Successfully Unemployed Show with Entrepreneurs Investors and Side Hustle

Updated: 09 Dec 2025 • 208 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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When Roger quit his 6 figure salaried job, he did it all wrong. In this episode he shares 3 important things that he had before he quit, and how you can get the greatest return on your time to help you become Successfully Unemployed. Mentioned in this episode: Income Building Live 2026 Join Dustin Heiner and hundreds o

16 min
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Zach Zimmer of The Passive Life opened his war chest and let us in behind the scenes of how he created wealth in his 30s and retied at 39 years old. His story is filled with exciting twists and turns, as well as 7 figure losses. Zach has truly walked the long winding road to financial independence, and is on a mission

60 min
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Teaching people how to play poker online and making money doing it! A membership business is a terrific way to make money and be successfully unemployed. Learn from Sky Matsuhashi of Smart Poker Study as he shows us how he started an online membership to make money. Get the BEST SELLING BOOK "How to Quit Your Job with

42 min
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When Roger quit his 6 figure salaried job, he did it all wrong. In this episode he shares 3 important things that he had before he quit, and how you can get the greatest return on your time to help you become Successfully Unemployed.

14 min
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14:28
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Culture specialist author, speaker, and consultant Jill Christensen joins us on the show to share her insights on how we can become successfully unemployed. With over 25 years in Corporate America, Jill has seen it all. She worked her way up to the C-Level corner office in a Fortune 100 company and found that once she

37 min
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What is an entrepreneur and how can you be a successful entrepreneur? Grant Sabatier has built many successful $1,000,000 businesses and he shows us how we can become entrepreneurs and be successfully unemployed. Learn from the millennial money man Grant Sabatier how to be an entrepreneur. Get the FREE Real Estate Inve

60 min
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