Much better the first time than the second.
The first time we sold, I had far exceeded any expectations I had as a founder. First, I barely believed I could be a founder at all. And second, with zero life savings and no “wins” to my name, selling for $50m in 12 months seemed amazing.
Indeed it was. I didn’t work for a year, I made my better half breakfast every day, I was in great shape.
The second time though, I knew. I knew how far the team and I could go. Once you know you can do it, it’s not quite as special. It becomes a business decision, and one with mixed emotions.
