The Cool Grandpa Podcast
Episode Summary In this episode of The Cool Grandpa Podcast, I sit down with Stefanie Shackelford, founder of Odyssey Travel, to explore how travel has evolved—and why experienced travel advisors matter more than ever, especially for grandparents planning meaningful trips with their grandchildren. With over 40 years in the travel industry, Stefanie shares how travel planning has shifted from handwritten tickets and phone-book-sized fare manuals to today’s digital-first world—while explaining what technology still can’t replace: human insight, experience, and relationships. Together,...
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Episode Summary: In this episode of The Cool Grandpa Podcast, I sit down with author, father, and former tech entrepreneur Kepler Knott to explore what it means to raise kids in an age of rapid change. Drawing from his book Raising Tomorrow: Talks to Prepare Our Kids for What Lies Ahead, Kepler shares why adaptation, resilience, and values matter more than ever—and how parents and grandparents can guide kids without hovering over them. Together, we discuss how to talk with kids (not at them) about meaning, work, money, technology, relationships, and values. The conversation highlights the...
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Summary: Choosing senior living for a loved one can feel overwhelming, emotional, and deeply personal. In this episode of The Cool Grandpa Podcast, I sit down with Jeannie Duckworth, co-founder of Blue Magnolia Senior Living Advisors, to unpack what families really need to know when navigating senior care options. Jeannie shares her journey into senior living, shaped by years of hands-on experience inside communities and a deep passion for advocacy. She explains that Blue Magnolia Senior Living Advisors was built to serve families first—offering free, personalized guidance while...
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Show Notes: Santa Claus isn’t just a holiday icon—he’s a world-class leader. In this episode of The Cool Grandpa Podcast, I explore four powerful leadership traits modeled by Santa Claus and how grandparents, parents, and team leaders can apply them both at home and at work. Drawing from real-life experiences, generational insights, and leadership wisdom, this conversation reminds us that leadership is less about titles and more about vision, trust, consistency, and joyful service. Whether you’re guiding your family, leading a team at work, or mentoring others, these...
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Summary In this episode, I talk with historian Lisa Brunet, whose work explores the hidden world of grandparents in ancient Rome. Together, we unpack what grandparenting looked like 2,000 years ago—how elders shaped family identity, cared for young children, preserved memory through storytelling, and passed on family and cultural traditions. While grandmothers often stepped into hands-on roles, grandfathers frequently became the family's historians and memory keepers—sometimes proudly seeing themselves in a toddler learning to speak or scribble. Lisa explains how Roman law, marriage...
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Show Notes You are going to enjoy listening to the very first interview that I did for The Cool Grandpa Podcast. This episode originally aired back in May of 2020. This conversation still resonates with me, my wife Karen, and many other listeners to the podcast. If you heard it before, I hope you enjoy it again. If this conversation is new to you, you will get a lot of wisdom from Dean. In this heartfelt, post-Thanksgiving episode, I sit down with longtime friend and seasoned grandfather Dean Nielson. Dean—a Lean Six Sigma project manager, Eagle Scout mentor, devoted husband, dad of four,...
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Summary In this solo episode, I explore how the natural strengths of intentional grandfathers — presence, curiosity, encouragement, patience, and wisdom — translate into powerful leadership skills in today's workplace. Using stories about Legos, pancakes, and real-life team challenges, Greg reframes proven leadership ideas from Dale Carnegie, John Maxwell, and Dan Miller into an accessible, heart-first approach he calls Grandpa Leadership. Listeners will learn how to build stronger connections with their teams, empower younger employees, guide people through mistakes, and cultivate...
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In this follow-up conversation, I welcome back healthcare advocate and tech CEO Renee Balcom to discuss how grandparents and families can take control of caregiving decisions before a crisis hits. Renee shares practical insights on avoiding common caregiving mistakes, understanding medical and legal authority, and how technology, such as her new platform, Scroll.care, is changing the way families find trustworthy care providers. We explore why planning for aging is not about fear—but about empowerment—and how grandparents can build a legacy of compassion, preparedness, and advocacy...
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“Thou shalt honor the parents of your grandchildren. That’s the most effective way to build lasting family relationships.” — Neil Taft 🧩 Episode Summary In this heartfelt and insightful episode, I reconnect with author and grandparenting expert Neil Taft to explore the evolving role of grandparents in modern families. Neil shares insights from his newest book, Caring Grandparents, and explains how grandparents can both care about and care for their grandchildren. We discuss the emotional and financial realities of grandparents raising grandchildren, the importance of respecting...
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I welcome back longtime friend and repeat guest Dr. James Lott Jr., host of to discuss the rise of millennial grandparents and how shifting generational dynamics are reshaping modern family life. Together, we unpack everything from Millennials' and Gen Z’s futures as grandparents to how technology, social media, and evolving family structures have changed what it means to be a grandparent today. The discussion is full of humor, honesty, and insight — a lively cross-generational conversation about love, legacy, and laughter. Highlights: Why millennials are redefining what “young...
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In this episode of The Cool Grandpa Podcast, I sit down with author, father, and former tech entrepreneur Kepler Knott to explore what it means to raise kids in an age of rapid change. Drawing from his book Raising Tomorrow: Talks to Prepare Our Kids for What Lies Ahead, Kepler shares why adaptation, resilience, and values matter more than ever—and how parents and grandparents can guide kids without hovering over them.
Together, we discuss how to talk with kids (not at them) about meaning, work, money, technology, relationships, and values. The conversation highlights the unique and powerful role grandparents play in a child’s life, offering wisdom, perspective, and unconditional support that kids often hear differently than from parents.
This episode is a practical, thoughtful guide for fathers, grandfathers, mothers, and grandmothers who want to raise grounded, resilient kids while preparing them for a future none of us fully understands.
Key Topics Covered:
- Why adaptation and resilience are essential life skills
- Helping kids develop values through modeling, not lectures
- The difference between happiness and contentment
- Technology, attention, and the battle for our kids’ focus
- Teaching money as “stored energy” in a digital world
- Why boredom, independence, and responsibility still matter
- How grandparents uniquely influence grandchildren
- Turning everyday moments into meaningful conversations
🎯 Call to Action for Fathers
Fathers:
If you’re navigating tough conversations about values, technology, work, or identity with your kids, Raising Tomorrow gives you a practical framework to prepare—not preach. Pick one chapter, read it alongside your child, and use it as a starting point for conversations that build trust, resilience, and independent thinking.
🎯 Call to Action for Grandfathers
Grandfathers:
Your role matters more than you may realize. Kids often hear wisdom differently from grandparents—without the pressure or tension of daily parenting. Raising Tomorrow is a powerful tool to help you guide your grandchildren with perspective, patience, and grace. Use it to reinforce values, spark meaningful talks, and support the parents you love.
Links:
👉 Learn more and explore the book at RaisingTomorrow.org
You can use this email address to reach out to Kepler: connect@raisingtomorrow.org
Here is the link to follow Kepler on Facebook: https://www.facebook.com/RaisingTomorrowCommunity
We talked about and referenced "Moore's Law" about technological advancement. Here is the Wikipedia link about that law. https://en.wikipedia.org/wiki/Moore%27s_law
We both mentioned the book The Anxious Generation by Jonathan Haidt. Here is the Amazon Link: https://www.amazon.com/Anxious-Generation-Rewiring-Childhood-Epidemic/dp/B0C9N2L56X/ref=sr_1_1?crid=2H8M4SK2LVZAW&dib=eyJ2IjoiMSJ9.AYLrmEEAErPNx2RGaRJxhOElKKHk5Bxo4woqlvzz-Zl3Nigo6O4PUOIbeK2xnmdbSNLrSJdplfViZYmOC7k_17z-dnG0hWIAMbE7JrzkDaAp8Q8G7ao1enL8d_YmbK4_Cc_-ZGVSa1EglmXK88K0vTgLUqvpQkWntGt-D2CB3aNbzdTEtwxzK1-yR8z8MM33nyESImFRxSAtRzQI2wyFp6ZKhPCO47wyB1eXuGwHUoA.OkSBZteDUVy3GIBReLNavBQDrAB2limybmuAUJVhw9g&dib_tag=se&keywords=anxious+generation+book&qid=1768444451&sprefix=anx%2Caps%2C166&sr=8-1
You can watch this fun conversation on YouTube by using this link: https://youtu.be/-XCyGvQXEJg
I would appreciate it if you could support the show. You can support the show through “Buy me a Coffee” and donate a few dollars by clicking HERE. (https://buymeacoffee.com/coolgrandpa)
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