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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

I really wonder where this guy is now. Really unfortunate that 2008 YouTube could only handle 10min videos.

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