I am not convinced that most lose their shirts. I know several companies that lease trucks to carriers and even provide the drivers. Those drivers are W-2 employees, not some 1099 driver kind of thing. IRS frowns on the 1099 for a driver thing.
I could easily do it profitably if I had the motivation to do it. My single truck operation is an LLC with a S Corp tax structure, and the truck is leased on to a carrier. I am an "employee" driver of my own company, and I am the President of the company. Just one truck. I pay myself a weekly W-2 salary. Profits from the company are passed on to me as distributions from my company. And my company even pays for medical insurance for me and the wife (BCBS 5 million dollar coverage policy) and other stuff. I paid myself $3000 in August as a driver ($750 a week irregardless of miles and time off which is average W-2 truck driver salary for my area of the country), and the net profit after payroll and all expenses was $6300. Even paying a W-2 driver $1000 a week would be profitable based on my operation.
It is possible when actually set up and run as a true business instead of some Billy Bob trucking operation. Gman is not way off the reservation as you seem to imply.