How one person crashed, burned, reinvented and created two new companies. With Damion Lupo. Ep. 019.

Many baby boomers have experienced bankruptcy, foreclosure, business loss, divorce, humiliation, and other traumatic experiences. Those life events can become a personal identity that lingers for years, unless there is a process of introspection, re-wiring, and re-inventing.

Our guest today, Damion Lupo, had great success in his twenties, only to crash and burn. He went through a process before reinventing himself, writing three books, and now owning two successful financial services companies. On his journey he has started 30 businesses, and shares lessons learned.

He is mission and purpose driven with many lessons in this episode.

Expect a future episode about creating a Qualified Retirement Plan that will give you a totally new perspective on Wall Street and investing.

Feature Segments

  • Why he does not like the word “retirement.”  (2:25)
  • Why would you stop contributing? (4:00)
  • When stop using your mind and engaging. (4:55)
  • Having the financial trappings. (6:20)
  • Problem when he created his first financial empire. (7:30)
  • Being the “golden child.” (8:19)
  • People do not see under the hood of outwardly successful people. (8:35)
  • Damion’s mistakes. (8:30)
  • What Damion did to get his confidence back. (10:50)
  • Trigger events. (11:10)
  • His process after the trigger event. (11:47)
  • The moment. (12:12)
  • The difference-he surrendered and sought the truth. (13:35)
  • It’s about ownership. Could take 5 minutes or 5 years. (15:10)
  • Asked what could I do that would benefit other people? (16:29)
  • The pain of regret vs. the pain of discipline.  (22:02)
  • The fear of failures for baby boomers. (24:00)
  • Tip toeing safely to death’s door. (26:50)
  • Damion’s Music, which will be listed below.
  • On death and dying. (32:10)
  • Looking back from 95 years old to his youth of today. (33:28)
  • Final take away. (37:20)


These are two bands and songs that I never paid much attention to. Just goes to show how much great music and lyrics there are. Not just for baby boomers. This message whispers loud.

Contact Damion Lupo


Visit for copies.

  • Life ReInvented.
  • Guide to Qualified Retirement Plan.
  • Quick and Dirty Guide to Gold and Silver.

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