This is the video that initially popped into my mind, it's from 2008 titled:
Homeless Man Used to Be a Banker Before the Recession

Sucks it's only 10 minutes long due to 2008 YouTube, because his story is wild and pretty heartbreaking at some points:

• ran away from home at 12 with hippies
• returned home after 1 year, kicked out for good
• spent ~2 months in every US state over the next 15 years
• settled in LA, got job in the investing arena (diamonds, indie films, oil/gas)
• evicted from his home
• loses storage unit with all of his belongings, including 10,000 pages and a book to his daughter
• even more