The first place you should start is insurance. Unless you can get insurance you can't even get your authority. Without at least a couple of years experience you may find it difficult to get insurance. Commercial truck insurance is a very specialized segment of the insurance business. Progressive will usually insure inexperienced drivers, but you will be limited as to where you can go.
Although you have been driving a straight truck it will likely NOT be considered as experience by carriers or insurance companies unless you have had a CDL A license. Insurance companies usually check to see how long you have had your CDL. If you have had your CDL A for a couple of years then that may suffice to qualify you with some insurance companies.
Due to your lack of experience I would suggest that you go to work for another carrier to gain some experience. Pulling a flat is a bit more involved than hooking to a box or van. It can save you a lot of headaches. If you don't want to go to work for a flat bed carrier for a while then you will need to find someone who is willing to train you in load securement.
If you decide to proceed with your own authority you will need to have registered agents in every state in which you plan on doing business. OOIDA will do this at no charge for current members. There are services that will do it for an annual fee. A registered agent is someone who will accept service for you in a state should you get sued for any reason.
Once you have your insurance and registered agents on file you can apply for motor carrier authority. This can be done online for $300. Again, there are services that will do this for you, but I can't see paying someone to do what I can do for myself. I would allow 3-6 weeks to get your authority once you have submitted all the paperwork. If you want to pay someone to do it for you OOIDA and others will do it for a fee in addition to the filing fee charges by the feds.
If you are to pull a flat around you will need a trailer, tarps, chains, binders, straps, etc., Trailers can range from about $5,500-15,000 for a used flat. Securement equipment should run about $2,200-2,500 for new.
There have been a few members who have started without any experience. Without experience you should plan on having a good amount of cash to keep you going until the money starts to come in. There will also be a learning curve. It takes time to learn any new business. It is a big leap going from driving a straight truck for a company locally to a flat bed over the road under your own authority.
You need to have some knowledge about operating costs. OOIDA has a spreadsheet on their website which might help you. It isn't 100% accurate, but it is a good start. You can plug in your personal numbers and find your estimated cost of operating your business. Unless you know your operating costs you won't know if a load is profitable for you or not. Remember each load is a negotiation.
Starting out with no experience there is another obstacle you will need to overcome that we don't discuss much with new people and that is where to run. There are some areas of the country that are best to stay away from due to the cheap rates and lack of available freight. You can subscribe to some loadboards to help find loads. It is important to establish good contacts as you go along. I rarely use loadboards. When things slow or I am in a bad area, I may use them. I prefer to rely on my personal contacts that I have made over the years.
One other thing that I would caution you about starting out is how much you pay for your equipment. If you plan on financing your equipment I would suggest keeping your payments as low as possible. I would not want to have a payment more than $1,200/month. In fact, the lower the better. You should be able to find some good deals around. Getting financing can be a challenge these days. Since you don't have any experience financing equipment it could be even more difficult. A good down payment would help in getting financing. Another factor they consider is how much experience you have in the type of equipment you want to finance. You should be able to buy a decent flat and tractor for $25,000 or less. As the economy slows there should be better deals around.
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