4 ms·

You only be hit by a tax bill if you chose to exercise the option, which only make sense if the stock is worth more than the strike. If you are "given" somethin

You only be hit by a tax bill if you chose to exercise the option, which only make sense if the stock is worth more than the strike. If you are "given" something that is worth more than $1, the IRS will want a piece of it. If you worked at a startup (not a small business), the most likely outcomes after 4 years is either 1) Company went bust, 2) Company grew. The option protects you from the not having to pay anything if scenario #1 happens. If scenario #2 happens, then you should be happy: you have an option to pay X for something that is usually worth multiples of X after 4 years. I actually think the IRS is being nice not to tax the at-the-money option grant. They essentially assume zero time value, which would be quite high for a startup given the high volatility and the potentially long term for the option.

novok 5y ago
Startup engineers are often young and do not have much savings. Options are a cost, often in the 5 to 6 figures range to exercise. If you exercise at time of hire, your cost can be significant for something that will probably perform less than putting it into bitcoin as far as expected value goes. If you count exercise cost as part of the 'salary', then startup salary is even worse than it usually is. When you leave, the options expire away typically after 90 days. If you exercise, even if they are ISOs, AMT tax can easily make the exercise cost 6 figures anyway. Most engineers in their mid 20s do not have 6 figures in savings unless they already worked at FANG for the first 4 or 5 years of their career. You have to choose, do i put most of my savings into something that will probably go nowhere? Most do not and lose out on the significant compensation they would of at FANG. It's a system that favors the already wealthy and young adults with wealthy parents. Companies actively try to prevent giving liquidity to employees through restrictive clauses. The best case scenario is an employee that works hard and then forfeits their equity due to the above math. The company has a financial incentive to screw employees over and seduce them with unlikely projections of life changing wealth. ----- On the other hand, founders have stock at the start, valued at $0. Even if they have a vesting schedule, they can pre-exercise for no cost. Since it's extremely unlikely that they will sell in the first year, all of their income from that stock in the future will be taxed at LTCG rates. Since the average employee can't afford to pre-exercise (or they get RSUs), they pay at income tax rates, so if they do get lucky, they've compressed 4-8 years of equity compensation in one year, which means they pay %25-%35 more in income tax alone. Employees are often subject to 6 month lockups after IPO, which means if it drops, they have to pay tax on a value that is much higher than they can liquidate with the stock they actually have. Founders often get special liquidity access that employees don't, in secret, during funding rounds. VCs do this to align the founder's interests with theirs, which is going for an outlier $10B IPO vs. liquidate at $300 million at series B, because if the founder has %20, that is a life changing $60 million, taxed at LTCG rates, that makes you an ultra high net worth individual, but is basically a failure from the VCs perspective.
NeverFade 5y ago
> If you worked at a startup (not a small business), the most likely outcomes after 4 years is either 1) Company went bust, 2) Company grew. Right, so the bottom line is this: After 4 years working at the startup, unless it already went bust, you will typically want to exercise, and then you'll get hit by a big tax bill for purchasing a security which is still very likely to end up at zero. It's a risk no matter how you look at it. Unless you happen to work at a startup that became a unicorn, which is very rare, you will end up paying good money for something that may be entirely worthless. So in the best case scenario, you take a risk for an upside that may put your comp around the same level as what you'd get for simply working for FAANG. Worst case, you pay a big tax bill that drops your comp even farther below what your friends at FAANG are making, which is already going to be twice or more to begin with. Surely you see the problem here, especially for risk-averse engineers.

novok 5y ago

Startup engineers are often young and do not have much savings. Options are a cost, often in the 5 to 6 figures range to exercise. If you exercise at time of hire, your cost can be significant for something that will probably perform less than putting it into bitcoin as far as expected value goes. If you count exercise cost as part of the 'salary', then startup salary is even worse than it usually is. When you leave, the options expire away typically after 90 days. If you exercise, even if they are ISOs, AMT tax can easily make the exercise cost 6 figures anyway. Most engineers in their mid 20s do not have 6 figures in savings unless they already worked at FANG for the first 4 or 5 years of their career. You have to choose, do i put most of my savings into something that will probably go nowhere? Most do not and lose out on the significant compensation they would of at FANG. It's a system that favors the already wealthy and young adults with wealthy parents. Companies actively try to prevent giving liquidity to employees through restrictive clauses. The best case scenario is an employee that works hard and then forfeits their equity due to the above math. The company has a financial incentive to screw employees over and seduce them with unlikely projections of life changing wealth. ----- On the other hand, founders have stock at the start, valued at $0. Even if they have a vesting schedule, they can pre-exercise for no cost. Since it's extremely unlikely that they will sell in the first year, all of their income from that stock in the future will be taxed at LTCG rates. Since the average employee can't afford to pre-exercise (or they get RSUs), they pay at income tax rates, so if they do get lucky, they've compressed 4-8 years of equity compensation in one year, which means they pay %25-%35 more in income tax alone. Employees are often subject to 6 month lockups after IPO, which means if it drops, they have to pay tax on a value that is much higher than they can liquidate with the stock they actually have. Founders often get special liquidity access that employees don't, in secret, during funding rounds. VCs do this to align the founder's interests with theirs, which is going for an outlier $10B IPO vs. liquidate at $300 million at series B, because if the founder has %20, that is a life changing $60 million, taxed at LTCG rates, that makes you an ultra high net worth individual, but is basically a failure from the VCs perspective.

NeverFade 5y ago

> If you worked at a startup (not a small business), the most likely outcomes after 4 years is either 1) Company went bust, 2) Company grew. Right, so the bottom line is this: After 4 years working at the startup, unless it already went bust, you will typically want to exercise, and then you'll get hit by a big tax bill for purchasing a security which is still very likely to end up at zero. It's a risk no matter how you look at it. Unless you happen to work at a startup that became a unicorn, which is very rare, you will end up paying good money for something that may be entirely worthless. So in the best case scenario, you take a risk for an upside that may put your comp around the same level as what you'd get for simply working for FAANG. Worst case, you pay a big tax bill that drops your comp even farther below what your friends at FAANG are making, which is already going to be twice or more to begin with. Surely you see the problem here, especially for risk-averse engineers.