Hi cs-szazz. I remember being in your situation; it's frustrating because you can't Google for answers. Here is advice I was given when in a similar situation.

- Find the other people at the company in your situation (size of grant, type of options). Share your learnings with each other. Consider getting professional advice, the Bay is full of attorneys and CPAs for whom this is a familiar situation.

- If you're at a unicorn, you probably have co-workers who are veterans of other unicorns and have been through this before. Ask them for advice (or an introduction to their source of professional advice)

- As a group, consider asking your board to arrange a limited second market sale to cover exercise costs and taxes. Many institutional investors are happy to buy a little extra stock, especially if it helps with keeping senior staff happy and focused on the right things.

- If you're going to be doing anything involving stock without board approval (like trying to build some kind off house-of-cards, pseudo-legal collateral package for a loan shark) you really need to hire an attorney.

- if you only have options, you might not be a shareholder. Your rights and access to information might be different once you've exercised a share.

- You can't extend the 90 day exercise window on ISOs, that's a federal law thing. The company can convert to NSOs to extend the window, but the setup for that conversion is complicated and expensive.

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!

Options being dangled in front of employees to trick them (only later to find out they can't afford to exercise it) is infuriating - it's almost fraud imo.

100% agree. I'm in the low 7-figures right now (on paper), and will probably be mid-7 with the next round of funding. So I have 0 chance of affording the taxes if I wanted to leave, and am kind of at the whim of the board if they want to extend my window.

It's not a great feeling, especially when you contributed a lot to the company at a very early stage. I am glad there's companies popping up to help with this problem, like ESO Fund, but in my opinion the companies should be trying to fix this instead.

Without knowing your exact situation, one thing to keep in mind is that the preferred value (last valuation / # of shares) of a share is generally a good bit higher than the tax liability (value of a common share from the 409a minus your strike). Still likely a big tax hit, but perhaps slightly better. IMO changes to tax law for illiquid assets is the best but most unlikely option here.

Yeah it's a good call out, in this case FMV is about 1/3rd the preferred. Sadly the that still puts it out of reach for me, but means I can afford to exercise at least some.