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. 🌟

🔗 Watch or listen now and join the conversation about what it truly means to be an operator in life and business. #AmericanOperator #Entrepreneurship #Leadership #MountainLife

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https://mainshares.com/

n this episode of American Operator, JC sits down with Travis McAshan, founder and visionary leader of Glide Design, a trailblazing marketing and design firm based in Austin, Texas. Travis shares his entrepreneurial journey, from leaving the corporate grind to creating a company centered on “beauty and results.” Together, they dive deep into the power of user-centered design, the importance of continuous improvement, and the mindset needed to embrace failure as a stepping stone to success.

Travis reveals his personal and professional philosophies, including how writing daily “Be" statements has transformed his life and leadership style. He also opens up about the messy reality of entrepreneurship, sharing insights from his 21-year journey of running a business, overcoming burnout, and reconnecting with his purpose.

Whether you’re a seasoned entrepreneur or just starting your journey, this episode is packed with actionable wisdom and inspiration to help you define your purpose, lead with integrity, and navigate the challenges of business ownership. #operatorinsights #operatorlife #acquisition #buyabusiness

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Follow Mainshares on LinkedIn https://www.linkedin.com/company/mainshares/

https://mainshares.com/

In this special team room session of The American Operator, JC goes behind the curtain with Judd Goodrich, Head of Capital Markets, to explore the world of small business ownership, investment, and operations. Whether you're an aspiring owner-operator or a seasoned entrepreneur, this episode is packed with actionable insights and candid advice.

Judd shares his journey from Minnesota to the startup world, offering lessons learned from supporting thousands of business founders and operators. Together, they discuss the challenges and rewards of taking over small businesses, from managing labor-intensive industries to balancing growth with sustainability. With an emphasis on the human element, Judd reveals why empathy and respect for a business’s history are critical for success.

Listeners will gain valuable tips on:

• Navigating the complexities of small business acquisitions.
• Building trust with employees and stakeholders.
• Setting achievable goals to drive sustainable growth.
• Leveraging the right support networks and investors.
• Why starting small often leads to big successes.

This conversation is full of real-world examples, practical advice, and engaging stories from the frontlines of small business operations. Whether you’re buying your first business, managing a growing portfolio, or just curious about what it takes to succeed, this episode delivers honest and relatable insights for every stage of the journey.

Subscribe to our Youtube Channel: https://www.youtube.com/@AmericanOperator

Follow Mainshares on LinkedIn https://www.linkedin.com/company/mainshares/

https://mainshares.com/