Successfully Unemployed Show with Entrepreneurs Investors and Side Hustle
Master Passive Income
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
https://successfullyunemployed.co
Episodes
Mentioned books

Jan 27, 2026 • 45min
Become An Actor and Start Acting w Brian Chambers
Learn how to become an actor from this retired teacher, turned actor. He will show you all the steps you need to take to become a successful actor and quit your job to be successfully unemployed. So, lets learn how to become and actor. Brian shows us how to act and make a living in an acting career to make money and retire early.Get my free real estate investing course: https://masterpassiveincome.com/freecoursesuYoutube Channel: https://successfullyunemployed.co/youtube// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipster//OTHER RESOURCES:Bank I use: https://successfullyunemployed.co/bankWebsite hosting I use: https://successfullyunemployed.co/sitegroundMembership Tools I Use for My Online Business: https://successfullyunemployed.co/kartraNOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Jan 20, 2026 • 1h 6min
How to Make Money Online for Beginners with Dollar Sprout's Jeff Proctor
Making money online for beginners is all about producing content for your audience. In today's show, Jeff Proctor of Dollar Sprout helps us to learn how to make money online for beginners.Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesuLearn even more about being successfully unemployed here: https://www.successfullyunemployed.co/62Youtube: https://successfullyunemployed.co/youtube// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Jan 14, 2026 • 49min
Excuse Eliminator Kelly Charles Collins Leaves Attorney Work to Impact Millions
Kelly Charles Collins has done it all. Mother. Attorney. Author. Speaker. She left her attorney career behind to become a professional speaker and voice of value on TEDx stages, and for Fortune 100 companies. She's sought after all over the world and her interview will encourage and inspire men and women alike to pursue a life of being Successfully Unemployed!"We WON an AWARD!! Top 20 Side Hustle Podcasts! Check us out here! https://podcast.feedspot.com/side_hustle_podcasts/Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesuYoutube: https://YouTube.com/iamrogerwesley// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!
Dec 29, 2025 • 43min
It's Not IF You Get Laid Off Or Fired... It's When.
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," and he's here to share insights for those of us on our journey to becoming Successfully Unemployed!"We WON an AWARD!! Top 20 Side Hustle Podcasts! Check us out here! https://podcast.feedspot.com/side_hustle_podcasts/Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesuYoutube: https://YouTube.com/iamrogerwesley// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!
Dec 23, 2025 • 17min
Are You The Most Competent You Can Be? 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// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!
Dec 9, 2025 • 15min
Is It Faith or Fear Leading You?
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.
Dec 2, 2025 • 60min
Retired at 39, Zach Zimmer's Journey to Financial Independence
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 to help others do the same. This interview is one for the books, and one you certainly don't want to miss out on."We WON an AWARD!! Top 20 Side Hustle Podcasts! Check us out here! https://podcast.feedspot.com/side_hustle_podcasts/Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesuYoutube: https://YouTube.com/iamrogerwesley// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!
Nov 25, 2025 • 43min
Making Money by Online Memberships with Sky Matsuhashi
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 Passive Income" FREE: https://www.successfullyunemployed.co/freebookytLearn even more about being successfully unemployed here: https://www.successfullyunemployed.co/20// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipster//OTHER RESOURCES:Bank I use: https://successfullyunemployed.co/bankWebsite hosting I use: https://successfullyunemployed.co/sitegroundMembership Tools I Use for My Online Business: https://successfullyunemployed.co/kartraNOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Nov 11, 2025 • 37min
Ex C-Suite Exec quit to impact 500,000+ people, Jill Christensen
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 got there, she wasn't fulfilled. Pursuing her passion for improving culture all around the globe she took to becoming a professional speaker and consultant that has spoken all over the world over 360 times in less than 10 years. Best selling author of two books and highly sought after, she will encourage you on your journey to becoming successfully unemployed."We WON an AWARD!! Top 20 Side Hustle Podcasts! Check us out here! https://podcast.feedspot.com/side_hustle_podcasts/Get the FREE Real Estate Investing Course: https://masterpassiveincome.com/freecoursesuYoutube: https://YouTube.com/iamrogerwesley// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!
Nov 4, 2025 • 1h
Millionaire Entrepreneur Teaches How to Start Your Own Business with Grant Sabatier
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 Investing Course: https://masterpassiveincome.com/freecoursesuLearn even more about being successfully unemployed here: https://www.successfullyunemployed.co/52Youtube: https://successfullyunemployed.co/youtube// WHAT TO WATCH NEXTStart a Podcast: https://youtu.be/YdKKwSSOnJAMake Money Online: https://youtu.be/WDkRHg3uxR0Flea Market Flipper: https://youtu.be/MYEoeQPT-5E//BEST BUSINESS COURSES I RECOMMENDStart an Online Business: https://successfullyunemployed.co/p24Start a podcast: https://successfullyunemployed.co/podcourseMake money on Etsy: https://successfullyunemployed.co/goldcityCreate a Facebook Ads Agency: https://successfullyunemployed.co/laptopempiresMake $ from nothing as a Flea Market Flipper: https://successfullyunemployed.co/fleamarketflipperLearn how to invest in land: https://successfullyunemployed.co/retipsterLearn more about Dustin and find resources to build an automatic real estate investing business:https://masterpassiveincome.com/NOTE: This description may contains affiliate links to products we enjoy using ourselves. Should you choose to use these links, this channel may earn affiliate commissions at no additional cost to you. We appreciate your support!Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy


