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My First MillionHow he beat the S&P 500 for 11 years doing (almost) nothing
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CHAPTERS
- 0:00 – 2:44
“Zero Action” investing: outperforming with ~3 trades per year
Sam describes meeting a retired founder who invests in public stocks and has averaged roughly 22% annual returns over about a decade while making very few buy/sell decisions. He and Shaan react to how unusual it is to beat the market while doing almost nothing, including multi‑year stretches with zero trades.
- •Sam recounts reviewing the investor’s brokerage account after meeting him in Hampton
- •They used Claude to estimate how many buy/sell “decisions” he made per year
- •The investor averaged about 2.9 decisions per year, with some years at zero and a max around six
- •Shaan reads the comparison showing his returns vs. the S&P 500 and notes he beat it most years
- •Sam highlights the contrast between “movement” and real progress, calling it “Zero Action”
- 2:44 – 4:20
What he actually does day-to-day: deep research, detailed notes, then waiting
Shaan presses on whether the investor is truly passive or actively researching. Sam shares the investor’s explanation: he studies a small set of understandable businesses deeply, documents his thinking, and waits for pricing/opportunity windows before acting quickly.
- •Shaan asks what kinds of stocks the investor owned; Sam gives broad categories without naming specifics
- •Shaan asks whether the investor is “set it and forget it” or researching constantly
- •Sam reads the investor’s text: deep study of a few things he understands, with detailed notes
- •The investor watched a company for months, felt it was expensive, then bought when it became cheap enough
- •The “waiting” period is the strategy: long preparation followed by a decisive move
- 4:20 – 7:46
Patterns Sam sees in great decision-makers: few big decisions, don’t sweat reversible ones
Sam connects the story to other high performers they’ve interviewed or met, saying many make surprisingly few major decisions. He also describes a framework: distinguish reversible decisions from irreversible ones and stop agonizing over the reversible category.
- •Sam says investing is appealing to analyze because decisions and outcomes are clearer than in startups
- •He quotes Warren Buffett’s idea of “lethargy bordering on sloth” as a cornerstone
- •Sam recalls Kevin Ryan saying he gets roughly one good idea a year
- •Sam says admired people make few decisions but avoid overthinking small ones
- •Sam proposes sorting decisions into reversible vs. irreversible to reduce needless stress
- 7:46 – 10:11
Premortems, journaling, and avoiding “resulting”
Sam adds more common traits he’s noticed: knowing one’s circle of competence and writing things down. He introduces premortems and explains the importance of judging decisions by the quality of inputs rather than outcomes alone.
- •Sam describes “circle of competence” as a reason to say no even to good-looking opportunities
- •He notes disciplined people turn down things simply because they don’t understand the industry
- •Sam explains premortems: writing down everything that could go wrong in advance
- •He warns against “resulting” (calling a decision bad only because the outcome was bad)
- •He lists journaling and writing arguments to oneself as recurring habits among thoughtful decision-makers
- 10:11 – 14:53
Jack Dorsey’s failure list and Zuckerberg’s “victory lap” mindset
Shaan shares a story about Jack Dorsey writing a long list of reasons Square could fail to stay grounded. The conversation pivots to Mark Zuckerberg, with Shaan describing Zuckerberg’s recent public confidence and a philosophy of being judged by big wins rather than mistakes.
- •Shaan tells the story of Jack Dorsey writing “140 Reasons Why Square Will Fail” and sharing it
- •He relates premortems to “avoid the elephant in the room” and design around failure modes
- •Shaan says Zuckerberg has been doing lots of press and seems to be on a “victory lap”
- •He describes Zuckerberg’s public persona shifts (including dropping profanity in interviews)
- •Shaan contrasts investing’s “don’t lose money” framing with entrepreneurship’s tolerance for mistakes if the wins are huge
- 14:53 – 20:51
Why Zuckerberg picked Alex Wang: strategy, communication, execution, talent density
Sam challenges whether Alex Wang is being described as a great operator/leader or merely a technical contributor. Shaan clarifies what Zuckerberg praised: strategic thinking, clear communication, and strong execution beliefs—especially around keeping teams small and flat to maximize talent density.
- •Sam questions how to reconcile leading a very large company with being “the smartest in the room”
- •Shaan lists the attributes he says Zuckerberg credited: strategic mind, clarifying communication, execution strength
- •Shaan recounts a specific view: small, elite teams can outperform large groups in certain contexts
- •He describes the organizational preference for a tight, flat structure with fewer voices
- •Sam summarizes the point as leadership ability rather than doing all the work personally
- 20:51 – 21:36
Leaders seeking input: crisp writing, humility, and constant “high-signal” feedback loops
Shaan describes how Zuckerberg solicits perspectives informally and frequently, and how his communication style stands out. Sam generalizes that many highly successful leaders actively gather opinions—even from people who feel “less qualified”—as a kind of superpower.
- •Shaan recounts Alex Wang saying Zuckerberg sends long, thorough WhatsApp replies quickly
- •He says Zuckerberg regularly asks many smart people what Meta may be getting wrong, outside formal meetings
- •Shaan suggests Zuckerberg uses these exchanges both for insight and to assess others’ signal quality
- •Sam contrasts secretive, opaque decision-making with more consensus-driven styles
- •Sam says it’s common for top performers to ask for input, even when the other person feels less accomplished
- 21:36 – 22:37
Comparison and self-judgment: hiring a coach and defining “the game you’re playing”
Sam describes hiring an executive coach and feeling overly self-critical from constant exposure to extreme outliers. Shaan offers his coping frame: stop comparing across incompatible goals by getting clear on which “game” you’re actually playing.
- •Sam says being around world-class people makes him judge himself harshly
- •He recounts the coach telling him he’s more ambitious than he claims
- •Shaan says comparison is hard but manageable if you define your own game
- •He argues many people can’t articulate where they’re trying to be in five years
- •Sam agrees that even driven, successful people often lack a clear end-state they’re aiming for
- 22:37 – 30:16
How “games” shape identity: NBA examples and the book concept Shaan references
Shaan develops the “game” metaphor with sports examples, describing different players pursuing different aims. He explains a framework of intention and obstacle, and shares a book idea: choosing a game determines what you want and who you must become to win.
- •Shaan gives examples of different “games” athletes might be playing (legacy, proving oneself, earning a contract)
- •He frames stories as intention plus obstacle and applies it to life stages
- •He reflects on how their own “game” shifted from ‘trying to make it’ to a different set of priorities later
- •Shaan says people can become defensive or confused when asked directly what game they’re playing
- •He describes a book idea: the game you pick reshapes your behaviors and even personality
- 30:16 – 31:25
“Keep your sails up”: quotes about action, momentum, and staying ready
Shaan shares an Elon Musk fable about rebuilding immediately after total failure, then ties it to other action-first quotes. He recalls Scott Galloway’s “keep your sails up” metaphor—staying ready for opportunity even when things are going badly.
- •Shaan tells a story where Musk would start building again within 24 hours after losing everything
- •He connects it to a Napoleon quote about acting first and having the plan emerge from action
- •Shaan recounts Scott Galloway’s line about keeping your sails up to catch the wind when it comes
- •He acknowledges “motivation corner” can feel cheesy but still useful
- •Sam and Shaan discuss when motivation is most helpful (early striving and later meaning-making)
- 31:25 – 33:46
Turning a slump around with small wins: routines, environment, and momentum
Shaan shares a low point from an early company era and how their living situation mirrored their business stress. He explains how changing routines—getting small unrelated wins—improved attitude, creativity, and productivity without changing the business strategy first.
- •Shaan describes a period of hardship and letting business problems degrade daily life
- •He says they lacked a “next play” mentality and carried yesterday’s losses into today
- •A simple reset (like taking a hike) created an immediate psychological lift
- •He emphasizes stacking small “life wins” (cleaning up, routines, basic improvements) to regain momentum
- •Sam agrees small, seemingly silly changes can create outsized impacts
- 33:46 – 38:47
Sam’s panic/claustrophobia breakthrough: the DARE method and a real flight test
Sam explains his long-running fear of flying and how a book changed his approach to panic. He walks through using the DARE framework to invite and confront panic—then stress-tests it during an unexpectedly tense flight situation.
- •Sam says he used Xanax for flights for years and recently attempted a drug-free flight
- •He outlines the DARE steps: dismiss, allow, run towards, engage
- •Sam describes deliberately building excitement for the panic moment at the airport and on the plane
- •He recounts a mid-landing surprise: taking off again due to brake issues and diverting with firetrucks waiting
- •Sam says the approach worked “night and day,” even under the heightened scenario
- 38:47 – 41:39
Training for scary moments: exposure, rehearsals, and replicating fight-day conditions
Sam connects fear management to how elite fighters prepare, describing a coaching approach that simulates every detail of the real event. He applies the idea to business situations like difficult conversations, arguing that rehearsing the full “walkthrough” can reduce nervous-system shock.
- •Sam says his panic is driven by claustrophobia and describes small exposure steps (like short subway rides)
- •He discusses how MMA coaches study fear because fighters face extreme stress in public
- •Sam recounts a method: months ahead, simulate fight-day meals, gloves, outfit, walkout music, and lighting
- •He says replicating granular details helps the nervous system get used to the experience
- •He proposes using similar rehearsals for negotiations, firings, and other high-stakes conversations
- 41:39 – 46:08
Anticipation vs reality: using acceptance to blunt fear (and why it helps)
Shaan reflects on how anticipation can exceed the actual experience, causing either disappointment or dread amplification. He shares how acceptance helped him with skydiving fear, and he and Sam connect this to why rehearsing feared events can make the real moment feel less intense.
- •Shaan notes research suggesting enjoyment often peaks in anticipation, not during the event
- •Sam relates this to purchases: the research phase can feel better than owning the item
- •Shaan suggests anticipation can be used strategically: rehearsal makes feared events feel less novel and intense
- •He tells a skydiving story where acceptance (“it’s happening”) reduced fear substantially
- •They close by reiterating DARE’s steps and joking about how it could be framed like an old PSA-style commercial
