Episode 780: The Ten Best and Worst Decisions of My Life - Part One (Worst Decisions)

Uncategorized Aug 17, 2025

What is a "bad decision" if not a lesson in disguise? And what do you do once you've learned that lesson? Today, I'm sharing the ten worst decisions I've made across my 18 years in business and life. From costly business partnerships and legal missteps to personal regrets and missed financial opportunities, I'm pulling back the curtain on my biggest screw-ups so you don't have to make the same ones. 

This isn't a conversation about regret; it's about reflection. Tune in now and to let us know which of these you can relate to the most, and make sure to tune in next week for Part Two, where I’ll be revealing the best decisions I’ve ever made!

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In this episode you’ll hear: 

  • Why doing it yourself is sometimes the best option, and how I learned this lesson the hard way through multiple business partnerships
  • The crucial importance of getting every agreement in writing
  • Why you should invest in yourself sooner and the single decision that changed my business trajectory after years of struggling 
  • How the habit of investing, no matter how small the amount, is more critical to financial success than how much money you make
  • What I learned after selling Bitcoin and passing on real estate opportunities out of fear
  • Why the desire to "improve" something that's already working can lead to costly mistakes and how I learned this lesson the hard way 
  • The importance of keeping your guard up and not trusting easily 
  • Why a bad decision is only a true mistake if you don't learn from it and apply the lesson to future choices

  

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