The problem is is that you are a pessimist not an optimist. You believe that the probability of failing is better than that of succeding and you are terrified of failure. An optimist would not be afraid to take calculated risks, is not afraid of failure and would be prepared with ways to mitigate the damages should that happen. That's the description of a savvy business owner.
If he was going to finance, expand, etc. he would be sure that he had the reasonable expectation of future income to cover the costs. That's just common sense. Financing equipment with the hope of getting enough business to cover the cost is like buying a lottery ticket then buying a new car in the hope it will pay off.