When Your "Worst" Trade Teaches You the Best Lesson

I sold Amazon in 2014 because I hated the Fire Phone. Sounds stupid now, right? The stock went on to become a 14-bagger while I was sitting on the sidelines mad about a device that flopped anyway.

Here’s what I got wrong: I was so focused on short-term failures that I missed the founder’s long-term vision. Bezos wasn’t afraid to swing and miss—he tried AWS, Whole Foods, Prime, advertising empire. Some ideas worked, some didn’t. But the willingness to experiment is what separates 14-baggers from mediocre stocks.

Fast forward to today. I own TransMedics (TMDX), and guess what—management just bought an aviation company. My first instinct? “This kills the margins, I’m out.”

But I learned my lesson. I didn’t panic-sell. Instead, I gave the founder-led company room to execute.

Two years later, the stock has tripled from its lows. Transplant revenue up 32%, logistics up 35%, net profit margin at 17%. The aviation unit? Now used in 78% of transplants. The “dumb” acquisition became a competitive moat.

The pattern is clear: founder-led companies with bold ideas often look crazy in year one and genius in year three. The mistake isn’t believing in innovation—it’s expecting it to work immediately.

I’m not selling TMDX. I’m adding to it. Some founders actually know what they’re doing.