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.
Ep 37 · Douglas Song
Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song
What happens when an entrepreneur spends decades helping founders transition, scale, and protect the businesses they’ve built?
Ep 36 · Daniel Innovaté
Stop Planning. Start Building. (His Rule Will Challenge You) | Daniel Innovaté
There’s a new kind of builder emerging. Not slower. Not more careful. Just… faster, sharper, and a little harder to categorize.
Ep 35 · Andy Marshall
What It Really Takes to Build a Brand People Love | Andy Marshall
Most people think they’re building a business. But every now and then, you meet someone who’s building something deeper, something rooted in people…
Ep 34 · Eve Peeterson
Why Mentorship Is Broken (And How to Fix It) | Eve Peeterson
There’s a moment in every founder’s journey where the question shifts. Not “What am I building?” But “Who am I becoming?” In this conversation, Mark sits…
Ep 33 · Dakota Simpson
Why Founders Don’t Succeed Alone | Dakota Simpson
In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Dakota Simpson, Chief Program Officer…
Ep 32 · Stephanie Johnson
Operational Debt Is Slowing Your Company | Stephanie Johnson
In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Stephanie Johnson, a fractional CEO…
Ep 31 · Amy Henderson
Strategic Alignment of Talent, Tech & Data | Amy Henderson
In this episode of the Parallel Entrepreneur, Innovation Series, Mark Cleveland and Johnny Anderson sit down with Amy Henderson, Director…
Ep 30 · Meg Chamblee
Women in Tech, Real Relationships & Nashville’s Growth Story | Meg Chamblee
In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Meg Chamblee, Executive Vice President…
Ep 29
Designing for Trust: Customer Experience, Bias & the Human–Automation Balance
Great experiences don’t happen by accident. They’re designed. In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny…
Ep 28
Why Today’s Leadership Playbook Breaks in the Age of AI
The leadership playbooks that built today’s successful organizations were designed for a different world.
Ep 27
Why the Future of Entrepreneurship Starts in Schools
In this Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Dr.
Ep 26 · Jon Hilton
Why AI Strategy Fails Before It Starts | Jon Hilton
Why do AI initiatives often stall? What does it take to build AI strategies that scale inside real businesses?
Ep 25
Stop Doing Tasks AI Can Handle: Shauna Sprague on Automation & Human Potential
In this special Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Shauna Sprague, an AI…
Ep 24 · S3 CEO Rod McDaniel
Why Community Is Nashville’s Superpower — A Conversation with S3 CEO Rod McDaniel
In this special Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Rod McDaniel, CEO of S3…
Ep 23 · Mark Blaze
Nashville’s Tech Future: Why the Pieces Are All Here | Mark Blaze
What happens when a city stops waiting for permission and starts acting like the technology hub it already is?
Ep 22
Michael Built a Cybersecurity Empire—Then Let Competitors Use His Tools
What happens when a cybersecurity veteran automates the work his competitors still struggle to deliver? He builds the future—and lets them use it.
Ep 21
The Power of Curiosity: Carla Bailo on Smart Cities, Boardroom Wisdom, and Transforming Mobility
In this episode of The Parallel Entrepreneur, Mark Cleveland welcomes Carla Bailo—an industry visionary who’s helped shape the future of mobility,…
Ep 20 · Matthew Joynes
Part 2 - Currency Chaos, AI Freedom & The Future of Value | Matthew Joynes
Welcome back to The Parallel Entrepreneur for part 2 with British-American polymath Matthew Joynes.
Ep 19
Part 1 - AI Will Erase 20th Century – Parallel Entrepreneur Matthew Joynes on Money, Cap Tables & Super-AI
What happens when super-AI makes lawyers, accountants—and even capitalism—obsolete? British-American “apex” parallel entrepreneur Matthew Joynes (PGA…
Ep 18
Start Paralleling: Mark Cleveland on Multiplying Your Impact
Stop juggling. Start PARALLELING. Entrepreneur, community‑builder and podcast host Mark Cleveland takes the Creative Mornings stage to share why…
Ep 17
From Basement Startup to Global Brand: Tim Ozgener’s Parallel Journey
Looking for inspiration on juggling multiple business passions? Tim Ozgener might just be your blueprint.
Ep 16
From EdTech to CyberTech: Justin’s Parallel Entrepreneur Path
AI and security compliance could make or break your next venture. In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Justin…
Ep 15 · Robert Hartline
The Human Side of Hustle Ft Robert Hartline
What happens when a merger you can't control threatens to destroy your 22-year business overnight?
Ep 14 · Dr. Michael Sprintz
Surviving to Serve: A Parallel Entrepreneur’s Comeback Ft Dr. Michael Sprintz
How do you launch a thriving medical practice, then pivot to a fast-scaling software startup—all while staying laser-focused on patient care, personal…
Ep 13 · John Farkas
Mastering Leadership, AI, and Organizational Alignment Ft John Farkas
Wondering how to nurture alignment throughout M&A integration? In this episode John Farkas, founder of Ratio and Candor—two companies that help businesses…
Ep 12
From Startup to $90M Exit: Silas Deane on Innovation, Risk, and Resilience
Are you a serial entrepreneur juggling multiple ventures and hungry for breakthrough growth?
Ep 11 · John Cerasuolo
Scaling Success: Leadership, Acquisitions, and Culture with John Cerasuolo
Unlock the secrets of building an acquisition empire from someone who's done it well.
Ep 10 · Plum.io
How Caitlin MacGregor is Unlocking Human Potential with Plum.io
Ready to discover how to hire for potential rather than past credentials—and why it could transform your business?
Ep 9
How Multipreneur Christian Paro Built the Coolest Co-Working Space in Nashville
Get ready for a masterclass in multi-venture entrepreneurship from Christian Paro, founder of Center 615, Studio 615, Five Points Alley Shops—three of…
Ep 8 · Craig Fuller
The Journey of FreightWaves Ft Craig Fuller
Ready to master the art of running multiple ventures without losing your sanity—or your shirt?
Ep 7
Small Ideas, Big Wins: Nitin Rai’s Blueprint for Multi-Venture Success
How do you juggle multiple ventures and keep your cool under pressure? Meet Nitin Rai — seasoned founder, investor in 70+ startups, and champion…
Ep 6
Scale, Sell, Repeat: Roger Brown’s Playbook for Parallel Entrepreneurs
How do you scale, sell, and still come back for more? Meet Roger Brown — a serial founder who’s built (and exited) four different ventures, from physician…
Ep 5 · Jason Putnam
Redefining Success Through Human-Centric Leadership Ft Jason Putnam
’m joined by Jason Putnam, a two-time award-winning executive (Globee Executive of the Year, Silver Stevie Award) and a 2024 Inspiring Leader.
Ep 4 · Francisco Gonzalez
Bridging Passion and Purpose in Business Ft Francisco Gonzalez
In this engaging conversation, Mark Cleveland and Francisco Gonzalez explore the essence of entrepreneurship, focusing on the importance of community…
Ep 3
Serial Exits & Roll-Ups: John McDonald’s M&A Roadmap for Parallel Entrepreneurs
How do you build a company that buyers can’t wait to acquire—and still keep your entrepreneurial spark alive?
Ep 2 · Ania Rodriguez
Building a Competitive Edge Ft Ania Rodriguez
Join me, Mark Cleveland, as I sit down with Ania Rodriguez, CEO & Founder of JourneyTrack.io, to discuss her journey as a serial entrepreneur and her…
Ep 1 · William Klehm
Innovating Beyond Boundaries Ft William Klehm
In my very first episode, I sit down with visionary Parallel Entrepreneur, William Klehm, to unpack the lessons he learned from building, scaling,…