Would someone here be able to help think through exercising startup options? I’m currently partially vested at a Series C (soon to be D), and considering taking a new role at a seed stage (soon series A). Both companies are updating 409As now, and it sounds like early exercising at the seed stage company might be on the table. Current company is well-known, run by a famous CEO, has been around for a while, but isn’t profitable yet. I know that after 90 days ISOs turn into NSOs.

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Posting as :
works at
You are currently posting as works at

So...if companies are updating their 409A, it will very likely go up. You may already be in a blackout period at one or both companies, unless they are willing to go with the old 409A (unlikely). So you may have to wait.

The C/D stage company may mean that exercising causes a pretty hefty tax bill. Make sure you have the cash for that.

Whether you exercise or early exercise, you are starting the cap gains clock at that time. If you early exercise, don't forget to file your 83(b) election timely.

Lots of good advice by my former colleague Mary Russell at stockoptioncounsel.com.

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Thanks!

Wow this is the post I’m looking for. Similar situation. How do you find a CPA / tax advisor that knows all of this type of stuff in the startup world?

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Call Mary and ask fir a rec! She works w all of them in Silicon Valley.

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