Here's what I would do if I were you, blake. I would wait till the season hits(coming up quick), then just quit your job and try to go out on your own. This way if you realize that its harder than you thought, and you have to throw in the towel, your old boss might still hire you back, cause he knows your a good worker. But, if you wait till he fires you, then your ARE on your own. Also, IXT is right about the accounting, it will cost more than you know. I am lucky enough to have a family member do my accounting, but if you do pay your taxes, you will be surprised at the headache that keeping track of every reciept, logging every mile, etc. will be for your business. I would just use what you've got till you can afford a dump truck that is 5-6 years old. then you won't have to play mechanic every day like I do with my 80's era chipper, and 1999 grapple truck! You can do it, Im only 23, so your not the youngest guy trying to go out on his own.. I would'nt underbid your boss ever.. just try to get jobs that he's not bidding on.