Lots of investors are quite happy to fund an entrepreneur who's run companies in the past. They feel that he knows the grind; he understands what's involved in running a startup , and has the experience and the expertise needed to be a good entrepreneur. This is especially true when he's run a successful startup in the past because success breeds success.
A key question every entrepreneur needs to answer on Day 0 is whether the business being “built to run” or being “built to flip”.