Estate Planning Nightmares .....and how to avoid them!

Jonathan Braddock

Welcome to "Estate Planning Nightmares...and How to Avoid Them!" - the podcast that delves into the fascinating and often unsettling world of estate planning gone awry, while providing you with invaluable insights to ensure your own estate planning journey is smooth and stress-free. Join us as we uncover real-life stories of estate planning gone wrong - from contentious family disputes over inheritances to legal battles that could have been prevented. Our goal is to help you "Make Things Easier For Those You Love!

  1. Aug 12

    The Photograph That Survived Gettysburg: What Will Survive You?

    What if one photograph was all that remained to tell your story? In this powerful return episode of Estate Planning Nightmares and How to Avoid Them, Jon Braddock welcomes back Pennsylvania estate planning attorney and Civil War historian John Benson for a fascinating journey from the battlefield of Gettysburg to the digital world we live in today. John shares the remarkable story of Sergeant Amos Humiston who was killed at Gettysburg and found with no identification, only a photograph of his three children in his hands. That single photograph was circulated across the country, ultimately allowing his wife to identify him and learn what had happened to her husband. But that's only the beginning. John shares two additional stories of wounded Civil War soldiers whose final written words preserved something no will or legal document ever could: who they were, what they believed, and what mattered to them in their final moments. Then the conversation becomes deeply personal when John shares what happened after his own mother died. Just days before her funeral, he discovered a handwritten letter she had intentionally left for him alongside her estate planning documents. As John explains, receiving her words at the very moment he most desperately wanted to hear from her was something on which he could never put a price. That raises an important question for all of us: We may be the most documented generation in human history, but are we actually preserving any of it? We have thousands of photographs, texts, emails, videos, social media posts and digital files. Yet without passwords, context, organization and intentional preservation, much of our personal history could disappear with us. Jon and John explore why true estate planning must go beyond the documents and beyond simply deciding who receives the house, money and possessions. Because there are really two questions every family should answer: What do you want your family to HAVE? And perhaps more importantly... What do you want your family to KNOW? You'll discover why photographs need stories, why personal letters and videos may become priceless family treasures, how technology can actually cause us to preserve less rather than more, and how a secure digital vault can help preserve not only important information but the stories, values, memories and messages behind a life. John also offers a simple piece of advice anyone can act on immediately: Get started! And Jon adds an even simpler challenge: Take out your phone. Hit record. Tell one story. Five minutes. Because your family can inherit your house, your money and your possessions. But they can't inherit a story you never told. In this episode: * The incredible story of the unidentified soldier found at Gettysburg holding a photograph of his children * Three Civil War stories that redefine what it means to leave a “last testament” * The emotional letter John's mother left him before she died * Why future generations may know the big events of our time—but lose the stories of the people who lived them * The danger of leaving thousands of digital photographs without names, context or access * Why estate planning should preserve more than assets * How letters, photographs, journals, recordings and videos become part of your legacy * Why “hope is not a plan” * One simple thing you can do today to begin preserving your story An estate is what you leave behind. A legacy is what continues because you were here. And perhaps the biggest lesson from Gettysburg: Your legacy isn't simply what you leave behind. It's what you intentionally preserve. Contact John Benson Website ⁠https://www.penglaseandbenson.com/⁠ LinkedIn ⁠https://www.linkedin.com/in/john-benson-esquire-2892179/⁠ Facebook ⁠https://www.facebook.com/penglaseandbenson/

  2. Jun 30

    From Navy JAG to Estate Planning: Why Every Family Needs a Plan Before It's Too Late

    For more than a decade, Kate Tanner served as a Lieutenant Commander in the U.S. Navy Judge Advocate General's Corps, prosecuting crimes, advising military commanders, and helping service members through some of the most difficult moments of their lives. But after years of dealing with the legal consequences of life's worst days, she realized she wanted to help families avoid those crises altogether. In this episode of Estate Planning Nightmares...and How to Avoid Them, Jon Braddock sits down with Kate to discuss her remarkable journey from Navy prosecutor to estate planning attorney and why she believes estate planning is one of the greatest gifts we can leave the people we love. Together they discuss: • Kate's path from human trafficking advocacy to the Navy JAG Corps • What she learned while prosecuting cases and advising military leaders around the world • Why she chose estate planning after leaving military service • Why estate planning is for every family—not just the wealthy • The advantages of trusts over wills • How advanced healthcare directives can provide clarity for families facing dementia or Alzheimer's • The unique planning considerations facing LGBTQ+ individuals and families • Why financial literacy should be part of every family's legacy • How estate planning helps preserve not only assets, but also stories, values, and peace of mind Kate's passion for making estate planning accessible to everyone shines throughout this conversation. She shares thoughtful, practical advice while reminding us that the greatest value of a good estate plan isn't found in legal documents—it's found in reducing stress, preventing conflict, and making life easier for the people we love. If you've been putting off your estate plan because you think you're too young, don't have enough assets, or simply don't know where to start, this episode is for you. To learn more about Kate Tanner and Tanner Life & Estate Planning, visit https://tannerestateplanning.com/ or follow her on Instagram https://www.instagram.com/tanner_esq/

  3. Jun 10

    The Trust Trap: Why DIY Estate Planning Often Ends in Disaster

    Most people believe that once they create a trust, their estate plan is complete. Unfortunately, that's often where the problems begin. In this episode of Estate Planning Nightmares... and How to Avoid Them, Jon Braddock sits down with estate planning attorney Michael Stewart, founder of Stewart Legacy Law, to discuss some of the most common and costly mistakes families make when planning for the future. Michael shares his journey from the world of big-law litigation to helping families create meaningful estate plans that protect loved ones and preserve legacies. Along the way, he reveals why so many DIY trusts fail, the critical difference between a will and a trust, and why estate planning isn't just for wealthy families. You'll discover: • Why improperly funded trusts are one of the biggest estate planning failures • The common misconceptions people have about wills and trusts • Why young families need estate planning just as much as retirees • How proper planning can prevent family conflict and court involvement • The importance of communicating your wishes before a crisis occurs • What legacy truly means beyond money and legal documents Michael also shares a personal story about helping his own grandmother avoid probate and create a smoother path for future generations. If you've ever thought, "I'll get around to my estate plan someday," this episode may change your mind. Because the goal isn't simply transferring assets. It's making things easier for those you love. Michael's Contact Information: Michael Stewart Stewart Legacy Law Email: Info@StewartLegacyLaw.com Website: https://www.stewartlegacylaw.com/ LinkedIn https://www.linkedin.com/in/michaelstewartlegacylaw/ Instagram: https://www.instagram.com/michael_stewart_legacy_law/

  4. Apr 21

    Why Estate Plans Fail in Real Life (Even When You Have One) | Lauren Klein, ESQ.

    Most estate plans don’t fail because people didn’t do them… They fail because no one followed through. In this episode of Estate Planning Nightmares… and How to Avoid Them, Jon Braddock sits down with estate planning attorney Lauren Klein, co-founder of Flourish Law Group, to break down what’s really going wrong in modern estate planning—and why so many families still end up in probate, confusion, and chaos. Lauren shares her journey from finance to law and reveals the three biggest issues she sees every day: • Planning that’s reactive instead of proactive • Failure to properly fund and retitle assets • Little to no follow-up as life changes The result? Plans that look great on paper—but fall apart when they’re needed most. This conversation goes beyond documents and into what actually makes a plan work: • Why “set it and forget it” is dangerous • The real risks of DIY estate planning • How poor communication leads to “morbid scavenger hunts” • What families should be doing right now to avoid costly mistakes If you already have an estate plan, this episode is a must-listen. Because the biggest mistake isn’t having no plan… It’s thinking you’re covered when you’re not. Contact Information: Lauren A. Klein, ESQ., LL.M. Flourish Law Group 954-698-4570 laurenklein@flourishlawgroup.com Website https://flourishlawgroup.com/ Follow Lauren on: Instagram https://www.instagram.com/lawyerlaurenklein/ https://www.instagram.com/flourishlawgroup/ LinkedIn https://www.linkedin.com/in/lauren-a-klein-esq-ll-m-a39a5a35/ https://www.linkedin.com/company/flourish-law-group/posts/?feedView=all

  5. Apr 7

    From the Flight Deck to Financial Reality: The 7 Money Milestones Most Families Miss

    Most people think they’re doing okay financially. They’re working hard…earning money…maybe even saving or investing… But what if the real problem isn’t income—it’s understanding? In this episode of Estate Planning Nightmares… and How to Avoid Them, Jon Braddock sits down with U.S. Navy veteran and financial educator Sheik Kuyateh for a powerful conversation about money, discipline, and what most families get completely wrong. Sheik’s story doesn’t start on Wall Street. It starts in the D.C.–Baltimore area during the 1980s drug wars—where money wasn’t taught, and the wrong examples were everywhere. From there, he found structure and purpose in the U.S. Navy—serving 8 years on active duty, including deployments during Iraqi Freedom and Enduring Freedom, working on aircraft carrier flight decks under intense pressure. But it was during deployment that everything changed. A single moment—watching another sailor trade stocks—opened his eyes to a truth most people never learn: Just because you make money… doesn’t mean youunderstand it. Today, Sheik is on a mission to eradicate financial illiteracy—what he calls one of the biggest crises in the world, impacting over 5 billion people. In this episode, he breaks down his powerful framework: The 7 Money Milestones: And here's where it gets real..... Jon connects the dots between financial literacy and estate planning—because what he sees every day are families dealing with the consequences of skipping these steps. Because building wealth without a plan…often leads to confusion, conflict, and unnecessary loss. In this episode, you’ll learn: “I think I’m doing okay financially…” This episode might challenge that. Contact Information: Sheik Kuyateh How Money Works Educator WealthWave | The How Money Works Company 7310 Miramar Rd.  Suite 450 San Diego, CA 92126 E: sheik.kuyateh@wealthwave.com    Take the Free Financial Literacy Quiz  https://financialliteracyindex.com/skuyateh/quiz   Get the Money Books  (also free)  https://howmoneyworks.com/skuyateh/books

Ratings & Reviews

4.5
out of 5
4 Ratings

About

Welcome to "Estate Planning Nightmares...and How to Avoid Them!" - the podcast that delves into the fascinating and often unsettling world of estate planning gone awry, while providing you with invaluable insights to ensure your own estate planning journey is smooth and stress-free. Join us as we uncover real-life stories of estate planning gone wrong - from contentious family disputes over inheritances to legal battles that could have been prevented. Our goal is to help you "Make Things Easier For Those You Love!