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Ask HN: Former employees' RSUs at risk after startup's IPO

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Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#41
I've never had RSUs as an ex-employee. But as a current employee I've seen net share withholding and sell to cover. With net share withholding, the company figures your witholding %, issues you the net shares after withholding and pays the withholding from cash. A new IPO company may prefer to use its cash for other things.

Given that there's one month until the date, and stock plan stuff always takes a while, it's probably too late to ask them to change their plan.

I think you should be able to finance this withholding, most likely, you'll be able to pay back the loan once the RSUs are tradable, about 30 days later. If the stock drops too far though, you'll need to sell the stock, and then marry someone with a lot of capital gains to cancel out, and have your new spouse help pay back your loan :P

Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#42
post #28

Earlier quoted context omitted.

Right. Instead of the IPO date, or the end of the lockup date, they chose 3/15 as the date to settle the vested RSU. And require us to estimate our tax, based on the fair market value of that future date, with this formula, and pay cash, otherwise the vested RSU will be canceled: Number of vested RSUs * the estimated fair market value of the stock at the settlement date * the appliable highest marginal federal, state…

(Again, not an accountant, I repeat that because I might be wrong and I'd hate anyone to suffer because of that..) There are a couple of different risks here. One is that you pre-pay the company for more than the FMV ends up being; it sucks, especially with interest rates being as high as they are, but you'll get the money back with your tax return filed next year. A different risk is that the price is spiked high at…

Price is mostly flat since IPO (up or down within ~10% mostly), looks the stock is thinly traded, daily volume is less than 100k shares.

Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#43
post #30

re #3, if your RSU windfall is substantially large, you might be eligible for the 100%/110% safe harbor that won't penalize you for tax underpayments (assuming you are a US taxpayer) e.g., you make $200K in 2024 and $5 million in 2025 (which includes the RSU windfall). Assuming you pay at least 110% of what you paid in taxes in 2024 in 2025, you need not pay estimated tax or anything beyond statutory withholding amou…

The issue is not that they want their withholding to be correct for the taxes they owe. The issue is the company needs to follow the withholding rules, and probably for cashflow reasons or maybe for tricky equity law reasons, would like the former employee to provide the withholding, rather than a net share settlement or sell to cover.

This should count as a supplemental wage payment. The 22% rate for supplemental wages only applies if income is under $1M and the person was paid wages by the employer this year or last; details in publication 15 https://www.irs.gov/publications/p15#en_US_2025_publink10002...

Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#44
Wait - there’s a lot of assumptions being made in this thread. Is everyone you’re referring to a former employee? Are you sure you had RSUs, proper, as opposed to options?

If you have options, this is entirely because of the different treatment between ISOs and NSOs.

Is it possible you thought you had RSUs but instead had options?

Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#46

Wait - there’s a lot of assumptions being made in this thread. Is everyone you’re referring to a former employee? Are you sure you had RSUs, proper, as opposed to options? If you have options, this is entirely because of the different treatment between ISOs and NSOs. Is it possible you thought you had RSUs but instead had options?

Yes, all former employees (current employees that hold RSUs are offered sell-to-cover, no worries on upfront tax by cash). And yes, they are RSUs. As for options, ex-employees need to pay to buy options when leaving the company within 90 days.

Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#49

Earlier quoted context omitted.

I commented with a correction. March 15, 2025 is 140 days from the IPO day. This is before the lockup periods ends and they require us to estimate our tax, based on the fair market value of that date, with the following formula, and pay cash, otherwise the vested RSU will be canceled: Number of vested RSUs * the estimated fair market value of the stock at the settlement date * the appliable highest marginal federal,…

anyway, mail me at username at googles service. Some chance I have an answer

Sent the email. Thank you!

Re: Ask HN: Former employees' RSUs at risk after startup's IPO

#50
post #46

Wait - there’s a lot of assumptions being made in this thread. Is everyone you’re referring to a former employee? Are you sure you had RSUs, proper, as opposed to options? If you have options, this is entirely because of the different treatment between ISOs and NSOs. Is it possible you thought you had RSUs but instead had options?

Yes, all former employees (current employees that hold RSUs are offered sell-to-cover, no worries on upfront tax by cash). And yes, they are RSUs. As for options, ex-employees need to pay to buy options when leaving the company within 90 days.

Well, for options it's more complicated than that - you can have ISOs that convert to NSOs to allow people to defer having to exercise illiquid options when they leave the company. So that's where my options question was coming from - the scenario you describe is VERY common in a scenario where ISOs have converted to NSOs upon leaving the company.

But okay, you have RSUs - how familiar are you with your agreement? It could have been a double trigger vesting arrangement, where the shares "semi-vest" over time, but then they don't fully vest until a liquidity event, at which point poof suddenly all of those ghost shares become REAL shares. If that's the case, they likely baked in a process for employees to have those shares withheld, or auto-sold during the lockup period. It's all tied in with their HR system and other payroll processes to make that easy.

Another scenario is that at some point since you left, or right before the IPO, they re-issued everyone's shares to be a different share class, because they wanted to clean up their cap table before going public. For employees they could just fix that for them, because again - all baked into the existing systems. For previous employees (and people who were gifted stock and former board members and advisors and angel investors and whoever else), they don't have an easy way to fix this. The old stock class technically doesn't exist because its been converted, so they can't sell to cover, and when they convert, they couldn't automate that because they don't have your withholding information and other payroll details for compliance purposes.

In either scenario, it's worth either reading your agreement carefully and/or talking to an attorney. Regardless, however, if this was related to an IPO, the legal and compliance stuff on this is going to be buttoned up and carefully done, so assume that (however unfair) they either have to do this in this fashion or it's much easier for them to do it this way (or some combination of both). It is possible to do very shady things during a private transaction, even a private transaction with a publicly traded company, but not for an IPO.

There are companies that will loan you money to cover vesting costs or these types of situations - they'll do it at shitty rates, but if the options are losing out on a windfall or losing an extra 10-20% on the windfall, it's worth considering.

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