Should AI Manage Your Investments? What Retirement Investors Need to Know

Artificial intelligence is everywhere right now, including investing. But should AI be trusted to build an investment portfolio?

In this episode of Cowboys & Cufflinks, Jeff Mathies and Caleb Moore break down how AI works, where it can be useful, and why long-term investing decisions still require context, judgment, and a coordinated plan.

Topics include:

  • Why AI relies heavily on past data

  • Why markets move for reasons beyond numbers

  • Crypto volatility and risk considerations

  • The thinking behind the MYFIT retirement planning process

More episodes and resources: cowboysandcufflinks.com

Have specific questions to ask Jeff, Caleb or the team at Mathies Financial Partners? Schedule a phone call here: https://calendly.com/jeff-mathies/15-min.

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Episode Video

Jeff Mathies, CFEd®
CEO, Mathies Financial Partners

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.