Hello everyone! Thank you for taking the time.
I’m soon to turn 22M and currently working as a yard jockey at a company named after a South American rainforest. Been working inside the warehouse since 18 and at 21 I became a yard jockey as I’ve always been around trucking and fuck the inside work. They’ll be sending me to CDL school in April and upon completion, I will keep working there over the summer as I finish my degree (they help pay a bit) in cybersecurity. While I stay and finish my bachelor’s, they schedule us for “runs” 150mi radius nothing crazy so I’d be getting road experience although not much.
My father has been a diesel mechanic all his life and has dabbled in trucking here and there but doesn’t last long as being a mechanic is his passion. He’s always buying cheap trucks and flipping them after some work and cosmetics. He has this 99 Freightliner FLD Classic that he’s been wanting to custom out as a project but never gets around it and wants to pretty much give it to me… I’d be a fool not to take this truck right ?? I don’t wanna sound spoiled or anything as we come from the gutter and definitely understand the value of things but I say this to say I’m in an extremely blessed position in my eyes which I’m grateful for and I want to take FULL advantage of it.
I have done everything on the business side of things except IFTA and Insurance as I still have time before I want to proceed. LLC, MC, DOT, DUNS, EIN, etc are good to go. Insurance is going to be a bitch but others around my age and younger have done it so why can’t I?
Question is: If you were in this situation, you got a CDL and a Truck, would you go Owner Operator or go be a company driver for a bit then take a shot at it as OwnerOp?
If you do go OwnerOp, in this situation, would you try your luck on load boards or lease on to a company? Would you lease on to a mega or someone smaller? Everything has its pros and cons but If the OwnerOps of Reddit had to do it in this situation how would you go about it?
THANK YALL IN ADVANCE!
(please don’t bring up or mention anything about going into IT with my degree. This is my backup plan if this doesn’t work out for me. I am not a fool.)

