This week on Irregardless, Shep Hickey sits down with Sean Bailey, Territory Sales Manager at Smokiez Edibles, for a conversation that spans from cannabis to the Chilean mountains. Sean gives us a behind-the-scenes look at Missouri’s evolving cannabis industry—how the shift from medicinal to recreational use reshaped his career and opened up new opportunities.

But that’s just the beginning. Sean dives into his time with the National Outdoor Leadership School (NOLS), where he spent six months living off the land in Patagonia, Chile. From survival skills and leadership to the Leave-No-Trace philosophy, Sean shares what it really means to thrive in the wild—plus a few hilarious stories and the most intense challenge his group faced in the mountains.

He also reflects on how returning home after such a life-changing experience shaped his worldview—and how his path as an Eagle Scout helped prepare him for it all.

Tune in for a conversation full of grit, growth, and the kind of leadership that only comes from life off the beaten path.