In this episode, JC sits down with Riley Siddoway, the ultimate "operator's operator," at the headquarters of Uphill Pursuits in Bozeman, Montana. From his early days exploring mountain peaks to a decade as a mountain guide, Riley shares the lessons learned in leadership, grit, and decision-making at high altitudes—both literal and figurative.

Riley dives into his entrepreneurial journey, offering insights on building businesses that can thrive beyond their founders, the importance of sticking to the process, and why balancing risk is key to success. Whether it’s navigating a treacherous summit or acquiring a business, Riley’s philosophy stays consistent: “Getting to the top is optional. Getting back down is mandatory.”

If you’re passionate about adventure, small business ownership, or just love hearing real stories about perseverance and purpose, this episode is for you.