I am going to get a CDL through the local college which will be basically a one-on -one training. I can get a certificate for another $100 and a few extra tests. Is the certificate that valuable in getting work? Also; I have been a driver for over 5 years contracting (independent contractor) with various companies hauling freight local and out of state including 2 years for Fed Ex. I have driven everything I can legally drive without a CDL , mostly 26’ straight trucks or trucks pulling 25’ trailers. Does this experience count when getting work or will companies only count CDL experience?

If by CDL work you mean tractor trailer the answer is a big no. It does not count for anything.

If you are talking about driving a straight truck the answer is maybe. In this case it will all depend on the company.

Like the other post said it depends. I drive a straight truck for a mail contractor and one of their requirements were you must have 2 years over the road exp. I thought they were blowing smoke about this since it is a straight truck, but we had a guy to put in an application and he was denied because he did not have 2 years experience and he had a CDL-A I heard that the post office and the insurance companies are VERY VERY VERY VERY strict about this policy and it must be enforced because is written in the contract and the contract can be terminated if the driver or drivers do not have the minimum experience. So it all depends on who you ask or want to drive for.

Thanks for your comments.

I'm planning on CDL-A. If I went the route of owning my own truck would the lack of CDL-A experience keep me from getting regular work? Do brokers and individual companies look into how long you've been CDL? Long term I prefer to be O/O and run my own business (I have over 15 yrs in running my own business).

You might consider requiring yourself to have a minimum of 2 years OTR experience, before hiring yourself, to drive for yourself. You may have experience in running a business, but you lack Trade knowledge. Your prior skills will be very useful, and you should learn quickly. Learn on someone else's dime. Don't be in such a hurry. You have much to learn..and mistakes will be a natural progression.

I ran a Construction business myself, but I didn't get my State license and go into business, until I spent almost 7 years learning the trades. It took me about 4 years by the Grace of God to learn business after I hung my shingle.
So, I do believe in the entrepreneur spirit. Good luck.

Not having the experience will bite in your a$$ here. It is going to be very hard to get some insurance company to give you a policy. I don't know for sure about this 300 miles radius insurance but you might want to look into it. I have been driving trucks for 18 years and I would not buy a truck unless I am guaranteed $100,000 bring home pay not gross pay. I know that is impossible for me so thats why I drive for a company. Before you try your luck as an O/O drive for a company for at least 5-10 yrs get your dollars lined up and as you drive for that company try to keep a list of potential clients you may want to pull for. My dad is an O/O and he is doing well but he said the slow freight is not a problem for him its the fuel prices. The good thing for him is all the kids are grown, the house is paid for, and truck and trailer is paid for but he said if had kids and house and truck payments he would have left a long time ago. Please do not rush into a decision that could ruinig you credit, finaces, and most important your life please just drive for a company' you can found a company that will hire you. You can make good money as a company driver, I made $44,000 last year and will make over $45,000 this year.