It appears to me that you prioritize the friendship over the financials, which can be a valid decision. If that's the case, you might just have to accept that you worked for free to nurture or sustain this friendship.
But if this is about a girl, then I worry that you already lost. Even today, most women still subconsciously expect their boyfriend to be able to provide for them, if it becomes necessary. For that criteria, a boyfriend that cannot successfully negotiate deals to his favor is an unsafe choice. That's why guys who pretend to have complete control do so well.
That said, it seems like you got one very good lesson on accounting for software development here, which will help you avoid similar issues in the future.
When I do free work, I always send invoices and then simultaneously grant the start-up a timely unlimited credit on the amount. That way, they don't have any cash flow issues, which is the main worry for any startup. But you'll be listed as "payed in $ X in working time" in their bookkeeping, which means both you and them and their investors know precisely how much money to send your way to pay you off.
The only annoyance with having invoices in their books is that you have to pay profit taxes on the owed amounts. But of course you get those taxes back should they tank and not be able to pay you anymore.
But overall, I believe that most CEO and sales types will not value anything that isn't listed in their finance books. So make sure you show up in their term sheet with a high $$$ amount next to it, or else they won't take you seriously.
Oh and in most countries, the tax and legal stuff is really cheap. I would be surprised if that is anything more substantial than a tactic to get you to commit quickly.
But if this is about a girl, then I worry that you already lost. Even today, most women still subconsciously expect their boyfriend to be able to provide for them, if it becomes necessary. For that criteria, a boyfriend that cannot successfully negotiate deals to his favor is an unsafe choice. That's why guys who pretend to have complete control do so well.
That said, it seems like you got one very good lesson on accounting for software development here, which will help you avoid similar issues in the future.
When I do free work, I always send invoices and then simultaneously grant the start-up a timely unlimited credit on the amount. That way, they don't have any cash flow issues, which is the main worry for any startup. But you'll be listed as "payed in $ X in working time" in their bookkeeping, which means both you and them and their investors know precisely how much money to send your way to pay you off.
The only annoyance with having invoices in their books is that you have to pay profit taxes on the owed amounts. But of course you get those taxes back should they tank and not be able to pay you anymore.
But overall, I believe that most CEO and sales types will not value anything that isn't listed in their finance books. So make sure you show up in their term sheet with a high $$$ amount next to it, or else they won't take you seriously.
Oh and in most countries, the tax and legal stuff is really cheap. I would be surprised if that is anything more substantial than a tactic to get you to commit quickly.