Jack’s covered so many miles, his quads could probably get verified. But this episode isn’t about distance—it’s about depth.

From Calendar Year Triple Crown thru-hiker to dirtbag mentor to outspoken activist, Jack’s evolution has been public, personal, and full of hard choices. In this intimate, funny, and sometimes heavy conversation, we cover:

• The shifting why that fuels his steps today

• Why he canceled a 1,776-mile protest hike out of fear for his safety

• The new plan he’s carving out instead—and what keeps him grounded

• Dirtbag ingenuity when gear fails big time

• Wild stories from the trail (and the weirdest item he’s seen someone carry)

• Who’d play him in the biopic of his life—and what scene has to be included

If you’ve ever felt torn between purpose and protection, activism and adventure—this one’s for you.

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