Start with what you know:
You wrestled in school.
You played football.
You've beat down a few twerps.
He's not as big or crazy as you, so the last lesson, apply in reverse.
Do slow wrestling with him. Just get on the floor and talk to him while he tries to roll you around.
Then stand against a wall or fence and wrestle with him. Teach him how to get the advantage position and not bore in, but push off, get behind, get past you. I call this goon surfing. Wrestling with you, who he cannot overpower, as you speak with him calmly, will help him relax and seek the advantage position. Mario Sperry, "the Zen Machine" a top BJJ/MMA pioneer recommended doing Jiu Jitsu against a vertical surface, not on the floor. You get your head kicked in by third parties on the floor.
Next go to boxing. I will send you a copy of The Punishing Art. For him, all he needs is a pair of boxing gloves. Let him hit your palms without bringing them to him. Hold your hands steady and resist the temptation to meet his punches. Alternately, place your free hand on his head and sometimes shoulder, letting him know that his goal is to hit both of your hands without you touching him with either. You might not feel confident in your knowledge of boxing. But, your wrestling ability is a better governor for his self-defense boxing ability than most references. The danger to a boxer, in a self-defense setting, is getting grabbed by some big redneck out of the Utah wilderness.
As far as coaching him in boxing, some of the best boxing coaches never boxed. You just have to understand what you are seeing. You don't have to be able to do it.
Good luck and address any specific questions to me and I'll answer them.
Thriving in Bad Places
James, this could be a very valuable thread. I hope you keep up with this topic.
Ishmaelmy two cents' worth would be 1.) to get him interested in building basic bodily strength to go along with skills and tactics. What I used to do with my kids was "pennies for pushups, nickels for chinups". Their allowances were based on the (observed) number of those exercises they did each day. 2.) Give him a path to developing a warrior self-image. Reading the Robert E. Howard books would be an example of giving a boy an idealized image of what he could become, if he was willing to put in the effort.
Thanks Shep, the hardest thing for me to wrap my head around is the laziness, they do not understand what it takes to build a strong body, plus their parents have been to easy on them. I explain my path as a young man, they look at me like I have horns growing out of my head, at 14 I was throwing baled hay, summer hauling, winter feeding, most all the young men had jobs like this, we also had sawmills to work in, try the green chain for a day, it was hard but a great time to be alive, the sawmills ranches, dairys, are gone, it prepared me for the real world!
Muay Thai involves a lot of grappling and Greco-Roman style wrestling.
I think Tony Blauer is the best place to start for quickly learning self defense.
For strength, pick up "Starting Strength"
Ishmaelhang in there. You are doing a good thing by being a mentor to this lad. Normal boys in our society are desperate for masculine role models. Any improvement you can help this kid make is a step in the right direction.
More:
biggerfasterstronger.com/uploads2/13_JanFeb_26.pdf