The Information reported [1] Friday that Stripe is trying to raise $4B at a $55B valuation for “a huge tax withholding bill that comes due when it modifies employees’ stock grants that are set to expire before a potential public listing”.
I did a bit of research, but couldn’t figure out what sort of tax laws are at play here? Why is Stripe looking at such an enormous bill, and hypothetically what could happen if they can’t raise all the money?
Well 'relatively', what I mean is it's still Stripe right, I'm no insider but I'm sure they'd have no trouble raising it as debt on decent almost traditional/established company ish terms. It's not the same as random fledgling startup seeks 10%.
> In the case of payments group Stripe, RSUs worth millions of dollars will start expiring from 2024 and risk being forfeited unless the company buys them out, changes the terms of the awards or launches an IPO.
> Employees face a personal tax liability when RSUs vest. But staff are unable to sell any of these shares without the company launching a flotation. To get around the problem, Stripe wants to withhold a portion of the stock equivalent to the tax liability from employees’ awards. Separately, it plans to sell stock to investors, using the money raised to pay the employees’ tax bills and buy up any stock they wish to sell.
> Stripe intends to raise enough to cover the tax bill associated with the RSUs handed out to many of its 8,000 employees since 2017, and will hold back some of the value of employees’ shares as compensation, according to a person familiar with the matter.
> “Stripe has realised they have to help the employees out,” said Glen Kernick, Silicon Valley leader at valuations provider Kroll. “When they [RSUs] vest, that’s a taxable event. As an employee, you now own the shares and owe tax but you don’t have the ability to pay your tax bill by selling shares. That’s obviously viewed as a hardship.”
TLDR stripe needs cash to pay taxes to provide employee liquidity if they don’t IPO, and this ain’t a great macro to IPO
Tangentially, private equity in the tech startup space on the secondary market is currently transacting at a ~40% discount.
They should've IPOed when valuations went into massive bubble territory in 2020/2021... have to wonder what kind of logic they were using to wait so long.
If you can IPO at a ~100x sales multiple, what more do you really need? Hard to feel sorry for those that chose to stay private for a decade+ while the getting was good
So 7 years would have “been to early” (e.g., like Meta did it and we all know how that ended…)? Or 5 years in the case of Google? Or 2 years for Amazon?
It's generally hard to do anything with vested RSUs in a non-public company. For one, they often require time and a liquidity event in order to vest; but even if they were vested into shares, it's hard to sell non-public shares.
Essentially we have another story of people being offered equity compensation in a non-public company as though it were real compensation. Now they're even potentially being hit with tax liability for that equity despite having no way to realize the income.
This sounds like stripe does not actually have the cash to cover the withholding even then, and if they can't I think that means the employees are getting $X of "income" being taxed on that, and then having to put some significant % of that value aside, from their own assets, to cover that tax burden. Because stripe insisted on equity compensation with no method for equity compensation to have a non zero real world value despite its non zero tax value? "cool" I really hope stripe's equity compensation is a significant multiple of other companies to make up for this ... if they ever actually go public. Otherwise the "equity" remains fictitious zero value BS.
Hardships like taxing illiquid stock is the main reason for only taxing _realized gains_.
Since Stripe wants employees to cherish their vested interest in the company, the corporation goes ahead of law here and facilitates. This also means that employees are less likely to either forfeit and sell the stock to third parties.
Legislators promoting entrepreneurship may in future encourage this behaviour to strengthen employee ownership of companies, when RSUs become commonplace for most employees, not just executive officers.
> Hardships like taxing illiquid stock is the main reason for only taxing _realized gains_.
This seems like an over simplification which ignores people’s abilities to still draw cash on their illiquid stock. It’s not hard to imagine that early employees with millions in stock can take a loan against them, or they can sell their shares on the secondary markets too. This is especially true for Stripe.
The idea of taxing only realized gains is why we have problems like prop 13 in California with two neighbors paying radically different property taxes on the same valued homes.
That in my opinion would be a horrible idea for property taxes which are an important part of local and state taxes. According to this source[0] property taxes make up more than 30% of a state’s revenue, so having reliable constant revenue streams would be gone if it happened on sale.
I think there’s other issues too like how property taxes accumulate and can surpass the value of the home in which case you do what?
They are double-trigger (source: I am a Stripe RSU holder). However, they also have an expiration date. The expiration provides the "substantial risk of forfeiture" that the IRS requires in exchange for not taxing the RSUs at the time you receive them.
I did a bit of research, but couldn’t figure out what sort of tax laws are at play here? Why is Stripe looking at such an enormous bill, and hypothetically what could happen if they can’t raise all the money?
[1] https://www.theinformation.com/articles/inside-stripes-55-billion-pitch-to-investors