sucks to hear about your friend...ive been jumped too, by 5 or six when i was young, on a dirt road- came out of it with both set of teeth thru top and bottom lips, broken rib, raw (pizza) knees and elbows, two broken ear drums, broken nose, two black eyes and broken blood vessels in both eyes to the point where there was no white left in either eye, misc bruises and lumps everywhere and two broken knuckles in my right hand from puntching back without looking.
getting jumped sucks as it is one of the most powerless feelings you can have.... the best thing to do is run if you can or get yourself to the safest spot you can away from any walls or corners so that if you can escape you can do it easier. mace or pepper spray is good to carry as well because this kind of thing often happens around bars where you cannot bring your pistol, if you were going in, so your weapon will most likely be in your truck if you have a cwp.
the one i like the most is a pepper spray fountain pen. it looks just like a pen and is very easy to carry without it bugging you like a can of bear spray or larger unit will. i allways have one on me when im in central america or mexico as you can stay out of machette range and still hit the assailant with the spray
the heel hook and the arm bar are two fairly simple submissions to learn. i imagine that you can google either of these and find some simple instructions for them. it is no guarantee by any means but is about the best chance you have other than a rear naked choke where you can put the unlucky one that gets caught in it on top of you with your back on the ground and protect yourself with his body to some extent as he will pass out in about 20 seconds and you can use his limp body for some protection while still havin ome limited protection for you head...
when you get jumped chances are you will be on the ground no matter how tough you think you are and both of these submissions(heel or the arm) are easy to get on someone when there are multiple sets of legs and arms around ya.. the unlucky one who gets caught by the submission will scream so loud that he will beg his friends to stop...even still, as soon as you can, escape and run
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"time is but the stream I go a-fishing in"- Henry David Thoreau