I Made Six Figures A Month On Wall Street...Then I Was Eating Out Of Garbage Cans

Rise Above with Kevin Lanning · Oct 7, 2026 · 1h 17m

Ray Rapaglia had the life most people chase — a six-figure-a-month Wall Street career, a nightclub he owned with other brokers, celebrity parties, models, Ferraris. But none of it was ever enough. Over 34 years, his drinking and drug use progressed from beer and cocaine to a decade of smoking crack, and finally to a crushing OxyContin addiction that cost him everything: four marriages, his relationship with his father and kids, his money, and his will to live. By June 2010 he was homeless, eating out of garbage cans, and sleeping under a tree in a cemetery — convinced his life was over.

Then…