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The Dirt Path

The Dirt Path

By: Grayson Harris
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The Dirt Path Podcast celebrates those who choose to live and work differently. The world pushes us toward the "highway" of conventional jobs and lifestyles. But some brave people choose the "dirt path," with no signs or lights guiding the way. We interview these "dirt path trailblazers" to uncover: What led them to the path? Their biggest challenges and actionable tips for the "dirt path curious." This show is for anyone unaligned with their current job or lifestyle, seeking motivation to make a change. New episodes: Wednesday 6am EST (Video available on Spotify and YouTube)Grayson Harris Personal Development Personal Success
Episodes
  • Doubling Down Amidst Uncertainty & Building Community | 28 Mandy Reynolds
    Jun 24 2026

    Mandy Reynolds is a commercial real estate agent, developer, and the co-founder of Union + Co. coworking space in Bath, Maine. She shared her dirt path journey rescuing a historic, 24,000-square-foot "white elephant" building, creating a community cornerstone in a small town, and the mental stamina it takes to continue amidst massive uncertainty.


    Expect to hear:

    - Unconventional Path: How Mandy started her career doing ESG research, transitioned into real estate, and eventually co-founded a coworking space

    - Doubling Down Amidst Uncertainty: Why Mandy chose to invest more into Union & Co after a rocky start, and how they mentally persevered throughout.

    - Third Space Emergence: The rise of third spaces after covid and the unexpected impact a coworking space provides

    - Bigger than a Coworking Space: Mandy's vision of creating a community center point in a small town in Maine, and how they differentiate themselves from other coworking spaces.


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    Timestamps:

    (00:00) Bath Coworking Dream

    (01:05) Closing Deals Variety

    (02:13) Commercial vs Residential Real Estate

    (06:05) Maine Roots & The Border Town Reality

    (08:13) New Zealand Study Abroad & The Liberating Side of Travel

    (12:19) ESG Research Career & The SINS Blueprint

    (18:28) Remote Work Coworking & The Isolation Trap

    (21:21) Real Estate Turning Point & Build Maine

    (27:04) Broker Investing Dilemma & "Rich Dad Poor Dad" Influence

    (32:13) Union & Co Origins: A Historic Fairytale Downtown

    (37:04) Opening Day And First Members

    (40:58) Sticking With It: From 5 Founders to 2

    (47:22) Why Coworking Matters: Getting Out of Your Bubble

    (55:12) New Building Redevelopment: Tackling a 24,000 Sq Ft Monster

    (59:25) Community Programs And Art

    (01:04:17) Advice For New Operators: You Must Own the Bricks

    (01:07:53) Frankisms And Farewell: Knowing How to Get Out


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    Connect with Mandy:

    - Union + Co Website: https://www.unionandco.me/the-team

    - Union + Co Instagram: https://www.instagram.com/unionandcomaine/

    - Mandy's LinkedIn: https://www.linkedin.com/in/mandy-reynolds-aa779155/


    Support the podcast:

    - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/

    - Email your questions: thedirtpathpodcast@gmail.com

    - Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

    Show More Show Less
    1 hr and 16 mins
  • Why We Stopped the Digital Nomad Life for a Small Town in Maine | 27 Wanderers
    Jun 16 2026

    After 5 years living the digital nomad life around the world, we decided to make a major life change: we are settling down in a small town in Maine.

    In this month's dirt path wanderer's episode, we are sharing why we are stopping full-time travel, why we chose Bath, Maine, and reflections from our recent trip to South Korea.Expect to hear: • The South Korea Safe Flex: why Koreans leave their most expensive possessions to save seats. • The 2-Year Prank: For 2 years Paige has been working towards this moment. It finally manifested in a big way. • No More Nomadding: why we are stopping full-time travel and how it will look for us going forward. • Why Bath, Maine: Out of everywhere in the world, why did we choose a small town in Maine for our new homebase. ------------------------------Timestamps: (00:00) We Stopped the Digital Nomad Life (01:19) Reflections from our South Korea Vacation (04:06) Red Clay Barefoot Parks(10:21) Paige's 2 years prank on Grayson Comes to Fruition (13:53) Grayson’s South Korea Roses: walking and tranquility(19:23) Food highlights: Gochujang Octopus and Kimchi Burnout(24:35) Why We Paused Full-Time Travel (27:00) Searching for our New England Homebase(28:36) Returning to a Repeat Apartment for the First Time Ever (32:24) Needs vs. Wants: How Constant Moves Reveals Your True Home Base Non-Negotiables (35:41) Why Bath, Maine Checked Every Single Box (44:59) The Future of The Dirt Path: Local Artists, Craftsmen, and In-Person Interviews------------------------------Related Links:- Paige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/- Grayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/Support the podcast:- Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/- Email your questions: thedirtpathpodcast@gmail.com

    Show More Show Less
    48 mins
  • 8 Life Lessons From 5 Years as a Digital Nomad | 26
    Jun 10 2026

    I just celebrated my 5-year digital nomad anniversary (nomadiversary). Here are my 8 life lessons after living in 5 continents, 24 countries, and making 57 unique moves. For most of my time traveling the world, I was an electrical engineer working remotely in a traditional industry. I later transitioned to HR and recently stepped onto the dirt path as an online entrepreneur.


    Expect to hear:

    • The 5-Year Nomad Statistics: A breakdown of my last 5 years living around the world

    • Deconstructing the Fear Algorithm: How traditional media distortion and viral social media loops completely twist our perception of international travel safety

    • The Trap of Lifestyle Labels: Why obsessing over industry titles like "remote worker," "slow-mad," or "expat" can quietly sabotage your autonomy

    • Human Relationships vs. Remote Destinations: Why learning to love a new country is a lot like loving a partner

    • Conditioning the Mindset Muscle: The unexpected psychological benefits of facing constant micro-challenges and small discomforts while living abroad

    • The Ultimate Medium for Personal Growth: Why intentional, curious travel completely outperforms standard personal development books and podcasts for long-term self-improvement


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    Timestamps:

    (00:00) Celebrating a 5-Year Nomadiversary

    (01:13) My Nomad Stats: 5 Continents & 57 Moves

    (05:44) Lesson 1: Deconstructing the Media's Fear Algorithm

    (10:11) Lesson 2: The Illusion of Lifestyle Labels

    (12:51) Lesson 3: Designing Environments Around Specific Hobbies & Goals

    (17:53) Lesson 4: Trusting Your Lived Experiences Over Thoughts

    (22:21) Lesson 5: No Place Is Perfect

    (27:52) Lesson 6: Why Small Discomforts Generate Ultimate Empowerment

    (31:57) Lesson 7: "I’m the Problem" — The Confronting Mirror

    (36:05) Lesson 8: Curious Travel and the Art of Popping Cultural Bubbles

    (44:57) Celebrating 6 Months of the Podcast


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    Support the podcast:

    - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/

    - Connect with Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

    - Email your questions: thedirtpathpodcast@gmail.com

    Show More Show Less
    47 mins
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