I'd take the baby step to owner operator first leased to a carrier. Your plan could work if you've built an extensive contact list over the past years.
There is nothing wrong with starting your own business as long as you have the experience and money to see you through your start-up. Another is whether you are someone who is well organized. Just because someone is a good driver doesn't necessarily mean that they are a good businessman. Some people are better off staying a company driver. It is difficult to offer someone this type of advice without knowing them. You can make good money running your own authority. You can also lose your shirt. Leasing to a carrier is a good way to transition to getting your authority. If you want to get a good feel as to what it is like to run your authority, then you may want to lease to an agent based carrier such as Landstar or Jones. There are other carriers who are agent based and pay percentage. Landstar will not hold your hand. You will need to be proactive in finding your own loads, much as you would running your own authority. It is a good way to see if running your authority is for you, without having all the risk.
If you have the resources and desire to be successful and are highly motivated, then you could be successful running your own authority. There are some on this board who seem to be making it with little or no experience and plenty of money in the bank. With 19 years driving experience, you certainly know how to move freight from one point to another. Whether you can run a successful trucking business is something only you can answer. Over the years I have seen a lot of successful drivers fail as owner operators and running their authority. Many have gone back to being company drivers. Running a business is not for everyone. It takes a lot more effort to find good paying loads and do all the paperwork involved in running a business. You need to learn how to manage your time.
I have had several former owner operators who have come to work for me after not being able to make it as an owner operator. Most of them bought a truck they could not afford and little or no money to see them through difficult times. In most cases, they had a major equipment failure and didn't have the resources or credit to repair their truck. That is not a good way to become a successful owner operator. You are taking a great risk if you start out without decent credit and cash in the bank. It costs a lot of money to run a truck, whether it is as an owner operator or running your own authority. If you have been driving a truck for 19 years you should have a good nest egg by now. A good businessman takes measured risks.
Thank you GMAN I appreciate the advice. I am taking my time, and doing a lot of research. It is something I am going to do it is just a question of when. 17 years in Teamsters, #31 on a 140 driver board, 5 weeks vacation. I will admit I am not the sharpest knife in the drawer. My father told me that any time you can be your own boss, it is better than having one. Thank you all for your comments.