082: Recovering from Bankruptcy and Creating a Legacy of Love with Ken Wimberly

Ken Wimberly hasn’t just gone bankrupt – he’s lived to tell the tale. After having success in the real estate industry, overspending and the Great Recession forced Wimberly to shrink his financial life and pay off hundreds of thousands of dollars in debt. 

As he rebuilt his financial life, Ken also founded Legacy of Love: a digital parent-to-child or grandparent-to-child journaling platform. It’s a place to capture moments, save memories, leave lessons, document photos, or videos, voice notes, voicemails, and capture little moments of life that might otherwise pass with time. 

Today, Ken joins the podcast to share the story of his financial mistakes and comeback, the power of digital scrapbooking, and the importance of passing along knowledge – financial and otherwise – to future generations.


Please note: For this special giveaway of Job Optional*, we do not currently offer international shipping. Residents outside of the U.S. may obtain a copy of Job Optional* via eBook format upon request to info@howardbailey.com.

In this podcast interview, you’ll learn:

  • Why so many pre-retirees fear they’re going to need to declare bankruptcy, why you may want to, and what alternatives you have.
  • What percentage of debt is viable in real estate investing – and when you need to worry about being overleveraged. 
  • How Ken keeps his assets organized and tracks his many streams of passive and active income. 
  • The ripple effect of having purpose – and the power of mentorship, even in retirement. 
  • How Ken set off on a powerful personal fitness journey – and what you can do to push your body to new levels of achievement, regardless of how old you are or if you don’t have access to any fancy equipment.

Inspiring Quotes

  • “You may think you’ve got it all figured out or you may have no clue what you’re going to do, and guess what, it doesn’t matter, because you’re going to get through so many different parts of your life that are going to be vastly different than what you ever thought they would be.” – Ken Wimberly
  • “My best advice to anyone that finds themselves in that (debt) situation to get out of it is to get into a career, which they can be compensated for the value they create, rather than trading dollars for hours.” – Ken Wimberly

Interview Resources


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