It's a little different if you held into 2020, though. Then you'd be on the hook for the higher taxes, but again, you should still be able to eventually claim the loss, so as long as you're in the same tax bracket, it'd be OK.
You were taxed the minimum amount (37%) when they vested, but likely need to pay a lot more than that yourself.
The IRS gives you some time to pay the difference; I think if they get their money in the tax year, they're happy. So if you owed those taxes but knew you'd sell in November, the loss would offset the gain, and it'd be like you never owed the taxes. It would work out so you'd pay taxes on the sale price as though it were all short term capital gains. The problem comes if you don't sell in 2019. First, you'd owe those taxes on gains you never really saw. When you realize the loss, you'd be owed the taxes back, but as an offset to gains elsewhere the year you sell, or in $3000 increments for the rest of your life.
Employees' RSU agreements stated that Uber would deliver their shares 6 months post-IPO. A few days before the IPO Uber decided to amend the agreement and accelerate the vesting, so shares would be available on IPO day itself.
Why did they do this? Uber is legally required to withhold taxes during a vesting event. The most common way to do this is to sell a percentage of the shares immediately on vest. This, however, increases the total number of shares in the market and depresses the stock price. To avoid this, Uber decided to pay for the taxes out of their own pocket and claim a percentage of the shares for themselves (basically a private stock buyback).
By moving the vest date up, Uber gambled on the fact that the stock price would be higher in 6 months, and the move would thus benefit both themselves (less out of pocket spend for withholding) and the employees (difference taxed as capital gains rather than regular income). Instead the opposite happened and both parties lost out. More importantly Uber reduced their own risk by locking down their total liability at the IPO date itself and exposed their employees to the whims of market fluctuations.
tl;dr Uber accelerated vesting of employee grants so that they happened during the lockout period. Also they could have proactively taken more out to cover taxes for the employee but chose instead to take the minimum out.
They didn't do this for the same reason - they were paying for the withheld taxes themselves.
The article makes it look like Uber tried to short change employees, but if the stock had rocketed up, they would have saved employees a ton of money in taxes because the gain from IPO price to the price when the lock-up expired would have been taxed as capital gains.
They also make it looks like these people are all making pennies because the stock didn't do well, which we all know is obviously not the case (especially if they are engineers).
Side note: when people bash ISOs because they are evil or something, I just think of tax implications like this. This wouldn't happen if they were options instead of RSUs.
Uber delivered shares to its employees on the day of its IPO in May 2019, meaning employees would be taxed at the price of $45 a share. But the employees were restricted from selling their shares for six months, by which point the price had fallen to around $27 a share.
This definitely sucks for the employees. But it isn't really clear that Uber did anything wrong. In cases where there's an IPO pop, and employees want to hold on to the stock for a while, this can be good for employees, because more of their income happens via capital gains.
To me, the real lesson is that our tax code is stupid, because it treats "a share of stock that you are given on day X, but may not sell until day X+180" and "a share of stock that you are given on day X+180" in different ways, even though they seem exactly the same to the employee.
He means that if I offered you stock with a 6 month lockup, or a stock with no lockup, you would prefer the second, and value it much higher.
