Putting together a business plan...

I understand the Desire to become an o/o right away.

But if you are a new driver, You might want to consider hiring on to a Company.
#1 To get the Training you need initially.
#2 To learn the different things about the industry, things you may not have thought of. Best trucking lanes, What type of Hauling is best for you, make contacts in the business, etc.
#3 If you are going through Passes, Snow, Ice, etc.. It is better to "Learn" these techniques in Someone elses $100,000 + Set-up!!
And finally, Just to get the Experience under your belt.
You may find that you Do not Like the Lifestyle as much as you thought you did. Better to find this out BEFORE you spend all your money.

BoR Thoughts.........

 

Just because you have the money and credit history to achieve the goal of purchasing the trucks and paying for everything else that goes along with it doesn't mean that you will succeed.
The first issue I see with your plan is you want to hire drivers and drive too. I won't say it's impossible, it can be done, I did it for a short time, it was a huge mistake. I spent more time doing the paperwork, resolving issues, and so many other things that I was too tired to do a good job with my truck that I eventually put a driver on my truck as well just so I could deal with all the things that you have to deal with and stay on top of.

Rule of thumb that I live by. Own trucks in odd numbers. Why? Because one truck can support itself, two trucks cannot support two trucks if one is in the shop, three trucks can carry the expenses of the one in the shop along with their own operation expenses and payments.
Just because you are leased to a company (I wasn't) doesn't mean that they handle all the problems and responsibilities that come with owning a company and having employees. It makes it easier as you don't have to be concerned with lining up the loads for all the trucks and dealing with the different clients or doing the billing etc. You do however have to keep up with it all and make sure that the trucks are being maintained and taken care of. It's not fair to the drivers to expect them to keep up with the maintenance of the truck although good experienced drivers will because that's the way they are. Of course I know I have a Type A personality which is a headache sometimes, however I could tell you anything that you needed to know about my company, drivers, clients etc. People think because they lease to a company that they have all the bases covered when in fact that adds one more thing to keep an eye on. Most companies are honest but there are some out there that aren't and you need to keep up with everything that they do for you because ultimately you are responsible. One other thing that I found, the more the company does for you while you are leased to them the more it cost. Administrative charges can get pretty expensive and in some cases you'd be better off staying in the office and paying yourself to handle all the paperwork taxes, building up your client list for the day that you can stop being leased and have your own company if that is ultimately your goal.
I say DO get a CDL and DO learn to drive and get the experience because you will need it to handle the drivers and other things that you will come into contact with in the trucking industry. I say start as a driver, work as a driver for 5 years, then decide if having your own company is what you truly want then go for it. You'll be much more prepared for it and have an idea of what you are getting into.

 

I wouldn't have a friend as an employee. It never works out and you loose a friend fast that way. If anything hire two drivers and keep it all on a business footing.

 

I'm sure you have thought of this already since you have a business background, but I'll throw this out to you anyways:

1) Buy Business Plan Pro software -- it will help you budget and get a gameplan together for all types of contingencies. You'll be able to keep focus in estimates in revenues and expenses.

2) The Entrepreneur Magazine put out a really good book on starting a business. Yes, it's a general business book but it gives you a good idea about all facets of starting up a company.

3) There are a couple trucking books for start-up. I'll have to go back and find those for you.

I'm in the same boat as you. I'm targeting a year to start a company with 5 trucks. I haven't been in the business long (2 years) but I have gained a good knowledge of lanes, rates, etc to know that I can do this on my own.

Hope this helps...