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If they were the earliest employees the stock should have been at par value, making the tax payment minimal. Later employees typically get options, which don't

by raylad 4y ago

If they were the earliest employees the stock should have been at par value, making the tax payment minimal. Later employees typically get options, which don't have the tax issue. So I'm still unclear where the tax bill is coming from.

yieldcrv 4y ago
Because they didn’t get options. Stripe was flirting with going public for so long that they gave RSUs and people were trading the shares on private secondary markets. Those secondary markets have dried up in the general macroeconomic environment, so now this practice is leaving people with their pants down, complete illiquidity.
- raylad 4y ago
  If they didn't get options, tax would have had to be paid as each RSU vested if it was not paid with an 83b election. So again, I don't see why Stripe has a tax bill now.
  - deleted 4y ago
    [deleted]
  - kasey_junk 4y ago
    RSU don’t allow an 83b. Stripe issued double trigger RSU so the tax is only due when the second trigger occurs, which hasn’t happened yet. Some of the RSU have upcoming expiration dates as required by IRS rule. To avoid those expiration dates Stripe wants to do something. That something probably involves a big tax withholding for Stripe that must be paid in cash. Stripe doesn’t intend to go public soon so is seeking an alternate way to come up with that cash.
bzax 4y ago
I don't know why you believe later employees get options. It is true that at public companies, employees often are compensated with options, but at "startup"s where the FMV of a new employee grant would be prohibitively expensive to either early exercise or pay income taxes on, employees get RSUs. Options are for small companies, and 83b elections when the exercise price can be paid by the employee upfront. RSU are for unicorns. Once the company is public and there is liquidity you can do whatever. Except backdating stock options...
- raylad 4y ago
  Someone here is confused, and it might be me. As I understand it: In a company where the fair market value share price is $1/share, if you get granted 100 options, you owe tax on $0 because options are not taxable. If you get granted 100 RSUs which are all fully vested, you owe tax on $100 because stocks are taxable. If the RSUs are 0% vested you don't owe any tax yet. Then, if the share price goes up to $2 a share, you still owe $0 tax on your options, but if you have RSUs and 50 of them now vest, you immediately owe tax on $100 (50 x $2) - unless you did an 83b election and paid taxes on the 100 shares at $1 a share at the time you got the grant. If you exercise the options, now you owe tax on $200 (100 x $2), whether or not you can sell the stock. So again, I don't understand why Stripe would have a tax bill under any of these scenarios. The employees would have a tax bill connected with vesting of RSUs if they had not done an 83b election, but no one else would have any tax due until they (exercise in the case of options) and then sell the stock.
  - bink 4y ago
    If I'm understanding it correctly, the employees won't have a tax bill if they let the options expire, but they are presumably worth millions so they don't want to just throw that money away. If they exercise then they will owe taxes and they will also have no way to sell the shares (currently) to pay the tax bill.
    - raylad 4y ago
      Sure, but options don't expire while you are an employee. So if Stripe wants to let employees sell stock, they only have to exercise options equal to the number of shares they will sell, then they can use the proceeds to pay the tax. I still don't understand why there is a tax bill for Stripe.
      - theIV 4y ago
        > Sure, but options don't expire while you are an employee. ISOs (not totally sure about NSOs) have a 10 year expiration from grant date[0]. [0]: https://www.law.cornell.edu/cfr/text/26/1.422-2 https://www.law.cornell.edu/cfr/text/26/1.422-2
fatnoah 4y ago
They way I'm reading the article is that there are employees that would incur large tax liabilities by exercising their options, but have no way to sell those option, so Stripe is looking to cover those taxes. Whether those employees may or may not have been able to ameliorate this by making an 83b election is moot at this point. They clearly didn't, so now something has to happen if the company wants to keep them around.
- s1artibartfast 4y ago
  I can't read the whole article but are they planning to buy back some of the stock to cover the tax, or simply pay it as some kind of a perk. Edit: after reading the archive link, it seems that the former case is the most likely.
  - fatnoah 4y ago
    Yeah, I think it's the former, so it'll feel more like "sell to cover" for the employee. I'd have to imagine that paying it as a perk would trigger its own tax liability.

by raylad 4y ago

yieldcrv 4y ago

Because they didn’t get options. Stripe was flirting with going public for so long that they gave RSUs and people were trading the shares on private secondary markets. Those secondary markets have dried up in the general macroeconomic environment, so now this practice is leaving people with their pants down, complete illiquidity.

raylad 4y ago
If they didn't get options, tax would have had to be paid as each RSU vested if it was not paid with an 83b election. So again, I don't see why Stripe has a tax bill now.
- deleted 4y ago
  [deleted]
- kasey_junk 4y ago
  RSU don’t allow an 83b. Stripe issued double trigger RSU so the tax is only due when the second trigger occurs, which hasn’t happened yet. Some of the RSU have upcoming expiration dates as required by IRS rule. To avoid those expiration dates Stripe wants to do something. That something probably involves a big tax withholding for Stripe that must be paid in cash. Stripe doesn’t intend to go public soon so is seeking an alternate way to come up with that cash.

bzax 4y ago

I don't know why you believe later employees get options. It is true that at public companies, employees often are compensated with options, but at "startup"s where the FMV of a new employee grant would be prohibitively expensive to either early exercise or pay income taxes on, employees get RSUs. Options are for small companies, and 83b elections when the exercise price can be paid by the employee upfront. RSU are for unicorns. Once the company is public and there is liquidity you can do whatever. Except backdating stock options...

raylad 4y ago
Someone here is confused, and it might be me. As I understand it: In a company where the fair market value share price is $1/share, if you get granted 100 options, you owe tax on $0 because options are not taxable. If you get granted 100 RSUs which are all fully vested, you owe tax on $100 because stocks are taxable. If the RSUs are 0% vested you don't owe any tax yet. Then, if the share price goes up to $2 a share, you still owe $0 tax on your options, but if you have RSUs and 50 of them now vest, you immediately owe tax on $100 (50 x $2) - unless you did an 83b election and paid taxes on the 100 shares at $1 a share at the time you got the grant. If you exercise the options, now you owe tax on $200 (100 x $2), whether or not you can sell the stock. So again, I don't understand why Stripe would have a tax bill under any of these scenarios. The employees would have a tax bill connected with vesting of RSUs if they had not done an 83b election, but no one else would have any tax due until they (exercise in the case of options) and then sell the stock.
- bink 4y ago
  If I'm understanding it correctly, the employees won't have a tax bill if they let the options expire, but they are presumably worth millions so they don't want to just throw that money away. If they exercise then they will owe taxes and they will also have no way to sell the shares (currently) to pay the tax bill.
  - raylad 4y ago
    Sure, but options don't expire while you are an employee. So if Stripe wants to let employees sell stock, they only have to exercise options equal to the number of shares they will sell, then they can use the proceeds to pay the tax. I still don't understand why there is a tax bill for Stripe.
    - theIV 4y ago
      > Sure, but options don't expire while you are an employee. ISOs (not totally sure about NSOs) have a 10 year expiration from grant date[0]. [0]: https://www.law.cornell.edu/cfr/text/26/1.422-2 https://www.law.cornell.edu/cfr/text/26/1.422-2

fatnoah 4y ago

They way I'm reading the article is that there are employees that would incur large tax liabilities by exercising their options, but have no way to sell those option, so Stripe is looking to cover those taxes. Whether those employees may or may not have been able to ameliorate this by making an 83b election is moot at this point. They clearly didn't, so now something has to happen if the company wants to keep them around.

s1artibartfast 4y ago
I can't read the whole article but are they planning to buy back some of the stock to cover the tax, or simply pay it as some kind of a perk. Edit: after reading the archive link, it seems that the former case is the most likely.
- fatnoah 4y ago
  Yeah, I think it's the former, so it'll feel more like "sell to cover" for the employee. I'd have to imagine that paying it as a perk would trigger its own tax liability.