[kneath]

Yes, there are several strategies. Each of them impacts significant discount on sale price, requirements to make a sale, or significant risk to option holder.

Kind of like saying "anyone can buy a car without having a job or savings" — it's true, but those deals aren't comparable to those that can buy a car with cash.

[toomuchtodo]

There are funds/financial firms that will fund your options exercise, and take nothing if your common shares go to zero (they take a cut if there is an IPO or other significant liquidity event). Its an equity-backed loan with no recourse.

Appears to be a reasonable option if you have a large amount of options and prefer the cash now vs later.

> All of these deals require approval by the company. Which means you don't get to choose the firm, you get to deal with the firm they approve of.

EDIT: These transactions require no agreement from your company in order to execute.

[kneath]

I … oof. I'm sure this stuff does look good from the outside. From experience, it is not anything close to that.

Most stock options have short expirations (10 year is still very uncommon). There is no "now vs. later" choice, it's a "now or never choice"

All of these deals require approval by the company. Which means you don't get to choose the firm, you get to deal with the firm they approve of.

That kind of deal is in the 1% of deals they make. Almost all require option holders either repay loans or take on significant risk.

I know this stuff sounds great on paper, in practice it is another world. Not to mention the absurdity of giving away half or more of your gains to a private equity firm from options you earned, just because the company has made a weird rule.

[jeremymcanally]

Typically these transactions are practiced on exercised options (i.e., shares) not options. I've never seen that offer for options.

And they're right, it is fairly risk free. The investors understand (and sign a lot of paperwork indicating that) they understand it's extremely high risk and will possibly end up that (a) the shares will be worth nothing or (b) the company may never, ever offer a liquidity event. In the event that they do, the shares or derived value thereof transfer to the lender/investor. In the event that they don't, the instrument performs exactly like a loan/promissory note backed by the equity the shareholder owns with no vehicle for enforcing repayment beyond derived value from the shares.