Lead Like a Grandpa: The Heart-Centered Leadership Your Team Needs EP - 246
Release Date: 11/21/2025
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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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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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 loyalty by showing genuine care. I also introduce my three-part Grandpa Formula for Connection and share a weekly challenge to help leaders put these ideas into action.
Key Takeaways
- Lead with presence, not pressure. Your team needs to feel seen, valued, and supported.
- Let people build "their ship." Encourage creativity and ownership instead of rigid compliance.
- Practice real curiosity. Ask questions that show you care about your people's work and dreams.
- Encouragement = fuel. A slight nod, a quick thank-you note, or celebrating tiny wins builds massive confidence.
- Loyalty follows care. People may not feel loyal to an organization these days, but they will be loyal to a leader who shows up for them.
- Be the calm center. Like a seasoned grandparent, bring steadiness, patience, and wisdom when stress hits.
- Guide people without taking over. Present options, help them think, and let them choose — that's how they grow.
The Grandpa Formula for Connection
- Be Present
Put the phone down. Give undivided attention. It builds trust instantly. - Be Curious
Ask about projects, challenges, and motivations. Curiosity creates belonging. - Be Encouraging
Praise progress, not perfection. Your encouragement becomes someone's confidence.
Links and Resources
Click HERE to download your free copy of my Grandpa Leadership Connection Worksheet.
To listen to Dan Miller's interview about supporting grandchildren's creativity, click on this link: https://cool-grandpa.us/2021/09/10/ep-48-growing-creativity-with-grandchildren/
As always, you can watch this video on YouTube using this link: https://youtu.be/I3_S8E1UhjY.