At Cowboys and Cufflinks, Main Street values meet Wall Street insight. Built on trust, clarity, and common sense, our show helps everyday American families and mainstream investors cut through the noise of confusing financial jargon.
We believe that building wealth isn’t just for the elite. It’s for hardworking people who want to protect their families, pursue their dreams, and secure their future.
With a straight-talking style rooted in integrity, Cowboys and Cufflinks brings real strategies, timeless principles, and a touch of grit to help you invest with confidence and live life on your terms.
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Steve is an investor coach, entrepreneur, and co-host of Cowboys & Cufflinks. With a background in investment services, counseling, and business ownership, Steve brings a people-first approach to financial coaching and leadership. His passion for helping others build confidence and clarity has guided his career for more than two decades, helping families pursue financial peace of mind through practical planning and real conversations.
Outside the office and podcast studio, Steve enjoys country swing dancing, exploring the Colorado Rockies, hiking, biking, and spending time outdoors whenever he can.
Jeff Mathies is a retirement strategist, entrepreneur, and host of Cowboys & Cufflinks. After getting his start in the insurance industry in 2003, Jeff founded Mathies Financial Partners in 2008 and has spent years helping families navigate retirement through education, planning, and real-world experience. As a Certified Financial Educator (CFEd®), he is passionate about simplifying financial concepts and helping people make confident decisions for the future.
Based in Pueblo, Colorado, Jeff enjoys ranch life with his wife and their five children. Outside the office and podcast studio, you’ll usually find him mountain biking, hiking, golfing, or spending time with his kids and grandkids.
Caleb is a Colorado-based Investment Advisor Representative, outdoorsman, and co-host of Cowboys & Cufflinks. With more than 20 years of experience coaching business and financial management for the State of Colorado, Caleb has dedicated his career to helping people build confidence through financial literacy, leadership, and practical guidance. His passion for coaching and servant leadership continues today as he helps families and individuals prepare for long-term financial stability.
Outside the office and podcast studio, Caleb enjoys mentoring youth hunters and fishermen, spending time outdoors, and sharing life with his family, dogs, and horses in Pueblo, Colorado.
