[berberous]

The strike prices of options are set based on a 409A valuation.

These are "cashless" loans, which are recourse for tax purposes (so that the IRS respects this as a true purchase of shares, in order to start people's LTCG and QSBS clocks). The terms were likely very favorable, i.e. set with an interest rate equivalent to the AFR. This is not a situation in which the company is trying to make money as a lender.

This is no riskier than deciding whether or not to exercise your options, which typically employees have to decide within 3 months of leaving a startup.

The risk is not in the terms of the loan, but in whether the employee wants to exercise and lay out the cash (or the promise to pay the cash); in each case, it's an investment decision to decide whether it's worth it given that the stock is risky and could eventually be worth zero.

Note that all these issues are driven by tax rules, and generally not the startups. Startups are damned if they do, damned if they don't.

Every type of equity has pros/cons. If it's an immaterial amount of money, the employee should be a big boy and just decide whether or not to risk the cash. If it's a material amount of money, the employee should really be speaking to their own advisors, which if they have a material amount of equity, they should be able to afford to do.

[synu]

If you can’t afford to buy your options, but take out a personal loan to buy them, that must have been a riskier approach than just buying them if you had the cash, no? The leverage increases the personal risk at least as I understand how that works.

Unless there was an agreement to forgive the loans if the options go underwater, which I haven’t seen reported here.

[SamReidHughes]

It depends on what your future income stream looks like. If you're a 22-24 year old software developer, getting to take on low-interest debt in an inflationary environment is a great deal. It's losing money on the stock that is the problem here.

[synu]

If it requires predicting the future isn’t that by definition riskier?

The potential outcomes if you spend money you have are that you recover your money (break even), lose the money, or make a profit.

The outcomes if you take a loan are that you break even, make a profit, or acquire a debt that you by definition weren’t really able to afford in the first place (or you would have just used the resources you have to fund the exercise).

I feel sorry for anyone who was hoping they were young and had tons of upside potential, who now needs to service a loan that they will never see a corresponding asset for, who is about to face a quite difficult job market for juniors.