Exercising Startup Stock Options and Tax Implications (2018)

Stock Options at an early startup sucks, until it doesn’t.  Basically until the company goes public (IPO), sells to another company, or grows big enough to know it’s not going to fail, these stock options are a costly gamble.  Purchasing my stocks and paying the taxes cost me about $33k!  Since these options were part of my compensation package, it’s really hard to leave them on the table though.  I’ve got too much FOMO to not buy them!  Here’s the story of my 2nd options exercise and how it affected my taxes.

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