He never tied his own assets to the businesses, which is fairly smart, could also mean he had a set salary within the company just the same(a figure that can be easily tracked by financial scrutinizes like the IRS.)

A business can fail for many reasons outside the control of the business.
Anyone that thinks otherwise should ask everyone that lost their business due to Covid, BLM, or changes in government regulation. Could also be internal issues, some moron in the middle screws things up and the top doesn't become aware of it until the business is already falling into a pit it can't get out of.