[s1artibartfast]

I don't think the company would be in trouble with the IRS if the rsu's are not exercised. I also don't think it would be breaking the social contract if the employees were granted new replacement rsu's with term limits that aren't contingent on employment. It's not that different then unemployed sitting on vested stock waiting for an IPO or liquidity event.

Maybe I don't understand something in the tax law, which is entirely possible.

Whether this is a good deal for the employees remains to be seen and depends on the spread between the current buyback value and the eventual IPO price.

[alecbz]

The whole point of the double-trigger RSU situation is to create a "meaningful risk of forfeiture". It's only that condition that makes the IRS okay with not taxing the RSUs until they're liquid. If employers just top up employees when their old RSUs expire, there really isn't any meaningful risk of forfeiture anymore.

I don't have a full understanding of exactly what language in which laws/documents govern this, but my general understanding is that the IRS would definitely not be happy about that, as it undermines the whole point of the double-trigger RSU.

[gibolt]

Sitting on vested stock is different than being granted new stock (as a replacement) without being a current employee. That may open Stripe up to some additional tax/liability.

[kgwgk]

> I don't think the company would be in trouble with the IRS if the rsu's are not exercised. I also don't think it would be breaking the social contract if the employees were granted new replacement rsu's with term limits that aren't contingent on employment.

But the company and employees would definitely be in trouble with the IRS if they were granted new replacement rsu's with term limits that aren't contingent on employment.