I'm not familiar with Stripe's situation, but there are non-public markets available for this kind of stock sale. You just can't buy from them unless you're already rich. I'd guess that long-term employees do have an amount of flexibility in that regard.
Unfortunately many companies have clauses in their options grants that prohibit employees from selling shares to any investor not approved by the company board (e.g. EquityZen).
This is already a thing, large investors like Fidelity do exactly this.
e.g. Fidelity has a significant investment in SpaceX through a handful of their mutual funds, which you can then purchase and basically invest in SpaceX indirectly.
Publicly traded organizations can have any kind of private investment. I wonder, though, if there is regulation around how much of the public org’s capital can be put in private stock purchases…