

Ask HN: How to exercise stock options expired due to founder's mistake? - startupemp

tldr; Early employee at a startup who couldn&#x27;t exercise a part of my options as founder and HR intentionally didn&#x27;t respond to my emails within 90-day expiration period. what are my options?<p>I was an early engineer (&lt;5) at a startup and joined them in the first 6 months of inception. I worked (hard) for over 5+ years and left them recently due to limited growth opportunities within the startup. I believe the startup will have a decent exit (nothing remarkable, but =~$50M to $100M) based on steady growth and its valuations in last few rounds.<p>After leaving the startup recently, I sent an email to the founder and HR attaching executed exercise notice but without any payment (as I didn&#x27;t know where to wire the money etc.). I didn&#x27;t receive any response from them until 5 days after the vested options expired due to 90-day expiration rule of ISO options set by IRS. I followed up multiple times (before expiration) but didn&#x27;t hear back.<p>A week after expiration, I received a response from founder (who cc&#x27;ed the lawyers) saying that I could exercise the options and send them a check. Within few minutes of his emails (yeah, it was a setup), the lawyers replied saying I couldn&#x27;t exercise them as I was past 90-days which IRS mandates.<p>Now I understand that IRS has a 90-day rule here. but what are my options considering the startup founder&#x2F;HR intentionally didn&#x27;t let me exercise?<p>Notes:
1. I took paycuts for the options early in the startup tenure (a mistake which I fixed later). so I hate to see the options just go away like this. 
2. If options are part of compensation, why do vested options expire after 90-days? I understand ISO rule by IRS, but shouldn&#x27;t startup employees opt for NSO&#x27;s etc.? The vested options correspond to work that I already did in the past. I fail to understand this rationally. Are there any other favorable equity structures that startup employees should push for?
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throwaway420
The best advice anybody is likely to give you is that you should probably
delete this and consult with a lawyer.

