Helping Grandkids Graduate Without Debt With Jeannie Burlowski - EP 232
Release Date: 05/30/2025
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...
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Grandparenting in the Roman Empire with Dr. Lisa Brunet EP - 247
The Cool Grandpa Podcast
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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Bonus Show - How Grandkids Stretch Us: Lessons from Dean Nielson
The Cool Grandpa Podcast
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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Lead Like a Grandpa: The Heart-Centered Leadership Your Team Needs EP - 246
The Cool Grandpa Podcast
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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Empowered Caregiving; with Renee Balcom EP - 245
The Cool Grandpa Podcast
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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Caring Grandparents Insights from Neil Taft EP - 244
The Cool Grandpa Podcast
“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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Millennial Grandparents; Insights From James Lott Jr. - EP 243
The Cool Grandpa Podcast
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...
info_outlineIn this episode of the Cool Grandpa podcast, Jeannie Burlowski discusses how grandparents can effectively support their grandchildren's college finances. She emphasizes the importance of creative strategies for college savings, the impact of personal letters from grandparents, and the significance of career assessments in guiding students toward debt-free education. The conversation highlights practical steps grandparents can take to leave a lasting legacy and ensure their grandchildren's success in higher education.
In this conversation, Jeannie Burlowski shares insights on how grandparents can play a pivotal role in helping their grandchildren navigate the complexities of education and career planning. She discusses the importance of strengths assessments, innovative scholarship strategies, and the pitfalls of relying solely on financial aid.
Jeannie emphasizes the need for early career planning and shares success stories of students who have graduated debt-free. Additionally, she highlights the benefits of utilizing 529 plans and Roth IRAs. She introduces the FIRE movement as a pathway to financial independence.
🎯 What You'll Learn:
- Why a heartfelt letter and a $20 college contribution can mean more than the latest toy
- How 529 college savings plans can be used meaningfully — and what to do with leftover funds
- Why career assessments at age 15 can shape lifelong success
- Creative alternatives to scholarships and financial aid that reduce college costs
- How grandparents can lead the charge with strategic planning (even if the parents are overwhelmed)
Jeannie also shares success stories from families that have used her advice to graduate with zero debt—and, in some cases, money in the bank.
Whether you're a grandparent looking to make a difference or a parent hoping to lighten the load, this episode delivers practical steps and emotional resonance.
🧡 Highlight Quote:
"The message matters more than the money — you're saying to your grandchild: You are worth investing in." — Jeannie Burlowski
🛠 Resources & Links:
- 📘 Launch: How to Get Your Kids Through College Debt-Free and Into Jobs They Love Afterward
➤ Available at libraries or for purchase on Jeannie's site - 🌐 Free Monday Newsletter & Tribe Membership
➤ Sign up here: https://debtfreecollege.us - 🎥 Watch Jeannie's age-specific 10-minute strategy videos:
➤ https://debtfreecollege.us - 📚 Article: Why You Might Want to Talk Your Kid Out of the Ivy League
➤ Google: "Burlowski Out of Ivy League" - 📖 Recommended Reading:
➤ The Simple Path to Wealth by JL Collins
➤ FIRE (Financial Independence Retire Early) Movement on Facebook