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.

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Some companies execute a 3-5 year plan and then revert to average returns. Others 'win by winning'—their success creates new opportunities and network effects, turning them into decade-long compounders that investors often sell too early.

Contrary to the instinct to sell a big winner, top fund managers often hold onto their best-performing companies. The initial 10x return is a strong signal of a best-in-class product, team, and market, indicating potential for continued exponential growth rather than a peak.

To avoid emotional, performance-chasing mistakes, write down your selling criteria in advance and intentionally exclude recent performance from the list. This forces a focus on more rational reasons, such as a broken investment thesis, manager changes, excessive fees, or shifting personal goals, thereby preventing reactionary decisions based on market noise.

The asymmetrical nature of stock returns, driven by power laws, means a handful of massive winners can more than compensate for numerous losers, even if half your investments fail. This is due to convex compounding, where upside is unlimited but downside is capped at 100%.

The sign of a working diversification strategy is having something in your portfolio that you're unhappy with. Chasing winners by selling the laggard is a common mistake that leads to buying high and selling low. The discomfort of holding an underperformer is proof the strategy is functioning as intended, not that it's failing.

Even for the world's greatest investor, success is a game of outliers. Buffett made the vast majority of his returns on just 10 of 500 stocks. If you remove the top five deals from Berkshire's history, its returns fall to merely average, highlighting the power law effect in investing.

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.

McCullough advocates for a "promiscuous" investment strategy, quickly moving capital to where signals are strongest. He argues that emotional attachment to winning positions, or "bag holding," is the primary way investors lose ground. The goal is to compound returns by avoiding drawdowns, not by marrying a single investment thesis.

Buy businesses at a discount to create a margin of safety, but then hold them for their growth potential. Resist the urge to sell based on price targets, as this creates a "false sense of precision" and can cause you to miss out on compounding.

Suboptimal selling is often driven by fear: a position gets "too big" or you want to lock in gains. A better approach is to only sell when you find a new investment you "love" more. This forces a positive, opportunity-cost framework rather than a negative, fear-based one, letting winners run.