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From all the owner operators and lease operator I know personally, none of them remained in the trucking business. They seemed to be happy when I first met them, but now they don't care about trucking at all. They just tell me that it had caused them too much headache.
One guy is now working for US Postal in the office and another guy opened a Mexican Restaurant in Kuwait. None of them are in the trucking business anymore.
I think you can have more success as a Freight Broker/Agent.
Owner Operator:
An owner-operator is a driver who either owns or leases the truck they are driving. A self-employed driver.
DAC:
Drive-A-Check Report
A truck drivers DAC report will contain detailed information about their job history of the last 10 years as a CDL driver (as required by the DOT).
It may also contain your criminal history, drug test results, DOT infractions and accident history. The program is strictly voluntary from a company standpoint, but most of the medium-to-large carriers will participate.
Most trucking companies use DAC reports as part of their hiring and background check process. It is extremely important that drivers verify that the information contained in it is correct, and have it fixed if it's not.