This is a very difficult sell at most startups, particularly those who have done A rounds, as it requires legal maneuvering in most cases.

If you want startup stock, I'd think "Charge biggest/most sophisticated companies a LOT of money, reinvest a portion into angel rounds." This does mean that you'll have stock from companies you didn't work for.

Note that angel investing is, for most angel investors, a fun way to lose money. (I have three small angel investments.)

An angel who invests $50k into a startup at a $5 million valuation gets a MUCH better deal than an employee who is offered 1% of the company, by the way. Ask me why if this isn't immediately obvious to you.