Buffett in the age of mania: Lessons from 1995-1999 letters

There is a certain kind of investing advice that sounds smart—until you try to follow it. "Buy great businesses." "Don't overpay." "Think long term." All true. But what does any of that actually mean when you are staring at a frothy market surrounded by hype, and your broker is begging for attention? That is why I keep returning to Buffett's letters from the late 1990s. These were the years when the world was losing its mind over dot-com stocks and the Nasdaq was making millionaires out of college kids. But Buffett? He stuck to the basics. He didn't just repeat the old lines—he explained what they meant, why they mattered, and when they broke down. From the brutal truth about retail business to why most M&A deals are just ego wrapped in spreadsheets to how insurance becomes a money-printing machine if you do it right—his letters from 1995 to 1999 are a masterclass in staying sane when the market goes manic. This is our attempt to decode them, one idea at a time. To read our take on his earlier letters, follow this story series. Retail traps Back when I was in college, there was this bookstore chain that everyone in town loved. They had beanbags, free coffee, and a cool vibe that made you feel more cultured just by stepping inside. The place was packed. Then, one day, it was not. The chain went bust in a few years. I thought of that store when I read Buffett's 1995 letter. "Retailing is a tough business," he wrote. Not just tough—brutal. Even the best-run retailers, the ones posting glowing ROEs and steady same-store growth, can cra

This article was originally published on April 11, 2025.