During the dot-com bubble, investors who sold at the first sign of a wobble missed massive gains. Analysis shows that even after the crash, buy-and-hold investors were profitable, while those who sold early were not. The worst financial outcome is panic-selling at the bottom of a crash, which locks in losses.

Most turnarounds fail. Instead of investing on the announcement, wait 12-24 months for early evidence in leading KPIs before they hit the bottom line. This improves your odds, as turnarounds that start working rarely revert. The probability gain is worth more than the initial upside you miss.

Gaonkar identifies her biggest error with NVIDIA wasn't selling too early, but failing to re-evaluate and buy back in later. The psychological pain of "sunk cost bias" makes it incredibly difficult to re-enter a position at a higher price, even when the fundamental thesis has improved.

For VCs, the financial impact of passing on a generational company far exceeds the losses from investments that go to zero. Author Eric Reiss emphasizes that investors must be psychologically resilient to these misses, as opportunity cost is the most expensive mistake.

Since it's impossible to know upfront which investments will generate outlier returns, the key isn't picking them but holding them. The biggest mistake is 'cutting your flowers to water your weeds'—selling winners to invest in underperformers. You must 'circle the wagons' around your core assets.

A conservative bias can lead VCs to sell promising assets prematurely, foregoing significant future gains. According to Foresight Capital's Jim Tanenbaum, this mistake has a far greater negative impact on fund performance than investing in companies that fail.

Investors often focus on losses, but the biggest financial mistakes come from selling compounding winners like Costco too early. This happens when short-term IRR calculations, heavily dependent on unpredictable exit multiples, overshadow the long-term value of a great business.

Investors fixate on selecting the right companies, but the real money is made or lost in the decision of when to sell or hold a winning position. The timing of an exit can create a 100x difference in outcomes. Having a disciplined approach to portfolio management and liquidity is more critical to fund performance than the initial investment choice.

Wilson advised against trying to perfectly time the peak of a successful company's dominance. Competition will eventually emerge, but anticipating its impact is futile and often leads to premature selling. He believed you can make a fortune by riding a winner for years before the problems become acute.