I gotta say that I appreciate the honesty and self-reflection. Unlike several others I don’t see this as a “my sucks because I made a lot of money-you should pity me”, but more of a “I made a lot of money and discovered that the pursuit of it didn’t make me a better person — I wonder why” post.
Clayton, I sincerely appreciate the time you spent writing this. And I absolutely LOVE your elevator test. I think I’ve literally read this post 10 times at this point because it resonated with me so much. I definitely appreciate the feedback and hope that we can stay in touch.
Hi Kenan, I run an internet company which I bootstrapped with my co-founder. We’re around the same size as you when you had your exit (5M/year or so)
I have experienced many of the things you’ve written about. Can I ask you a question? Do you talk to people in elevators?
Having been on the receiving end of a lot of unwanted (and unreported) sexual harassment from male colleagues and bosses over the years, I want you to know Dave: it really eats away at your soul. You try to ignore it or make a joke about it. You feel embarrassed and ashamed. What have I done to deserve this? Sometimes your female colleagues say stuff…