I have a friend (for real this time), who is a longtime pilot, flys at least 150hours a year and probably has had is license for 25+years. Holds a private license owns his own single engine 6 seater. Problem is he has no problem flying IMC busting ifr. Doesn’t file flight plans. Doesn’t go up when it’s horrible mind you but doesn’t let weather stand in his way. Went up last week for an hour flight and will causally admit he was IMC for 10 min in a 1 hour flight. A mutual friend has and continues to give him a lot of crap about it. We have tried to push him to get his IFR rating. I am currentlt getting my IFR rating and working hard at it. My buddy is an IFR and commercial pilot. We both kind of lean on this guy and he just passes it off, excuses range from “I can’t pass the written..” “don’t have time to do it..” ect. I actually thought that by me going for my IFR it would stimulate him to just get it done. Advice on how to approach him differently?? I don’t want to see him get hurt one day nor do I really want to be in the air in IMC when I see his plane out of the hangar either. You’d think sooner or later a controller would flip. We fly out of an uncontrolled airport though.