Suppose that I want to build a startup with independent contractors and want to compensate them with non-qualified stock options (NSOs). I expect the business to take some time to stabilize and become profitable, and I do not want to force the contractors to prematurely exercise their options and pay income taxes on the stock received before the business is a proven success.
I therefore would like to set the NSO expiration date to, say, 20 or 30 years from grant date, rather than the usual 10. For similar reasons, I would like to omit (or greatly extend) the typical requirement that NSOs be exercised within 90 days of leaving the company.
Is all of this possible while still keeping the NSOs exempt from 409A treatment? (A variety of online articles discuss stock options and 409A—see here and here for examples—but I haven't yet found any that give a clear answer to this question.)