I'm seeing a surprising number of comments describing catastrophic tax outcomes due to exercising options with a large spread and holding the stock long enough

I'm seeing a surprising number of comments describing catastrophic tax outcomes due to exercising options with a large spread and holding the stock long enough for it to tank before selling, while still being stuck with a massive tax bill. This situation is easily avoided by filing your 83b and early exercising your options immediately, or at least before a subsequent funding round/term sheet valuation cycle. None of the comments describing those outcomes mention this. For those reading and new to the startup game, read up on the 83b. When you're an early employee at a startup, the cost of early-exercising even a substantial number of shares is often not cost-prohibitive. And should you leave the company before it all vests, you get a check for the unvested remains. It's a NO-BRAINER when the exercise cost is small. https://blog.wealthfront.com/always-file-your-83b/ https://blog.wealthfront.com/always-file-your-83b/