Do you have the cash and definitely want to take all the risk of an exercise? I used ESO Fund in the past to buy shares that were too expensive in exchange for a chunk of the upside.
I think the IPO is a matter of when. But question is if I switch companies - would I still keep those options to be exercised after I leave or before I leave? If the company goes IPO, the question is moot
That depends on what your stock agreement says. Each company has its own rules. Look for it in your offer package.
Don't know your specific contract but most companies give 90 days after leaving to exercise options. Whether the company has IPO'd in the interim is irrelevant to your ability to buy them.
No one wants to buy your WeWork stock. Just except its worthless.
I think the problem is you are likely not going to get much from a private marketplace since the IPO devaluation is well documented. In other words wework had a hard time finding buyers in the first place so that will only be worse for you as an employee. That is a big risk IMHO.
I may not want to sell the exercised options till I see how IPO performs. But I'm wondering I can still have the option to purchase the stocks at the strike price. Hopefully all of this verbiage is in bold letters in my Grant docs. Tx for the feedback!
Search for secondary markets. Also check your agreement
Are you afraid the company won't make it to IPO? Anyway, from a quick search you can either get your company to buy them back from you, or you have to find someone to buy them. It looks like there a few marketplaces for this type of thing, just gotta search for it.