Ask HN: How to figure out if your stock options are worth exercising?
What are some of the indicators that you use to evaluate your current company and see if it's worth exercising your vested stock options?
Firstly, you need to know where the company is at on the funding chain, and understand the key financials as it stands today. If the company is late series stages you should have many more options, including potentially a private exchange after you exercise. Also the larger % you hold gives you more options as well, someone holding < 1% really isn't in the same position to negotiate as someone holding 10%.
If the company is at the seed stage and hasn't raised their Series A then exercising the options will almost never pay off. As a general rule, after the series A the reason to exercise gets stronger with each successive round, which should be obvious. But outside of that it is hard to generalize IMO.
Maybe someone else has some generic rules to follow, but I feel it takes a lot of details to be able to formulate a reasonable decision here.
Also, my main issue is that the exercise price is around $1.00, and I have around 30K options, so I might be spending a good chunk of money.