Low-Frequency Investing: The 2.9-Decision Portfolio

A man at a gathering for entrepreneurs called Hampton once told one of the hosts of this show that he sold his company for eight figures and now invests for a living. Curious, the host asked to see the brokerage account on the spot (00:57). What came back, once the twelve years of trades were fed into the AI assistant Claude, was not a story about picking winners. It was a story about almost never picking anything at all.

The investor had owned around fifteen stocks over a decade, give or take five. But across those twelve years he made an average of just 2.9 decisions annually, where a decision means a single stock bought or sold (01:14). In three of those years he made zero trades. His busiest year, six. The result: a 21.8% average annual return against 13.5% for the S&P 500, and he beat the market in eleven of eleven years, losing only in 2022 (01:59). Run the arithmetic forward and ten million dollars invested at the start would have grown to roughly sixty million (02:27).

"He only made 2.9 decisions a year. And we put together this cool graph, and there were some years, I believe, three out of the last ten years, he made zero decisions." — Sam Parr [01:39]

Asked how he actually spends his time, the investor said he studies a few companies he can truly understand, keeps detailed notes, and waits. He researched one company for about six months before COVID, decided he liked it but thought it was priced too high, and kept writing notes until the market made it cheap. Then he bought it that same day (04:02). Warren Buffett has described his own approach in similar terms: lethargy bordering on sloth (05:10). The common thread among people who are good at this, the hosts argue, is that they know their circle of competence, meaning the narrow set of things they genuinely understand, and they decline everything outside it without treating the refusal as a verdict on the opportunity itself (07:55).

The other habit worth borrowing is the pre-mortem: writing down, before starting anything, every way it could fail. Jack Dorsey, who helped create Twitter, reportedly wrote a list titled "140 Reasons Why Square Will Fail" before launching the payments company Square, specifically to avoid getting high on his own reputation (09:16). The point of a pre-mortem is not to retreat from the risks. It is to build something that can survive them.

Judged by the Wins, Not the Losses

Investing punishes mistakes. Entrepreneurship, at its upper reaches, barely counts them. Discussing Mark Zuckerberg's recent media tour, in which Meta's founder has been candid about the roughly sixty billion dollars spent on the VR push once called the metaverse, about ten times what was spent developing the original iPhone, with little to show for it in adoption (13:32), one host pointed to Zuckerberg's own explanation of how he thinks about failure.

"You don't get judged by your mistakes. You're only judged by the things you got right, and how right you got them when you got them right." — Shaan Puri, recounting Mark Zuckerberg [13:55]

That logic explains Zuckerberg's pursuit of Alex Wang, the young founder of Scale AI, a data-labeling company that AI labs rely on to train their models, which Meta valued at around fourteen billion dollars before buying a large stake and bringing Wang aboard (15:25). Zuckerberg's stated reasoning was not that Wang is the smartest person in any room. It was Wang's strategic clarity and his conviction that winning in AI requires talent density: a small team of twenty to two hundred elite people who can hold the whole problem in their heads, rather than two thousand merely smart ones spread thin (16:05).

There is a psychological wrinkle here worth naming. The Dunning-Kruger effect describes how confidence about a subject often peaks early, right after someone learns just enough to feel capable, and then dips as real expertise reveals how much remains unknown (19:46). The most accomplished people the hosts have met tend to undersell their own competence and over-ask for other people's opinions, which looks like humility but functions as information-gathering.

That same conversation turned to a simpler question: what game is a person actually playing. Most people, even driven and successful ones, have never named it (22:55). The book The Score argues that the game chosen decides what someone wants and who they have to become to get it: charades rewards expressiveness, a lying game like Mafia rewards deception, and the same logic quietly reshapes a career (26:14).

Rehearsing the Thing You Fear

A story, possibly embellished, about Elon Musk circulated at a dinner where he was asked what he would do if both Tesla and SpaceX failed and he lost every dollar. His answer: move into the cheapest apartment he could find, buy a computer, and start building something new within twenty-four hours, not a week later (29:50). He reportedly said the loss of money would not bother him, but he would allow himself exactly one night of devastation over losing the companies before returning to work (29:31).

"The thing finds you. You just have to be building when it arrives." — Shaan Puri, recounting Elon Musk's view [30:08]

Napoleon Bonaparte, asked for his next plan, reportedly answered that he acts, and the plan emerges from the action (31:06). The through-line from investing patience to entrepreneurial motion is the same discipline aimed in opposite directions: know when to sit still, and know when stillness is just fear wearing the costume of caution.

Fear itself gets the most concrete treatment of the episode. One host described using a book called Dare, which lays out a four-step method for panic: dismiss the thought that panic matters, allow it to come, run toward it by wanting it to arrive faster, and then engage with something else once it peaks (35:48). He tested it on a flight to Jackson Hole and stayed off the anti-anxiety medication he had relied on for fifteen years, a test made considerably harder when the plane landed, then took off again after the brakes failed and had to divert to Salt Lake City (38:52).

MMA coach Firas Zahabi used a related idea to prepare the fighter Georges St-Pierre, who by his own coach's account did not relish fighting and felt real fear before bouts. Months out from a fight, Zahabi had St-Pierre eat the same pre-fight meal, wear the actual UFC gloves and outfit, train under the same bright lights, and listen to the opponent's walkout music, so his nervous system had already lived through fight day by the time it arrived (42:04). The same principle, one host noted, applies to a hard conversation or a firing: rehearsing the scene in detail beforehand blunts its power.

There is a related finding about anticipation itself: the peak of enjoyment, and apparently also the peak of dread, often sits in the buildup rather than the event (43:48). Heavy anticipation of something exciting tends to make the real thing a letdown, while heavy anticipation of something scary can make the real thing feel almost dull by comparison, because the nervous system has already spent its charge.

The clearest illustration came from skydiving. One host said he was not especially afraid going in, until the plane climbed above the clouds and a friend jumped first and vanished. What dissolved the fear was not bravery.

"The antidote to the fear was not really, like, bravery... It was just acceptance." — Shaan Puri [45:35]

He was hooked to an instructor who was also leaving the plane, which meant the jump was no longer a decision. It was simply already happening. Accepting that, he said, neutralized roughly half the fear on the spot, leaving something closer to excitement than terror. It is the same move, scaled down, as waiting four months to buy one stock, or writing a hundred and forty reasons a company might die before building it anyway: stop negotiating with the moment, and just meet it.