I think you hit the nail on the head, it's frustrating because there's no clear answers, very little resources on the topic.
I'm actually in Canada, so I'm not sure on the ISO -> NSO distinction.
I do think your advice about coworkers is good though, I know of a couple other early employees in my position (similar grant sizes, also unable to afford to fully exercise). I've often considered what would happen if all of us decided to push for an extended window (and convert to NSO's)
As for the secondary, I don't actually want to sell. I want the ability to wait until there's liquidity to sell, and do it on my terms. Selling now significantly reduces future upside. What I'm really trying to avoid is getting stuck at one company because I can't afford to leave in the future.
I do appreciate your advice though, always good to chat with someone who's been in a similar situation!
I'm actually in Canada, so I'm not sure on the ISO -> NSO distinction.
I do think your advice about coworkers is good though, I know of a couple other early employees in my position (similar grant sizes, also unable to afford to fully exercise). I've often considered what would happen if all of us decided to push for an extended window (and convert to NSO's)
As for the secondary, I don't actually want to sell. I want the ability to wait until there's liquidity to sell, and do it on my terms. Selling now significantly reduces future upside. What I'm really trying to avoid is getting stuck at one company because I can't afford to leave in the future.
I do appreciate your advice though, always good to chat with someone who's been in a similar situation!