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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…
Yes, I was very lucky. I was actually one of the first few employees, and I joined about a year before they raised their series A. Now they are a unicorn, and hopefully on their way to an IPO. I don't know if I would say I joined a "unicorn within unicorns". Every unicorn has at least 10 early employees with the same story, and according to this list [1], that's at least 1,850 people. I don't think the company was QS…
Under certain circumstances, QSBS (Qualified Small Business Stock) rules will significantly decrease your tax burden.