OK. I am trained to wax and have done it many times before.
To begin with. Any man who is going to wax his chest, back, shoulders, legs, etc. Their hair is much longer than a woman's because we shave and shave again before it get's too long. When a man wants to wax they need to shave first. Then let the hair grow back in for 3 ot 4 weeks. This ensures the hair is all the same length and thus will rip evenly. If the hair is too long, the har will just rip off and not out.
Second. Always apply wax or sugar with the grain of the hair. Place strip over wax and rub vigorously in the direction of the hair growth. Then, always rip against the grain. Make sure you leave yourself a good bit of strip to hang onto when ripping, otherwise it will not rip and you will have to yank many more times.
I cringed at the man waxing his own chest. You can do it at home, but it is better to get it professionally done. They are professionals and professionals for a reason. They have training in such areas where you (the the man) don't.