In this episode of Cowboys & Cufflinks, Jeff Mathis and Caleb Moore break down when to claim Social Security benefits, common mistakes retirees make, and how timing can impact your long-term retirement income.
They also discuss retirement planning, longevity risk, toxic financial relationships, and why having a personalized income strategy matters more than ever.
What You’ll Learn
• When it may make sense to claim Social Security early
• How delayed claiming impacts your monthly benefit
• What provisional income means for Social Security taxation
• Common Social Security claiming mistakes
• Why retirement income planning requires more than just “rules of thumb”
• How longevity impacts retirement planning decisions
• Why stress-testing a retirement plan matters
The conversation also touches on toxic financial relationships, retirement planning mistakes, longevity risk, and even the growing role of artificial intelligence in investing decisions, all through the lens of protecting your future and building a retirement plan designed to adapt.
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.
