1. Do consult a lawyer. The state you’re in matters and if you’re in the Bay Area you should be able to get a lawyer to provide advice at no cost. I would stru

1. Do consult a lawyer. The state you’re in matters and if you’re in the Bay Area you should be able to get a lawyer to provide advice at no cost. I would structure their equity as an option grant. You still have a long way to go to make this successful so they should be vesting over the future. You could give them credit for the time since the company was founded. 2. This is not a great way to structure this payment. Really you should just pay him a very high commission rate for closing those first few deals so he can cover the debts. Mixing it with a stock transaction will look shady to future investors/regulators. Be upfront with your investors about this and they should understand.