The Lesson That Cost Me a Fortune (But Made Me Rich)

Here’s the brutal truth: my biggest investment mistake turned into my best teacher.

Back in 2014, I dumped Amazon stock right before it became a 14-bagger. Why? Because I hated the Fire Phone. I was so cocky after tripling my money that I thought I knew better than Jeff Bezos. Spoiler: I didn’t.

The real lesson? Founder-led companies earn the right to fail. Bezos went all-in on that doomed phone, but it didn’t stop him from building AWS, Whole Foods integration, Prime, and an ad empire. One bad swing doesn’t end the game.

I applied this lesson to my current core holding: TransMedics (TMDX)—a medical device company that keeps donor organs viable during transport. When management announced an aviation acquisition in 2023, the market panicked. Stock got cut in half. My initial gut? Disaster.

But I didn’t sell. I gave the founder-CEO time to execute.

Fast forward two years: stock tripled from the lows. Transplant revenue up 32%, logistics up 35%, net margins hit 17%. The aviation unit now handles 78% of transplants in their program. Turns out the logistics network was the play all along.

TransMedics is aiming for 10,000+ transplants (vs current levels) plus kidney markets and international expansion. Yeah, there are real risks—new product categories, execution questions, margin concerns.

But here’s the thing: I’m not selling this founder’s next swing. The Fire Phone taught me that lesson too well. Sometimes the best returns come to investors patient enough to let visionaries fail their way to victory.

Warren Buffett said it best: “It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes.” I learned from both.