I can't agree with the comment above enough.

I have seen this situation far too many times (both with myself earlier in my career and with friends) - employees feel loyalty to their employer, but it is a one-way street. You have the added pressure of shouldering all of the technical work for the company.

There are too many red flags in your story (legal fees being too high to give you stock should tell you how much they really value your work). I think it is shocking that they didn't put you on a stock vesting schedule as soon as your trial period is up, considering that you are building the product. You should be the CTO/VP of this company, and part of that founding group - yet they want you to build the tech but treat you as a low-level employee.

Find a new role and quit asap. You were smart enough to see that the company is sinking, so use the experience you have gained from working for this company to find yourself a good role in another startup, or work on your own and teach these lessons to others as a consultant.

The alternative is an example that I went through myself. I was in a similar situation - in the financial field with a solid group of founders, the only tech guy etc. The company (this was 99-00) was running out of money. I re-negotiated my role to be the CTO, negotiated a solid slice of the company stock and built a fresh new prototype of our platform in 6 weeks - complete with integrated analytics, customer management and support (using a third party platform). We used the prototype and business plan to raise a new round - I got a pay kick at that point and a budget to bring in 5-6 developers. We fired a lot of the business people who were not doing a lot (they bought their big financial company work ethic with them to the startup). 18 months later we were acquired by a large financial firm, which was a solid outcome for all involved.

Why do they only want to give you a share when they're revenue-neutral?

A limited company, their liability is extremely limited, I'm assuming it's not a partnership. There's no reason for them not to give you equity right now.

From what they said was that to give out shares at this point would require additional lawyer fees. They are already formed as an S corp (I believe), so I'm not sure how much lawyer fees would be required, but nevertheless, I was young and naive when I first started (this is my first startup) and probably should have pushed a bit harder.

The truth is that they might actually believe that they'll give you a "big slice of the pie" once the money starts rolling in but in reality what will happen is that they'll a) get greedy and b) be able to afford someone(+) to replace you if you complain too much.

It's just aaahhh business and you're out of a job with no pie.

A startup whose founders can go on holiday for a week can afford lawyer's fees.

Vacations needn't be expensive. Sure, there's a loss of one week's income generation, but it's possible to have a fantastic week away on what it would cost to talk to a lawyer for half an hour. Some examples: camping and fishing, eating what you catch to save on food; rock climbing; backpacking; etc.

yeah, but the opportunity cost is pretty high.

"give out shares at this point would require additional lawyer fees" -> translate: they don't want to give you shares.

Don't get too excited about randomly leaving unless you have a particular plan in mind. If you don't have equity, it's definitely a good idea to separate yourself emotionally - but if you've got a steady paycheck, there's no reason not to keep cashing them until you have your next step sorted.

This is spot on. I think at this point I'm seeing the light, but just because things are looking like they'll end badly doesn't mean I'll put myself in a worse position because of it. Good call.

Actually, I'd counter that.

Getting out of there will make you way more available for opportunities. And almost any opportunity is better than what you're doing now, so I would get out in a hurry.