I don't bother him too much about it as long as his grades are good and responsibilities around the house are met. Every so often i'll scroll through his phone but haven't found anything you wouldn't expect from a typical 8th grader. I don't come down on him for language or crude jokes or anything like that, i'm looking for actual danger and not 14 year olds being 14. He knows I have the pin to his phone and he could change it to make it a bigger issue between us but he never has and in return i won't confront him unless i feel like it's a very serious issue.
Data point: everyone in my HS's class of 1200 who was "cool" is now more or less a bagger in a grocery store, or dead from drug overdose. Everyone who was ostracized and a "loser" is successful.
Do you want your kids to have a happy high school time (4 years) or a happy life being able to afford fun things(~60 years)?