Skip Gen Travel with Stefanie Shackelford EP - 251
Release Date: 01/30/2026
The Grandparenting Blueprint: With Richard Eyre EP - 257
The Cool Grandpa Podcast
Summary: In this episode of The Cool Grandpa Podcast, I welcome returning guest Richard Eyre to discuss his latest book, The Grandparenting Blueprint. Together, we explore how grandparents can intentionally build meaningful relationships with their grandchildren by sharing wisdom, stories, and what Richard calls “Grandfather’s Secrets.” Richard explains how shifting from lectures and advice to storytelling and interactive conversations opened the door to deeper engagement with his own grandchildren. Even more unique—23 of his grandkids helped write the book, contributing their own...
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From Author to Entrepreneur: Kevin Hall's Journey EP - 256
The Cool Grandpa Podcast
Episode Summary What happens when a retired programmer decides he’s not finished building? In this powerful and practical conversation, I welcome back author and marketing mentor Kevin M Hall to discuss: Reinventing yourself after retirement Building an author platform from scratch Marketing books without spending thousands Navigating AI in publishing The courage to ask (because when you don’t ask, the answer is always no) And what 50 years of marriage can teach us about grace and love Kevin shares real-world strategies from his upcoming book Book Marketing on a Budget and...
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Transitions Are the Curriculum EP - 255
The Cool Grandpa Podcast
🎙 The Magic of Transitions In this episode of The Cool Grandpa Podcast, I explore the theme of transitions in life, particularly focusing on the journey from fatherhood to grandfatherhood and the responsibilities that come with these roles. My observations delve into the emotional and relational aspects of these transitions, emphasizing the importance of embracing new identities and the role of mentorship in guiding younger generations. T In this reflective solo episode, I also explore the truth every man eventually faces: Transitions are inevitable. From boy to man. From son to...
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An Understanding Heart For Grandparents EP - 254
The Cool Grandpa Podcast
🧭 Episode Summary In this solo episode of The Cool Grandpa Podcast, I explore insights from Dan Miller’s book and apply them to modern grandfatherhood. Greg shares three powerful themes—listening as a legacy skill, curiosity over correction, and emotional presence in a distracted world—along with personal stories and practical steps grandfathers can use today to deepen relationships with their grandchildren. 👂 Listening as a Legacy Skill Listening isn’t passive—it’s an active gift that teaches empathy and builds lifelong connections. I reflect on the...
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Presence Over Pressure: A Cool Grandpa Lesson EP - 253
The Cool Grandpa Podcast
Summary In this episode of the Cool Grandpa Podcast, I discuss the importance of communication and listening in building meaningful connections with grandchildren. I emphasizes that presence is more powerful than pressure and introduces the 'Three, Two, One Grandpa Rule' to enhance interactions. The episode highlights the significance of asking questions, reflecting on conversations, and creating a safe space for grandchildren to express themselves. Key Takeaways 🧩1. Presence Beats Pressure Just being calm and physically present can create a sense of safety and trust for...
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The Grandpa Effect: Belief, Confidence & Legacy EP -252
The Cool Grandpa Podcast
What do your grandchildren believe about themselves because of you? In this solo episode of The Cool Grandpa Podcast, I draw on the timeless wisdom from Chapter One of The Magic of Thinking Big and apply it to one of the most underestimated leadership roles in a child’s life: the role of a grandfather. David Schwartz opens his book with a bold claim—success begins with belief. Not intelligence. Not talent. Belief. And when you view that idea through the lens of grandfatherhood, it raises an important question: What beliefs are our grandchildren borrowing from us—intentionally or...
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Skip Gen Travel with Stefanie Shackelford EP - 251
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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Raising Tomorrow with Kepler Knott - EP 250
The Cool Grandpa Podcast
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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Navigating Senior Living with Jeannie Duckworth EP - 249
The Cool Grandpa Podcast
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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Leadership Lessons from Santa Claus EP - 248
The Cool Grandpa Podcast
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...
info_outlineEpisode 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, we dive into:
- The hidden value of working with a professional travel advisor
- How multi-generational and “skip-gen” travel is reshaping family experiences
- Why grandparents are uniquely positioned to create unforgettable travel memories
- How travel agents personalize trips based on family dynamics, budgets, and kids’ ages
- The growing appeal of national parks, cruises, trains, and cultural experiences
- What to look for when choosing a travel agency—and red flags to avoid
- Why travel insurance matters more today than ever
This conversation is a must-listen for grandparents who want to travel smarter, reduce stress, and build deeper bonds with their grandchildren through shared experiences.
If you’re a grandparent dreaming about meaningful trips with your grandkids—but don’t want the stress of planning—this episode is for you.
👉 Listen now and discover how experienced travel advisors help grandparents create unforgettable, age-appropriate adventures that build lifelong memories.
Links
Click on this link to visit Odessy Travel: https://www.team-odyssey.com/
Here is Stefanie's email address: sjs@team-odyssey.com
You can use this phone number to reach out to Stefanie and Odessy Travel: 707-343-7112
You can watch this fun conversation on YouTube by using this link: https://youtu.be/wfWvWW3Dg1o
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)
Here is a link to my webstore: https://cool-grandpa.us/shop/