Bootstrapping a business in some ways seems more like solving chicken and egg problems.
It is harder to hire since you don’t have a team. Harder to build a team since it is hard to hire.
Harder to get customers since you don’t have customers. You don’t have customers since it is harder to get customers.
You don’t have credibility since you don’t have enough customers. You don’t have enough customers since you don’t have credibility.
It is harder to raise money since you don’t have money. You don’t have money since it is harder to raise money.
Most problems in building a business boils down to chicken and egg problems. Once you are past that, you either have the chicken or the egg, the general economics and theories start to apply. Before that you have to solve the problem. I guess that is the main challenge of bootstrapping a business. That is the hard part. And maybe that is why it gets easier after one success.
There are multitudes of ways on how to get past them in every scenario. They have costs associated with them. Costs in terms of risk, investment, effort and time.
But modeling the bootstrapping process in this way simplifies them in a way. It is not that the world is coming against you, you simply are solving for something else. The perspective helps you see the problem in a different light. And thus helps you to look forward past it.