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 balances operational intensity with deep personal discipline. If you're building more than one thing—an...
May 22, 2025•53 min•Ep. 22
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 serve every citizen. Carla's bold curiosity and relentless learning has had great impact on transpo...
May 15, 2025•1 hr•Ep. 21
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 mechanics of fiat liquidity. • AI-driven disruption—from accountants to animation studios—and the rise of “...
May 08, 2025•55 min•Ep. 20
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 LifeMed AI replaces 90,000 manual billing jobs with 120 staff and a neural network ▸ The fatal cap-tabl...
May 01, 2025•1 hr•Ep. 19
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 will give you: • A new definition of success (alignment, not hustle) • Real‑life examples from the P...
Apr 24, 2025•11 min•Ep. 18
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: • Following Your Heart: Why Tim chose cigars and contemporary art • Improv & Entrepreneurship: Le...
Apr 17, 2025•58 min•Ep. 17
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, Justin’s story is a masterclass in spotting trends and executing effectively. Key Highlights: • Oppor...
Apr 10, 2025•1 hr 9 min•Ep. 16
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, harnessing AI for decisions, and leading from a place of love. Key Highlights: • Secrets of a $100M Scale – ...
Apr 03, 2025•1 hr 1 min•Ep. 15
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 growth, and 24 years in recovery? In this episode, Mark Cleveland welcomes Dr. Michael Sprintz, an anesthesiologist-turned-tech-entrepreneur tackling chronic pain, addiction, and complicated billing structures in healthcare. Dr. Sprintz shares how resiliency, authentic leadership, and “flow” guide his parallel ventures. Highlights: • From OR to Re...
Mar 27, 2025•1 hr 1 min•Ep. 14
Wondering how to nurture alignment throughout M&A integration? In this episode John Farkas, founder of Ratio and Candor—two companies that help businesses master M&A integration—discusses how to unlock growth-ready alignment. From creating synergy across different offerings to leading teams through high-stakes transformations, John shares real-world lessons on balancing purpose with performance, leveraging “context switching,” and staying ahead of rapid market shifts. Highlights: • Paral...
Mar 20, 2025•45 min•Ep. 13
Are you a serial entrepreneur juggling multiple ventures and hungry for breakthrough growth? In this candid conversation, Silas Deane reveals his battle-tested blueprint—from bootstrapping a game-changing fintech solution in an unlikely industry to executing a $90M exit without investors. If you’re ready to unlock the secrets of scaling, pivoting, and innovating across diverse markets, this episode is your must-watch playbook. Highlights include: • How Silas bootstrapped VendEngine from idea to ...
Mar 13, 2025•52 min•Ep. 12
Unlock the secrets of building an acquisition empire from someone who's done it well. In this exclusive interview, John Cerasuolo, CEO of Leap Partners, reveals the unconventional strategies and hard-won lessons that propelled his journey from the Naval Academy to leading a thriving home services network. If you're a parallel entrepreneur looking to scale or dreaming of launching your own network, this conversation is your blueprint for success. Highlights include: • His transformative journey f...
Mar 06, 2025•43 min•Ep. 11
Ready to discover how to hire for potential rather than past credentials—and why it could transform your business? In this episode of Parallel Entrepreneur, Mark Cleveland sits down with Caitlin MacGregor, CEO and Co-Founder of Plum, to talk about building a high-growth company while raising a family and defying the usual startup playbook. If you’re juggling multiple ventures—or planning to—Caitlin’s journey will inspire you to embrace change, experiment with collaboration, and double down on wh...
Feb 27, 2025•1 hr 8 min•Ep. 10
Get ready for a masterclass in multi-venture entrepreneurship from Christian Paro, founder of Center 615, Studio 615, Five Points Alley Shops—three of the most dynamic co-working and creative spaces in Nashville—and a new 49-acre trail-oriented development, featuring artist lofts. Hosted by Mark Cleveland, this episode of Parallel Entrepreneur explores how Christian turned a park-management background into a cutting-edge real estate empire that thrives on community, collaboration, and creativity...
Feb 20, 2025•41 min•Ep. 9
Ready to master the art of running multiple ventures without losing your sanity—or your shirt? Join host Mark Cleveland and Craig Fuller, the pioneering founder of FreightWaves, as they rip open the playbook on “Parallel Entrepreneurship.” From launching data-driven freight tech to buying iconic media brands—and even building an aviation empire—Craig spills the secrets behind owning your audience, harnessing AI for growth, and seizing opportunities most people miss. If you’re tired of thinking s...
Feb 13, 2025•1 hr 9 min•Ep. 8
How do you juggle multiple ventures and keep your cool under pressure? Meet Nitin Rai — seasoned founder, investor in 70+ startups, and champion of underrepresented talent. In this eye-opening episode, host Mark Cleveland uncovers Nitin’s secrets to mastering delegation, cultivating mindful leadership, and building “small” ideas into life-changing success stories. Discover why he believes failure is not an option, why women-led startups excel, and how a single headstand (yes, you read that right...
Feb 06, 2025•46 min•Ep. 7
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 services to cannabis testing labs. In this power-packed interview, Roger reveals how to create genuine value in a business (not just revenue), the art of spotting the right time to sell, and why trusting your team is your ultimate superpower. He also dishes on where AI fits in modern marketing, the pitfalls of overvaluing your own company, and...
Jan 30, 2025•41 min•Ep. 6
’m joined by Jason Putnam, a two-time award-winning executive (Globee Executive of the Year, Silver Stevie Award) and a 2024 Inspiring Leader. Jason’s the Chief Revenue Officer at Plum, where he’s revolutionizing the talent space with psychometric data to build inclusive, thriving teams. In this conversation, we dive into: - Why “failing fast” can spark rapid innovation - How psychometric data transforms hiring and retention - Cultivating a culture that scales alongside your business - Personal ...
Jan 23, 2025•54 min•Ep. 5
In this engaging conversation, Mark Cleveland and Francisco Gonzalez explore the essence of entrepreneurship, focusing on the importance of community, mentorship, and the entrepreneurial mindset. Francisco shares his journey from early entrepreneurial experiences to founding Fearless Journeys, a community aimed at connecting aspiring entrepreneurs. They discuss the emotional aspects of entrepreneurship, the significance of listening to customers, and the role of fear in decision-making. The conv...
Jan 16, 2025•41 min•Ep. 4
How do you build a company that buyers can’t wait to acquire—and still keep your entrepreneurial spark alive? In this episode of The Parallel Entrepreneur, we sit down with John McDonald, Co-Founder and Senior Managing Director of Kensington Park Capital, who’s closed 300+ M&A transactions. John shares: Highlights: • The biggest mistakes founders make when selling • How to spot the perfect buyer (it’s not just about price!) • The HVAC & Home Services roll-up wave: Who’s buying and why • ...
Jan 09, 2025•1 hr 3 min•Ep. 3
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 mission to revolutionize customer experience. Ania shares her insights on building enterprise-grade SaaS platforms, raising capital as a female founder, and scaling multiple businesses simultaneously. Highlights: • How Ania leveraged her background in customer experience and innovation to launch JourneyTrack. • The importance of listening to yo...
Jan 03, 2025•42 min•Ep. 2
In my very first episode, I sit down with visionary Parallel Entrepreneur, William Klehm, to unpack the lessons he learned from building, scaling, and selling multiple businesses. From spinning off a $28 billion asset at Ford Motor Company to leading groundbreaking startups in e-bikes and artificial intelligence, Bill shares his journey of innovation, leadership, and impact. Chapters: 00:00:00 Welcome to the Parallel Entrepreneur 01:18:00 Lessons from Ford: The Foundation of Entrepreneurship 04:...
Dec 06, 2024•1 hr•Ep. 1
The Parallel Entrepreneur Podcast, hosted by Mark Cleveland, dives into the journeys, challenges, and insights of entrepreneurs who simultaneously manage multiple ventures. Through candid conversations, we uncover what drives these visionaries to juggle diverse enterprises, how they navigate risks and failures, and the lessons that have shaped their paths. Guests share practical advice on scaling businesses without losing their edge, balancing energy and focus across ventures, and finding inspir...
Sep 30, 2024•37 sec
