He had better insight into the legal issues than we (or any of the lawyers we talked to) did.
I still think it failed primarily because the economics changed under our feet (prices went from $2-3k to $20-30 within 2 years), and because we didn't raise enough money. The team could have been a bit better (and would be, today; I was like 20 years old back when we did this, and none of us had done a traditional startup before), but the brick wall we were up against on pricing and financing was pretty much a deal killer.
I don't think any of this is strong evidence against a similar effort working today (not an offshore platform for hosting, but cryptographic systems, or offshore for HR/visa compliance, or just for cost advantages).
The basic strategy of trying to push only a single challenge (technical or legal or whatever) vs. trying to innovate on everything at once, is valid.