I am often asked if experience is helpful? Simple answer is yes. I have worked with thousands of entreprenurs. I have been directly involved in almost 200 startup. But I am still surprized from time to time. I can never tell who is going to succeed but I can tell with great accuracy, who is not. This has served me well as an investor.
First time entreprenur is an even bet. One never knows who will transform and rise to the occasion. A once failed entreprenur is a great bet if he owns his failure. He has twice the fire in his belly, he has something to prove. The failed entreprenurs who blame others for the failures are likely to blame others again. I don’t want to be the one who gets blamed.
First time successful entreprenurs are a poor bet, genrally speaking. They think they have the magic. They don’t sweat the small things any more. They delegate rather than do. They want a much bigger success. They already are living a good life, the success will not transform their life in any meaningful way. Failure will not hurt as much either.