I think Jackson, Bryce and other social media influencers showed him how to manage, produce and survive a life style that allows you to live in a mansion, have paid sponsorships and give a short term wealth but, his association/ friendship with Michael and Anthony have taught him the long term of maintaining that look and life of wealthy and famous. Micheal, I suspect, charges everything to a business account and so Dylan can say, in truth, that Michael does not spend "his" money on those lavish trips and hotels, that expense goes to his company and is a tax write off. Only one of them pays to rent the private jet, which I'm sure is shared by others of their rich inner circle. They all help each other, Dylan wants in on these connections to one day contribute and feel like one of the elite. Spend a little, get more back.