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01181008on What I Wish I'd Known About Equity Before Joining a Unicorn

QSBS is a tax thing, not a specific company thing. On the face of it (tech company, exercised very early) it seems like you'd be eligible. The company lawyers should be able to tell you the QSBS eligibility period (something like "options exercised before MM YYYY, when TECH CORP's gross assets exceeded $50 million")

01181008on What I Wish I'd Known About Equity Before Joining a Unicorn

Sure, I can relate :). Have a few thoughts:

$20k to $5-10m is incredible. That implies 250-500x valuation growth (for example you joined at series A with $20m valuation and the company is worth $10b), which means you hit a unicorn within the unicorns!

Was the company QSBS-eligible when you exercised? There are huge potential tax savings there.

Your shares were NSOs, correct? There are weird potential issues with 83bs and vesting ISOs.

It's worth thinking through how to factor your paper money into your investment portfolio. You could model it as $0 and have an otherwise standard asset allocation (e.g. whatever WealthFront recommends for your risk profile). Alternately you could include it as a huge illiquid stake in a US tech company -- as if your portfolio was 80% in GOOG -- and mitigate your overexposure in the other 20%. Or something in between.