Any words of wisdom on hiring an outside C.E.O? Cautionary tales?
I don't have any personal experience, but here's an article that's been posted here before:
The Pmarca Guide to Startups, part 9: How to hire a professional CEO
Take your time.
Understand the new CEO's motivations.
Create a new board seat for the CEO: http://www.venturehacks.com/articles/ceo-board-seat
Bring him on board as an Advisor or Director first and see how that works out.
The Jim Cramer book (of all books) Confessions of a Street Addict chronicles his hiring and firing of a few clueless/alcoholic CEOs when he started his web venture.
Why are you hiring an outside CEO? (Note: I'm not trying to second guess you. I just think your story might be valuable to people on this forum.)
Cautionary tale: Fernand Serrat.
Hm, been googling him but not much comes up besides mentions that he was lousy and made a surprise resignation at Linuxcare...
Oops, spelled it wrong: Fernand Sarrat. Try googling with words such as 'lawsuit', and 'sexual harassment'. Also look around for 'Doug Nassaur' (not the object of Sarrat's affections, but hired by him).