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REDDIT

Tech startup options expiring and I can't afford tax hit to exercise. Where to find investors who would be interested in a fire sale on pre-IPO options?

C
Mar 24, 2025 · 22:14

I worked at a tech startup ten years ago and the first equity grant I received is going to expire in a month. I didn't know about 83b elections back then so the tax hit for me to exercise at the current FMV is astronomically higher than I can personally afford to float.

Company has been legitimately close to IPO for a few years now, Goldman was preparing an offering for them right when the IPO market shit the bed so they called it off, but they've managed to maintain value pretty well in the post-COVID era (hence why I can't afford exercise) and are broadly aiming to go public within the next couple of years.

At this point I would honestly sell my shares for like 1/8 of FMV because otherwise I get nothing from them, but I don't personally know any wealthy people and the pre-ipo options-trading platforms seem to be very dead these days. Any ideas about how to find someone?

Happy to identify the company and give numbers around share count/price if that would be helpful, just didn't want to accidentally break a rule or something.