Work Worth Doing

Dean Reilly
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Everyone wants the freedom to book a flight on a days notice without asking for time off... but getting there takes work. That work is what this podcast will help you do, by turning your knowledge into money Learn from entrepreneurs and inspiring individuals who’ve encountered all the challenges you'll face on your path. Expect the confidence and tools to reclaim control over your time. IG: @heydeanreilly

  1. 11/03/2025

    The Hidden Danger of Having a “Good” Salary

    Bit of backstory - https://youtu.be/GdtDj76dIUw Follow me on IG - https://www.instagram.com/heydeanreilly Book a 15 min Call - https://calendly.com/work-worth-doing/work-worth-doing-airbnb-mentoring

    16 min

  2. 10/15/2025

    Adam Williams - What it's ACTUALLY like to leave Tech Sales...

    Granular Airbnb Intro Video -  https://youtu.be/eoBN-JGVzhE Follow me on IG - https://www.instagram.com/heydeanreilly Work with Me - https://calendly.com/deanreilly/work-worth-doing-airbnb-mentoring1

    1h 2m

  3. 09/03/2025

    Julia Gao Miller - Finding Her Passion After Being Fired from a 9-5

    Give this a watch 👉 https://www.youtube.com/watch?v=GdtDj76dIUw Follow Julia on IG 👉 https://www.instagram.com/fightnomadjulia/Follow me on IG 👉 https://www.instagram.com/heydeanreilly Work with Me 👉 https://calendly.com/deanreilly/freedom She got fired, had no backup plan. But then blew up to 300K followers on Instagram. In this episode of Work Worth Doing, Julia shares her experience of build a life she actually wanted after feeling trapped to her 9-5. You’ll learn: - What getting fired taught her about safety- Why 100K followers left her burnt out and broke- How she rebuilt from scratch with no niche and no backup plan- The moment she realised her “freedom” business still felt like a trap- How slowing down became the only way forward

    1h 7m

  4. 07/08/2025

    Darren Lee - Journey From a Corporate 9-5 to a $4m Business

    Give this a watch next 👉  https://youtu.be/uBfXZE3POx4 Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share From $0 to $4M… but Darren Lee didn’t do it by chasing views. He built a business that lasts, by learning to play the Infinite Game. In this episode, we go deep on how he scaled a podcast agency that now makes $4M/year, and why so many founders fail by chasing a game they can’t win. You’ll learn… The mindset shift that saved his businessWhy most people stay broke (even with skills)How the podcast became the businessWhat the Infinite Game really means, and how to win itWhy the best founders don’t try to “escape”

    1h 25m

  5. 06/21/2025

    Business & Life Update

    Book a Strategy Call with Me 👉 https://calendly.com/deanreilly/discovery-call-path Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share A solo update on where I’m at, life, business, mindset, and what's been going on lately:  → The numbers from my Airbnb + coaching businesses → What I’ve learned from shitty hires and messy ops → Why I am in Baii

    20 min

  6. 06/18/2025

    Sol Hyde - London 9-5'er to Bali 6-Figure Business Owner

    Book a Strategy Call with Me 👉 https://calendly.com/deanreilly/discovery-call-path Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share Sol smashed $100K in 100 days. But what makes his story powerful isn’t the revenue, it’s the system that got him there. In this episode, we unpack the three ingredients that changed everything for him, and the sneaky beliefs that hold most creators back. You’ll learn… Why “views” don’t matterHow to test your way into a 6-figure offerWhat batch content gets wrongHow sales is actually about self-worthThe hidden cost of staying in the 9-5 too long Instagram: @sol.hyde @heydeanreilly @work.worth.doing.podcast Newsletter: workworthdoing.transistor.fm

    55 min

  7. 06/09/2025

    Dan Kelsall - Making Content That Actually Sounds Like You

    Book a Strategy Call with Me 👉 https://calendly.com/deanreilly/discovery-call-path Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share Dan Kelsall is the founder of Offended and one of the most irreverent voices on LinkedIn. But what makes him powerful isn’t the swearing, it’s the clarity behind it. From getting rejected by clients for being “too much” to building six-figure campaigns for KFC, this episode is a no-bullshit look at what it really takes to stand out. You’ll learn…– Why your content feels forced (and how to fix it)– The real difference between a personal brand and a sellable brand– Why building a business ≠ posting more– How to gamify backlash so you stop fearing it– What makes people actually buy from you Dan's Linked In- https://www.linkedin.com/in/dan-kelsall/ Work with Me 1to1- https://calendly.com/deanreilly/discovery-call-path

    53 min

  8. 06/02/2025

    Biliana Stoyanova - How to Get Good at Content and Sales

    Book a Strategy Call with Me 👉 https://calendly.com/deanreilly/discovery-call-path Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share Biliana is a sales and marketing strategist for solopreneurs, but what makes her story powerful isn’t the revenue, it’s the clarity behind her process. From years of helping creators “sell without the sleaze” to building offers that convert without burnout, this episode explores what actually moves the needle. You’ll learn…– Why most founders feel awkward about sales (and how to fix it)– The magnesium vs. sleep analogy (and why your offer isn’t landing)– Why conviction matters more than confidence– How to tell if it’s a content problem or a positioning one– Why authority isn’t built in carousels — it’s built in stories IGBiliana IG - @myonlinemarketingcoachBiliana LinkedIn - https://www.linkedin.com/in/bilianastoyanova/Me - @heydeanreillyPod - @work.worth.doing.x

    56 min
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About

Everyone wants the freedom to book a flight on a days notice without asking for time off... but getting there takes work. That work is what this podcast will help you do, by turning your knowledge into money Learn from entrepreneurs and inspiring individuals who’ve encountered all the challenges you'll face on your path. Expect the confidence and tools to reclaim control over your time. IG: @heydeanreilly

Information

  • Creator
    Dean Reilly
  • Years Active
    2024 - 2025
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © 2026 Dean Reilly
  • Show Website
    Work Worth Doing