I think the calculus is different for exercising options after leaving than the scenario the GP described, in which the company is pitching current employees on a stock purchase scheme.
There’s nothing inherently wrong in the latter, but it’s super unusual, and it’s pretty safe to be wary of startups shouldn’t do unusual things with their financing / cap table.
Exercising options post departure, on the other hand, is par for the course with any option-based compensation (note that this shouldn’t apply to RSUs, since those are usually owned outright after vesting).
A similar question arises with payment of taxes for 409a elections. Can be pricey, but it doesn’t raise the same red flags as a founder asking you to pay to work there.
There’s nothing inherently wrong in the latter, but it’s super unusual, and it’s pretty safe to be wary of startups shouldn’t do unusual things with their financing / cap table.
Exercising options post departure, on the other hand, is par for the course with any option-based compensation (note that this shouldn’t apply to RSUs, since those are usually owned outright after vesting).
A similar question arises with payment of taxes for 409a elections. Can be pricey, but it doesn’t raise the same red flags as a founder asking you to pay to work there.