An Investor Beat the S&P 500 by Making Just 2.9 Decisions a Year

A Hampton member showed Sam Parr a brokerage account after telling him he had become a public-stock investor following the sale of a company. Parr said the investor had made nearly 22% annually over the period he was describing. What caught his attention was how few trades sat behind that performance.

There are two time spans in the account as the hosts described it. Parr said he and the investor exported the brokerage history and asked Claude to count buys and sells over roughly 12 years. The displayed chart, however, labels the account’s 22 total moves—10 buys and 12 sells—as occurring over 7.5 years. It also shows three years without activity, from 2022 to 2025. The figures describe different periods in the source; they should not be collapsed into a single account-history window.

The chart compares a hypothetical $100 invested in 2014, showing $1,063 for the investor and $457 for the S&P 500. It gives annual returns of 21.8% and 13.5%, respectively, and says the investor beat the market in 11 of 12 years. Puri noted that 2022 was the one year in which he did not. These are the figures displayed and discussed by the hosts.

Parr’s point was less that others should copy the portfolio than that the results challenged his own reflex to stay busy. He and Shaan Puri both talk about patience, Parr said, yet often move quickly and mistake movement for progress. An average of 2.9 decisions a year suggested long intervals of research and waiting—not a stream of trades.

The account was not presented as a search for obscure stocks. To protect the investor’s privacy, Parr described the holdings only in broad terms: among them were a large travel company and a popular clothing company. The investor told him that he studies a few businesses he understands, keeps detailed notes, and waits for a price he finds attractive. In one example, he had studied a company for about six months before Covid. He liked the business but thought it was expensive, so he read annual reports and documented his thinking. When the price became cheap enough, he bought.

That process is more active than “set it and forget it” might suggest. The investor was doing work before the trade; the low decision count described what he did with the account, not how little attention he paid to the companies. Parr’s account of the investor’s method puts the effort in preparation and the restraint in execution.

Parr connected that pattern to a line he attributed to Warren Buffett: “Lethargy bordering on sloth” was the cornerstone of Buffett’s investment style. He also recalled Kevin Ryan saying he gets about one good idea a year. Parr saw a related discipline among people he admires: they do not necessarily generate more ideas or make more decisions; they try to reserve attention for the ones that matter.

That distinction applies to smaller choices, too. Parr said he often agonizes over decisions and suggested asking whether a choice is reversible. If it is, he argued, it usually does not warrant prolonged deliberation. Puri described his own default as not caring about most things unless there is a reason to care. Parr’s default, by contrast, is to treat small mistakes as evidence of larger sloppiness—as if a typo might predict bad business judgment. Their contrast makes restraint less like a universal personality trait than a practice: some people need to stop treating everything as consequential; others need to notice what deserves attention.

Parr also described investors he admires as knowing the limits of their competence and writing down their reasoning. A person can decline an opportunity without deciding it is a bad one; it may simply fall outside what they know how to judge. Writing down the case for and against a decision, or listing how it could fail, makes the reasoning easier to examine later.

Puri offered Jack Dorsey’s preparation before starting Square as an example. As Puri recounted it, Dorsey wrote “140 reasons why Square will fail.” Puri connected the exercise to the idea of identifying where a company might die before committing to its success story. The point, as he put it, was to face possible failure modes rather than leave them unspoken.

That kind of premortem is not a guarantee against failure. Parr’s distinction was between judging a decision by its result and judging it by the quality of its inputs and reasoning. A bad outcome alone does not show that the original decision was bad; the decision has to be considered in light of what was known and how it was made. Writing down the risks gives that later assessment something more concrete to work with.

The hosts also distinguished investing from entrepreneurship. Puri contrasted Buffett’s emphasis on not losing money with a founder’s willingness to make mistakes in pursuit of a much larger win. He invoked the baseball analogy attributed in the discussion to Jeff Bezos: a great hit in baseball can produce at most four runs, while a successful business decision can produce far more. That does not make every risk sensible. It means that, in Puri’s framing, a business can survive mistakes if the potential payoff from getting a major decision right is large enough.

The investor’s restraint and the founder’s risk-taking are not the same strategy. Both, though, depend on knowing what kind of mistake is tolerable. The investor waits for a price that fits his analysis; a founder may accept setbacks in pursuit of an outsize result. In either case, the question is not simply whether to act, but what the decision could cost and what it could make possible.

Parr said an executive coach challenged his description of himself as lazy and not ambitious. The coach thought he seemed ambitious. Parr found the comparison difficult: his work puts him in contact with people at exceptional levels of wealth, influence, or achievement, and beside them he can feel as though he is falling short.

Puri’s response was to ask what game a person is playing. People can compare themselves with someone pursuing a different goal without first naming the difference. Puri used athletes to make the point: one player might be trying to extend a career and cement a legacy; another might be trying to prove himself after leaving a team; another may chiefly want to enjoy the work and earn well while the opportunity lasts. The same profession can contain different ambitions.

The question also changed over time for the two hosts. Puri said that in their twenties they were trying to “make it”—to become successful and make money. In their thirties, his own priorities shifted toward building a family while remaining successful, but without the same relentless grind. The point was not that one game is better than another. It was that pursuing an old definition of success can keep a person working toward an outcome they no longer want in the same way.

Puri used The Score: How to Stop Playing Somebody Else’s Game to describe how a game shapes its players. As he summarized the book’s idea, choosing a game affects both what you want and who you need to become to get it. Charades rewards expressiveness and communication; Mafia calls for deception. The rules define more than the route to winning. They make certain traits useful and others less so.

That helps explain why “I’m trying to build something great” may not settle what a person is pursuing. Parr said that when he asks people where they want to be in five years, some have never worked out what the end state looks like. Puri suggested that someone seeking more success or prominence may be trying to prove something to themselves, but that motive can be uncomfortable to say aloud. If the game remains unnamed, its goal can keep moving.

The practical question is what the person wants the current pursuit to accomplish. Building wealth, proving a capability, making room for family, and enjoying work while it lasts can overlap, but they are not interchangeable. A decision that advances one may make another harder. Naming the game does not require a fixed life plan; it makes the trade-offs in the present more visible.

Parr described using a method from Dare, a book about panic attacks, to fly without the Xanax he had relied on for years. The acronym stands for dismiss, allow, run towards, and engage. He described the practice as treating the anxiety as something he could allow and approach, then redirecting his attention to an activity after it peaked.

He started the exercise the night before a trip, when he was anxious about leaving his children for four nights. At the airport, he imagined the moment the plane door would close and told himself he was ready to feel panic. He said he flew without medication for the first time in 15 years.

The flight became more difficult than he expected. After landing in Jackson Hole, the plane took off again. Parr said he began to worry, then heard the pilot explain that the brakes had failed and that the plane would divert to Salt Lake City. The pilot said they would use reverse thrust and that fire trucks would be waiting. Parr said he remained drug-free through the next 45 minutes, though he did panic somewhat. He described the method as useful in that experience, not as a way to eliminate fear.

He connected it to his claustrophobia, which had kept him from taking the New York subway for years. He said he began working on it through exposure, starting with the shortest subway trip he could find. He also described the idea of being on a cruise ship in the middle of the ocean as intensely frightening. His approach was to try situations rather than wait to feel unafraid.

A story Parr recalled about MMA coach Firas Zahabi and fighter Georges St-Pierre offered another model of preparation. Parr said Zahabi recreated aspects of fight day in training: the meal, UFC gloves and clothing, the opponent’s walkout music, and bright lights around the practice octagon. As Parr told it, St-Pierre did not like fighting or approach it with the eager aggression of someone who wanted to hurt people. Rehearsing the conditions of the fight was a way to get used to them.

Parr applied the same idea to situations such as negotiations, firings, or difficult conversations. He said he had often approached them without practicing the actual experience, even if he had thought about what to say. He wanted to walk through the situation in advance, down to how it would feel to enter the room. Before flights, he had sometimes packed his suitcase or repeated other parts of the routine. It felt silly, he said, but useful.

The point in these examples is not that rehearsal makes a difficult event easy. It gives a person a chance to meet some of its details before the stakes are immediate. Puri added that people can spend more time anticipating an event than experiencing it. He speculated that anticipating a frightening situation might make the real event less novel and therefore less overwhelming. Parr recognized the pattern from races and difficult conversations: the lead-up can be more miserable than the event itself.

Puri’s example was skydiving. He said he was not especially frightened beforehand, but became afraid in the plane when he saw a friend jump and disappear from view. What helped was accepting that he was attached to an instructor who was going out of the plane. Once he stopped bargaining over whether he would do it, he could try to meet the experience rather than resist it. He described acceptance, followed by a willingness to feel the rush, as changing the character of the fear—not removing it.

Not every uncertain situation calls for the same response. The investor’s method was to study and wait until a particular opportunity met his standard. Parr’s account of preparation was about meeting an event already approaching. And Puri’s retelling of a story about Elon Musk pointed to a different problem: what to do when the next direction is not yet clear.

Puri explicitly said he did not know whether the Musk story was true and offered it as a fable if nothing else. In the story, Musk was asked what he would do if Tesla and SpaceX both failed and he lost his money. The reported answer was that he would find the cheapest apartment he could, buy a computer, and begin building something within 24 hours. Puri’s interest was in the idea of starting before knowing exactly what the next thing would be. He connected it to a line attributed to Napoleon: “I act, and the plan emerges from my action.”

Puri also recalled Scott Galloway advising people to “keep your sails up”: remain ready for the wind to return rather than letting a bad stretch determine how you live. He illustrated the idea with a period when the company he and Parr were building was struggling. They slept on an air mattress and hung a garbage bag on a nail instead of using a trash can. Puri said they were letting the company’s problems spill into their living conditions and their attitude toward themselves.

A hike in Boulder did not fix the business or supply a new strategy. Puri said that after he and Parr climbed the Flatirons, they came back with a sense of having completed something difficult. That unrelated win improved their mood and, in his account, helped them generate and believe in better ideas. His examples were modest: clean the room, get a trash can, take the hike, put on a good outfit. They were ways to interrupt what he called a “last play” mentality, in which yesterday’s bad result governs the next attempt.

Waiting, rehearsing, and acting before the plan is complete are different responses, not a single rule. The investor’s patience depended on having studied an opportunity; Parr’s preparation addressed a fear-provoking event he expected to face; the Musk anecdote, which Puri did not claim was verified, concerned restarting after a hypothetical collapse. The common thread is not simply doing less or doing more. It is matching the next move to the uncertainty at hand.