The tricker one for me, personally, was a slight variation on this:
- We pay you decently enough - below market rate but enough - and since you have stock options...
Due solely to my own stupidity, it took nearly a decade of hard work before I realised that gambling on other peoples' success wasn't the best long-term option for me.
Gambling on your own success is also not always a good idea. See many startups.
If you're gonna take a bet, you might as well hold all the cards.
In any case, I think you are making it sound more easy than it actually is.
Usually, the way to handle this is to build a really cheap, quick & dirty prototype and put that in front of users. Etherpad did this for collaborative editing, then got bought by Google, with the functionality folded into Google Docs. Google Cardboard did this effectively for augmented reality, and I'd bet that they're taking the learning from it right now for Google's 2nd-gen AR/VR products.
Is it inconceivable that you might think a bet on someone else is better, at least in the current time?
I'd certainly value equity in a startup founded by a successful entrepreneur with previous huge exits over equity in a startup which I don't even have a good idea for.
Of course, you should still demand a good salary. Particularly because the companies with the most valuable equity are also the ones who can pay you well. The startups paying peanuts are also, in general, useless.
You might think it is, but that's probably before you realize that, even if the company does work out, you're going to get fucked by the founders and VCs.
The thing is - if this is actually the situation, it'll usually be pretty apparent. You'll get super excited just interviewing with them. If you feel like you're "taking a bet" on working with someone, you probably are, and it isn't likely to be a good bet.
That's not really true. Businesses fail for lots of reasons which are not related to the founders doing something wrong.
If asked to bump salary (paying their technical lead, me, $60K sans benefits), they'd say "we have no money to do so". If asked to provide more equity (because that's how companies have traditionally handled having little cash-on-hand), they'd say "we can't issue more options".
That continued inflexibility, plus other things, meant it was time to leave.
There's no shame in picking a suboptimal solution if it addresses stability and anxiety concerns--it's just important not to stay if things get better and you can't upgrade the solution.
To be clear unless you are running your own independent shop you are doing this by default.
You are either chasing your dreams or someone else's - it really is binary.