First, senior leaders often have much of their emotional equity invested in the past. The average age of an S&P 500 CEO is currently fifty-eight, up three years since 2008. Average tenure is eleven years, the longest since 2002. While veteran leaders may have the benefit of experience, they’re weighed down by legacy beliefs. Many of their assumptions about customers, technology, and the competitive environment were forged years or decades earlier, and reflect a world that no longer exists.

It is one of the big benefits of being a private company. When I first bought these lands from major oil companies, they were looking ahead one quarter or one year. They wanted to get the assets ‘off their books’ to make their financial ratios look better. We can do more with these businesses because we don’t suffer the crazy pressures that are put on a public company.

By contrast, the problems affecting General Motors in 2008 were created by decades of entropy combined with inertia due to embedded obsolete routines, frozen culture, and chain-link systems. Bankruptcy may not be enough to fix this difficult situation. I expect to see the company fragment further and sell off valuable brand names over the next decade.

The business magazine Fortune published a list of the largest 500 US corporations in 1955 and has continued to do so annually ever since. The subsequent fate of the initial top ten provides a powerful rejoinder to the claim that large businesses acquire a scale that leaves them masters of their environment.

In 2020 the Fortune 500 looks very different. Fortune now includes service businesses, so the two top companies by sales are retailers – as would also have been true in 1955. But the current leaders are retailers that did not exist in 1955: Walmart and Amazon. No fewer than four companies are names that probably mean little to non-US readers – they are intermediaries in the fabulously costly US healthcare system. United Health is an insurer, McKesson and Cencora (previously known as AmerisourceBergen) are distributors of pharmaceutical products and CVS Health is both insurer and retailer.