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My First MillionBusiness Tricks We've Learned From Gamblers, Pickup Artists, & Feynman
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Ed Thorp: The Math Prodigy Who Beat Blackjack
Sam introduces Ed Thorp, a poor-born math prodigy turned professor. He explains how Thorp tested card counting at home with distractions, then proved it in Las Vegas with a mob-connected backer's money.
- •Thorp grew up poor and scored at the top of California's standardized tests as a young teen
- •He applied probability theory to blackjack and published a paper on card counting
- •He rehearsed with smoke and shouting friends to simulate a casino
- •A backer named Manny fronted $10,000 and the pair made $11,000 profit in a weekend
- •His book became a hit and casinos came to recognize him, so he wore disguises
Roulette Wearable and the First Quant Hedge Fund
Thorp moves on to roulette, using a small computer and a two-person team, then turns to investing. Sam covers his options-based hedging, the Buffett introduction, and the fund's long run of returns.
- •The roulette setup used small computers with buttons in shoes and an earpiece, described as the world's first wearable
- •After losing early in the market, Thorp learned options and hedging
- •He ignored company fundamentals and treated investing as a math game
- •A professor connected to Buffett introduced them, and Thorp launched one of the first hedge funds
- •He earned roughly 20-25% a year for 30 years and shut the fund down in 2005
The Game, Being Interesting, and Pursuing Hobbies
Sam connects Thorp to The Game and the idea that working on yourself makes you more interesting. He argues that Thorp and Feynman started with silly, rudimentary hobbies that grew over time.
- •Sam and Shaan both read The Game as young men, and Shaan recounts the cube test
- •Sam says being ambitious and passionate about hobbies makes people attractive
- •Sam feels less interesting now because of expectations and social-media distraction
- •Thorp bought a $500 roulette table at auction just to see if the game could be counted
- •Feynman tested simple questions like how dogs smell, starting at basic principles
Jack Smith: Curiosity-Driven Projects After Vungle
Shaan describes their friend Jack Smith, who built Vungle with first-principles thinking. After selling it, Jack followed his curiosity with projects like building an ergonomic chair.
- •Jack challenged the CPM ad model by charging for actions (CPA) instead
- •Vungle's playable mini-game ads worked better than video ads
- •He sold Vungle for roughly $700-750 million at age 29
- •After selling, he researched chairs, bought 52 of them and built his own
- •He answers what he's up to honestly, without a status-driven answer
Shaan's Filter: Do Things Because the Doing Is the Reward
Shaan shares Naval's idea that retirement means doing things for their own sake. He explains how he turned it into a filter for every activity rather than finding one "thing."
- •Naval's quote on the day activity itself becomes the reward
- •Shaan asks whether he's acting for deferred payoff or for enjoyment
- •Applying it to workouts led him to boxing and basketball
- •He says he spent about 35 years on the "this sucks now, pays off later" model
- •He feels more switched on since making the shift
Is Following Your Interests a Privilege?
Sam calls this approach privileged and says most people must grind first. Shaan disagrees, citing his podcast and engineers with side projects, and they discuss what share of successful people took each path.
- •Sam says it requires luck and paying dues, noting a blue-collar worker with three kids has little time
- •Shaan says he'd welcome being called privileged and that wasting freedom is a mistake
- •Shaan started the podcast expecting to lose $10,000 a year
- •Sam guesses 60-70% of wealthy people they know found their path miserable, and about half then pursue real interests
- •Both agree the biggest successes are often interest-driven but the average ones are not
Y Combinator, Pivots, and Playing the Game of Business
Sam argues that YC pushes founders to pivot to whatever works. Shaan counters with Paul Graham's advice to scratch your own itch, and observes that many friends are really drawn to the game of business itself.
- •Sam says 12 weeks pushes founders toward ideas that simply get a win
- •Shaan cites Paul Graham warning against "playing startup"
- •Airbnb and Coinbase came from founders' own lives
- •Sam and Shaan agree the biggest successes are itch-driven but not the average
- •Shaan says Jack and others are passionate about playing the game of business more than any industry
The Roger Bannister Effect: Knowing a Solution Exists
Shaan shares stories showing that merely knowing a breakthrough is possible raises your odds of finding it. This runs from OpenAI's Q* rumors to Kaggle, the four-minute mile and his own marketing channel.
- •The Q* leak led researchers to explore that technique and publish strong results
- •Claude Shannon's brother gave him a vague hint that was enough to solve a puzzle
- •Kaggle teams reproduce a rival's jump without knowing how it was done
- •Several runners broke four minutes soon after Bannister
- •Shaan's team found a channel breakthrough after hearing someone else was winning on it
The MFM Paradox and Newsletter Parallels
Shaan names the effect the MFM paradox: following someone's success helps even without knowing their methods. Sam gives the parallel of Morning Brew and The Hustle, and praises Shaan's additions to the Thorp story.
- •Hearing others' results can inspire you without copying their tactics
- •A friend's goal of making a million dollars in three months sparked Shaan's own ideas
- •Sam and Austin found they had been replicating each other's success in newsletters
- •Sam credits Shaan for tying the episode together
Step Zero: Believing It Can Be Done
Shaan says Thorp's first step was believing the house could be beaten, and shares a Tony Robbins event story about Simon Says. He explains the virtuous cycle of belief driving action and results.
- •Cheesy but true ideas are underrated because smart people dismiss them
- •At the Tony Robbins event, only about 5% of the audience believed they could win Simon Says
- •Most people are not playing the game, and many who play don't believe they can win
- •Belief drives action, action drives results, and results reinforce belief
- •If stuck, he suggests raising your belief by reading about or talking to people who did it
Shaan's Blackjack Misadventures and the Lesson on Leverage
Shaan tells how he and friends tried card counting on a South Carolina riverboat, then ran an underground blackjack game. He explains the plans failed, ending with the lesson that leverage matters more than an edge.
- •Trevor counted, Shaan signaled and Dan played the drunk "whale"
- •Dan missed the signals and bet $1,000 at a bad count, wiping the team out in two hands
- •They then tried to be the house, but a friend threatened to call the cops to get his $800 back
- •Shaan concluded leverage is more important than an edge
- •He says modern casinos use six decks and auto shufflers, which remove the edge
Publisher timestamps
- 0:00Ed Thorp and the mathematics of gambling
- 7:51World's first hedge fund
- 12:12Sam and Shaan revisit “The Game”
- 16:06The Feynman technique for learning
- 21:14Shaan's one criteria for action
- 24:58Why you don't need privilege to start
- 29:06Playing "the game" of business
- 33:37Switching to better games
- 36:15How the Roger Bannister Effect crushes limiting beliefs
- 40:13Step 0: Believe it can be done