Best Legacyplanning Podcasts (2025)

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3 Unbelievable Executor Mistakes That Cause Family Nightmares 3:48

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10d ago3:48

3:48

Are you listed as an executor in someone's will—or think you might be someday? Discover the one tiny detail that can save you weeks of stress, expensive headaches, and family arguments. In this episode, David shares real listener stories and breaks down the practical tips you need to avoid common estate pitfalls. Don't let small oversights cause bi…

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She Turned Heartbreak Into Help: The Story Behind Elayne's Mission 21:17

16d ago21:17

21:17

What if estate planning didn't have to feel cold and clinical? On this episode, discover how Adria Ferrier, founder of Elayne, turned heartbreak into a mission—and built an innovative platform that transforms legacy and loss into something deeply human. If you want to rethink how families navigate one of life's toughest moments, this conversation w…

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What REALLY Happens When You Die Alone: Stories From a Death Doula 32:16

23d ago32:16

32:16

Have you ever struggled to talk about death or support someone grieving? This episode is for you. Join David and death doula Marlene Morrow as she shares her journey, the moving work she does, and essential wisdom about advanced care planning, supporting children, and how we can all bring more comfort during life's hardest transitions. Listen in—th…

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The Eco-Friendly Goodbye: Discover Green Burial's Surprising Legacy 31:04

30d ago31:04

31:04

Did you know your funeral could become your greatest act for the environment? Join David as he has a conversation about the world of green burial with Sasha Honsl from Green Burial Ottawa Valley. Learn what makes green burials different, why they matter, and how they just might be the ultimate gift back to Mother Nature. If you care about your lega…

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Dementia, Laughter, and Legacy—Why Every Family Needs This Talk 42:54

1M ago42:54

42:54

What if talking openly about death could actually help you live a fuller life? Join David for a conversation with hospice social worker Lisa Pahl, co-creator of the Death Deck. Discover how humor, honesty, and heartfelt stories can break the stigma around end-of-life discussions—and why these conversations might be the key to deeper connections wit…

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From Shattered to Strong: One Woman's Guide to Surviving Grief 32:51

2M ago32:51

32:51

Have you ever wondered how people find their way forward after losing someone they can't live without? In this episode, David is joined by Carol Banens—grief coach and author—who opens up about losing her husband, the unexpected realities of grief, and the gentle steps she took to rediscover joy. Tune in for real talk about grief that goes beyond c…

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Behind Closed Doors: The Untold Challenges of Grieving at Work 41:44

2M ago41:44

41:44

What happens when grief follows you to work? In this episode, David sits down with Janet Gwilliam-Wright and Mekel Harris of Bloomwell—two compassionate experts helping employers and employees navigate the storm of loss. If you've ever wondered how workplaces can become truly supportive environments in the toughest times, you'll want to tune in. Fo…

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Confronting Death, Finding Purpose: How Kelly Turned Pain Into Power 32:11

2M ago32:11

32:11

If you think legacy is only about wills and wealth, think again. Join David as he has a conversation with legacy coach Kelly Campbell. Kelly reveals how personal tragedy, family challenges, and hard-won wisdom led her to redefine what legacy means—both for herself and those she helps. You don't want to miss this moving and practical conversation. F…

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When Grief Meets Chaos: Inside the Messy World of Unplanned Family Estates 29:23

2M ago29:23

29:23

On this episode David is joined by Katelyn Magnuson—financial expert and host of the Wealth Witches Podcast—for an honest conversation about the importance of estate planning and what really happens when families avoid those difficult conversations about death and money. Katelyn opens up about her own family's approach: how watching her parents tak…

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What to Consider When Retirement Planning, Ep #80 24:18

3M ago24:18

24:18

We like to think of Money Mile as standing at the corner of triathlon and personal finance, and we believe that age group triathletes are the lifeblood of our sport. This summer, we are going to take the opportunity to highlight some of our favorite “Questions on Course” segments from the last several months. In this episode, we're going to bring b…

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Retirement Planning: Questions about 401(b) Loans and Social Security, Ep # 79 21:47

4M ago21:47

21:47

Welcome to the Money Mile podcast. I'm your host, Justin Waller, and I am happy you are here. We like to think of Money Mile as standing at the corner of triathlon and personal finance. This summer, we're taking the opportunity to highlight some of our favorite “Questions on Course" segments from the last several months. In this episode, find out w…

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When Families Fight: The Emotional and Financial Cost of Inheritance Battles 35:05

4M ago35:05

35:05

In this "Best of" edition The Executor Help Podcast , we're diving headfirst into those tricky, emotional waters: sibling rivalry, family feuds, and inheritance showdowns. David has conversations with estate planning expert Jeffrey Condon and veteran mediator Charles Ticker—two guys who have seen more family drama over cottages and cold hard cash t…

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Smart Strategies for a Strong Financial Future, Ep # 78 10:55

4M ago10:55

10:55

This summer, we will take the opportunity to highlight some of our favorite “Questions on Course" segments from the last several months. In this episode, we are going to bring back focus on the retirement planning side of things. I share my thoughts and advice when someone says, “I’ll never be able to retire”. You will want to hear this episode if …

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The Psychological Journey of Retirement 33:59

4M ago33:59

33:59

This is a best of Executor Help Podcast Episode and here's why it is worth another listen. David revisits his conversation with Dr. Riley Moynes, author, speaker, and creator of the groundbreaking "The 4 Phases of Retirement." If you missed it the first time around—or even if you've already listened—this episode is absolutely worth another spin. Wh…

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Exploring Grandparenting Superpowers and Emotional Bonds 37:06

4M ago37:06

37:06

Imagine having a superpower that makes you the coolest person in your grandchild's life. That's what being a grandparent's all about, in this Best of Executor Help Podcast David has a conversation with Shirley Hershey Showalter co-authored of the book, The Mindful Grandparent, The Art of Loving Our Children's Children. Tune in to learn more about t…

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Unlocking Wealth and Happiness with Die with Zero 4:16

5M ago4:16

4:16

In this Best of Episode of The Executor Help Podcast, David explores the thought-provoking book "Die With Zero" by Bill Perkins. David discusses how the book challenges traditional views on saving and legacy, urging listeners to focus on living fully and using wealth to create meaningful experiences, nurture relationships, and make a positive impac…

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Cherie Gruenfeld’s Story: From World Record Triathlete to Transforming Lives, Ep #77 42:47

5M ago42:47

42:47

Today we have a special guest on the show, Cherie Gruenfeld. Cherie has been competing in triathlons for 33 years and completed her first Ironman triathlon when she was 48 years old. She is currently the oldest woman to complete the Iron Man World Championships at the age of 78 and the Iron Man 70.3 World Championships at the age of 80. She holds 1…

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Secrets to a "Good Death" (and What Most Families Get Wrong) 27:46

5M ago27:46

27:46

Most people avoid talking about death—but what if facing it head-on is the greatest gift you can give your family? In this episode, David chats with Julie Saeger Nierenberg about her book "Journey's End," the power of end-of-life planning, and the importance of having the hard conversations now. If you want to learn what it takes to create a sense …

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Strengthening Relationships Through Prenups and Honest Money Talks 18:35

5M ago18:35

18:35

In this episode, David is joined once again by Emily Bouchard—social worker, blended family expert, and author of "The Beginner's Guide to Purposeful Prenups" After discussing the complexities of blended family estate planning in their last conversation, David and Emily have a conversation on another tricky topic: prenuptial agreements. Emily break…

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Love, Legacy, and Legalities: Purposeful Planning for Blended Families 28:04

5M ago28:04

28:04

In this episode David Edey has a conversation with Emily Bouchard, an expert on family dynamics in estate planning. She is co-author of Estate Planning for the Blended Family. They discuss the complexities of estate planning for blended families—covering everything from updating beneficiaries to navigating difficult family conversations and making …

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A Joy Mindset in Triathlon with Mira Panek, Ep #76 43:20

5M ago43:20

43:20

Mira Panek shares her joyful mindset about her success as a self-proclaimed “accidental athlete.” She tells us how she got involved in Triathlon, her training and racing experiences, as well as her volunteer coaching of teens in the sport. Her story demonstrates how embracing opportunities can lead to fulfilling achievements. Similarly, embracing p…

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What Will Matter: Preparing for Life's Transitions and Leaving a Legacy 19:32

6M ago19:32

19:32

If tomorrow was your last day, what would matter most? Join David and guest Peter Christman on This Best Of: Executor Help Podcast for a heartfelt episode exploring business exits, personal epiphanies, and the importance of living—and leaving—a life of value. Peter opens up about his own mortality, the power of honest conversations, and the poem th…

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Grief, Trauma, and Sex: The Conversation You've Never Heard Before 38:32

6M ago38:32

38:32

Grief isn't just about death—it's woven into the fabric of everyday life, and we often wear masks to hide it. On this episode, join David and grief expert Edy Nathan author of It's Grief for an open, compassionate conversation about navigating loss, honoring your feelings, and finding small ways to move forward. Edy brings empathy and hope to a sub…

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Navigating College Costs with Howard Freedman, Ep #75 43:05

6M ago43:05

43:05

Welcome to Money Mile. Today’s guest is Howard Freedman. Howard holds an MBA and has worked in various fields, including industrial engineering, consulting, education, payroll systems, and writing. He transitioned into mentoring the younger generation, prioritizing honest financial guidance over profit-driven sales. His focus is on helping others m…

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"Why Not Me?": A Widow's Journey Through ALS, Loss, and Healing 30:38

6M ago30:38

30:38

If you've ever wondered how to navigate the darkest moments of life, this episode is for you. Join David as he has a conversation with Rachel Schneider author of The Widow Chose Red. Rach recounts her experience of losing her husband to ALS, raising young sons as a single mother, and discovering ways to celebrate life amid heartache. It's a convers…

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Forget the Money: The Real Reason Family Empires Crumble 32:23

6M ago32:23

32:23

Have you ever wondered why some families lose their wealth—and their connections—after just a generation or two? On this episode, David has a conversation with wealth psychology coach Shayla T Locklear , as she peels back the curtains on what really keeps a legacy alive. It's not just about smart investments or ironclad wills; it's about trust, pur…

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The One Conversation That Will Change How You See Death Forever 33:39

7M ago33:39

33:39

When life pushes you to the edge—career changes, family illness, overwhelming responsibility—how do you find your way back to what makes you happy? David has a conversation with Minnelle Williams from Ending Well with Minnelle. Hear how a journey from funeral homes to international travel led her to help others write their legacy stories and live w…

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From Ironman to Advocate: Bob Babbitt’s Journey to Empower Adaptive Athletes, Ep #074 55:30

7M ago55:30

55:30

Meet Bob Babbitt, a true legend in the athletic and humanitarian worlds. As a Co-founder of the Challenged Athletes Foundation, Bob has helped transform the lives of thousands by making sports accessible to individuals with physical challenges. His passion for storytelling shines through as the host of Babbittville Radio, where he shares inspiring …

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How One Sugar Bowl Tore a Family Apart: Unbelievable Inheritance Stories 30:26

7M ago30:26

30:26

Ever thought settling an estate was just paperwork? Think again. In this episode, David has a conversation with author Gina Brown reveals the tangled web of grief, family drama, and even pet dilemmas that unfolds when a loved one passes away. Drawing from her own experience—and a hundred stories she gathered from friends. You will laugh, cry, and t…

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How a Daughter Found Peace in Her Father's Final Moments 24:38

7M ago24:38

24:38

In this episode David has a conversation with Julie Sager Nierenberg, the author of "Daddy, This Is It." In her heartfelt book, Julie opens up about her emotional journey of being with her father during his final days. It's a touching and genuine portrayal of saying goodbye to someone you love. For David's book, other resources and more visit www.d…

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How a Voicemail from Dad Sparked a Healing Revolution! 27:39

7M ago27:39

27:39

In this episode David has a conversation with Estrella Quiroz, the cofounder of Last Farewells—a platform that helps people leave lasting, meaningful messages for loved ones after they're gone. Estrella shares the deeply personal story that inspired this venture and talks about finding joy and purpose in the face of life's toughest moments. So Tune…

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Why Money is a Taboo Subject in Families 25:45

7M ago25:45

25:45

In this episode David has a conversation about the complexities of family, money, and legacy with Ruschelle Khanna author of Inherited Trauma and Family Wealth. They discuss the impact of inherited trauma on how families handle wealth and the importance of having open conversations about money. Learn how early experiences shape our money habits and…

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Don't Regret Your Last Words: A Heartfelt Journey with Robin Nathaniel 32:47

8M ago32:47

32:47

In this episode David's guest is Robin Nathaniel, a TEDx speaker and social media leader. Robin shares his personal journey through family trauma and loss, emphasizing the importance of leaving conversations on a positive note, whether with close loved ones or strangers. Listen in as Robin highlights the dangers of pride and the need for reconcilia…

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Why Embracing Death Could Be the Most Beautiful Part of Life! 34:05

8M ago34:05

34:05

In this episode David has a conversation with Dr. John Horton, co-author of "Good to Go." Dr. Horton shares compelling stories from his 50 years of medical practice. They discuss the five key understandings that can guide us to a dignified departure. How nurturing our relationships and finding inner peace can transform our final moments into someth…

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The Surprising Power of Legacy Planning for Entrepreneurs! 22:41

8M ago22:41

22:41

In this episode David learns about the essence of legacy, business planning, and leadership. His guest is Steve Ramona, a passionate entrepreneur who learned from his father the profound impact of serving others. They explore the significance of having a solid plan for business growth, the importance of mentorship, and fostering a team-centered cul…

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Diana Hassel: From Successful Triathlete to Inspired Coach, Ep #73 34:54

8M ago34:54

34:54

In this episode, we’re joined by Diana Hassel, a 25-time Ironman finisher with 14 age group podiums at Ironman Hawaii. Diana is also a professor of equine emergency surgery at Colorado State University and has transitioned into coaching triathletes, offering personalized training and a focus on nutrition. Diana’s coaching journey began after friend…

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How to Laugh Your Way Through Death and Taxes 31:14

8M ago31:14

31:14

In this episode of The Executor Help Podcast, David has a conversation with Barb Amsden, the author of How to Laugh at Death and Taxes. Barb shares her journey from becoming an executor for her godparents to writing a book filled with humor and practical tips for handling wills and estates. They explore the unexpected challenges, the therapeutic po…

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Blake Anderson: Taking A Systemic Approach to Triathlon and Real Estate, Ep # 72 33:43

9M ago33:43

33:43

In this episode, Blake Anderson, a top real estate agent and endurance athlete, shares how his commitment to systems and relationships has led to success in both real estate and triathlon. From overcoming addiction to becoming a record-breaking ultramarathoner and innovating in real estate with a flat-fee model, Blake’s approach offers valuable ins…

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Is Joy the Answer to the World's Negativity? Steven Petrow Weighs In! 39:03

9M ago39:03

39:03

In this episode David welcomes back award-winning journalist and author, Steven Petrow, to discuss his latest book, "The Joy You Make." Building on their previous conversation about aging and loss, David and Steven explore the concept of joy and its vital role in our lives, particularly during these challenging times. They discuss the differences b…

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The Child-Free Approach to Legacy and Wealth 23:54

9M ago23:54

23:54

In this episode David has a conversation relating to the unique challenges faced by individuals without children and the issue of estate planning with expert Bri Conn of ChildFreeWealth. Whether you're single or in a child-free partnership, listen in to discover actionable insights on making meaningful legacy decisions that will reflect your values…

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Amy Woolsey’s Journey in Triathlon, Ep #71 37:40

9M ago37:40

37:40

Amy’s journey into the world of triathlons is a story of passion, perseverance, and inspiration. What began as a simple bucket list item in 2002 quickly turned into a lifelong pursuit that has shaped not only her physical fitness but also her personal growth. From her first Sprint race to completing multiple Ironman triathlons, Amy’s path is one of…

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Preserving Family Legacies with Life's QR 28:37

9M ago28:37

28:37

Grief affects us all differently, but what if there was a way to celebrate and remember our loved ones' lives beyond a newspaper obituary? In this episode David has a conversation with Jennifer Blakely from LifesQR. Jennifer shares the story behind Life's QR, an innovative platform that helps families create digital legacies for their loved ones. H…

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Unlocking the Secrets of Selling Dead People's Things! 29:40

10M ago29:40

29:40

In this episode David welcomes a fascinating guest, Duane Scott Cerny, a master of estate sales, collector, and author of "Selling Dead People's Things." Cerny dives into his 35 years of experience in the vintage business, sharing how he turned a passion for collecting into a thriving career. Duane talks about some of the most interesting and pecul…

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Dr. Torkil Faero: How Your Heart Rate Variability Affects Your Health, Ep #70 58:44

10M ago58:44

58:44

In this episode, we explore the power of Heart Rate Variability (HRV) as a window into your heart health—and how you can improve it. Joining us from Norway is Dr. Torkil Faero, a seasoned General Practitioner and emergency physician with 26 years of experience. Dr. Faero has practiced medicine across Norway and in war-torn Angola with Doctors Witho…

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Why You're Making Downsizing Harder Than It Needs to Be 43:00

10M ago43:00

43:00

David explores the world of downsizing and estate management with expert Barry Gordon, CEO of Gordon's Downsizing and Estate Services. Barry shares tips for making the tough decision to downsize and offers guidance for executors handling estates. From the emotional challenges of leaving a cherished home to the practicalities of managing property an…

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How to Avoid Family Drama During Illness and Loss! 33:31

10M ago33:31

33:31

David has a conversation Tracy Heath, an author Before Goodbye. Tracy shares her journey of turning personal grief into a guide for others. It is written to assist families in preparing for terminal illnesses and avoiding future regrets. They explore grief management, and navigating family complexities during illness. Tune in as Tracy offers practi…

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Balancing Family, Triathlon, and Business with Kirsten Miller, Ep #69 49:56

10M ago49:56

49:56

Today, we’re joined by Kirsten Miller, a seasoned triathlete with over 22 years of experience and a board-certified sports nutritionist. Kirsten’s dedication to her family and her strategic approach to balancing training, racing, and home life have been the cornerstone of her longevity in the sport. Beyond her personal achievements, she’s passionat…

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How Skateboarding Unlocked the Secrets to Life and Death 26:17

10M ago26:17

26:17

David welcomes Michael Brooke, a lifelong skateboarder and author, who shares his journey from the world of skateboarding to becoming a funeral director's assistant. At 60, Michael finds himself exploring the unexpected parallels between the energy of skateboarding and the deep realities of life and death. Through his experiences in the skate indus…

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The Art of Grandparenting: How to Transform Love and Values into a Lasting Legacy! 38:12

11M ago38:12

38:12

In this season 5 episode debut David learns about the heartwarming world of grandparenting with Shirley Hershey Showalter, co-author of "The Mindful Grandparent." Explore the unique superpower of being a grandparent, the joy of creating special moments, and the profound connection across generations. Shirley shares insights on embracing mortality, …

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Triathlon, Recovery, and Lifestyle Medicine: Michele Cellai’s Inspiring Journey, Ep # 68 47:46

11M ago47:46

47:46

In today’s episode of Money Mile, we’re joined by Michele Cellai, a triathlete and nurse practitioner, to discuss her journey in triathlon and her career in health and wellness. Michele's passion for the sport started in the early 1980s after watching Julie Moss’s iconic Ironman finish, and she’s been racing ever since. Michele also shares her work…