[chamomeal]

Your options haven’t expired since leaving those startups?

I recently left a job at a startup where I had some options vested. It would be like 6k to exercise them. I was leaning towards leaving em, and now this thread has kinda convinced me

[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.

[whstl]

Sorry, my mistake. It's all shares, I don't know why I said stocks/options.

But it's all shares. First from being early in a marketing startup that recently closed, second from being one of the first engineers of an event ticket marketplace that's holding on for dear life, third from a tourism unicorn that paid half my salary with instant-vesting shares during Covid.