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After being fired by client Sandy Gottesman at the start of a lunch, Charley Ellis pivoted and asked for his favorite investment. The answer was Berkshire Hathaway, which Gottesman planned to hold "forever." This single piece of advice led Ellis to invest his firm's contingency fund, yielding a nearly 100-fold return.
Warren Buffett's history, which includes significant misses like IBM and passing on Amazon, proves that a perfect track record isn't necessary for success. The immense, compounding returns from a few great investments can more than compensate for the inevitable mistakes and missed opportunities in a portfolio.
An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.
Past winners of the auction for a charity lunch with Warren Buffett have leveraged the access into career opportunities, such as Ted Welcher, who became a Berkshire investment manager after winning twice. This demonstrates that high-stakes networking can function as a direct, albeit expensive, form of career investment.
Unlike most professions where deep specialization is crucial, legendary investors like Warren Buffett and Charlie Munger have thrived by being generalists. Their success comes from applying broad mental models across various industries, a stark contrast to the specialist approach that dominates other fields.
Greg Abel’s $25 million flat salary at Berkshire Hathaway works because his alignment stems from his significant personal wealth tied to the company's success. Having invested over $100 million of his own money into Berkshire stock, his motivation is intrinsic ownership, avoiding the short-termism often induced by typical performance-based CEO compensation plans.
Over 58 years, Warren Buffett made ~400 investment decisions, but only 12 truly mattered—a 4% hit rate. The crucial insight is not just buying right, but holding these few exceptional businesses for decades, allowing compounding to work its magic.
The insurance-float investment model isn't copied more because it requires a principal's mindset. Agents must constantly explain decisions and get buy-in, constraining independent action. Principals, acting as if it's their own money, can endure the psychological discomfort of being different from the herd.
Buffett strategically used Berkshire's and Coca-Cola's inflated stock prices as currency to acquire Gen Re. This swapped his overvalued equity risk for Gen Re's stable bond portfolio, which acted as a ballast and protected Berkshire during the subsequent market crash. He allowed the deal to be publicly perceived as a mistake, masking its strategic genius.
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.
Warren Buffett's successor, Greg Abel, is investing his entire $15 million salary into Berkshire Hathaway stock. This is a powerful form of "eating your own dog food" that signals ultimate confidence in the company's future to the market, aligning his personal financial success directly with shareholder outcomes.