Mar 19, 2025 · 1h 17m · bigdeal
$250 Million Founder: What I Did Wrong & How To BUILD BIG | Ankur Nagpal
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In this episode of The Big Deal Podcast, entrepreneur Ankur Nagpal joins Codie Sanchez to break down his journey from building and selling Teachable for $250 million to launching Carry, sharing actionable lessons on startup culture, unconventional fundraising, and the psychology of wealth. Nagpal provides candid reflections on immigrant resilience, high-performance hiring, and transitioning from financial scarcity to true abundance.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Codie holds 36.5% of the talking time here. How this is scored →
Codie as informed peer 4.9 Guest teaching 5.2 Guest disagreement 2.1 Codie pushing back 1.8
speaking balance: gold is Codie, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 3:08 Dismissing entitled workplace culture
Ankur aggressively mocks employee demands around unionization and snacks, bluntly remarking that tech workers are not working in coal mines.
Hardest push from Codie ▶ 36:41 Pushback on business ownership statisticsCodie rejects Ankur's loose definition of business ownership, pointing out that paper LLC creation distorts real revenue-producing small business data.
Biggest teaching moment ▶ 15:38 Venture fund fee structure mechanicsAnkur breaks down how typical 2% management fees compound over ten years into an effective 20% guaranteed payout regardless of performance.
Codie holds their own ▶ 55:29 Codie's State Street MBA deal structureCodie demonstrates sharp institutional finance savvy by detailing how she got State Street to pay for her Georgetown MBA while keeping her full salary and negotiating out the clawback clause.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Codie as informed peer | Guest teaching | Guest disagreement | Codie pushing back | Why |
|---|---|---|---|---|---|---|
| Startup Culture Shifts and Managing Team Mindsets | 6 | 3 | 4 | 2 | Codie and Ankur find instant common ground complaining about corporate cultural softness and entitlement among modern employees. Codie shares her own management experience from institutional finance with rigid quant firing systems. | |
| Early Hustles, Facebook Apps, and Supporting Family | 3 | 5 | 1 | 1 | Ankur recounts building viral Facebook quiz apps at Berkeley, generating up to $50k a day as an immigrant student. Codie actively listens and validates his early hustle. | |
| The Teachable Exit, Infinite Money, and Playing for the Sport | 4 | 4 | 1 | 1 | Ankur details his salary progression at Teachable and what walking away with nine figures felt like. Codie reflects on how Twitter distorts financial reality for ordinary entrepreneurs. | |
| Raising $70M on Twitter and Aligning Investor Incentives | 5 | 7 | 2 | 2 | Ankur educates listeners and the host on the hidden economics of 2-and-20 venture management fees over 10-year fund lifecycles. Codie concurs with syndication math and sharing risk. | |
| Mastering Cold Outreach and High-Profile Interactions | 5 | 6 | 2 | 2 | Ankur provides cold outreach heuristics, citing the equal response rate across seven follow-ups. Codie shares a personal DM confrontation with Mark Cuban regarding price caps. | |
| Teachable's Inception and Silicon Valley's Youth Culture | 4 | 6 | 2 | 1 | Ankur explains the inception of Teachable and contrasts Silicon Valley's respect for young founders against hierarchical international business cultures. Codie adds context regarding speed and technology leverage. | |
| Fintech Architecture, Domain Acquisition, and Tax Code Perks | 5 | 6 | 2 | 2 | Ankur discusses founding Carry to productize tax loopholes and retirement plans for small business owners. Codie contributes domain name war stories and personal branding trade-offs. | |
| Failed Sports Ambitions and Cultural Entrepreneurship | 6 | 4 | 2 | 4 | Ankur and Codie explore demographic entrepreneurial tendencies and Indian immigrant business ownership. Codie pushes back on business ownership statistics, clarifying LLC creation versus cash-flowing operations. | |
| Hybrid Work Innovations and the Second-Time Founder Dilemma | 4 | 5 | 2 | 1 | Ankur explains his hybrid company policy of working 11 months in-office and 1 month fully remote in February, alongside his increased fear of public failure as a second-time founder. | |
| Wealth Mindset, Gratefulness, and Breaking Scarcity Habits | 5 | 4 | 2 | 2 | Ankur and Codie discuss overcoming scarcity mindsets and whether to maintain a poor-kid mentality after achieving substantial wealth. | |
| Creation vs Consumption, Dating in NYC, and Startup Geography | 4 | 5 | 2 | 2 | Ankur reflects on the rise of digital consumption traps versus creation and the decentralization of startup hubs away from Silicon Valley to cities like New York and Austin. | |
| Pandemic Exits, Higher Education ROI, and Pricing Strategy | 7 | 6 | 3 | 2 | Ankur and Codie break down the economics of higher education, MBAs, and course pricing psychology. Codie showcases her corporate negotiation prowess with her employer-funded Georgetown degree. | |
| Hiring A-Players, Fast Execution, and Market Moats | 6 | 6 | 2 | 1 | Ankur and Codie exchange philosophies on vetting high performers, moving with extreme speed, and establishing regulatory moats against AI commoditization. |
Statements from this episode (28)
Nagpal: Startups become less fun to manage once headcount hits 100
“At least for me, I would say up to about 50 was really fun. When it got to a hundred, it started feeling less fun.”
Nagpal: Overplaying mission over winning attracts hires who struggle under pressure
“Last time, I think we overplayed the mission side because like, again, mission is important, but we still wanted people who are primarily there to win. But last time we're like, Hey, you know, education is really important, but then we ended up getting a lot o…”
Nagpal: Facebook apps scaled to $50,000 daily, making $1M before age 21
“It started my freshman summer, and at the end of my freshman summer, I was making, like, 20 dollars a day, but all the way scaled to 50 grand a day, and making a million bucks before I was 21.”
Nagpal: College Facebook apps reached 4–5M daily users, beating Yelp and LinkedIn
“Like at our peak, we had more traffic than LinkedIn, Yelp, about the same as New York Times. We had like, I think like four or five million teenagers basically using it every single day.”
Nagpal: Teachable's $250M acquisition was half cash, half stock
“I mean, half of it was cash, half of it was stock.”
Nagpal: Raised a $70M venture fund via Twitter DMs
“When I fundraised for my fund, I raised about seventy million dollars on Twitter DMs with, I want to say like maybe under five actual meetings.”
Nagpal: 2-and-20 VC structures guarantee managers 20% in cumulative fees over 10 years
“What people don't understand is it's actually closer to 20 and 20. It's one of the best kept secrets because venture funds charge those fees for 10 years. So if you raise a hundred million dollars, The investor makes twenty million bucks, maybe even 25, regard…”
Nagpal: Took zero management fees and funded 25% of his fund
“What I did with my fund is I took zero management fees, which was absurd for a fund of that size and a quarter of all the capital was mine.”
Nagpal: A $10 million net worth is not in the top 1% of households
“Like, if you make ten million, if you have a net worth of ten million dollars, you are not in the top one percent of households. It's crazy. You're like one top one and a half, but you're on the top one percent with a ten million dollar net worth.”
Nagpal: Response probability remains constant through seven cold outreach emails
“I forgot the data, but like, I think with the first seven emails you send or something, the chance of getting a response are the same, which means you should send seven emails, because if you have a five percent chance, you'll have a five percent chance even t…”
Nagpal: Mark Cuban replied every time Nagpal emailed him as a teenager
“Even when I was 1819 years old, every time I emailed Mark Cuban, he replied.”
Nagpal: Teachable reached $40K-$50K monthly sales within nine months
“The first month we processed maybe like 3000 dollars in course sales. But every single month after that, we process a little bit more until eight or nine months in, we were doing 40, 50,000 dollars a month in course sales across, I want to say 15, 20 creators.”
Nagpal: 18-to-20-year-olds hold a golden window for high-profile networking
“If you're. 1819, or 20, you're in a golden window where a lot more people will be willing to meet with you because of your promise and your potential.”
Nagpal: Carry surpasses $2M ARR and $100M in customer assets
“So we're a little bit over two million in annualized revenue. We custody a little bit over a hundred million dollars in customer assets which is good.”
Nagpal: Startups can easily fix their branding years later
“You can fix brand later on. People don't realize that. Like you can fix brand a year and two years in at any given point, like even now we're, you know, a little bit over two years in. But 10 years from now, almost all of our customers 10 years from now are in…”
Nagpal: Carry operates in-office 11 months and remote during February
“The default expectation is we're in the office every single day, but we're remote for one month. And partially it's because for anyone in New York, winter in New York can be soul crushing. So we're remote in February, in the office, 11 months of the year, whic…”
Nagpal: A single remote month boosts employee enthusiasm for office work
“The thing that's been interesting is when most people come back, their reaction is not like, that's sick, why can't we do it always? Like, they're like, yeah, it was great, but they're like, oh, I missed the office. I missed, I kind of missed being around ever…”
Nagpal: Knows multi-hundred-millionaires who are sad they aren't billionaires
“I know people who have made hundreds of millions of dollars, where sad they're not a billionaire.”
Sanchez: Business class seats are nicer than most private jets
“A nice, Business class seat, way nicer than a seat, except on the biggest jet out there. So I think a lot of this is just flexing on the internet.”
Nagpal: Teachable doubled ARR from $25M to $50M three months post-sale
“Our business, like we sold the company at about twenty five million in ARR and we doubled to 50,000,003 months later.”
Nagpal: Almost never hires MBAs, doing so only despite their degree
“Like, I'm, I almost never hire MBAs. And once in a while, if they do, it's despite their MBA.”
Nagpal: 50% never open online courses, but higher prices increase completion
“Like, 50% of times people wouldn't open the thing. When you charge more money, you actually got better results, ironically. A lot of people were more likely to take the course, more likely to report a happier satisfaction just by charging more”
Nagpal: Most course creators can double prices without hurting conversion rates
“What we found is most creators could double their price and see no change in conversion rate.”
Nagpal: Initial job performance never reverses; test hires as contractors
“I will get one out of every four hires wrong. And if you work with that constraint, you can be smart about it. So wherever possible, I love to have people contract or do something for a couple of months, because you can always tell after you start working with…”
Nagpal: Performance improvement plans do not work and harm both sides
“I don't think, like, you know, pips and performance improvement plans really truly work, and sometimes I think they do a disservice To both the employer and the employee.”
Nagpal predicts a billion-dollar one-person company will emerge soon
“There'll be a billion dollar Company soon with one person and all of that, but for now, yeah, it's getting there.”
Nagpal: Distribution will become most valuable as building costs drop
“I think distribution is probably going to become more important than it already was. Because if the cost of building something goes down to almost nothing, reaching people becomes the most valuable thing.”
Nagpal: Regulatory compliance creates enduring business moats against AI
“We're, you know, RIA. We're going to be a broker dealer. Even if AI makes it really easy to do stuff, the SEC is not going to approve people in two days. FINRA is not going to approve people in two days. So regulatory modes, I think are real and will continue …”