Successfully Unemployed Show with Entrepreneurs Investors and Side Hustle

Master Passive Income

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In their own words

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

As heard by us

Based on 6 episodes we listened to · September 2026

Detailed guest interviews connect financial independence to the operating choices behind rental property, online businesses, and multiple income streams.

Successfully Unemployed turns the pursuit of financial independence into a series of operating questions. Across interviews hosted by Dustin Hiner and Roger Wesley, guests explain how they built income beyond a salary, while the conversation keeps returning to the choices,…

Read our full review in PlayNext →

Why you'd press play

Dustin calls your J-O-B 'just overbroke' and wants you to think like a landlord.

Press play if you want

  • to see how lot rent figures into a mobile home park deal before the freedom talk carries you away
  • to hear why a money site slowed its publishing instead of feeding Google more articles
Read the full recommendation in PlayNext →

Talks about

Best episodes of Successfully Unemployed Show with Entrepreneurs Investors and Side Hustle

Short reviews from the PlayNext desk, based on the episodes we processed.

3X Your Profit w/ Mid-Term Real Estate Investing with Paul David Thompson

A practical look at mid-term rentals as a middle path between long-term leases and short-term stays.

Mid-term rentals are framed as a workable middle path between year-long leases and short-term stays. The discussion stays grounded as it follows how furnished units can serve traveling nurses, corporate travelers, and military stays, with the claim that the model can generate…

From CNN to PR Marketing Expert

A practical guide to matching expertise with the places the right audience already pays attention.

This episode treats visibility as a practical job, not a branding exercise. Roger Wesley and Elizabeth Howell focus on podcast guesting, reporter outreach, and smaller niche channels, with the clearest advice landing in the middle: set the business goal first, figure out where…

Become An Actor and Start Acting w Brian Chambers

Acting is framed as a practical career path built on craft, proof, networking, and persistence.

Brian Chambers' move from teacher to working actor is framed as a practical path: learn the craft, build proof, and keep moving until opportunities start to open.

Invest in Apartment Complexes with Michael Blank

A direct case for apartment syndications as a path to financial freedom.

This episode makes a straightforward case for apartment syndications as a route to financial freedom. Dustin Hiner introduces a guest who walks through multifamily deals of 50, 60, 70 units and larger, while also explaining how outside investors can come in alongside the…

NY Firefighter Invests In Apartments to Retire Early

A practical real estate pitch centered on starting small and building toward financial independence.

The episode works best when it follows the firefighter's move into apartment investing and keeps the focus on practical choices: starting with what is familiar, matching the lane to risk tolerance and goals, and treating financial independence as a long game.

Got Multiple Streams of Income? Here is how...

A direct case for building income outside a single paycheck.

Dustin Hiner keeps the discussion squarely in quit-the-J-O-B territory, but the point lands because it stays practical. The advice is simple enough to use: notice when work comes easiest, test whether an idea is worth paying for, and be honest about whether there is enough skill…

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Episodes

  1. 1

    Never Pay Taxes Again w/ the Trifecta Plan | Mark Kohler

    ·51m
  2. 2

    Pay Your House Off in 3 Years!

    ·43m
  3. 3

    Is It Faith or Fear Leading You?

    ·14m
  4. 4

    Retired at 39, Zach Zimmer's Journey to Financial Independence

    Zach began with two houses.

    ·1h·4 clips
  5. 5

    I'm NOT a Salesman

    Roger Wesley hosts an episode challenging the belief that some people are not salesmen, arguing that everyone sells in personal relationships and daily life.

    ·13m·1 clip
  6. 6

    AI Is Taking Over And You MUST Invest In Real Estate To Afford To Live

    Dustin Hiner opens fast and loud.

    ·38m·2 clips
  7. 7

    Are You The Most Competent You Can Be? 4 Levels of Competency

    Roger Wesley shares a mindset lesson on the four levels of competency, discussing how to overcome self-sabotage, build consistency, and develop communication skills for entrepreneurial success.

    ·17m·1 clip
  8. 8

    From CNN to PR Marketing Expert

    Hidden gem

    Host Roger Wesley interviews Elizabeth Howell, a PR expert with 25 years experience including CNN, about how entrepreneurs can use media interviews and podcast guesting to build their businesses.

    ·41m·4 clips
  9. 9

    Excuse Eliminator Kelly Charles Collins Leaves Attorney Work to Impact Millions

    Hidden gem

    A lawyer brings a speaker's discipline and urgency to Roger Wesley's mic.

    ·49m
  10. 10

    Turning a Blog Into A Media Company and Travel the World with Josh Summers

    Dustin Hiner opens by framing financial freedom as something you build, not something you wait for.

    ·44m·2 clips
  11. 11

    How to Make Money Online for Beginners with Dollar Sprout's Jeff Proctor

    Jeff Proctor, founder of Dollarsprout.com, shares his journey from a low-paying internship to building a successful affiliate marketing blog.

    ·1h 6m·5 clips
  12. 12

    Got Multiple Streams of Income? Here is how...

    Hidden gem

    Dustin Hiner starts with a hard push to move beyond the J-O-B.

    ·57m·3 clips
  13. 13

    NY Firefighter Invests In Apartments to Retire Early

    Hidden gem

    Dustin opens with his financial freedom pitch and introduces a New York firefighter who invests in apartment complexes.

    ·49m·3 clips
  14. 14

    Copyrighting to Sell Anything by Building a Storybrand with Eric Upton

    Hidden gem

    Dustin Hiner interviews Eric Upton about StoryBrand-style messaging and why he says wasted marketing usually comes from unclear copy, not a bad product.

    ·42m·2 clips
  15. 15

    2008 Crash Again?! Private Credit Crunch And Economic Stagflation

    Hidden gem

    Dustin Hiner says Oracle’s 30,000 layoffs are a warning sign that AI is compressing white-collar work across tech, finance, consulting, and design.

    ·32m·2 clips
  16. 16

    3X Your Profit w/ Mid-Term Real Estate Investing with Paul David Thompson

    Hidden gem

    Dustin Hiner interviews Paul David Thompson on midterm real estate investing and says furnished units can produce up to 3x the revenue of long-term leases.

    ·37m·2 clips
  17. 17

    It's Not IF You Get Laid Off Or Fired... It's When.

    Hidden gem

    Roger Wesley frames the episode around a blunt question: “What would you do if you lost your job today?” and says his guest, Steve Jaffe, was laid off four times before writing The Layoff Journey from Dismissal to Discovery.

    ·43m·2 clips
  18. 18

    Invest in Apartment Complexes with Michael Blank

    Hidden gem

    Dustin Hiner opens with his usual push to leave the J-O-B behind.

    ·44m·2 clips
  19. 19

    How to Invest in Land with Land Investing Expert Seth Williams

    Hidden gem

    Roger Wesley interviews Seth Williams, who says his first land deal was a $331 purchase that later sold for $1,900 and that his land income overtook his banking salary after about two to three years.

    ·30m·2 clips
  20. 20

    Become An Actor and Start Acting w Brian Chambers

    Hidden gem

    Brian Chambers says he built an acting career from Houston, Texas, without moving to New York or Los Angeles, while also teaching online English and coaching swimmers.

    ·45m·3 clips
  21. 21

    Is It Faith or Fear Leading You?

    Host Roger Wesley shares his personal journey of leaving a six-figure job to pursue entrepreneurship, emphasizing that conviction, faith, and belief are more important than having all financial details in order.

    ·15m·1 clip
  22. 22

    How To Invest In Mobile Home Parks w/ William Parmer

    Hidden gem

    Host Dustin Hiner welcomes William Palmer, a Master Passive Income student-turned-coach who transitioned from law enforcement to successful real estate investor.

    ·1h 4m·2 clips
  23. 23

    Millionaire Entrepreneur Teaches How to Start Your Own Business with Grant Sabatier

    Grant Sabatier built his own lane.

    ·1h·1 clip
  24. 24

    Ex C-Suite Exec quit to impact 500,000+ people, Jill Christensen

    Hidden gem

    Roger Wesley frames Successfully Unemployed around people who leave W-2 work, and Jill Christensen fits that theme as a Fortune 500 executive turned business speaker.

    ·37m·2 clips
  25. 25

    Multi-Family Real Estate Investing with Whitney Sewell

    Hidden gem

    Dustin Hiner frames multifamily syndication as a path away from the J-O-B and points listeners to his free real estate course by texting “rental” to 33777.

    ·45m·2 clips
  26. 26

    How to Make $10,000,000 Investing In Real Estate

    Dustin Hiner teaches how to turn one property into $10 million by building a real estate business focused on income, not speculation.

    ·23m
  27. 27

    Invest Now Or Never Be Able To Invest In The Future

    Dustin Hiner explains why you must invest in real estate to achieve financial freedom in the age of AI and unaffordable homes.

    Apr 14, 2026·39m
  28. 28

    Making Money by Online Memberships with Sky Matsuhashi

    Host Dustin Hiner introduces the show's mission to help listeners achieve financial independence through entrepreneurship, side hustles, and investments, sharing his own success with rental properties.

    Nov 25, 2025·43m
  29. 29

    There IS An Elevator to Success

    Roger Wesley interviews a guest who wrote 'The Wealth Elevator' about achieving financial independence through entrepreneurship and investing.

    Sep 9, 2025·49m
  30. 30

    From Employee to Commercial Real Estate Investor: Charles Seaman's Journey

    Host Roger Wesley interviews successful entrepreneurs who have quit their jobs to build businesses and passive income streams, focusing on real estate investing.

    Aug 26, 2025·42m
  31. 31

    College Student to Real Estate Mogul

    Host Roger Wesley interviews successful entrepreneurs and business owners who left traditional jobs to build passive income through real estate investing.

    Aug 19, 2025·37m
  32. 32

    Avoid This Mistake IF You Want to Be Financially Free

    Aug 12, 2025·23m
  33. 33

    Escaped the US Treasury to be a Health and Fitness Coach: Brian Douglas

    Aug 5, 2025·31m
  34. 34

    The Biggest Competitor You'll Face

    Jul 15, 2025·8m
  35. 35

    Kirby Atwell Helps Student Create $6000 in Monthly Cash Flow!

    Jul 8, 2025·50m
  36. 36

    Transform Your Life: Escape the 9-to-5 Grind

    Jun 30, 2025·1h 13m
  37. 37

    International Real Estate Investing with Dr. Axel Meierhoefer

    Jun 24, 2025·44m
  38. 38

    When Will You Be Successfully Unemployed?

    Jun 17, 2025·14m
  39. 39

    2nd Generation Immigrant to Financially Independent, Maurice Philogene

    Jun 10, 2025·55m
  40. 40

    Pro Hockey Player Turned Business Genius, JR Butler is Changing the World

    Jun 3, 2025·43m
  41. 41

    How Brittany Durphey Built 2 Successful Businesses in 12 Years

    May 20, 2025·40m
  42. 42

    From Homeless to Financial Success | The Keys To Success In Life

    Mar 11, 2025·23m
  43. 43

    Dustin Heiner's Passes the Baton to Roger Wesley

    Mar 4, 2025·40m
  44. 44

    Explode Your Business with Social Media w/ Jeff Pfitzer

    Dustin Hiner interviews an expert on using social media to build a brand and grow a business, aiming to help listeners achieve financial independence and quit their jobs.

    Mar 3, 2025·47m
  45. 45

    Become Flea Market Flippers to Quickly Make Money From Anything

    Feb 24, 2025·33m
  46. 46

    How to Become A Youtuber With Jeff Rose

    Host Dustin Hiner interviews Jeff Rose about building multiple income streams through blogging, YouTube, and freelancing to achieve financial freedom.

    Feb 18, 2025·49m
  47. 47

    $500+ A Day On Facebook Marketplace w/ Andrey Kozlov

    Feb 10, 2025·25m
  48. 48

    Grow a Successful Business to Quit Your Job with Steve Feld

    Host Dustin Hiner interviews business coach Steve Feld about how he quit his job and built a successful coaching business.

    Feb 3, 2025·51m
  49. 49

    Secrets of Successful Land Investing with Mark Podolsky

    Jan 27, 2025·45m
  50. 50

    How to Start a Business to Live the Dream Life with Tom Sylvester of Lifestyle Builders

    Dustin Heiner introduces the show's mission to help listeners achieve financial freedom through entrepreneurship and side hustles, and previews an interview with an expert on building businesses to fund lifestyles.

    Jan 20, 2025·39m