01/20/2026
Everyone assumes I sold Commercial Defeasance in 2006 because I saw the crash coming. I wish I could say I predicted the whole thing, but that’s not what happened.
When you’re a first-time entrepreneur, your entire net worth is tied up in one business. That’s a terrifying position to be in, especially when you’re watching the kind of growth we had. We went from doing three or four defeasance transactions in our first year to doing thousands annually. That trajectory doesn’t last forever, and I knew it.
The decision to sell wasn’t about being brilliant or seeing around corners. It was about being realistic. When an offer arose that let me take some chips off the table, I took it. That’s not market timing genius, that’s just understanding that concentrating all your wealth in one asset is how you lose everything when conditions change.
Looking back, the timing worked out incredibly well. But in the moment, I was just trying to make a smart decision about risk management. Sometimes the choice of diversifying and reducing exposure is the one that saves you.
