[pcl]

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.