I'm under intense pressure to deliver the update with the idea that it will enable them to generate enough money to pay off their debt, but this seems fundamentally wrong to me. Is there some other deal that we could work out quickly that would be fair to both parties and something that their board might agree to?
Secondly, do not deliver the update. That's the only thing you have that might give you some leverage. If they can't pay now, don't count on them being able to pay later. As others have suggested, a sizable portion of the company stock might be another option if you like to gamble. You'll have to think about the valuation, of course, and what the company might be in the future: a reasonable compensation might be 0.1, 1, 5, or 20% of the company. Given the current state of affairs, the stock becoming worthless is also one fair possibility.
If the company is as penniless as it seems there's no point in even suing to get paid. Next time, stop deliveries after one month if payments stop coming in.
Spoiler: because it's easier and cheaper for them to sucker you into doing work for IOUs.
Ask for the cash or a piece of the company. Once you hand over the code, you don't have a lot of leverage.
Hard truth: the chances of you getting any of the money you’re owed, and any more on top of that is incredibly small. So small that the probably might as well be 0%.
Businesses that are going to be successful do not have a year+ of unpaid debt. And they are not betting their farm on an outsourced deliverable. The people you’re dealing with are “playing business” the way children “play house” except they’re doing real economic damage to everyone around them, yourself included.
That said, I can’t imagine this is real and is likely just someone trolling which is becoming increasingly common on HN.
Make dam sure the company does not have access to the code in the interim.
If the company is in as dire straits as you believe there's every chance you're never going to see your money.
Sales projections for the new release are just hot air, the may come true and they may not. If the principals are so sure of the sales projections they can go and find some investors to raise the $250K. In the meantime you not providing the update may leave you open to various types of legal pressure and that's just one of the reasons you need legal representation.
I've been in this position for much, much less money. Like you the amount outstanding slowly, slowly grew and because I was more interested in tech than money I allowed it to happen. Don't allow the same thing to happen to you.
Firstly, on the face of it, it looks like you are taking all the risks of equity without the possibility of a payday.
Secondly, if the business is owner-managed you’re in a strong position to ask for an equity stake in lieu of cash payment. That might be preferable to you.
But as suggested above, legal advice would be useful at this point.
Do not deliver the work until you get paid or they give you equity.
If it's not you they owe, you shouldn't be doing anything different than your contract specifies.
Do you mind working for me instead? My projections are $20M revenue in 6 months after deployment. I estimate it will only take you 6 months of free labor to finish my project.
Also, if they have a board, it sounds like they're not actually a small client, which means they can easily pay you what they owe you. Can they pay the salaries of their management? Then they can pay you.
Var DFN: you do deliver, they fail and don't pay
Var DSN: you do deliver, they succeed and don't pay
Var DSP: you do deliver, they succeed and .. pay you? Why should they?
Your chance is 1/4 at best and 1/8, 12.5% realistically.
You credited them with $250k (1/40 of a potential revenue?), you won't find a quarter of million lying around.
As others already said - forget about that $250k. You now have a gambling chance to get something (way lower than $250k), but only if you demand the cash upfront.
PS: technically there is a variant NSP: you don't deliver, they succeed .. and pay you. It is only interesting in what it lowers your chance to 1/10. *grin*
case 1: it resolves the situation. you probably get paid? case 2: it won't. you loose a lot of money
your bargaining chip is the update and you should use it as collateral. as one can easily misstep by impulsive action, you should get advice from a lawyer how to proceed to secure as much payment as possible. probably additionally implementing kind of a kill switch so your moneymaking update cannot be used after bankruptcy without your help/key. from my own experience: when we talk about bankruptcy it helps to act fast, so speed and options to pressure money from them help most. threats will just complicate the situation so please get a competent lawyer involved as soon as possible as you are entering a legal minefield; doing it yourself just guarantees higher risk to step onto a mine.
good luck