A vicious cycle beats a virtuous one: How Warren Buffett’s Geico fell behind Progressive in the auto insurance race

Warren Buffett’s failure to capitalize on the economy’s digital shift over the last two decades has hurt his otherwise enviable track record as an investor. His blind spot regarding tech didn’t stop at the stock market: It bled into how he ran Berkshire Hathaway’s operating companies as well. Across many of his wholly owned businesses, Buffett neglected technological upgrades, and Berkshire’s business value has suffered as a result.

It’s important to understand this because the majority...