Failure 1: Worked for a friend's company. As employee #1. I was to have all kinds of freedoms and responsibilities. Sounded really awesome. Failure 2: Was too

Failure 1: Worked for a friend's company. As employee #1. I was to have all kinds of freedoms and responsibilities. Sounded really awesome. Failure 2: Was too conflict-shy to draw firm boundaries, and likewise was he. This friendship of 20 years is no more. (While working for said friend) Failure 3: Offered a hair-raisingly badly thought-out fixed-price bid. Both my friends's mistake and mine. We probably sunk about 5x what we stood to make from it, and then abandoned the project, embarrassing a relative in the process. There's plenty more of course, but these bother me.