[hkarthik]

Sounds like you're on the fence about leaving, first step is decide if you want to leave or not. Then plan how to exit and retain some value in the equity (if it's worth it). Be open about your plans to exit the company and if the founders trust you, they'll work it out with you.

You should try to negotiate a conversion of your ISO shares to NSO shares, and extend the exercise window by 7 years. This will change the tax profile a bit for the shares, but allow you to keep your equity and still leave to do something else. It's a common option, but not given as an option to every employee, only those who are well vested. But it's way better than losing your shares with a 90 day exercise window.

If they won't go for that, you should ensure that you know what the current 409a value is for the company. Ask one of the finance folks to help you answer that question. If it is lower than the strike price on your ISOs, you are underwater on the options and you should not exercise and instead let them expire. You'd be better off investing the $25K on something else with better returns.

[marloc]

Thank you! I wasn't aware of the conversion from ISO to NSO. The FMV is above the strike price but as I just said above it is also below the "share price" the company communicates internally. It is just 3 times the strike price.