My First Million

I spent 24hrs with a blue collar millionaire

It's a rare case of a founder handing over the actual purchase price, build cost and sale price on three deals in a row, so you can judge a romantic-looking business on its real margins.

1. 01Mark O'Brien, 63, buys wrecked New York brownstones and resells them restored — 94 Bank Street in the West Village cost $5.5 million and he expects $17 million.
2. 02The constraint on a landmark brownstone is permitting, not building: 94 Bank Street sat two and a half years on approvals while carrying cost ran.
3. 03Finishing the rubble cellar is close to free square footage for O'Brien, because floor area ratio excludes below-grade space from the allowance.
4. 04The Fort Greene townhouse pencils at $2.8 million to buy and about $2 million to build against $6.2 million out — roughly $500,000 a year over three years.

Howard Marks: how I make money while you worry about a market crash

One of the most respected investors alive walks through his actual decision process during the 2008 crash — doubt included — instead of the cleaned-up retrospective version.

1. 01Howard Marks upgraded his December AI-bubble memo two months later after his VC son Andrew pushed him, arguing autonomy is what no earlier technology had.
2. 02Oaktree raised an $11 billion distressed-debt fund before the 2008 crash — four times the largest ever — by naming a market that had stopped saying no.
3. 03Bruce Karsh deployed an average of $450 million a week for 15 weeks after Lehman failed, with no data and no precedent to work from.
4. 04Marks frames the Lehman-era bet as asymmetry rather than conviction: if the financial world ended nothing would matter, so the only mistake was not investing.

The $150B dollar business hiding in plain sight

One episode connects a secretive 160-year grain dynasty, the mechanics of family trusts, and a genuinely useful mental model for why AI probably creates more work than it destroys.

1. 01Cargill has been America's largest private company for 40 years, is 88% owned by one family, and books about $150B a year.
2. 02Cargill's edge was physical position: grain elevators built beside the railroad, then expansion into barges, meatpacking, salt and a $10B+ hedge fund.
3. 03Every part of a single hamburger — seed, fertilizer, feed, beef, salt, corn syrup, fry oil — passes through Cargill's hands.
4. 04Cargill's 80/20 rule sends 80% of profits back into the business and 20% to the family, which is how the hosts explain 160 years of compounding.

We found an app that lets you buy anything for $0

One sitting gets you a genuinely strange consumer trend, a clean explanation of Nick Sleep's shared-scale-economies idea, and the credence-goods lens on why grading businesses print money.

1. 01Korean dopamine apps like Food Never Comes sell the browsing and checkout ritual with nothing ever delivered, alongside virtual smoke-break chat rooms.
2. 02Kevin Ryan's playbook, which Sam Parr calls Hondification: launch at low quality and low cost, then raise quality for years while holding the price flat.
3. 03Nick Sleep's shared scale economies: Costco and Amazon hand scale savings back to customers, building a surplus that never shows up on the P&L.
4. 04Costco charges about $100 a year for membership, returns roughly $1,000 in bulk-buying savings, and books nearly all its $5 billion profit on memberships.

I dropped out of college and built a $3.6B company from scratch

Levie narrates the turn-down-half-a-billion decision from inside — the offsite, the reasoning, the lack of secondary — instead of the sanitized version, and is equally specific about therapy and his reading list.

1. 01Aaron Levie started Box in 2005 with three friends from middle and high school, and all four dropped out of college to do it.
2. 02Box's pivot from consumers to enterprises took months of wandering rather than one meeting, and Levie was the last of the four founders convinced.
3. 03Consumers would pay $5 a month and enterprises $5 million a year, which is why Levie calls consumer storage a death pit once Google and Apple bundled it.
4. 04The four founders drove to Yahoo in a failing Nissan minivan hoping for $5–10 million and got a polite rejection email two weeks later.

Ray Dalio: The principles that made me a billionaire

Dalio answers with actual numbers — the 15-streams math, the 5-15% gold allocation, 11.8% a year for 31 years, a bubble gauge at 75% of 1929 — where most principles interviews stay at the aphorism level.

1. 01Dalio called Mexico's 1982 default, was wrong about the fallout, lost his clients' money and borrowed $4,000 from his father after laying off all five employees.
2. 02The holy grail Dalio teaches is roughly 15 good uncorrelated return streams, which by his math strips out about 80% of risk without cutting return.
3. 03Dalio built Bridgewater mechanically: every decision backtested against history, written up as a timeless and universal rule, then programmed into a computer.
4. 04Bridgewater returned roughly 11.8% a year for about 31 years with only around three losing years and no correlation to the stock market.

5 ruthless business lessons from one week in NYC

Transcript available; summary, chapters and takeaways are on their way.

How to find your arbitrage (from the guy who’s done it 3x) ft. Nick Kokonas

A trader turned restaurateur turned software founder walks through the actual mechanics and numbers behind three arbitrages, which is rarer than the usual founder advice.

1. 01Nick Kokonas changed careers about every 10 years: Chicago options trader, then Alinea's owner with chef Grant Achatz, then founder of booking software Tock.
2. 02Nick Kokonas's first big arbitrage was a direct line from a Chicago futures pit to New York ETF traders, skipping a 30-second paper ticket relay.
3. 03Kokonas says the ETF arbitrage made over $100 million in one year and reached a couple percent of American Stock Exchange volume within six months.
4. 04Every arbitrage window closes, Kokonas says: by 2002 trading volumes fell, partners earned far less, and he quit trading after a hard 2001.

We spent 8 hours finding the best stuff on X. Here it is.

It is a fast tour of what founders were arguing about on X this month, with two operators giving blunt verdicts on which ideas hold up as businesses.

1. 01Ben Levy, Shaan Puri's business partner, says he spends about eight hours a day on X and brought his best recent finds to My First Million.
2. 02Congo Brands is Sam Parr's model for creator products: two little-known Ohio operators built Prime with Logan Paul and KSI and own more of it than they do.
3. 03Elon Musk's pledge of one SpaceX share to each of about 72 million American children is worth roughly $10 billion, by Shaan Puri's estimate.
4. 04Pieter Levels now trusts only moats like proprietary data and network effects, and Sam Parr says he would not want to own a software company right now.

This 3-hour Elizabeth Holmes doc broke our brains

It is a spoiler-heavy debrief that turns a much-praised documentary into a live argument about whether Elizabeth Holmes believed her own story.

1. 01Nathan Fielder lived with Elizabeth Holmes for 34 days before she went to prison to make the documentary You Can See Everything.
2. 02Elizabeth Holmes tells Fielder on camera she has never lied, and Shaan Puri faults the film for skipping her trial admission about Pfizer logos.
3. 03Shaan Puri cites a ChatGPT summary saying only 12 of about 300 Theranos small-sample assays ever ran on the company's own machines.
4. 04Billy, Holmes's partner, asked the filmmakers for a share of the upside, pointing to the $100 million Harry and Meghan got for their documentary.

Ex-Amazon VP tells us what it’s really like working with Jeff Bezos

Transcript available; summary, chapters and takeaways are on their way.

$100M hedge fund manager: Do not make the mistake of dying rich

Transcript available; summary, chapters and takeaways are on their way.