In a city known for breakout artists and bold founders, Mark Cleveland is building something less obvious but no less revolutionary. Through his Parallel Entrepreneur brand – anchored by a podcast, a growing network, and a forthcoming book – Cleveland is giving voice to a specific kind of business leader: the founder who doesn’t follow one path, but several at once.
“This isn’t about distraction,” Cleveland says. “It’s about design. Some of us are wired to build across domains. We’re not unfocused – we’re aligned differently.”
That insight forms the foundation of the Parallel Entrepreneur movement. For Cleveland, it’s not a theory – it’s how he’s operated for decades. His ventures span sustainable transportation, retail, civic innovation, manufacturing, media, and capital formation. From launching Swiftwick, a U.S.-made performance sock brand, to acquiring and selling Hobby Lobby International and the Dolphin Club in Brentwood. From leading Sea Bridge Freight, a maritime container-on-barge service, to his current work as Managing Director at Kensington Park Capital, Cleveland has consistently operated not in sequence, but in parallel.
And he’s not alone.
The Parallel Entrepreneur Podcast, which Cleveland hosts, features founders who run multiple businesses simultaneously. These are not “serial entrepreneurs” jumping from one idea to the next – they’re visionaries building integrated lives across multiple arenas. Guests include leaders like Craig Fuller, whose work in freight and aviation reveals how a single strategic framework can scale across sectors; Caitlin MacGregor, a tech CEO and mother navigating the layered demands of leadership; and Matthew Joynes, a global investor orchestrating a constellation of parallel ventures.
Cleveland believes it’s time this often-overlooked group of builders had a name – plus the tools and community to thrive.
“Most of the startup world still glorifies the solo founder chasing the unicorn,” he says. “But there’s a large, mostly unspoken tribe of founders who don’t fit that mold. They’re raising families, launching initiatives, managing teams, and creating impact on multiple fronts. This is who we serve.”
That service extends well beyond storytelling. The Parallel Entrepreneur Network offers workshops, business strategy services, and soon, proprietary AI tools like “Paralleling Agents” to help founders manage complexity without burning out. Regular meetups, called Lantern Circles, foster what Cleveland calls “companionship over coaching” – spaces built on trust, shared wisdom, and honest reflection.
“We’re not trying to scale another coaching platform,” Cleveland explains. “This is about real relationships that help you stay aligned, grow your ventures, and remember who you are.”
That spirit of integration runs through Cleveland’s upcoming book, Parallel: Build More. Burn Out Less. Drawing on podcast interviews, personal stories, and his wife Jenny Pruitt’s soulful reflections, the book lays out a philosophy where inner alignment becomes the foundation for outward momentum. Rather than offering a one-size-fits-all playbook, it invites readers to tune into their own instincts, energy, and rhythm.
“It’s not a how-to,” Cleveland says. “It’s more of a who-are-you.”
The book – like the movement – is intentionally non-linear. Its stories, tools, and insights can be picked up in any order, echoing the ethos of the parallel path: structured, but spacious. Focused, but fluid.
And Nashville, Cleveland says, is the perfect city to house this movement. “Nashville has a kind of creative permission built into its DNA,” he says. “You can be a musician and a startup founder, a teacher and an innovator.”
He believes the city’s collaborative spirit is a hidden superpower – especially for entrepreneurs walking parallel paths. “Musicians are masters of improvisation and collaboration. They know how to blend creative tension into something beautiful. That’s the same energy we’re channeling. In many ways, the creative class is part of our source code.”
He believes the city’s collaborative spirit is a hidden superpower – especially for entrepreneurs walking parallel paths. “Musicians are masters of improvisation and collaboration. They know how to blend creative tension into something beautiful. That’s the same energy we’re channeling. In many ways, the creative class is part of our source code.”
Through the podcast, platform, and community, Cleveland is doing more than building a brand. He’s giving a name to a way of working that many high-capacity leaders have practiced quietly for years.
“You don’t have to choose between your passions, your ventures, or your purpose,” he says. “You just have to find your rhythm – and your tribe.”
In a world that increasingly rewards creativity, adaptability, and multidimensional leadership, Cleveland’s message is clear: You’re not scattered. You’re scanning the horizon.
And in Music City – where possibility hums in every corner – that mindset might just be the new blueprint for what comes next.
Photos: Jenny Pruitt Cleveland and Jeremy Cowart
