Investors who wait for the perfect entry point are fighting a losing battle. Analysis of the Dow shows a 97% probability that any given purchase day will be followed by a future day with a lower closing price. This statistical certainty of seeing red post-purchase paralyzes investors and reinforces the value of systematic, unemotional investing.
The "Liking-Loving Tendency" causes investors to identify personally with their holdings. They ignore faults, favor associated things, and distort facts to maintain positive feelings. This emotional attachment leads them to rationalize bad news and hold deteriorating assets for too long, destroying capital.
The market is a 'Player vs. Player vs. Environment' game where retail investors play against pros trying to take their money (PvP) amid unpredictable global events (PvE). The only reliable winning strategy for the average person is to refuse to play the short-term PvP game and instead invest long-term.
Post-mortems of bad investments reveal the cause is never a calculation error but always a psychological bias or emotional trap. Sequoia catalogs ~40 of these, including failing to separate the emotional 'thrill of the chase' from the clinical, objective assessment required for sound decision-making.
Top tennis players like Rafael Nadal win only ~55% of total points but triumph by winning the *important* ones. This analogy illustrates that successful investing isn't about being right every time. It's about consistently tilting small odds in your favor across many bets, like a casino, to ensure long-term success.
Every investment decision feels uniquely difficult in the present moment due to prevailing uncertainties. This mental model reminds investors that what seems obvious in hindsight (like buying in 2009) was fraught with risk at the time, helping to counter behavioral biases and the illusion of past clarity.
Conventional definitions of risk, like volatility, are flawed. True risk is an event you did not anticipate that forces you to abandon your strategy at a bad time. Foreseeable events, like a 50% market crash, are not risks but rather expected parts of the market cycle that a robust strategy should be built to withstand.
Even if an investor had perfect foresight to buy only at market bottoms, they would likely underperform someone who simply invests the same amount every month. The reason is that the 'market timer' holds cash for extended periods while waiting for a dip, missing out on the market's general upward trend, which often makes new bottoms higher than previous entry points.
Warren Buffett's early partner, Rick Gurren, was as skilled as Buffett and Munger but wanted to get rich faster. He used leverage, got wiped out in a market downturn, and missed decades of compounding. This illustrates that patience and temperament are more critical components of long-term success than raw investing intellect.
Timing is more critical than talent. An investor who beat the market by 5% annually from 1960-1980 made less than an investor who underperformed by 5% from 1980-2000. This illustrates how the macro environment and the starting point of an investment journey can have a far greater impact on absolute returns than individual stock-picking skill.
The stock market is like a casino rigged for savvy players. Instead of trying to beat them at individual games (stock picking), the average investor should "bet on the game itself" by consistently investing in broad market index funds. This long-term strategy of owning the whole "casino" effectively guarantees a win.