Mark A. Cleveland

Parallel Entrepreneur with Mark Cleveland

Business EN ↓ 40 episodes

Mark explores the minds of visionary entrepreneurs who refuse to limit themselves to a single venture to learn how these trailblazers manage risks, innovate across industries, and turn ideas into impact. Whether you’re scaling your first business or juggling several, this podcast is your ultimate guide to thriving as a parallel entrepreneur.

Author

Mark A. Cleveland

Category

Business

Podcast website

parallelentrepreneur.com

Latest episode

Jul 7, 2026

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Episodes

How to Build an Extraordinary Life Without Following One Path | Ian Adamson 07.07.2026

What do engineering, world championship sport, product innovation, television production, and the Olympic movement all have in common? In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Ian Adamson , Chair of the World Pentathlon Multisport Obstacle Commission, to explore a career built on curiosity, continuous learning, and saying yes to opportunities most people would ne...

The AI Skill Every Working Adult Needs to Learn | Spencer Handley 23.06.2026

What happens when a musician, software engineer, educator, and entrepreneur all show up in the same person? In this episode of The Parallel Entrepreneur , Mark Cleveland sits down with Spencer Handley , Founder and CEO of Sonora, to explore a career built on curiosity, learning, and challenging conventional thinking. Spencer shares the story behind Sonora's growth from a guitar education company i...

Why Great Businesses Need Stewardship, Not Just Capital | Douglas Song 26.05.2026

What happens when an entrepreneur spends decades helping founders transition, scale, and protect the businesses they've built? In this episode of The Parallel Entrepreneur , Mark Cleveland sits down with Douglas Song , founder and CEO of Protos Capital, for a wide-ranging conversation on independent sponsors, lower middle market acquisitions, leadership, succession planning, AI, uncertainty, and w...

Stop Planning. Start Building. (His Rule Will Challenge You) | Daniel Innovaté 12.05.2026

There's a new kind of builder emerging. Not slower. Not more careful. Just… faster, sharper, and a little harder to categorize. In this episode, we sit down with Daniel Innovaté , product designer, creative entrepreneur, and one of the most naturally adaptive builders you'll come across. Daniel doesn't just talk about ideas. He turns them into real, working products, sometimes in minutes. We explo...

What It Really Takes to Build a Brand People Love | Andy Marshall 27.04.2026

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, place, and community. In this episode of The Parallel Entrepreneur , Mark sits down with Andy Marshall , Founder & CEO of A. Marshall Hospitality and the driving force behind Puckett's. From his early days in the grocery business to transforming a...

Why Mentorship Is Broken (And How to Fix It) | Eve Peeterson 08.04.2026

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 down with Eve Peeterson , an Estonian strategy and transformation leader who has led across private industry, government innovation, and national startup ecosystems. From working her way up in hospitality… To leading Estonia's startup strategy… T...

Why Founders Don’t Succeed Alone | Dakota Simpson 18.03.2026

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Dakota Simpson, Chief Program Officer at the Nashville Entrepreneur Center. Dakota is focused on a simple idea: founders don't succeed in isolation. They succeed when the right systems, support, and structure are in place around them. At the NEC, he leads the strategy and execution be...

Operational Debt Is Slowing Your Company | Stephanie Johnson 11.03.2026

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Stephanie Johnson, a fractional CEO and COO who specializes in helping companies eliminate what she calls operational debt. Most leaders recognize technical debt in software. Fewer realize the same concept exists inside organizations. Misaligned teams. Unclear processes. Decisions tha...

Strategic Alignment of Talent, Tech & Data | Amy Henderson 04.03.2026

In this episode of The Parallel Entrepreneur , Innovation Series, Mark Cleveland and Johnny Anderson sit down with Amy Henderson, Director of Infrastructure at HCA Healthcare Physician Services. Amy operates at the intersection of technical viability and business outcomes, aligning talent, technology, and data to drive enterprise growth inside one of the largest healthcare systems in the country....

Women in Tech, Real Relationships & Nashville’s Growth Story | Meg Chamblee 25.02.2026

In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Meg Chamblee, Executive Vice President for Tennessee at UDig. Meg launched UDig's Nashville office in 2020 and has grown it more than 10x, building not just a market presence, but a reputation rooted in trust, partnership, and long-term relationships. But this conversation goes far be...

Designing for Trust: Customer Experience, Bias & the Human–Automation Balance 18.02.2026

Great experiences don't happen by accident. They're designed. In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Suzi Earhart, CCXP, a Customer Experience and Organizational Change executive who believes better experiences begin with intentional design, empathy, and mutual understanding — and end in measurable business results. Suzi s...

Why Today’s Leadership Playbook Breaks in the Age of AI 11.02.2026

The leadership playbooks that built today's successful organizations were designed for a different world. In this episode of The Parallel Entrepreneur – Innovation Series, hosts Mark Cleveland and Johnny Anderson sit down with Amalia Goodwin, Global Managing Director of Adaptive Organizations at Slalom, to confront a reality most executives quietly avoid: Incremental change is no longer safe. It's...

Why the Future of Entrepreneurship Starts in Schools 04.02.2026

In this Innovation Series episode of Parallel Entrepreneur , hosts Mark Cleveland and Johnny Anderson sit down with Dr. Jeremy Qualls , Executive Director of the Entrepreneurship & Innovation Center (EIC) and College, Career & Technical Education at Williamson County Schools. Jeremy leads one of the most compelling early-stage entrepreneurship models in the region—where students don't just...

Why AI Strategy Fails Before It Starts | Jon Hilton 28.01.2026

Why do AI initiatives often stall? What does it take to build AI strategies that scale inside real businesses? What does responsible, human-centered AI look like in practice? In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland sits down with Jon Hilton, Shareholder-in-Charge of the LBMC AI Practice, to address these questions. Jon brings a rare mix of experience, enter...

Stop Doing Tasks AI Can Handle: Shauna Sprague on Automation & Human Potential 21.01.2026

In this special Innovation Series episode of Parallel Entrepreneur , hosts Mark Cleveland and Johnny Anderson sit down with Shauna Sprague , an AI strategist, architect, and TEDx speaker with 20+ years of experience helping Fortune 500 organizations navigate technology transformation. Shauna is known for helping leaders move beyond the AI hype and into confident execution—building clear roadmaps,...

Why Community Is Nashville’s Superpower — A Conversation with S3 CEO Rod McDaniel 14.01.2026

In this special Innovation Series episode of Parallel Entrepreneur , hosts Mark Cleveland and Johnny Anderson sit down with Rod McDaniel, CEO of S3 Recycling Solutions and Board Chair of the Greater Nashville Technology Council. Rod's journey, from growing up in public housing in Nashville to leading a nationally recognized, mission-driven tech recycling company, is a powerful example of what comm...

Nashville’s Tech Future: Why the Pieces Are All Here | Mark Blaze 07.01.2026

What happens when a city stops waiting for permission and starts acting like the technology hub it already is? You get Nashville's tech moment, and leaders willing to build it together. Mark Blaze is the kind of leader communities grow around. As President & CEO of the Greater Nashville Technology Council, he's less interested in headlines and more focused on connection, collaboration, and lon...

Michael Built a Cybersecurity Empire—Then Let Competitors Use His Tools 22.05.2025

What happens when a cybersecurity veteran automates the work his competitors still struggle to deliver? He builds the future—and lets them use it. Michael Peters is a rare kind of founder: one who leads both with technical depth and creative clarity. In this episode, we dive into the frameworks behind his companies Lazarus Alliance and Continuum GRC, the origin of the HORSE Project, and how he bal...

The Power of Curiosity: Carla Bailo on Smart Cities, Boardroom Wisdom, and Transforming Mobility 15.05.2025

In this episode of The Parallel Entrepreneur, Mark Cleveland welcomes Carla Bailo—an industry visionary who’s helped shape the future of mobility, from General Motors and Nissan to leading the Center for Automotive Research and winning the USDOT Smart City Challenge for Columbus, Ohio. Carla shares stories of innovation, mentorship, boardroom leadership, and the importance of building systems that...

Part 2 - Currency Chaos, AI Freedom & The Future of Value | Matthew Joynes 08.05.2025

Welcome back to The Parallel Entrepreneur for part 2 with British-American polymath Matthew Joynes. In this fast-paced sequel we dive into: • How Matthew rescued a bankrupt currency-trading firm and scaled it to $1 B+ in volume. • Why he calls Bitcoin “a collectible—like Beanie Babies” and predicts its slide back to reality. • Dollar dominance, tariffs as modern-day tribute, and the hidden mechani...

Part 1 - AI Will Erase 20th Century – Parallel Entrepreneur Matthew Joynes on Money, Cap Tables & Super-AI 01.05.2025

What happens when super-AI makes lawyers, accountants—and even capitalism—obsolete? British-American “apex” parallel entrepreneur Matthew Joynes (PGA producer, GameVice inventor, LifeMed AI founder) joins host Mark Cleveland to smash the china shop of old-school business. In this high-voltage conversation you’ll learn: ▸ Why Joynes says the real product of your company is its share price ▸ How Lif...

Start Paralleling: Mark Cleveland on Multiplying Your Impact 24.04.2025

Stop juggling. Start PARALLELING. Entrepreneur, community‑builder and podcast host Mark Cleveland takes the Creative Mornings stage to share why the future belongs to parallel thinkers—people who let multiple passions run side‑by‑side so each fuels the next. Whether you’re a founder with five side projects, an artist‑parent, or a multipotentialite who refuses to “pick a lane,” this 15‑minute talk...

From Basement Startup to Global Brand: Tim Ozgener’s Parallel Journey 17.04.2025

Looking for inspiration on juggling multiple business passions? Tim Ozgener might just be your blueprint. He helped take CAO Cigars from a basement startup to a global best-seller and then founded OZ Arts, a cutting-edge contemporary arts hub in Nashville. Now launching Oz Family Cigars, Tim blends art, science, and storytelling into every venture. In this episode, he and Mark Cleveland explore: •...

From EdTech to CyberTech: Justin’s Parallel Entrepreneur Path 10.04.2025

AI and security compliance could make or break your next venture. In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Justin Beals, co-founder of Strike Graph, to dive into frameworks, data risk, and that special systems-thinking spark that turns small wins into scalable success. Leveraging his EdTech expertise to tackle security compliance for billion-dollar enterprises, J...

The Human Side of Hustle Ft Robert Hartline 03.04.2025

What happens when a merger you can't control threatens to destroy your 22-year business overnight? Meet Robert Hartline—parallel founder who scaled his wireless stores to $100 million, only to face a brutal T-Mobile merger that forced him to shut down half his locations in months. In this candid episode of The Parallel Entrepreneur, Robert reveals why he believes in dancing through chaos, harnessi...

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