Operations Manager to O/O , am I crazy?

A little on my background. I have a bachelors degree in fine arts and worked in graphic design for many years until I decided I would get into my fathers trucking company. He had been a corporate at Southeastern Freight for many years and ended up starting his own reefer company in SC with a fleet of 20 trucks, a drop yard and a small brokerage. I started out cleaning trailers and doing yard checks, learned billing and dispatching and in a few years I was running most of the company while he played golf and maybe entertained a few customers. The plan was for me to take over the business until the recession hit and things got lean. To make a long story short, a man with his own private jet bought our company and Ive now been unemployed for over 6 months.
I have very little money but I'm a hard worker and one of the things Ive noticed about the drivers I've managed or the Owner Operators Ive hired is that they can make ALOT of money if they hustle and are smart. Ive always known you will never be rich working for someone else so Ive come up with a plan and Im hoping you salty road dogs can give me some advice.

I'd like to get a truck, bust ### enough to make a tiny bit of money and hopefully try to get a small fleet of 3 or so trucks in 5 years. I think with a few trucks I can run the operation with low overhead and make a little bit of money.

Heres the bad part. Im a manager not a driver, I dont have a cdl and all Ive ever done is practice backing with an ottawa in the yard a few times. I figure i will have to drive one truck for at least awhile.

also Ive heard so many horror stories from cr england drivers and other companies and I know that they dont make any money the first two years but after that you are golden as smaller companies can put you on insurance.

whats the best way to get driver training? Whats the best way to get truck financing? Am I ####### crazy? I have no customers now but once my no compete clause is up I think I can keep a few trucks busy. I guess I need a comprehensive plan and some good advice. Thanks guys! I look forward to hearing what you have to say

 

thanks so the company training is not the way to go? Before selling the company I had started to study to get a cdl but didnt really want it. If I had the foresight to see where I would be today I would have followed through while I owned 20 trucks and had a staff of professional drivers to instruct me. lol. Are you saying to get experience as a company driver before buying a truck? how long do you think it would take to get a good feel for the driving side? I know my insurance wouldnt let me hire a driver with less than 2 years experience and assumed it was that way in most of the industry