He obviously has talent that, properly nurtured, could lead to a career ... Personally, I would suggest that he try to get away from sounding like Sinatra ... how much of a career could he have as a "sound - alike" ? ...
When I first replied, I had in there that I don't know if he is trying to sound like Sinatra or not. Is he? Regardless, he could have a career with a Sinatra tribute, a crooner's tribute (several of which he could sing their hits), or, just doing his own thing. It's rare to have that kind of voice. And can play, too. With an Italian name and even looks Italian, haha. Heck, he can't lose.