The whole point of bootstrapping is that you risk almost nothing before you have some positive feedback that suggests you can risk more. You bet a nickel that you can sell something for a dime. Then you bet a dime that you can sell something for a quarter. Repeat until you're Bill Gates and you're betting a football team that you can make a lot of money leasing the Eiffel Tower.
If you lose at any point, you can take comfort in the fact that you haven't lost more than you know how to make.
I was never in the hole more than $60 plus my own time. Seriously, some days I think being a computer programmer is too darn easy to be legal. We bang away on a keyboard, whammo, value ex nihilo.
If you lose at any point, you can take comfort in the fact that you haven't lost more than you know how to make.