> But how are bootstrapped companies without access to large capital reserves or investment supposed to come up with the money to pay these tax bills while they wait it out?
You can go to the bank and take out a loan. It's called a "factor loan", and tax receivables are solid collateral.
Oh, it's worse. You also have to have your books in good enough shape for the bank, and submit them regularly. It's like doing taxes twice. Having your books in good shape is a good idea for many other reasons, but it's one more thing.
Better than bankruptcy, though, and it's often better than accepting VC terms.
You can go to the bank and take out a loan. It's called a "factor loan", and tax receivables are solid collateral.