[btilly]

Probably no.

The idea behind a deal like this is you get money now based on the valuation, and then when you're in a position to sell, you pay back on the valuation then. Which money you presumably have because you sell the actual stock you receive.

However there are a lot of ways this can go south. For a realistic instance Chartboost goes public, he gets hit with AMT taxes, and then finds out that as an insider he's not allowed to actually sell the stock for 6 months. He now has to cover both the current valuation and a tax burden he never knew about, but has no actual money.

I could multiply scenarios here. But the lesson is don't do this unless you have good legal advice. And the Wall St guy just wants to do the deal, carefully protecting the person providing shares is not a priority.