Parallel Entrepreneur with Mark Cleveland

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 r...

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 perfo...

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 episod...

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,...

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—Caitli...

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 backgr...

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,...

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...

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...

In this episode of the The Parallel Entrepreneur Podcast, I'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 fa...

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 entrepreneu...

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...

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 backgroun...

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 We...

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...