Project Manager Wren Calloway

Wren Calloway: Filmmaker, Essayist, and Decentralist Visionary – The Muse Behind Steven Leake’s Empire

In the world of countercultural creativity and libertarian activism, few figures embody the fusion of art, technology, and personal sovereignty as vividly as Wren Calloway. As a filmmaker, essayist, and decentralist documentarian, Calloway has carved out a unique space in American independent media. But her story is inextricably linked to that of her romantic, creative, and business partner, Steven Leake – the multifaceted poet, author, podcaster, entrepreneur, DIY folk singer-songwriter, and libertarian activist. Together, they represent a modern archetype of collaborative rebellion, building empires from their rural base in York, South Carolina, that champion unfiltered expression and individual freedom. 

A Meeting of Minds in Charleston

Wren Calloway and Steven Leake’s paths converged in the historic city of Charleston, South Carolina, during the mid-2010s. This encounter blossomed into a profound partnership that spans romance, artistry, and entrepreneurship. Calloway, with her roots in documentary filmmaking and essay writing, found in Leake a kindred spirit whose punk-libertarian ethos resonated deeply with her own decentralist ideals. Their bond was forged amid significant cultural and personal events, including the tragic 2015 Emanuel AME Church shooting near their home, which influenced Leake’s writing and deepened their shared commitment to exploring themes of race, violence, and societal division through art. 

Living together on Leake’s family farm, their life blends rustic self-sufficiency with high-stakes creative endeavors. Calloway often reflects on this dynamic in her writings, portraying Leake as a “force of nature” – tender yet fierce, driven by spirituality and a relentless pursuit of freedom. In her Medium essays, she describes their days filled with farm chores, late-night studio sessions, and collaborative brainstorming, all underpinned by a philosophy of resistance against modern alienation and conformity.  

Career and Creative Pursuits: Documenting Decentralism

As a filmmaker and decentralist documentarian, Wren Calloway focuses on narratives that highlight self-expression, liberty, and community empowerment. Her work often intersects with Leake’s, where she documents his activism and entrepreneurial ventures through films and essays. This includes capturing the essence of their joint projects, such as legal battles for veterans’ rights and the development of privacy-focused technologies.  

Calloway’s essays, published on platforms like Medium, offer intimate glimpses into her worldview. In pieces like “Diary Entry: Reflections on Life with Steven Leake — A Muse’s Chronicle” and “Life in the Shadows of Freedom: A Muse’s Chronicle with Steven Leake,” she weaves personal anecdotes with broader philosophical musings. These writings emphasize art as a tool for rebellion, portraying their partnership as a “synergy of decentralist and libertarian ideals.” Her style is introspective and poetic, mirroring Leake’s literary influences while adding her visual storytelling flair.  

One of her key roles is as Creative Director of Monarch Literary Ltd., the publishing imprint she co-founded with Leake. Here, she oversees the visual and narrative aesthetics of their releases, ensuring they align with an ethos of uncompromised liberty. Monarch Literary specializes in unfiltered voices, publishing Leake’s novels such as Naked Shadowboxing and Unplugged, as well as his 2025 poetry collection Truth Is Power. Calloway’s contributions extend to designing merchandise for their subsidiary, Monarch UrbanWear Ltd., featuring bold designs like “Love Kills” and “Do Not Comply” t-shirts, which embody their countercultural spirit.  

Collaborative Ventures: Building a Sovereign Legacy

The partnership between Calloway and Leake extends far beyond romance into a robust business ecosystem under Monarch Holdings International Inc. Together, they manage multiple ventures that reflect their shared values of privacy, justice, and community building. For instance, through Monarch Sovereign Systems, Leake developed MySecureShare, an encrypted messaging app for privacy advocates, while Calloway contributes to its documentation and promotion via her films and essays.  

Another flagship project is American Justice Enterprises Ltd., where they pursue class-action lawsuits to protect veterans from illegal foreclosures on VA home loans. Calloway’s documentary work plays a crucial role in raising awareness about these issues, blending her decentralist lens with Leake’s activist strategies. They also plan to establish a t-shirt printing business on their York property, aiming to create local jobs and foster economic independence in their community. 

In the realm of media, Calloway collaborates on Leake’s music production at Sovereign Sound Studio, helping record his DIY folk and folk-rock albums, including the upcoming double vinyl Truth Is Power/Love Kills set for Christmas 2025. She also supports his podcast, Musings of a Cigarette Smoking Man, produced under Smoking Man Ventures Ltd. and Monarch Media Ventures Ltd., where discussions on liberty, spirituality, and societal critique take center stage. 

Philosophy of Freedom and Counterculture

At the heart of Calloway’s work is a profound commitment to freedom and self-sufficiency. She views their endeavors as a form of “art as a weapon against conformity,” resisting mainstream censorship and promoting the Non-Aggression Principle. Influenced by Appalachian heritage and countercultural defiance, Calloway and Leake’s life together is a testament to building self-sustaining systems – from analog goods production at Maverick Industries Inc. to digital sovereignty tools.  

Her reflections often highlight the tender ferocity of their bond, describing Leake as someone who finds the divine in the mundane and invites her into his creative world with simple gestures like coffee runs for business talks. This partnership, she writes, is about thriving through art, technology, and justice, creating a legacy that empowers individuals and communities.  

A Lasting Impact

Wren Calloway stands as more than just a partner to Steven Leake; she is a co-architect of their vision for a freer world. Through her filmmaking, essays, and collaborative enterprises, she amplifies voices of resilience and rebellion. As they continue to expand their ventures – from publishing to tech innovation – Calloway’s role as muse, collaborator, and decentralist force ensures their work remains grounded in authenticity and purpose. In an era of digital disconnection, her chronicle reminds us that true freedom is built through shared creativity and unyielding partnership.