Long Lemonade
Betting on insurtech before the crowd
Early conviction

Lemonade was the highest conviction long position I’ve ever had. I discovered the opportunity, dove deep into the fundamentals, and immediately knew how special this company was — especially at the price it was trading at. It was under a $3 billion market cap at the time, and this was a large reason I started being active on X. The opportunity was so compelling that I had to tell people about it.
I generally don’t like telling people about stocks I’m in. I don’t talk about exits, and it creates complications. But Lemonade was so special I made an exception. This was just before Q3 2025 earnings — and after that day, Lemonade never saw a $3 billion market cap again.
When I discovered the opportunity, I went heavy with conviction — shares and LEAPS call options for a long-term position. This is a compounder. A multi-bagger. A long, long-term story. I was able to take profits and realize great gains on the options, but the Lemonade story still has a long way to play out. It’s the stock I’m most long-term bullish on currently.