Creating Startups in Gray Areas (centernetworks.com)

Rule of thumb #6: Find your ideal Co-Founder and partner. I think that increases the chances by far...

I was hoping for something about questionable legality, not just areas that don't already exist.

Especially with Web startups, following Tip 1 (Take Your Time) might mean you're still on the ground floor when a more ambitious someone has secured investment and begun executing despite poor economic conditions. She basically admits this herself in Tip 4 (Wear the Watch).

Ah... as in Grey skies...