This sounds a little nutty but if you want to be a bootstrapped Rippling, it's possible.
A trick I've found repeatable is to find an enterprise that doesn't shy away from big budgets (where six and preferably seven figure budgets are fine even for unproven vendors, because what's big/existential for you is negligible/experimental for them), and is willing to buy a product from you that requires "integration" (they love to spend money on integration, plus that means it doesn't work on day one!), where the "integration" cost is enough to bootstrap the product AND integration (and your ramen!) at your internal rates.
To avoid the bootstrap money going to overhead, to keep the money for product build (engineering instead of paperwork), you need to avoid getting "risk managed" like a mature vendor. Its best for you to be a pilot, or proof of concept, or pet project for a sponsor to show a concept they want the enterprise to do.
Pick your customers and product integrations carefully where the work will pay for the enterprise capabilities most likely to win your next sale. Use these big contracts like lilypads to cross the pond to the other side of Geoffry Moore's "chasm" between early adopters and early majoriy.
A trick I've found repeatable is to find an enterprise that doesn't shy away from big budgets (where six and preferably seven figure budgets are fine even for unproven vendors, because what's big/existential for you is negligible/experimental for them), and is willing to buy a product from you that requires "integration" (they love to spend money on integration, plus that means it doesn't work on day one!), where the "integration" cost is enough to bootstrap the product AND integration (and your ramen!) at your internal rates.
To avoid the bootstrap money going to overhead, to keep the money for product build (engineering instead of paperwork), you need to avoid getting "risk managed" like a mature vendor. Its best for you to be a pilot, or proof of concept, or pet project for a sponsor to show a concept they want the enterprise to do.
Pick your customers and product integrations carefully where the work will pay for the enterprise capabilities most likely to win your next sale. Use these big contracts like lilypads to cross the pond to the other side of Geoffry Moore's "chasm" between early adopters and early majoriy.