The father of value investing, Benjamin Graham, made the bulk of his net worth from a single stock: Geico. This concentrated, long-term holding of a compounding business directly contradicted his famous principles of broad diversification and selling assets once they reach intrinsic value, highlighting the power of selective flexibility.
Graham adopted philosopher Baruch Spinoza's idea of viewing things "in the aspect of eternity" to teach investors to focus on long-term intrinsic value rather than getting caught up in the market's daily emotional swings, promoting a disciplined, long-term perspective.
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%.
Cramer advises against 100% diversification into index funds. He suggests putting 50% of a portfolio in an S&P 500 fund as a safety net, while using the other 50% to invest in a small number of deeply researched stocks that you have a personal edge or conviction on.
Facing a massive tax bill on his appreciated Coca-Cola stock in the late 90s, Buffett used Berkshire's then-expensive stock as currency to merge with bond-heavy insurer General Re. This move diversified his portfolio into safer assets that rallied when the tech bubble burst, all without incurring taxes from a direct sale.
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.
According to Ken Griffin, legendary investors aren't just right more often. Their key trait is having deep clarity on their specific competitive advantage and the conviction to bet heavily on it. Equally important is the discipline to unemotionally cut losses when wrong and simply move on.
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.
Fisher rejected the common belief that blue-chip stocks are 'conservative.' He argued they are more likely to lose ground to innovative competitors. A truly conservative investment is a well-managed, dynamic enterprise that consistently grows and builds value, as these are the businesses that endure.
The effort to consistently make small, correct short-term trades is immense and error-prone. A better strategy is focusing on finding a few exceptional businesses that compound value at high rates for years, effectively doing the hard work on your behalf.
Contrary to Modern Portfolio Theory, which links higher returns to higher risk (volatility), Buffett's approach demonstrates an inverse relationship at the point of purchase. The greater the discount to a company's intrinsic value, the lower the risk of permanent loss and the higher the potential for returns. Risk and reward are not a trade-off but are both improved by a cheaper price.