Skip Gen Travel with Stefanie Shackelford EP - 251
Release Date: 01/30/2026
Aging Isn’t Just Physical with Erica Sell EP - 263
The Cool Grandpa Podcast
Show Notes In Part 2 of this powerful conversation, I sit down again with Erica Sell to explore the emotional, relational, and real-life challenges of aging—the side most families aren’t prepared for. While Part 1 covered the logistics of home medical equipment, this episode dives deeper into what really matters: - Difficult conversations - Resistance from aging parents - Family dynamics - Planning before a crisis hits Erica shares firsthand stories from families navigating aging in place, including the common struggles with “stubborn parents,” delayed decisions, and the emotional...
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Living in Crescendo with Cynthia and Kameron Haller EP - 262
The Cool Grandpa Podcast
SHOW NOTES In this inspiring episode, I visit with Cynthia and Kameron Haller to explore what it truly means to live a life of purpose—especially in the later years. With 6 children and nearly 28 grandchildren, the Hallers made a bold decision: step away from family for 18 months to serve a mission in Northern Ireland. What they discovered wasn’t just about service; it was about rediscovering identity, expanding influence, and living with intention. What You’ll Hear in This Episode: The Decision to Serve Why did they choose to leave family behind to serve The role of faith,...
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Winning the Battle for Connection: With Lee Ostler EP - 261
The Cool Grandpa Podcast
In this powerful episode of The Cool Grandpa Podcast, I sit down with Lee Ostler of the Heart of the Fathers Foundation to explore a transformative idea: 👉 If you want your family to change, you have to change first. Lee shares deep insights into emotional connection, generational influence, and why many grandparents struggle to truly connect with their grandchildren—not because they don’t care, but because they’ve never been shown how. Together, they unpack: Why emotional regulation is the foundation of strong family relationships The danger of “stealing the future” by...
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From Self-Sabotage to Self-Leadership with Mark Aylward EP 260
The Cool Grandpa Podcast
Episode Summary What happens when the identity you’ve built your life around—career, family role, or personal expectations—starts to shift or even fall apart? In this powerful return conversation, I sit down with Mark to explore why so many men experience self-sabotage, confusion, and identity loss as they move through their 40s, 50s, and beyond. Together, we unpack the emotional, cultural, and psychological forces shaping modern masculinity—and why today’s men often feel unprepared for this stage of life. Mark shares deeply personal experiences, including moments of loss,...
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Love Travels: How To Stay Connected with Helen Ellis EP - 259
The Cool Grandpa Podcast
Episode Summary In this episode of The Cool Grandpa Podcast, I sit down with Helen Ellis, author and researcher specializing in distance families—families spread across cities, countries, and continents. Drawing from her personal experience and groundbreaking research, Helen shares how grandfathers can build meaningful, lasting relationships with their grandchildren—even when separated by thousands of miles and multiple time zones. From practical strategies to emotional truths, this conversation explores how intentionality, empathy, and consistency can transform distance into deeper...
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Aging in Place with Erica Sell EP-258
The Cool Grandpa Podcast
Episode Overview Many grandparents want to stay in their homes as long as possible—but most families only begin planning when a medical crisis forces the issue. In Part 1 of this conversation, I sit down with Erica Sell, founder of , about how proactive planning and smart home design can help older adults maintain independence and dignity. Erica shares how growing up around the medical equipment industry—and a family emergency—led her to create a different approach: helping families understand all their options rather than limiting them to what insurance covers. This episode...
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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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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/