Hi,
Just wondering if anybody else thought about it already. We all know how hard it is to build a team until you're financed enough to be able to pay wages; even if you get a person on board, it is hard to estimate their actual commitment vs. what they promised and what their stake should be. Then, if that person quits for any reason before their stock is fully vested, it is another legal burden to manage.
What if instead of offering a stock compensation off the bat the company would issue convertible notes in a lieu of wages, with the cash value equal to the what that person would have been paid if there was cash in the company? Then, if that person quits before funding, the company still owes that person so if the company is getting liquidated or financed (or sold) the person would either get paid (w/ interest on top of it) or he would get a good discount for the dollar amount of services that he provided to date?
What do you think about this? Does it make any sense? Any caveats? Any legal reasons to avoid this scenario?
Unfortunately, I don't think this would ever work, due to income tax issues. As I understand it, the convoluted games startups play with equity grants are to avoid having the equity taxed at its real value; but I imagine that the IRS would demand that income taxes be paid immediately on the total wages, including the value of the debt -- which would very quickly create a cash flow crunch for all but the wealthiest employees.
If this were possible, though, it would make things much simpler -- just imagine, having founders, employees, and angel investors all hold the same form of equity!
EDIT: Just to be clear, I would say that the cash+debt model should continue indefinitely, rather than being limited to 4 years. The idea that someone's effective salary should drop dramatically 4 years after they were hired (i.e., when they are no longer vesting stock each month) seems absolutely loony to me.