My brother is the exact same way.
When I was in highschool, my parents told me that they would pay for my university education. I studied hard, got some scholarships, and also worked part time to contribute towards my education. And then my first tuition bill came in and my parents told me that they wouldn't be paying a cent towards my education. That was okay, their money their choice. I was a little upset because I would have saved even more if I hadn't been told that they would pay my way, but hey, paying for my education has taught me a lot of things. I didn't qualify for government grants, or government sponsored student loans because my parents make too much money. I finished with a little bit of debt, but nothing I can't take care of now that I've graduated.
My (younger) brother on the other hand... he knew that he wouldn't be getting help from my parents, and that he wouldn't qualify for government grants or government loans. Instead of getting a job in highschool, he signed up for a 40k line of credit, maxed it out, got my parents to co-sign on another 40k, and it just keeps going. I did 5 years of a professional degree while living in a very expensive city. He's done 3 years of a much cheaper degree while living at home.
My parents are terrible with money, and he seems to have learned from them. I wish there was something I could do, but nothing I have ever said to any of them sinks in. They make fun of me for "living like a monk", but to me, you can't put a price on peace of mind.