So if you exercise an option to buy a stock for $1, you have to pay taxes on the stock's current value, but if you had bought the stock outright at $1, you don't have to pay capital gains until you sell? That's absurd
Yes. Yes it is absurd. A lot of people have been screwed over by this situation.
I think it's basically a bug in US tax law. The scenario is such an edge case for most Americans.
The other not-so-nice aspect of this is that it disproportionately affects people who aren't already relatively wealthy. Theoretically you can avoid this trap by exercising your options as soon as possible and locking yourself into long-term capital gains. But if you're joining a relatively established startup it may well be pretty expensive to immediately exercise your options. If you don't have, say, 100k lying around you have to wait until there's liquidity, thus opening yourself up to this risk.
There are some downsides but this is one of the reasons that phantom stock and phantom stock options[1] can be good for employees as there is essentially nothing taxable until the actual payout, which is treated as regular income and can have taxes withheld like a normal bonus.
Phantom stock is super interesting. Do startups ever offer it? I'd be curious to know how it worked out.
It seems like it would be better than the worst case with traditional options but not as good as the best case. I mean, ideally you exercise your options early at a very low price and then enjoy long-term capital gains tax rates. Phantom stock means you'll always pay way more in taxes when you get your equity-based payout - 50%-60% vs 20%-30%. At the same time though you are never at risk of ending up underwater.
It seems like phantom stock would be great as an option for companies to offer employees - i.e. you could either get a traditional options structure or phantom stock. I wouldn't be surprised if there were negative accounting or tax consequences for the company though. And maybe the administrative overhead for offering phantom stock in addition to traditional options would be prohibitive for small startups.
This sounds reasonable, however that subsidy/gain is already paid for with the employee's labor, which cannot be recovered. Paying taxes on what is essentially a guaranteed gain sounds reasonable, but when it is a gain earned by putting in labor over several years, I'm not sure this is the best solution.
Yes, salary is paid for with labor, but a reduced rate that is offset with compensation in the form of stock options. You're correct that it is taxed, and the capital gains rate is lower than the salary tax rate. My comment was more an observation, but the thought hadn't been fully fleshed out.
