[7Figures2Commas]

> You will find hiring managers that literally have no idea how or why your options could be worth anything, and it's worth knowing when you're dealing with them.

Here's a different perspective for you to consider: most founders or hiring managers at early-stage startups don't have the ability to convince a reasonably skeptical person why the company's equity will ever be worth anything. It's basically a matter of faith. Most startups aren't going to have an outcome that delivers wealth to employee shareholders. You either believe that the company has the opportunity to defy the odds or not.

You say you are learning a lot, will have a good deal of responsibility and like your co-workers. In other words, it sounds like you're pretty happy and pleased with the prospect of continuing your employment with the company. A lot of people, even those who have maximized their compensation, are unhappy in their jobs, so you have something money can't buy.

This doesn't mean you shouldn't protect your financial interests and ensure that you're fairly compensated. But ask yourself what you stand to gain or lose from taking negotiations down a path that will ask your employer to convince you that whatever equity it offers you could be worth something.

The most important part of any negotiation is to determine what it is you want and need. Far too many people fail at negotiations because they don't do this. As a result, negotiations become focused on things that don't matter. You might win such a negotiation, but still come out a loser.

You like the idea of minor equity stake, ostensibly because you want to feel invested in a business that you're excited to be working for. If that's the case, you could do a lot worse than to pick a number, and tell your bosses you're really excited about the company's prospects and want to feel invested in its success. Chances are you'll have a far better outcome than putting your bosses on the spot and demanding that they predict the future.

[mvc]

> But ask yourself what you stand to gain or lose from taking negotiations down a path that will ask your employer to convince you that whatever equity it offers you could be worth something.

If you're going to be the head engineer in a startup, shouldn't you be having this conversation anyway as part of your job?

[7Figures2Commas]

As someone who has held hiring responsibility: there's a difference between asking a prospective employer for the information needed to make an informed career decision and challenging your prospective employer to convince you of its prospects to make you wealthy.

There are a number of perfectly reasonable questions prospective startup employees can and should ask that will give them the information needed to run their own exit scenarios. For instance, "What percentage of the fully-diluted outstanding shares does my option grant represent?" is always a good question to ask.

A prospective employee who demands that the company guesstimate how much he or she might make under random acquisition scenarios occurring at some unknown date in the future will stand out as being inexperienced at best and unreasonable at worst. Furthermore, no hiring manager can ethically meet such a demand.

In this case, the OP is already employed by the company he's negotiating with and it sounds like he's the one asking for equity. To request equity that hasn't been offered and then demand that the company prove it has value is a particularly awkward negotiating stance. Ostensibly he's asking for equity in the first place because he thinks it might have some value.