194: Kyle Depiesse | Slashing $380,000 of Debt in 38 Months

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A few years ago Kyle Depiesse logged on to the Social Security website and saw that he had earned a little over $1 million. He thought that was funny because he didn’t really have much to show for it. He asked his wife for her social security number and saw that she had earned about the same amount. So together they had about $2 million in lifetime earnings but they were $380,000 in debt. The debt wasn’t crippling, nor was it largely personal debt – most of it was their mortgage. But Kyle felt embarrassed and angry and resolved to tackle their finances differently from that moment on. In 38 months the debt was gone and Kyle and his wife were able to focus on investing for their future.

In This Conversation We Cover: 

  • [4:21] Kyle’s blue-collar upbringing and the beliefs he learnt about money
  • [6:56] Choosing new influences to change those beliefs
  • [14:23] Cutting up credit cards
  • [20:37] Gamifying debt reduction
  • [21:55] Screaming ‘We’re debt free!’ on The Dave Ramsey Show
  • [26:51] Leaving the corporate world to become a high school teacher
  • [27:56] Taking two years off to be at home with his son
  • [28:52] Kyle’s mastermind for men to find success in every aspect of their lives
  • [32:03] His morning routine

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Hi, I’m Rob!

Hi, I’m Rob! It has been said “You are not what you have learned, but what you’ve overcome.”


I have overcome my share of obstacles in order to architect the life of my dreams and uncover the key to lasting, meaningful success. Growing up in Queens (literally on the wrong side of the tracks), my early years were tumultuous, marked by hardship and violence.

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