Among the startup CEOs, there are ONLY two types worth investing in *(because you always back up the Leader, not just the product, or even the team!): 1. someone who did it (succeeded!) before and knows where he/she could have done better and is motivated to do much better, 2. someone who hasn’t done it yet, and is motivated to succeed or die trying. ANY OTHER KIND OF CEO IS A WASTE OF YOUR TERM SHEET.
The question here is, “What are the odds”? And, “What raises the odds?” As you can tell that odds are increase with the numbers of companies you start. Even then, before doing this research I would have thought that an IPO-ed startup CEO would have a more that 50% success rate with her next startup. But no, not so high.