Living at sea full time even surrounded by bright, talented and driven peers comes with many challenges that a start-up probably does not need to deal with (not even addressing the cost issue).
My credentials for saying so: I am a "geek" and a Yachtmaster 200t Ocean Instructor who worked on yachts and sailed across 2 oceans.
On the other hand, using a yacht in a harbour in SF bay, with "crew" on a b1/b2 visa working on startups should be investigated (yet again boats are expensive :P).
I think there may be some merit to your idea about the "live aboard" concept. It might work best someplace like Anacortes, where the boat could be moved across the border to Vancouver for a period of time.
Sailor here as well (out of Morro Bay, CA) and sail offshore regularly on my own boat.
