Community Spotlight: Josh Wilken-Simon & Legacy (Saturday Spotlight Edition)

Josh Wilken-Simon isn’t just building businesses, he’s building a movement rooted in legacy. As the founder of Legacy Cup, Legacy Glassworks, and Legacy Cannabis, Josh has spent nearly two decades fighting for cannabis legalization and creating spaces where the Minnesota cannabis community can thrive. His passion for music, art, and cannabis comes together this month at Legacy Cup VI, the Midwest’s largest cannabis festival and his story is just as inspiring as the event itself.

The Journey

Josh launched Legacy Glassworks in 2010 with a simple idea, to share his cousin’s hand-blown pipes with the world. What started as a few pieces sold at music festivals quickly became a way to spotlight an underground art form and bring more visibility to the glassblowing community. Those early days were full of long hours, road trips, and grassroots hustle, but they laid the foundation for something much bigger.

Over the years, Josh expanded his vision, founding Legacy Cannabis and later Legacy Cup, now the Midwest’s largest cannabis festival and a must-attend event for anyone passionate about cannabis culture. Each new project grew from his commitment to building something meaningful, not just for himself, but for the entire community.

For Josh, the most rewarding part of working in cannabis has been watching that community take shape and thrive. He admits that his excitement for the industry sometimes leads him to take on more than most people would dare, but with the support of a passionate, growing team, those big ideas have consistently transformed into major successes.

Community Impact

For Josh, community isn’t just an afterthought,  it’s the heart of everything Legacy does. From glass pipe gallery shows to intimate seshes, from Legacy Cup to Northern Haze, each event is designed to bring people together, celebrate the culture, and strengthen Minnesota’s cannabis community.

Josh firmly believes that collaboration is the foundation of a thriving cannabis industry. “I’d be working in a cubicle for some asshole boss if the community had not always supported us,” he says with a laugh, a reminder that Legacy’s success is built on the support of the people around them.

One of the events Josh is most proud of is Girls Kick Glass! - a groundbreaking gallery show that puts female glassblowers front and center. The event featured an inspiring mix of emerging artists and veteran pioneers, shining a light on their artistry while encouraging greater representation and recognition for women in the glassblowing world.

By championing events like these, Josh and Legacy are creating more than just businesses, they’re building a space where art, cannabis, and community intersect in powerful, meaningful ways.

Looking Ahead

Josh’s vision for Legacy’s future is rooted in supporting small, independent operators and preserving the craft culture of cannabis. He wants Legacy’s retail stores to serve as a platform for showcasing Minnesota’s best, from boutique growers to passionate hash makers, so that consumers can experience the highest quality, locally crafted products.

But Josh isn’t stopping there. He plans to build out a state-of-the-art grow lab, allowing Legacy to join the cultivation and production side of the industry. This will give his team the opportunity to experiment, innovate, and create unique products that reflect the brand’s commitment to excellence.

Josh is also watching Minnesota’s cannabis market closely and expects it to follow the same path as other recreational states, with large-scale consolidations and corporate players entering the scene. Rather than selling out, Josh is doubling down, forming strong partnerships with small, local businesses and positioning Legacy as a champion of independence. His goal is to keep Legacy community-driven, locally owned, and fiercely authentic, no matter how the market shifts.

Personal Insights

When asked what advice he has for new leaders in the cannabis space, Josh doesn’t hesitate: focus on people. “It’s all about the connections you make, with employees, the community, vendors, and even politicians,” he says. “Learn to work collaboratively, respectfully, and with passion, and success will follow.”

Josh’s biggest personal lesson has been to trust his instincts. “When red flags are waving and alarms are blaring, listen. Act decisively. Myself and many others have fallen victim to indecision and ignoring our instincts,” he admits. This ability to act with clarity and conviction has been key to Legacy’s growth and longevity.

For Josh, cannabis is about far more than business, it’s about creating spaces where people can connect, share ideas, and celebrate the culture together. Legacy Cup is the culmination of that vision, blending music, art, cannabis, and community into one unforgettable experience. If you want to witness the heart of Minnesota’s cannabis scene and see Josh’s passion in action, don’t miss this year’s Legacy Cup, it’s where the future of cannabis culture comes alive.

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