During due diligence, it's crucial to look beyond returns. Top allocators analyze a manager's decision-making process, not just the outcome. They penalize managers who were “right for the wrong reasons” (luck) and give credit to those who were “wrong for the right reasons” (good process, bad luck).

In a world of highly skilled money managers, absolute skill becomes table stakes and luck plays a larger role in outcomes. According to Michael Mauboussin's "paradox of skill," an allocator's job is to identify managers whose *relative* skill—a specific, durable edge—still dominates results.

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.

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.

In contrast to "Raiders" who sell for a quick 20% gain, the most successful "Connoisseurs" achieve outsized returns by letting their winners run. This long-term conviction, while seemingly boring, is where the majority of wealth is created in a portfolio.

Data over the last decade shows that 97% of professional stock pickers, despite their resources, fail to beat a basic market index. Ambitious individuals often fall into the trap of thinking they're the exception. The most reliable path to market wealth is patient, consistent investing in low-cost index funds.

Successful investing isn't about being right all the time; it's about making your wins exponentially larger than your losses. Top investors like Paul Tudor Jones only enter trades where the potential reward is at least five times the risk, allowing them to be wrong often and still profit.

Even sophisticated institutional investors exhibit significant behavioral biases. Research on their trades revealed that while their buying decisions added value, their selling decisions were so poor that a random selling strategy would have outperformed their actual sales by 100-200 basis points. They seem to apply discipline to buying but not selling.

The key to success is high-volume decision-making with a slight edge, not perfection. Like a casino, being right just over half the time on decisions with measurable outcomes guarantees long-term success. This mindset encourages action over analysis paralysis and accepts failure as part of the process.