Boris Berenberg
I Regret Selling My Startup
The author reflects on their regret of selling their startup, highlighting the mis-set expectations and personal incompatibility that led to their decision. They emphasize the importance of thinking deeply about the reasons for selling and the potential impact on one's life. The author shares their post-founder life experience, including the loss of identity and the struggle to find a new sense of purpose. They also discuss the lessons learned from the selling process, such as the need for mentorship, understanding motivations, and hiring the right team. Despite their regret, the author continues to work on new ideas and consult with other founders.
Another interesting learning was that I care a lot more about cash flows than wealth. What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. This is surprisingly hard, and amongst other wealthy people and former founders I now know, this is one of the most frequent preoccupations. In fact, one of the categories people are interested in are cash flowing software businesses just like the one I had sold. The best way to think about this is with a trite sports analogy of playing on offense vs defense. When I was the founder of a company I was always on offense working to grow and expand and find new success. Now I am working to defend what I have earned, while struggling with my inability to start something new. (View Highlight)