Successfully Unemployed Show with Entrepreneurs Investors and Side Hustle

Updated: 12 Aug 2025 • 204 episodes
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This is the place where ordinary people become extraordinary by building business, side hustles, and investments to quit their job and be successfully unemployed. In this show, Roger Wesley interviews successfully unemployed entrepreneurs and highlights how they quit their job and how you can too. https://successfullyunemployed.co

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Here Roger shares insights into one common mistakes that people make when on the road to Financial Freedom. This one mistake keep people from all levels of success, and disallow them from becoming Successfully Unemployed. Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesu Youtube: h

22 min
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From the US Treasury to the health and wellness community, former Professional Track Athlete Brian Douglas shares how he was able to walk away from his W2 to pursue his dream. In this episode he shares the steps he took to design his ideal life, pitfalls along the way, and valuable insights for those looking to make si

31 min
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29 Jul 2025 • EN

Laid Off. Now What?!

You've just been laid off. Your life has turned upside down, or has it? In this episode Roger interviews Steve Jaffe who was laid off 4 times over the course of his corporate career, and used what he learned from each experience to propel him forward. He's one of the brains behind "What Happens in Vegas, Stays in Vegas

42 min
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22 Jul 2025 • EN

4 levels of Competency

Roger discusses the 4 levels of competency that all of us face in everything that we do. He also shares how insights into why we encounter self-sabotage, and how to overcome this enemy in our lives. Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesu Youtube: https://YouTube.com/iamr

16 min
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Roger discusses some of the challenges he's faced while making the journey to becoming Successfully Unemployed, and offers guidance to those that are working towards that destination. "We WON an AWARD!! Top 20 Side Hustle Podcasts! Check us out here! https://podcast.feedspot.com/side_hustle_podcasts/ Get the FREE Real

7 min
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Kirby Atwell, Veteran of the US Army, decided that he needed to create more options in his life so he started investing in Real Estate. He's flipped over 70 properties, acquired over 35 short term rentals, and most importantly, given his Wife and 3.5 kids (baby 4 is due within a few months of this recording) a lifestyl

50 min
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