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What if one of the best ways to become a cooler, more connected grandparent was to learn something new alongside your grandchildren?
On this episode of The Cool Grandpa Podcast, Greg Payne talks with George Pillari, author of No Adult Left Behind: AI Is Learning. Are You?, about artificial intelligence, lifelong learning, and the opportunities technology creates for grandparents and grandchildren.
George draws on his background as a technology CEO and crisis manager who has worked with more than 100 companies. His interest in AI grew after seeing how dramatically the technology could simplify everyday problems and help people access information. He recognized that many adults were missing out because they viewed AI as intimidating or treated it like another search engine.
For grandparents, George believes the stakes are particularly meaningful. Technology is changing how younger generations learn, communicate, and solve problems. Rather than retreating from those changes, grandparents can approach them with curiosity and use them to build stronger family relationships.
George shares practical ways to get started, including using AI to explore a grandchild's interests, develop personalized stories, create illustrated books, and encourage children to imagine new inventions or business ideas. He also explains why the best results come from giving AI context, refining your questions, and treating its output as a starting point rather than unquestionable truth.
But this conversation isn't just about technology. George emphasizes that AI should augment our thinking, not replace it. He discusses the importance of screen-free conversations, critical thinking, checking multiple sources, maintaining intellectual discipline, and having the humility to learn from younger generations.
You'll also hear why George believes grandparents have plenty of road ahead of them and why continuing to learn can make the years ahead more rewarding.
In this episode, we discuss:
A Cool Grandpa takeaway: Your grandchildren don't need you to know everything. They need you to stay interested, keep learning, and be willing to explore the world with them.
Key takeaways1. Never stop learning. Grandparenthood can last for decades. Staying curious about new ideas, technology, and culture helps us remain engaged with the world our grandchildren are growing up in.
2. Use AI to connect, not just to save time. Start with something your grandchild already loves. Explore airplanes, animals, space, sports, or inventions together. AI can help turn a child's interest into an ongoing learning adventure.
3. Create something memorable together. George describes creating personalized, illustrated stories for his grandchildren. A story featuring a grandchild as the hero can become a keepsake and a conversation starter that extends far beyond the screen.
4. Give AI context, and keep refining your questions. Instead of entering a few keywords, explain what you want to accomplish, who the output is for, and what the final result should look like. Then ask follow-up questions to improve the result.
5. Let technology augment thinking, not replace it. AI can help generate ideas and organize information, but children still need to imagine, reason, question, and make decisions for themselves. Grandparents can model those habits.
6. Make room for screen-free conversations. George describes family mealtimes without phones or tablets and encourages conversations that challenge children to use their imagination. The goal isn't simply to turn off a screen; it's to use that time to think and connect.
7. Be willing to learn from your grandchildren. Pride can get in the way of connection. Letting a grandchild teach you something new demonstrates humility, shows that their interests matter, and creates opportunities for shared experiences.
Resources and Links Connect with George PillariCheck out Cool Grandpa gear: https://cool-grandpa.us/shop
Buy Me a Coffee using this link: https://buymeacoffee.com/coolgrandpa
Learn how grandfathers can move beyond fixing and providing to build deeper relationships through presence, connection, listening, and intentionality with Mike Elliott.
A Question for Every GrandpaThink about the people who matter most to you.
If your grandchildren were asked years from now, "How did Grandpa make you feel when you were around him?" what would you hope they would say?
And more importantly, what could you do today to help make that answer true?
Key Takeaways 1. Success can't substitute for connection.Mike's own story is a powerful example. He pursued external success believing it would resolve an internal sense of not being good enough, only to discover that what he was really seeking was connection.
2. Presence means more than simply being physically there.Mike describes presence as being sufficiently connected to yourself that you can accurately perceive and respond to another person's experience.
3. Slow down.Mike's phrase "the pace of connection instead of the pace of ambition" is one of the strongest concepts in the interview.
4. Grandpa doesn't always have to fix it.Sometimes grandchildren need a grandfather who is willing to be with them rather than immediately solving their problem.
5. Strength and vulnerability aren't opposites.Mike describes healthy relational strength as "strong back, soft front" and calls this gentle power.
6. We pass relational patterns to the next generation.Mike discusses both reactive patterns, such as anger, and repressive patterns, such as shutting down, people-pleasing, and avoidance.
7. Accountability doesn't have to become shame.A man can acknowledge that his behavior caused harm without concluding that he himself is fundamentally bad or broken.
8. Listen to someone else's truth without immediately making it your identity.Mike makes an important distinction between another person's experience and an absolute definition of who you are.
9. Your legacy is relational.Mike argues that many men eventually want more than a financial or material legacy. They want to be remembered for how they made the people they loved feel.
10. Practice relational hygiene.Mike's 30-day challenge is to inventory the relationships that matter most, consider how those people may experience you, identify relationships that need attention, and move toward ownership, apology, curiosity, and listening.
Mike's BioMike Elliott is a Relational Leadership Mentor and Men's Initiation Guide who works with men who want it all while building deeper, more meaningful relationships. Through his work with Relational Authority™, Mike helps men develop greater internal governance and lead with initiation, integration, and inspiration. Having been adopted twice and experienced the dark night of divorce, Mike rebuilt his life from the inside out. Today, he helps men transform their relationships, beginning with themselves, and create legacies of love, presence, and purpose. He is also the co-host of The Sacred We Podcast with Courtney Wren.
Links and Resources Connect With Mike ElliottMike Elliott is a Relational Leadership Mentor and Men's Initiation Guide who helps men develop Relational Authority™, beginning with themselves and extending into their relationships, leadership, purpose, and legacy.
Website: www.itsmikeelliott.com
Email: [email protected]
Newsletter: www.itsmikeelliott.com/newsletter
Community: The Initiated Man
The Sacred WeMike co-hosts The Sacred We with Courtney Wren. The podcast focuses on relationships and uses relationships themselves as a vehicle for personal growth and awakening. Mike specifically mentioned guests including Alison Armstrong, Gay and Katie Hendricks, and Harville Hendrix.
The Sacred We on Spotify
The Sacred We YouTube channel
Work With Mike & CourtneySacred Relating 2:2 Container
You can watch this conversation on YouTube by using this link: https://youtu.be/nQMrtAQPqrY Connect and support The Cool Grandpa Podcast
Check out Cool Grandpa gear: https://cool-grandpa.us/shop
Buy Me a Coffee using this link: https://buymeacoffee.com/coolgrandpa
What if one of the most important things a grandfather can do for his grandchildren is stop telling them what to do?
On this episode of The Cool Grandpa Podcast, I sit down with Perry Solomon, author of Grandpa Day, to talk about intentional grandfathering, following children's interests, building grit, and helping grandchildren become confident, independent problem solvers.
Perry brings more than 20 years of grandfathering experience to the conversation. His approach is simple but powerful: be attentive, listen, provide opportunities, facilitate experiences, and let grandchildren make decisions for themselves.
Rather than trying to solve every problem for our grandchildren, Perry believes grandparents can play a different and perhaps more important role: helping grandchildren learn how to solve problems themselves.
Following Their InterestsOne of the most memorable stories Perry shares involves his granddaughter discovering a chocolate fountain when she was just three years old.
Instead of dismissing it as a child's passing fascination, Perry paid attention.
That small moment eventually developed into a genuine interest in chocolate. Perry encouraged her curiosity by taking her on tours of craft chocolatiers throughout the Los Angeles area. Those experiences introduced her to people who became mentors and helped her develop knowledge, confidence, and relationships.
Years later, that interest took them to a chocolate convention in Amsterdam.
At just 13, Perry's granddaughter took notes, talked with people from around the world, learned about cacao science and genetics, and built relationships in the chocolate industry.
The lesson isn't really about chocolate.
It's about noticing what lights up a child's curiosity and helping them explore it.
Grandparents as FacilitatorsPerry describes the grandfather's role as that of a facilitator rather than a decision-maker.
Instead of telling grandchildren what they should do, grandparents can:
Perry believes grandparents have a unique opportunity to provide something children often don't get enough of: undivided one-on-one attention.
Even something as simple as sharing a meal can create an environment for meaningful conversations.
What Does Grit Really Mean?Perry draws on psychologist Angela Duckworth's work and defines grit as passion and perseverance toward long-term goals.
He uses his granddaughter's commitment to Division I soccer as an example. Her dedication, discipline, and willingness to work toward a long-term goal demonstrate what grit can look like in real life.
But Perry doesn't believe grandparents create grit by simply telling children to "work harder."
Instead, grit develops when children discover something they care about and then experience the process of pursuing it.
Let Them StruggleOne of the most challenging ideas in the conversation is also one of the most important:
If they aren't struggling, they aren't learning.
Grandparents naturally want to help. We want to protect our grandchildren, make things easier, and keep them from experiencing disappointment.
But Perry argues that grandparents should resist doing things for grandchildren they can do themselves.
Rather than handing over the answer, ask questions.
Rather than solving the problem, help them think through possible solutions.
Rather than rescuing them immediately, give them the opportunity to struggle, learn, and eventually succeed.
Mistakes aren't something we need to hide. They are opportunities to learn.
The Grandpa Who Helps Them See a Bigger WorldPerry and his wife have grandchildren who live in a suburban community in New Jersey. They intentionally expose those grandchildren to experiences outside their normal environment.
One example is taking them into Manhattan using New Jersey Transit.
For some of the grandchildren, it was their first experience in New York City.
One grandson stepped out of Penn Station, looked around, and simply said, "Wow."
Another saw the line of taxis and asked, "Can I drive?"
Those moments may seem small, but Perry believes experiences like these can have a lifelong impact.
A Grandpa Day Is Relational, Not RecreationalPerhaps the most important distinction Perry makes is between doing things with grandchildren and building relationships with them.
A trip to Disneyland doesn't automatically create a relationship.
Buying gifts doesn't create a relationship.
Taking grandchildren on expensive vacations doesn't guarantee a connection.
Relationships are built through authenticity, attention, listening, trust, and being present.
Perry's parting advice is simple:
Don't be the problem solver. Be the facilitator.
Listen. Encourage. Provide options. Let grandchildren experience the world.
And most importantly, resist the urge to impose your own agenda.
Sometimes the best way to become a Cool Grandpa is simply to become genuinely interested in what your grandchild is already interested in.
About Perry SolomonPerry Solomon is an entrepreneur and grandfather who has spent more than 20 years intentionally developing relationships with his grandchildren through shared experiences and what he calls "Grandpa Days."
His book, Grandpa Day, explores how grandparents can help nurture smart, resilient, and gritty children while building meaningful relationships that can last a lifetime.
Learn more at GrandpaDay.com.
Links and ResourcesHere is a link to Perry's book, GrandpaDay: https://www.grandpaday.com/
Sign up for Grandparents Week at Grandparents Academy: GrandparentsAcademy.com
You can watch this episode on YouTube using this link: https://youtu.be/5rhKSY0Up1E. Please remember to like and subscribe to this show on YouTube.
🛍️ Check out Cool Grandpa gear: https://cool-grandpa.us/shop
Buy Me a Coffee using this link: https://buymeacoffee.com/coolgrandpa
What if the best way to build a stronger relationship with your grandchildren is to start with their parents?
Neil Taft returns to The Cool Grandpa Podcast to talk about his new book, The Bridge to Your Grandchildren: What Their Parents Want You to Know.
Neil is a longtime grandparenting author, speaker, founder of Caring Grandparents, and a returning guest on the podcast. His work focuses on helping grandparents build meaningful relationships across generations while navigating the complicated dynamics that can come with adult children, in-laws, divorce, blended families, boundaries, and even estrangement.
His latest book grew out of an unexpected social media moment.
During a podcast appearance, someone asked Neil about the biggest mistake grandparents make. His answer was simple:
They fail to take really good care of the mother of their grandchildren.
That 71-second response went viral, reaching approximately 1.9 million TikTok viewers and generating thousands of comments. Neil says the response from younger mothers made him rethink his book's focus and dig deeper into what parents of grandchildren actually want from grandparents.
In this conversation, Neil and I explore what it means to become a bridge instead of a barrier in a family.
In this episode, Neil and Greg discuss:One of the most important messages in the conversation is that grandparents cannot control what their adult children do. They can control their own approach.
As Neil puts it, when a situation feels uncertain, his advice is simple:
"If it feels a little iffy, don't do it. You don't need to. Ask the parents."
That may sound simple, but it represents a significant shift in how many grandparents think about their role.
Neil's BioNeil Taft is a grandparenting author, speaker, TEDx presenter, founder of Caring Grandparents, and a great-great-grandfather whose work focuses on strengthening relationships between grandparents, parents, and grandchildren.
Neil has spent decades exploring what it takes to build intentional, lasting connections across generations. He has written five books on grandparenting and family relationships and has published hundreds of articles on intergenerational connection. His current work centers on helping grandparents navigate boundaries, communication, estrangement, modern family dynamics, and the changing role of grandparents.
His TEDx presentation, "The Bridge to Your Grandchildren," expands on the message of his latest book.
Neil is also a returning guest on The Cool Grandpa Podcast.
Key Takeaways 1. The relationship with the parents mattersNeil's central message is that grandparents who want a strong relationship with their grandchildren need to focus on their relationship with the people raising those children.
2. You cannot compel your adult childrenThe days of parenting a ten-year-old are over. Adult children are adults. Grandparents may have wisdom and experience, but they cannot force their adult children to accept it.
3. Curiosity beats criticismInstead of saying, "Why are you doing it that way?" try asking:
"Help me understand."
That simple change can transform a potentially confrontational conversation.
4. Good intentions are not enoughNeil makes an important distinction between intention and impact. A grandparent can mean well and still come across as critical, judgmental, or disrespectful.
5. Never undermine the parents in front of the childrenNeil considers this a "never-never." If a grandparent has an issue with the parent's decision, discuss it privately.
6. Trust takes time to rebuildIf a grandparent has crossed boundaries, one apology may not fix everything. Consistency matters.
7. Presence is pricelessNeil's practice of spending individual, distraction-free time with each grandchild demonstrates that meaningful connection often comes through simple moments rather than elaborate experiences.
8. The small things become the big thingsTexts, birthday cards, showing up at an event, sitting nearby, reading together, or simply being available can become treasured memories.
9. Estrangement does not have to mean giving upNeil encourages grandparents to continue making appropriate, non-manipulative gestures of love and connection.
10. Know when the stakes changeNeil makes an important distinction. Grandparents should generally respect parental authority, but situations involving abuse, addiction, or the safety of a child may require intervention and professional help.
Links and Resources The Bridge to Your GrandchildrenNeil's new book is titled The Bridge to Your Grandchildren: What Their Parents Want You to Know. Neil's current materials describe the book as written for both grandparents and parents, focusing on communication, boundaries, partnership, and navigating complicated family dynamics.
Learn more about Neil Taft's books.
Caring GrandparentsNeil's website provides articles and resources covering intentional grandparenting, communication, family relationships, estrangement, boundaries, long-distance grandparenting, and other challenges facing today's grandparents.
Visit Caring Grandparents
Neil TaftVisit Neil Taft's website
The Cool Grandpa PodcastVisit The Cool Grandpa Podcast
You can watch this episode on YouTube using this link: https://youtu.be/8wpundYZVQE. Please remember to like and subscribe to the channel.
🛍️ Check out Cool Grandpa gear: https://cool-grandpa.us/shop
Buy Me a Coffee using this link: https://buymeacoffee.com/coolgran
What if one of the most important things you can give your granddaughter isn't advice, money, or even wisdom?
What if it's simply becoming the person she knows she can call when life gets hard?
In this episode of The Cool Grandpa Podcast, I explore the unique role grandfathers can play in helping their granddaughters become confident, capable, and resilient young women.
From listening instead of fixing, to teaching practical skills, to showing her what a good man looks like, Grandpa's influence may be far greater than he realizes.
And for the grandfathers who aren't simply involved in their grandchildren's lives, but are actually raising them, I have a special message: you're not alone.
What does a young woman really need from her grandfather?
She needs someone who shows up.
Someone who listens.
Someone who believes in her.
Someone who challenges her to do things she doesn't think she can do.
And sometimes, she needs someone who gives her a safe place to talk.
In this episode, I explore how grandfathers can help their granddaughters develop confidence, resilience, competence, and a strong sense of identity.
I talk about why grandparents can offer a different perspective than parents, why listening may be one of a grandfather's greatest superpowers, and why confidence often grows from competence.
I also challenge grandfathers to look beyond appearance-based compliments and intentionally recognize qualities such as courage, perseverance, kindness, creativity, and problem-solving.
And there's a special message for grandfathers who are actually raising their grandchildren: you stepped into an extraordinary responsibility, and you don't have to do it alone.
The episode includes practical ideas, research-based resources, and organizations that can help grandfathers become more intentional in their relationships with granddaughters and grandchildren.
The Big IdeasHarvard's research emphasizes that resilience develops in supportive relationships and that reliable adults help children manage stress and build coping skills.
Harvard Center on the Developing Child – Resilience Resources (https://developingchild.harvard.edu)
Search Institute – Developmental RelationshipsSearch Institute identifies five elements of developmental relationships:
Practical actions include being dependable, listening, believing in a young person, encouraging effort, helping navigate difficult situations, empowering young people, respecting them, and creating opportunities for them to lead.
Search Institute – Developmental Relationships Framework (https://searchinstitute.org/resources-hub/developmental-relationships-framework)
Generations United – Grandfamilies & Kinship CareA national resource for grandparents and other relatives raising children.
Generations United reports that more than 2.4 million children in the United States live in grandfamilies, where grandparents, relatives, or close family friends are raising children because their parents cannot.
Generations United – Grandfamilies & Kinship Care (https://www.gu.org/explore-our-topics/grandfamilies)
Grandfamilies.orgOne of the best practical resources for:
Grandfamilies.org – Grandfamilies & Kinship Care Resource Center (https://www.grandfamilies.org/?utm_source=chatgpt.com)
GrandFacts – State-by-State ResourcesUseful for finding resources specific to your area.
GrandFacts State Fact Sheets (https://www.grandfamilies.org/State-Fact-Sheets)
Generations United – State of GrandfamiliesTheir report Building Resilience: Supporting Grandfamilies' Mental Health and Wellness examines both the strengths and challenges facing grandfamilies.
2023 State of Grandfamilies Report (https://www.gu.org/resources/2023-state-of-grandfamilies-report)
Resources Especially Useful for Granddaughters Girl Scouts of the USAA natural fit with the episode's emphasis on competence, leadership, outdoor skills, independence, and confidence.
Girl Scouts of the USA (https://www.girlscouts.org)
Girls on the RunPrograms designed to help girls develop confidence, character, caring, and connection.
Girls on the Run (https://www.gotr.org)
Dove Self-Esteem ProjectUseful resources around body confidence, appearance, and self-esteem—themes directly connected to your discussion about not making appearance the center of a girl's identity.
Dove Self-Esteem Project (https://www.dove.com/us/en/dove-self-esteem-project.html)
The Link to LT's episode that talked about being a lighthouse and not a snowplow: https://cool-grandpa.com/2026/08/12/when-the-door-is-closed-go-through-the-window-with-lt-lu-ep-276/
You can also watch this conversation on YouTube. Remember to like and subscribe to the YouTube Channel while you are watching our conversation: https://youtu.be/hOt-ISCtNcQ
Buy Me a Coffee – a great way to help out the podcast; use this link: https://buymeacoffee.com/coolgrandpa
What do you do when the door is closed?
Do you keep pushing against it? Walk away? Or look for another way in?
For LT Lu, the answer is simple:
When the door is closed, go in through the window.
On this episode of The Cool Grandpa Podcast, I talk with LT Lu, author of In Through the Window: On Forging Your Own Path to Success, about resilience, overcoming obstacles, finding your own path, and helping the next generation develop the confidence to solve problems for themselves.
LT's story is remarkable.
Born in China in the 1960s during the Cultural Revolution, LT grew up in circumstances where higher education was largely unavailable. He became the fourth student from his village to attend college, eventually making his way to the United States and building a career as a global business leader.
He later experienced another major "closed door" in his mid-50s when he lost his executive position following the acquisition of GE Appliances.
Instead of simply looking for another executive job, LT saw an opportunity.
He started his own company, NAVAC, which he describes as becoming an industry leader in HVAC tools.
That experience became one of the real-life examples behind his philosophy:
A closed door is not a closed future.
Resources Learn More About LT LuLT Lu's Website
Get LT's BookIn Through the Window: On Forging Your Own Path to Success is available through major booksellers.
Learn More About The Cool Grandpa PodcastCool Grandpa
You can also watch this conversation on YouTube. Remember to like and subscribe to the YouTube Channel while you are watching our conversation: https://youtu.be/88i8HfQVspM
When a father isn't actively involved in a boy's life, many grandfathers wonder what role they should play. Should they step in? How much influence is appropriate? How can they support their grandson without replacing his father or unintentionally undermining his mother?
In this episode of The Cool Grandpa Podcast, I explore the unique opportunity grandfathers have to become steady, trustworthy men in the lives of boys growing up without an active father.
Whether you're the father of the absent dad or the father of the child's mother, your role is different, but your influence can be profound.
I share practical advice for grandfathers who live nearby and those separated by distance, emphasizing consistency, respect for parental boundaries, and modeling the kind of man every grandson deserves to know.
Rather than trying to replace Dad, this episode encourages grandfathers to become another good man a young boy can trust.
In this episode you'll learn:"Don't ask, 'Can I replace his dad?' Ask instead, 'How can I become another good man in his life?'"
Resources MentionedCan grandparents influence our lives even if we never really knew them?
Author and former environmental attorney Sylvia Liu believes the answer is yes.
In this fascinating conversation, Sylvia shares the remarkable stories of her two grandfathers, both generals in Nationalist China whose lives intersected with some of the most pivotal events of the twentieth century. Although Sylvia met one grandfather only once and never met the other, their courage, sacrifice, commitment to service, and love of family profoundly shaped the generations that followed.
Sylvia and I also discuss immigration, education, family traditions, children's literature, and why every family should preserve its stories before they're lost.
This episode is a reminder that our greatest legacy isn't wealth or accomplishments—it's the values we pass from one generation to the next.
What You'll LearnSylvia Liu is an award-winning children's author whose books celebrate family, culture, courage, and resilience. Before becoming a full-time writer, she practiced environmental law for more than a decade, including work with the U.S. Department of Justice and Oceana.
Her books include A Morning with Grandpa, Manatee's Best Friend, and several acclaimed middle-grade novels featuring strong family relationships and multicultural themes.
Key TakeawaysSometimes the grandparents who influence us the most are the ones we barely knew.
Legacy isn't simply what we accomplish—it's what future generations remember, repeat, and build upon.
Family stories give children a stronger sense of identity.
Education, service, resilience, and curiosity can become generational gifts.
Every family has stories worth preserving before they're lost.
Links and ResourcesGrandparenting is one of life's greatest blessings—but it isn't always easy.
In this episode of The Cool Grandpa Podcast, Greg Payne explores three of the biggest challenges facing grandparents today, backed by current research and years of conversations with grandparents across the country.
You'll discover why family estrangement has become one of the fastest-growing emotional challenges for grandparents, why millions of grandparents are unexpectedly raising grandchildren, and how relationships with adult children can either strengthen or strain the entire family.
Whether you're struggling with one of these issues or want to become a wiser, more intentional grandparent, this episode offers practical encouragement and hope.
In This EpisodeHere is the link to the conversation that I had with Jamarl D. Clark and Mr. Robert Brown from Generations United: https://cool-grandpa.com/2024/04/19/ep-178-support-for-grandparents-with-generations-united/
You can watch this episode on YouTube at https://youtu.be/ZBQW6Ez9VKM. Please remember to like and subscribe to the channel.
🌐 Visit the website: https://cool-grandpa.us
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As a six-year-old boy in Louisville, Kentucky, I celebrated America's Bicentennial in 1976 with parades, flags, and neighborhood celebrations. Fifty years later, that little boy is now a grandfather himself, reflecting on what it means to leave a lasting legacy.
In this special Independence Day episode, we look at a side of America's Founding Fathers that rarely makes it into the history books: their roles as grandfathers, mentors, and family men.
What can Thomas Jefferson teach us about being present with our grandchildren? What does George Washington show us about family by choice? How did John and Abigail Adams build a multi-generational legacy? And why are Benjamin Franklin's stories still remembered centuries later?
Join me as we explore the timeless lessons these remarkable men can teach today's grandfathers.
In This Episode:You can watch this episode on YouTube using this link: https://youtu.be/NuuWGJnDRb0. Please remember to like and subscribe to the channel.
🛍️ Check out Cool Grandpa gear: https://cool-grandpa.us/shop
Buy Me a Coffee by using this link: https://buymeacoffee.com/coolgrandpa
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