Founders, unfiltered

The Parallel Entrepreneur Podcast

Mark Cleveland talks with entrepreneurs who refuse to stop at a single venture. Every episode below includes the full conversation and a complete transcript.

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Ep 40 · Joe De Sena

The Comfort Trap Every Entrepreneur Must Escape | Joe De Sena

Joe De Sena has built one of the world's most recognised endurance brands. As the founder and CEO of Spartan, he's spent decades proving that resilience…

Jul 21, 2026 · 45 min · Full transcript

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  1. Ep 39 · Ian Adamson

    How to Build an Extraordinary Life Without Following One Path | Ian Adamson

    Jul 7, 2026 · 59 min · Full transcript

  2. Ep 38 · Spencer Handley

    The AI Skill Every Working Adult Needs to Learn | Spencer Handley

    Jun 23, 2026 · 1 hr 20 min · Full transcript

  3. Ep 37 · Douglas Song

    Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song

    May 26, 2026 · 1 hr 22 min · Full transcript

  4. Ep 36 · Daniel Innovaté

    Stop Planning. Start Building. (His Rule Will Challenge You) | Daniel Innovaté

    May 12, 2026 · 54 min · Full transcript

  5. Ep 35 · Andy Marshall

    What It Really Takes to Build a Brand People Love | Andy Marshall

    Apr 27, 2026 · 1 hr 9 min · Full transcript

  6. Ep 34 · Eve Peeterson

    Why Mentorship Is Broken (And How to Fix It) | Eve Peeterson

    Apr 8, 2026 · 53 min · Full transcript

  7. Ep 33 · Dakota Simpson

    Why Founders Don’t Succeed Alone | Dakota Simpson

    Mar 18, 2026 · 22 min · Full transcript

  8. Ep 32 · Stephanie Johnson

    Operational Debt Is Slowing Your Company | Stephanie Johnson

    Mar 11, 2026 · 7 min · Full transcript

  9. Ep 31 · Amy Henderson

    Strategic Alignment of Talent, Tech & Data | Amy Henderson

    Mar 4, 2026 · 10 min · Full transcript

  10. Ep 30 · Meg Chamblee

    Women in Tech, Real Relationships & Nashville’s Growth Story | Meg Chamblee

    Feb 25, 2026 · 22 min · Full transcript

  11. Ep 29

    Designing for Trust: Customer Experience, Bias & the Human–Automation Balance

    Feb 18, 2026 · 13 min · Full transcript

  12. Ep 28

    Why Today’s Leadership Playbook Breaks in the Age of AI

    Feb 11, 2026 · 18 min · Full transcript

  13. Ep 27

    Why the Future of Entrepreneurship Starts in Schools

    Feb 4, 2026 · 16 min · Full transcript

  14. Ep 26 · Jon Hilton

    Why AI Strategy Fails Before It Starts | Jon Hilton

    Jan 28, 2026 · 16 min · Full transcript

  15. Ep 25

    Stop Doing Tasks AI Can Handle: Shauna Sprague on Automation & Human Potential

    Jan 21, 2026 · 11 min · Full transcript

  16. Ep 24

    Why Community Is Nashville’s Superpower — A Conversation with S3 CEO Rod McDaniel

    Jan 14, 2026 · 26 min · Full transcript

  17. Ep 23 · Mark Blaze

    Nashville’s Tech Future: Why the Pieces Are All Here | Mark Blaze

    Jan 7, 2026 · 12 min · Full transcript

  18. Ep 22

    Michael Built a Cybersecurity Empire—Then Let Competitors Use His Tools

    May 22, 2025 · 53 min · Full transcript

  19. Ep 21

    The Power of Curiosity: Carla Bailo on Smart Cities, Boardroom Wisdom, and Transforming Mobility

    May 15, 2025 · 1 hr · Full transcript

  20. Ep 20 · Matthew Joynes

    Part 2 - Currency Chaos, AI Freedom & The Future of Value | Matthew Joynes

    May 8, 2025 · 55 min · Full transcript

  21. Ep 19

    Part 1 - AI Will Erase 20th Century – Parallel Entrepreneur Matthew Joynes on Money, Cap Tables & Super-AI

    May 1, 2025 · 1 hr · Full transcript

  22. Ep 18

    Start Paralleling: Mark Cleveland on Multiplying Your Impact

    Apr 24, 2025 · 11 min · Full transcript

  23. Ep 17

    From Basement Startup to Global Brand: Tim Ozgener’s Parallel Journey

    Apr 17, 2025 · 58 min · Full transcript

  24. Ep 16

    From EdTech to CyberTech: Justin’s Parallel Entrepreneur Path

    Apr 10, 2025 · 1 hr 9 min · Full transcript

  25. Ep 15

    The Human Side of Hustle Ft Robert Hartline

    Apr 3, 2025 · 1 hr 1 min · Full transcript

  26. Ep 14

    Surviving to Serve: A Parallel Entrepreneur’s Comeback Ft Dr. Michael Sprintz

    Mar 27, 2025 · 1 hr 1 min · Full transcript

  27. Ep 13

    Mastering Leadership, AI, and Organizational Alignment Ft John Farkas

    Mar 20, 2025 · 45 min · Full transcript

  28. Ep 12

    From Startup to $90M Exit: Silas Deane on Innovation, Risk, and Resilience

    Mar 13, 2025 · 52 min · Full transcript

  29. Ep 11

    Scaling Success: Leadership, Acquisitions, and Culture with John Cerasuolo

    Mar 6, 2025 · 43 min · Full transcript

  30. Ep 10

    How Caitlin MacGregor is Unlocking Human Potential with Plum.io

    Feb 27, 2025 · 1 hr 8 min · Full transcript

  31. Ep 9

    How Multipreneur Christian Paro Built the Coolest Co-Working Space in Nashville

    Feb 20, 2025 · 41 min · Full transcript

  32. Ep 8

    The Journey of FreightWaves Ft Craig Fuller

    Feb 13, 2025 · 1 hr 9 min · Full transcript

  33. Ep 7 · Nitin Rai

    Small ideas that turned into big wins | Nitin Rai

    Feb 6, 2025 · 46 min · Full transcript

  34. Ep 6 · Roger Brown

    His repeatable playbook for building and selling companies | Roger Brown

    Jan 30, 2025 · 41 min · Full transcript

  35. Ep 5 · Jason Putnam

    What a Chief Revenue Officer actually does all day | Jason Putnam

    Jan 23, 2025 · 54 min · Full transcript

  36. Ep 4 · Francisco Gonzalez

    Building Fearless Journeys from the ground up | Francisco Gonzalez

    Jan 16, 2025 · 41 min · Full transcript

  37. Ep 3 · John McDonald

    How to exit, then do it again and again | John McDonald

    Jan 9, 2025 · 1 hr 3 min · Full transcript

  38. Ep 2 · Ania Rodriguez

    What it really takes to build and launch a startup | Ania Rodriguez

    Jan 3, 2025 · 42 min · Full transcript

  39. Ep 1 · William Klehm

    What Makes a Business Someone Actually Wants to Buy | William Klehm

    Dec 6, 2024 · 1 hr · Full transcript

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