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The article is right but misses the biggest problem with options: the need to spend money you may never get back in order to have a chance to be paid anything.

The article is right but misses the biggest problem with options: the need to spend money you may never get back in order to have a chance to be paid anything. There are two ways this happens: - You leave the company after 4 years and have 30-90 days to exercise. The exercise will cost you $20,000. The company is nowhere near an exit. Do you do it? - When you exercise you are either immediately hit with a tax bill for NSOs or you get screwed on AMT with ISOs. You suddenly owe money to the IRS simply because the company received a very high 409A valuation just before you left. A liquidity event is nowhere in sight. You've taken a huge gamble by joining a fledgling company that pays little with a low probability of success. You toil for years an overcome tremendous odds to just keep the company alive. But now when you leave the IRS and the company itself wants you to take a final gamble with your hard earned cash. I used to be an attorney who drafted option agreements. Now I've been at two startups as early employees. The reason why this never comes up is because employees do not know what they are getting themselves into. The options are worth very little BY DESIGN. Unless you are among the first 5 hires, you will have no leverage to negotiate a better deal.

nojvek 8y ago
A number of startups screw over their employees with options. 90 days is a terribly short exercise window. Kinda like a scam in a way. But not all startups are like that. Where I work (Mixpanel), that window is 5 years. Which I feel is a much generous and fair offer. With stock options, I pay no tax. If the company liquidates, then I convert the options to real stock (yeah i’ll have to pay money to do that). If things go better, I hold that stock for one year and when I sell, I pay capital gains tax at a much lower rate on the gains. But. Big BUT, there’s a lot of assumptions. Things may not go well, may it doesn’t get valued as much, may be it takes longer than 5 years. Lots of may be’s. That’s part of the startup gamble. We are hiring btw if anyone is interested in analytics space. DM me.
- chauzer 8y ago
  But you have NSOs though, not ISOs right? From what I understand, ISOs are required by law to have a 90 day exercise window, so companies that offer more than 90 days after leaving a company are having ISOs converted to NSOs. When you exercise the NSOs, you still will have a tax bill.

nojvek 8y ago

A number of startups screw over their employees with options. 90 days is a terribly short exercise window. Kinda like a scam in a way. But not all startups are like that. Where I work (Mixpanel), that window is 5 years. Which I feel is a much generous and fair offer. With stock options, I pay no tax. If the company liquidates, then I convert the options to real stock (yeah i’ll have to pay money to do that). If things go better, I hold that stock for one year and when I sell, I pay capital gains tax at a much lower rate on the gains. But. Big BUT, there’s a lot of assumptions. Things may not go well, may it doesn’t get valued as much, may be it takes longer than 5 years. Lots of may be’s. That’s part of the startup gamble. We are hiring btw if anyone is interested in analytics space. DM me.

chauzer 8y ago
But you have NSOs though, not ISOs right? From what I understand, ISOs are required by law to have a 90 day exercise window, so companies that offer more than 90 days after leaving a company are having ISOs converted to NSOs. When you exercise the NSOs, you still will have a tax bill.