It seems to me the best avenue to move from middle to upper class in the US has been real estate. If you start early, you can continually leverage your building equity to get loans for purchases of more property. US tax law is extremely landlord friendly, allowing you to write off "depreciation" of real estate, while you can also write off any cost of improvements, even as the market appreciates. Aggressively working on a real estate portfolio for 30 years gives a good chance of breaking out of the middle class. I can point to a couple of people that have done so. I bought a house with two other friends and rented it for a while. It was an enlightening experience. I wouldn't have been able to get started on my own, but after we flipped that house, I could have gone off on my own and expanded if I wanted to.