Serial Entrepreneurs are favored by everyone because of their experiences and record
A lot of people talk about how important it is to have experienced entrepreneurs who have successful exits to run a startup. I definitely agree. You would not bet money on a guy who’s playing a video game for the first time ever. If he has beaten a similar game before, he has much better odds. After all, everyone of us would be better than ourselves right now 10 years later.
Unproven Entrepreneurs tend to have more drive and work more crazy hours
However, experienced entrepreneurs who have successful exits in the past may also lose their drive compared to the first time they try. After all, they now have a comfortable life and it’s subconsciously it is fine if they lose. First time entrepreneurs don’t have that luxury and have a much stronger drive just because they might be living on their savings. They have to succeed. They are also looking to prove themselves while the successful entrepreneur has already proven himself successful.
Find good mixes of both
I think a good combo would be one founder with successful startups in the past, and another founder who is unproven but has the drive to push everything over his limit. Obviously successful entrepreneurs are difficult to find, so another good combo might be people who have failed 1-2 startups. They have the experience of what works and what doesn’t work, they spend a couple years developing relationships, and they still have the eagerness and drive to push themselves to the limits. The fact that they could fail a few times and get back to it shows their commitment.
If you are a successful entrepreneur who has strong exits in the past, make sure you don’t lose your drive. Always push yourself to the max regardless of how comfortable your backup is like. After all, you are there to make a bigger impact and create a new legacy.