early employees so their QSBS 5-year clock starts on day one.

Transfer credit card points to airlines instead of booking on the card site

Ankur says the single biggest credit-card-points mistake is redeeming on your card portal; transferring points to an airline loyalty program (Emirates, Air France/KLM) before booking can save ~70% of the points.

“So what you want to do instead is create an account with an airline. Like I do it with Emirates a lot because I fly internationally or with Air France, KLM, the international airlines are the best. Look up a flight on their loyalty program. Do the transfer. It takes like 30 seconds and you'll probably save 70% points right there.”

Steal thisNever redeem points on the card website — transfer them to an airline partner first to save ~70%.

Solo 401k: put away $69K/year if you have your own business

A Solo 401k lets a business owner contribute up to $69,000 a year (far above a corporate match) as a tax deduction, with the option to make it a Roth contribution — versus the $7,000 Roth IRA cap.

“So 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 'cause your company match is not enough. But with a solo 401, you can put in $69,000 a year, get that as a tax deduction. The second thing is you could do the whole thing as a Roth contribution.”

Steal thisIf you have any self-employment income, open a Solo 401k to shelter up to $69K/year.

Peter Thiel turned a $2,000 Roth IRA into a $5B tax-free fortune

Ankur recounts how Peter Thiel bought his PayPal founder shares inside a Roth IRA for about $2,000, which grew to $27M at sale and was reinvested (allegedly into Facebook), so he is set to have ~$5B tax-free.

“But what he did is he bought his founder shares at PayPal with his Roth IRA. So he spent like $2,000 to buy PayPal shares that became worth $27 million when PayPal sold. And then he had $27 million to just make all kinds of investments. He allegedly bought his like Facebook shares, 10% of Facebook from his Roth IRA. So he's going to turn 59 and a half in a year and he's going to have $5 billion tax-free, which is pretty wild.”

Buy your office building to deduct 20-30% via depreciation

Owning the real estate your business operates from (office, retail) lets you use depreciation to offset 20-30% of the purchase price as a business loss that year — why old-school businesses own their buildings.

“Just buying your office building, or if you have a physical building connected to anything you're doing, whether it's your office, whether you have a retail location, if you own that real estate, you can use depreciation to offset 20-30% of the purchase price as a business loss that year. So, which is why you'll see a lot of old school businesses, they actually own their properties.”

Steal thisIf your business has a physical location, own the building and use depreciation to offset 20-30% of the price.

Ankur's 4 happiness triggers

After selling Teachable, Ankur distilled his happiness to four repeatable components: constant movement, time outdoors, a higher purpose (work with meaning or religion), and relationships that count.

“But yeah, so happiness triggers movement, being able to spend time outdoors, having a higher purpose. For me, that's work with meaning, but for other people, you know, it's religion. It's just something that is like bigger than themselves. And 4 is like relationships that count. I can like simplify my life to these 4 components”

Steal thisAudit your life against four levers: movement, outdoor time, higher purpose, real relationships.

Indian Americans are 4-6x more likely to have heart disease and diabetes

Ankur states that an Indian person living in North America is 4 to 6 times more likely to have heart disease or diabetes, which he attributes largely to a default diet low in protein and high in fried carbs.

“Like an Indian person living in North America, right? So we have the same exact like upbringing, whatever, is anywhere between 4 to 6 times more likely to have heart disease, diabetes. Like it's just, it's real bad.”

Thinkific has a $1B+ market cap — investors are paying for the payments business

Sam notes course platform Thinkific went public with a $1B+ market cap on tiny sales. Ankur (Teachable founder, which sold for ~$250M on ~$25M sales) says the premium comes from saved-card payments revenue — once buyers start spending they keep buying.

“It's over a billion dollars their market cap is. And I asked Ankur. So our friend Ankur, he started this company called Teachable. When Teachable sold, they sold for, I think, $250 million.”