He thinks Jesse is kind of an idiot, but he can relate. At the very least he seems willing to help out folks, especially the younger ones. He mainly sees Jesse as a source of money, and maybe a bit of chill conversation and such. How Jesse managed to get so much money and not get arrested he isn't sure, but he'll roll with it. Deadpool doesn't really judge Jesse on his habits or business, after all its what he's been doing for most of his life. He's keeping it as business like as Deadpool really can for the most part. So long as you can pay, he'll do some jobs for you.