I have been thinking about this a lot recently

… I have been thinking about this a lot recently. A former boss and good friend who is incredibly smart and effective in the work place asked why the two of us had never gone the PE route and been more successful. While he is very successful by most standards, he sees people flying private jets all the time who do not appear more skillful, yet have been more successful. As I think on this, I feel I simply was never willing to go all in on the risk required to achieve that level of financial success. I tried co-founding a company once when I was 28 while engaged and importantly, before children. I felt I could take the risk and if I failed, could bounce back. I did fail - company did ok but my I ended up disliking working with my senior partner - and I did bounce back, ending up at GE. After that, I did not feel comfortable taking that level of risk until my children were off to college and no longer dependent on me an I had enough money saved that my wife and I would be ok for a long time. The people I know who have been jet-money financially successful took huge risks. …