Rafael Valle

How did you handle your stock option exercise window?

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Hey everyone,

I'm building StrikeRates and trying to understand how other people have navigated this. When I got laid off, I had 90 days to decide what to do with my vested options. I had no idea where to start. Every liquidity provider had different fees, different structures, different minimums. No way to compare them. No reviews from other employees. Just sales calls.

I ended up spending weeks building spreadsheets trying to figure out: do I self-fund? Take a non-recourse loan? Do a forward contract? What's the tax hit on each?

A few questions for anyone who's been through this:

  • Did you exercise your options or let them expire? Why?

  • If you used a liquidity provider, how did you find them? How did you evaluate them?

  • What information would have changed your decision?

I'm building free tools around this problem and would love to hear real experiences. Not looking to sell anything, just trying to make sure I'm solving the right pain points.

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