He can’t even acknowledge that he’s had a considerable boost in life that has nothing to do with him working hard.

It’s funny to get financial advice from somebody with a completely different economic background. If someone has their college paid for by their parents and receives financial support from them into adulthood, they are likely to assume that most everyone else has a similar economic background. Maybe for their group of friends, they’re right, but the advice they give probably won’t help someone who has financially supported themselves through college and is still paying off student loans they’ve had for 10 years. 

If you’re someone who came from nothing and worked hard for your entire life to build wealth, I think you have a right to complain about middle-class capable people who sit around and complain about their financial situation without putting in any work to change it. However, if you came from money and had a financial safety net set up for you by your family, you might want to think twice before saying someone else didn’t work hard enough for their money. Getting an inheritance or a cash gift from your parents is rarely the result of elbow grease.