Designed for active people looking to be active throughout their lifetime. We break down complex financial topics into mile-sized bits of education to help you make decisions confidently.
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Legacyplanning Podcasts
The podcast is filled with advice, tips, and many real-life examples demonstrating what can go wrong (and what can go right), depending on whether or not families plan accordingly in advance, communicate clearly with one another, and are willing to put petty and selfish differences aside. No one likes talking about death and inheritances before they absolutely have to, but as I have learned from personal experience, having these conversations earlier, rather than later, will save a lot of ti ...
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Exploring Grandparenting Superpowers and Emotional Bonds
37:06
37:06
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37:06Imagine 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
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4:16In 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
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41:11Today 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
27:46
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27:46Most 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
18:35
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18:35In 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
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28:04
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28:04In 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
43:20
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43:20Mira 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
19:32
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19:32If 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
38:32
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38:32Grief 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
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43:05
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43:05Welcome 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
30:38
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30:38If 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
32:23
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32:23Have 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
33:39
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33:39When 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
55:30
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55:30Meet 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
30:26
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30:26Ever 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
24:38
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24:38In 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
27:39
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27:39In 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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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
32:47
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32:47In 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!
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34:05
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34:05In 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!
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22:41In 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
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34:54In 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
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31:14
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31:14In 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
33:43
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33:43In 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
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39:03In 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
23:54
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23:54In 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
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37:40
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37:40Amy’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
28:37
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28:37Grief 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
29:40
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29:40In 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
58:44
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58:44In 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
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43:00
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43:00David 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
33:31
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33:31David 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
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49:56Today, 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
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26:17David 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
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38:12In 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
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47:46In 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…
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Grief and Paperwork: The Untold Struggles of an Executor!
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20:00In this Best of Episode, David has a conversation about the emotional journey and challenges of being an executor with Debbie Buehler. Discover her heartfelt story of managing her mother's estate—unexpected hurdles, the surprising demands of an executor's role, and the emotional toll it took on her journey. Whether you're an executor dealing with a…
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Unlocking the Secret Power of Handwritten Letters for Lasting Family Bonds
29:24
29:24
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29:24In this Best of Episode, David revisits his conversation with Lynette M Smith about writing special letters to say thank you to the important people in our lives. A special gift any time of the year especially during the holiday season. Lynette shares how her children inspired her dreams and why saying thank you with a handwritten note means so muc…
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Organic Coaching: Carly and Tyler Guggemos’ Journey to Helping Time-Crunched Triathletes, Ep #67
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43:01In this episode of Money Mile, I sit down with Carly and Tyler, the dynamic duo behind "Organic Coaching." They share the journey of how they built a thriving online coaching business that helps time-crunched triathletes balance training with their busy lives. From their impressive athletic achievements to growing a community of over 6,000 members …
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What Your Loved Ones Are Trying to Tell You from the Afterlife!
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46:28In today's "Best of" episode David revisits a conversation with the incredible Hospice Nurse Julie. This is all about the world of end-of-life care, Julie talks about the transition many of us fear but often feel too awkward to discuss. Spoiler alert: it's not all doom and gloom! Think of this episode as your go-to guide on how to be present for th…
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Behind Closed Doors: Family Secrets, Love Letters, and Life Lessons
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44:58
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44:58In this Best of Executor Help: Stories of Life, Death, and Legacy. David revisits one of his favorite conversations with journalist and author Steven Petrow. His story about dealing with sadness, love, and family will make you laugh and cry at the same time. Steven talks about what he learned from life. He shares a touching story about his friend J…
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From Horse Shows to Ironman: Brittany Vermeer on Triathlons and Blogging, Ep #66
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41:26
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41:26Brittany Vermeer is a triathlete and seasoned sports journalist. As a freelance writer and editorial consultant, she collaborates with top publications like Triathlete Magazine, Outside Run, Ironman, and Xterra. With six 70.3 triathlons under her belt, two World Championship qualifications, and her first full-distance Ironman completed in 2003, Bri…
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Family Heirlooms vs. Modern Values: What You Need to Know!
40:51
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40:51David has a conversation with Cynthia Kraft founder of Family Branch and Root. With over 20 years of experience, Cynthia shares her journey from genealogy to estate advisory. Their conversations range from addressing family dynamics, choosing the right executor, and navigating modern-day challenges like the generational shifts in values. Whether yo…
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Don't End Up Like Amy Winehouse: The Costly Mistake of Not Having a Will!
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35:35David's guest is Debbie Stanley, CEO and senior estate administrator of ETP Canada. With over a decade of experience guiding grieving families through the complexities of estate management, Debbie and David talk about the role of a corporate trustee, why more individuals are opting for professional expertise over personal executors. They explore th…
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In this episode David talks with Peter Morrison, a financial planner from Executors Friend. Peter shares his story and explains his job helping people who are executors—those in charge of handling someone's estate when they pass away. He talks about the importance of being prepared, organizing important documents, and having clear conversations abo…
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Welcoming Back “Beaker” McKee, Ep #65
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1:03:40We’re thrilled to welcome back Rebecca “Beaker” McKee to share her incredible journey at the Ironman Championship in Nice, France, where she placed 12th. In this episode, Beaker opens up about her experience with the course, the unique challenges of competing in Nice, and how it compares to her past races in Kona. But this isn’t just a story about …
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As part of the Make a Will Month series David has a conversation with Jill Chambers, the founder of Financial Concierge. It is Jill's mission is to guide vulnerable families, busy professionals, and older adults as they navigate the complexities of estate planning. In this episode Jill shares her insights on the importance of communication, the ris…
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Make A Will Month: Taking the First Steps Toward Peace of Mind
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32:53Do you have a will? If the answer is no, or you're unsure when you last updated it, this episode is a must-listen. David welcomes back Bruce Young, an expert in estate and trust advisory services, for a conversation on the importance of making and maintaining a will during part 1 in a series during 'Make A Will Month.' Discover how a little prepara…
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Driven to Triumph: Dana Bullard’s Inspiring Legacy, Ep # 64
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41:08Today, I'm joined by Dana Bullard, a former marathon runner turned accomplished triathlete. Dana has completed 26 Ironmans, including six finishes at Kona. After years as a competitive runner through high school, college, and into her post-grad marathon career, she began to feel burnout creeping in. When a colleague invited her to try a sprint tria…
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In this episode, "Wills Thrills & Legal Spills," David breaks down complex terms like wills, trusts and executor. Hear stories to demystify the essential documents for estate planning, such as power of attorney. Get ready to learn how to plan your estate as seamlessly as planning a journey to a theme park. Tune in and equip yourself with the knowle…
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