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by caseysoftware 2485 days ago
The single best source that I've found - short of a CPA familiar with stock - is David Weekly's book: https://blog.dweek.ly/introduction-to-stock-options-startup-...

I was an early employee at Twilio (#25) and much later at Okta. Following his advice saved me thousands when I early exercised in both cases. My only complaint is that I didn't find and apply his advice sooner.

The author is right. Most of the time it doesn't make sense to exercise. If you join early, the strike price will be lower but the risk will be higher aka the odds are lower. If you join later, the strike price will be higher but the risk should be lower aka the odds are better.

Regardless, having the liquidity at the right time can be hard, especially if you're caught in a layoff and don't have savings.