Ditto what everyone else said. Go drive for a big company and get your CDL there, for a number of reasons.
One of which (from an O/O standpoint) is that your dad won't be able to put you on his O/O insurance (if he's operating with his own DOT #'s and not leased onto anyone else) until you have a years experience.
I looked at going O/O out of the gate a number of years ago, and one of the biggest issues was not being able to get insured (aside from the insanity of making a near $200K capital investment just to get rolling).
Rick
A CDL is required to drive any of the following vehicles:
A department of the federal executive branch responsible for the national highways and for railroad and airline safety. It also manages Amtrak, the national railroad system, and the Coast Guard.
State and Federal DOT Officers are responsible for commercial vehicle enforcement. "The truck police" you could call them.
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Another "work for someone else" vote. The main reason fits with the rule "never be the one to teach your child how to drive". You will both end up in frustration and anger.
Also, as a new driver, the resources of a large company will help you get started better than relying on your old man for equipment and training. Once you have a few 100,000 miles under your belt, then talk to your father about driving together ... and with the experience issue out of the way, your drive insurance will be way less than as a rookie.