We put a multimillionaire’s portfolio into Claude (the results shocked us)
Episode of My First Million · October 19, 2026 · 49 min
Sam Parr and Shaan Puri discuss a low-activity investor's market-beating portfolio, Mark Zuckerberg's AI push, choosing your life's game, and techniques for overcoming panic and fear.
Summary
Sam Parr described meeting a Hampton member who sold his company and has since invested in public stocks, averaging roughly a 21.8% annual return since 2014 versus 13.5% for the S&P 500. After exporting the brokerage account into Claude, they found the investor made only about 2.9 buy or sell decisions per year, including three years with no activity. Parr drew lessons about patience, separating reversible from irreversible decisions, staying within a circle of competence, and writing down ideas and pre-mortems; Shaan Puri added the story of Jack Dorsey's list of reasons Square might fail.
Puri discussed Mark Zuckerberg's recent media appearances, which he called a somewhat premature victory lap, including Zuckerberg's praise of Alexandr Wang after Meta's large investment in Scale AI. Puri contrasted Buffett's avoid-losses approach to investing with entrepreneurship, where he argued only one's biggest wins matter, and relayed Wang's view that talent density and small, flat teams are key in AI. Both hosts observed that highly successful leaders often seek opinions widely, and Puri tied this to the Dunning–Kruger effect.
Parr said an executive coach told him he is overly self-critical, which he linked to constantly comparing himself with extremely successful people. Puri argued that most people never identify the game they are playing in life, citing LeBron James, Jaylen Brown and the book The Score. He also shared an Elon Musk anecdote, a Napoleon quote and Scott Galloway's advice to 'keep your sails up,' recalling how a hike in Boulder helped him and Parr break a downward spiral during their first company.
Parr recounted using the DARE method (dismiss, allow, run towards, engage) to fly without Xanax for the first time in 15 years, on a flight that aborted its landing at Jackson Hole due to brake failure. He described MMA coach Firas Zahabi's method of rehearsing every detail of Georges St-Pierre's fight day and proposed applying it to hard conversations. Puri closed with thoughts on anticipation and how acceptance neutralized his fear when skydiving.
Chapters
- 0:00
Zero action investing
Parr describes a Hampton member whose portfolio beat the S&P 500 while making only 2.9 decisions per year, as analyzed with Claude.
- 4:37
Lessons from great investors
Parr outlines traits of admired investors: few decisions, ignoring reversible choices, circle of competence and written theses.
- 8:19
Pre-mortems and Jack Dorsey
The hosts discuss pre-mortems and Dorsey's list of 140 reasons Square would fail.
- 9:56
Zuckerberg's victory lap
Puri discusses Zuckerberg's recent interviews, his praise of Alexandr Wang, and the contrast between investing and entrepreneurial risk.
- 15:10
What makes Alexandr Wang 'the guy'
Puri relays Wang's strengths and his account of Zuckerberg's crisp writing and habit of soliciting advice widely.
- 18:42
Consensus-seeking leaders and Dunning–Kruger
Parr contrasts secretive leaders like Vanderbilt with those who gather input, and Puri links humility to expertise.
- 21:09
Executive coaching and comparison
Parr shares feedback from his executive coach about self-criticism driven by comparing himself to the ultra-successful.
- 21:59
Identify the game you're playing
Puri argues most people never define their life's game, using NBA examples and the book The Score.
- 29:13
Motion over direction
Puri tells an Elon Musk anecdote, a Napoleon quote and Scott Galloway's 'keep your sails up' advice.
- 32:10
Breaking a downward spiral
Puri recalls how a hike in Boulder changed the hosts' mindset during their struggling first company.
- 34:43
The DARE method for panic attacks
Parr describes using DARE to fly without medication, including an aborted landing at Jackson Hole.
- 40:36
Rehearsing the scariest moments
Parr explains Firas Zahabi's fight-day simulations for Georges St-Pierre and applying them to hard conversations.
- 43:25
Anticipation, acceptance and skydiving
Puri discusses how anticipation shapes experience and how acceptance reduced his fear while skydiving.
Key points
What was said, by whom, with the exact words. Timestamps jump to the moment.
- Sam Parr
Parr reports that the investor he met has earned nearly 22% annually over the past decade.
“he's had nearly a 22% annual return for the last decade, which is amazing”
- Sam Parr
Parr says analysis in Claude showed the investor averaged just 2.9 buy or sell decisions per year.
“But what was interesting is that he only made 2.9 decisions a year”
- Sam Parr
Parr admits that he and Puri tend to confuse activity with progress despite preaching patience.
“We move a lot and we oftentimes mistake movement with progress”
- Sam Parr
Parr recommends sorting decisions by reversibility and not agonizing over reversible ones.
“you determine what decision is reversible and which isn't. And for the ones that are reversible, don't sweat over them”
Linked moment · 9:24Skip to 9:24 using a listen link in the info box.
Shaan PuriPuri says Jack Dorsey wrote a pre-mortem listing 140 reasons Square would fail before starting it.
“he created a list called 140 Reasons Why Square Will Fail”
- Shaan Puri
Puri considers Zuckerberg's AI victory lap premature because AI leadership shifts roughly every six months.
“Honestly, a little premature because like AI changes every, the leader changes every, you know, six months”
Listen from 10:41 · Meta Platforms artificial intelligence strategy
- Shaan Puri
Puri argues that unlike investing, entrepreneurship tolerates many mistakes as long as one's successes are large enough.
“Whereas entrepreneurship is the opposite. You can make tons of mistakes as long as When you do get something right”
- Shaan Puri
Puri relays that Alexandr Wang believed small, high-talent-density teams were key for Meta to win in AI.
“talent density was one of the most important factors in victory in AI”
- Sam Parr
Parr says highly successful people frequently ask others' opinions, which he views as a leadership superpower.
“I could tell that they're gathering information and I have found that to be like a superpower amongst a lot of leaders”
- Sam Parr
Parr discloses that he hired an executive coach and has done several sessions plus an assessment.
“I signed up for an executive coach, and I've done three or four sessions with him, plus this assessment”
- Shaan Puri
Puri argues that most people are not aware of what game they are playing in life.
“I don't think most people even are aware of what game they're playing in life”
- Shaan Puri
Puri summarizes The Score's thesis that the game one chooses defines one's goals and required identity.
“the game decides what you want and who you need to be to get it”
- Shaan Puri
Puri shares his father's advice that motion matters more than direction under uncertainty.
“It's about motion, not direction. And once you're in motion, it's a lot easier to figure out direction”
- Shaan Puri
Puri recalls that escaping a slump at their first company required only a change of routine, not strategy.
“And actually to switch it didn't require anything to change in our business. It didn't even require a new strategy. We just changed our routine”
- Sam Parr
Parr says the DARE method let him fly without Xanax for the first time in 15 years.
“I had to go to Jackson Hole the other day and I went sober. It was the first time that I've done that in 15 years”
- Sam Parr
Parr praises Firas Zahabi's approach of replicating fight-day details so the fighter's nervous system adapts in advance.
“they would get down to the very granular details of the fight and replicate it so your nervous system was used to it”
- Shaan Puri
Puri cites research suggesting enjoyment peaks during anticipation rather than the event itself.
“the peak of enjoyment comes in the anticipation lead up to the event, not the event itself”
- Shaan Puri
Puri says accepting that his skydive was inevitable neutralized about half his fear.
“Once I accepted that it is already going to happen, that already like neutralized, I don't know, 50% of the fear”
People
In the conversation
- Sam ParrEntrepreneur, founder of The Hustle and Hampton, co-host of My First Million
- Shaan PuriEntrepreneur and investor, co-host of My First Million, former Twitch executive
Discussed
- Warren BuffettAmerican investor and chairman of Berkshire Hathaway
- Mark ZuckerbergCo-founder of Facebook
- Alexandr WangScale AI founder and Meta chief AI officer
- Jack DorseyTwitter and Square co-founder mentioned as pushed out by investors
- Elon MuskEntrepreneur behind X, xAI and SpaceX, discussed in AI competition
- Georges St-PierreCanadian former UFC welterweight and middleweight champion
- Firas ZahabiCanadian MMA coach of Georges St-Pierre
- Kevin RyanAmerican entrepreneur and investor, founder and CEO of AlleyCorp and former CEO of DoubleClick
- Scott GallowayNYU professor and podcaster
- Charlie MungerAmerican investor quoted by Sam Parr
- Cornelius Vanderbilt19th-century American shipping and railroad magnate
- LeBron JamesLos Angeles Lakers forward cited as a longevity outlier
- Jaylen BrownBoston Celtics guard-forward at the center of the hosts' first-team All-NBA case
- David SenraPodcaster who interviewed Marc Andreessen
Topics
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From the publisher
Investing guide: 35+ money principles from investors/financial operators https://clickhubspot.com/tmgc Episode 873: Shaan Puri ( https://x.com/ShaanVP ) and Sam Parr ( https://x.com/theSamParr ) talk about an investor who makes 2.9 decisions a year, Zuck’s victory lap and what happened when Sam hired an executive coach. — Show Notes: (0:00) Zero Action Investing (7:55) Premortems (10:05) Zuck's Victory Lap (16:50) The Superpower of 100x Leaders (20:45) Sam Hires an Executive Coach (21:35) Identify the Game You're Playing (30:15) Keep Your Sails Up (33:45) Sam Attacks His Panic Attacks (38:55) Role Playing Hard Situations (41:00) How to Prep for the Scariest Moments — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
Summary, chapters and key points were generated from the episode transcript on November 1, 2026. Quotes are checked word for word against the transcript.