Drawing from Sun Tzu and Charlie Munger, the key to long-term investment success is not brilliance in stock picking, but systematically avoiding common causes of failure. By identifying and steering clear of ruinous risks like excessive debt, leverage, and options, an investor is already in a superior position.

Buffett emphasizes 'controlled greed.' His equally smart partner, Rick Guerin, was impatient and used margin loans. When the market fell nearly 70% in 1973-74, he was forced to sell his Berkshire shares back to Buffett for a pittance, missing out on generational wealth.

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.

Despite the focus on LTCM being 'too big' or 'too leveraged' in 1998, the capital deployed in similar relative-value strategies today is 10 to 100 times larger, suggesting the industry has amplified, not learned from, the systemic risks of scale and leverage.

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.

People justify high-risk strategies by retroactively fitting themselves into a successful subgroup (e.g., 'Yes, most investors fail, but *smart* ones succeed, and I am smart'). This is 'hindsight gerrymandering'—using a trait like 'smartness,' which can only be proven after the fact, to create a biased sample and rationalize the risk.

A skilled investor avoided a winning stock because his Limited Partner (LP) base wouldn't tolerate the potential drawdown. This shows that even with strong conviction, a fund's structure and client base can dictate its investment universe, creating opportunities for those with more patient or permanent capital.

A core discipline from risk arbitrage is to precisely understand and quantify the potential downside before investing. By knowing exactly 'why we're going to lose money' and what that loss looks like, investors can better set probabilities and make more disciplined, unemotional decisions.

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.