Jonathan Thomas McDermott
Welcome to the digital home of Jonathan Thomas McDermott of Chicago, a purpose-driven entrepreneur and community-minded innovator in the evolving world of cannabis lifestyle, real estate, and wellness. This platform showcases Jonathan’s journey as the founder of Stash Holdings Corp, where he has redefined the cannabis experience by creating immersive, socially engaging spaces that blend culture, connection, and care. With years of leadership dedicated to transforming operations into experiences, building inclusive communities, and advocating for mindful living, Jonathan has earned recognition for his vision, authenticity, and impact. Beyond his entrepreneurial pursuits, he is deeply passionate about parenthood, personal wellness, and cultivating meaningful relationships that spark growth. Through his thoughtful leadership and holistic worldview, Jonathan Thomas McDermott is not just shaping an industry—he is helping to reimagine how we gather, grow, and thrive in business and life.
Jonathan Thomas McDermott: Founder of Stash Holdings Corp, Wellness Advocate, and Purpose-Driven Entrepreneur
Jonathan Thomas McDermott, a Chicago-based entrepreneur and founder of Stash Holdings Corp, stands at the intersection of purpose, innovation, and community building. Since founding the company in 2019, McDermott has guided Stash through a period of ambitious growth, strategic transformation, and industry-defining creativity—all while cultivating a brand identity rooted in wellness, connectivity, and cultural relevance.
More than just a business owner, Jonathan Thomas McDermott is a storyteller and strategist—an individual who sees beyond profit margins to the human elements that define meaningful enterprise. His work at Stash reflects this ethos. What began as a vision to reimagine cannabis retail has evolved into a multi-dimensional lifestyle brand that includes immersive customer experiences, dynamic retail operations, and one of the largest consumption lounges in the United States. The lounge, at 15,000 square feet, is not simply a venue—it is a cultural hub, drawing people together through art, entertainment, and education. One of the brand’s standout community-building successes was a sold-out movie night featuring 21 Jump Street, where guests across generations gathered for a unique, cannabis-enhanced film experience, proving McDermott’s theory that modern dispensaries can—and should—function as social sanctuaries.
Yet, for all his achievements in the industry, Jonathan Thomas McDermott defies the tropes often associated with cannabis entrepreneurs. He is not interested in flashy financial narratives or recycled investor jargon. Instead, he prioritizes operations, customer experience, and visionary leadership. His passion lies not in raising capital, but in raising standards—rethinking what cannabis retail can look like when driven by authenticity, community, and innovation. As Stash expands into new markets like Missouri, McDermott has remained steadfast in his commitment to shaping not just stores, but experiences—spaces that foster openness, dialogue, and a sense of belonging.
At the core of McDermott’s approach is a refined understanding of human connection. A lifelong networker and natural communicator, he has always excelled in business development, relationship-building, and strategic partnerships. These strengths have allowed him to grow Stash Holdings Corp with an agility and resilience that few can match. He is known among peers and collaborators for his uncanny ability to find alignment where others see friction and to build bridges that outlast trends or transactional convenience.
But the Jonathan McDermott story is not confined to the boardroom. In fact, it is his personal narrative that most vividly illustrates the values that shape his work. At age 57, McDermott became a first-time father to a daughter who has since become the brightest light in his life. Now the proud parent of a three-year-old, he speaks candidly about the transformative experience of becoming a parent later in life. “There’s a kind of patience that only comes with age,” he has said. “You don’t rush through the moments—you savor them. You let them teach you.”
Fatherhood has grounded Jonathan Thomas McDermott in new ways, reinforcing the principles of mindfulness, presence, and emotional intelligence that have long guided his leadership style. This chapter of his life has also led him to revisit wellness practices that once lingered on the margins of his schedule. Most notably, he has returned to Transcendental Meditation, a daily ritual that now plays a central role in his personal and professional life. For Jonathan Thomas McDermott of Chicago, meditation is more than just a mental reset—it is a mechanism for staying deeply attuned to his vision, values, and responsibilities as both a father and a founder.
A lover of travel, Jonathan Thomas McDermott finds continued inspiration in the landscapes, philosophies, and lifestyles of Europe, especially Italy and Greece. These destinations, with their rich histories and vibrant cultures, have become his go-to sanctuaries for reflection and renewal. Whether walking along a cliffside village in Santorini or enjoying a slow afternoon in a Tuscan piazza, McDermott draws on the sense of timelessness, craftsmanship, and community that define these regions—qualities he seeks to mirror in the atmosphere of Stash’s stores and lounges.
Professionally, Jonathan Thomas McDermott is also focused on rebuilding his digital footprint to reflect this multidimensional identity. After stepping away from LinkedIn several years ago—citing challenges with platform restrictions around cannabis-related content—he is now working with a Philadelphia-based marketing agency to relaunch his profile with a renewed focus on storytelling, values, and vision. Rather than lead with financial transactions, he plans to highlight Stash’s operational evolution, its role in community engagement, and the distinct lifestyle experiences it delivers.
Through all of this, McDermott’s guiding principle remains simple but powerful: build something that matters. This philosophy fuels every decision he makes, from store layouts to hiring practices to how events are curated and marketed. It’s not about outpacing the competition or dominating market share. It’s about making sure every customer, every guest, every community member who steps into a Stash location leaves feeling seen, supported, and inspired.
In an industry still navigating its identity, Jonathan Thomas McDermott of Chicago represents a new kind of leader—one who understands that cannabis is not just a product, but a platform. A platform for culture, for wellness, for connection, and for reinvention. He doesn’t just sell something; he stands for something. And in doing so, he is building not just a company, but a legacy—one rooted in empathy, boldness, and the quiet confidence that the best stories are the ones still being written.