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. Sep 28

    You Paid the Premiums. So Why Won’t Life Insurance Pay? with Stephie Prestridge, Co-Founder of Life Claim

    You bought the life insurance. You paid the premiums. You named the beneficiary. So when you die, your family gets the money…right? Not always. In this eye-opening episode of Estate Planning Nightmares & How to Avoid Them, Jon Braddock sits down with attorney Stephie Prestridge, co-founder of Life Claim, to expose a side of life insurance most families never expect to encounter: delayed, denied and disputed death claims. Stephie spent nearly two decades as an estate-planning attorney. Then one of her clients died. The family had planned carefully. Life insurance was an important part of that plan—one policy was intended to help provide for the children, another to help take care of the surviving spouse and home. Then Stephie received the phone call. The insurance company wasn't paying. Her reaction? “That doesn't happen. It's life insurance.” Except it did. Stephie challenged the denial and won. But the experience led her to discover that life-insurance disputes were far more common and complicated than she had realized—and ultimately changed the direction of her career. In this conversation, Stephie explains the two-year contestability period, why even seemingly minor discrepancies on an insurance application can become important after death, and why “guaranteed coverage” does not necessarily mean a guaranteed payout. You'll also hear why that friendly phone call from the insurance company after a loved one dies may be more important than you realize. While you're grieving and answering seemingly innocent questions, someone may be taking notes—and those answers may become part of the insurer's investigation. Stephie shares what beneficiaries should consider doing instead and why documenting everything matters. And perhaps most importantly: If your life-insurance claim is denied, think carefully before filing an appeal yourself. Stephie explains why the rules can vary depending on the policy and why, with certain employer-sponsored policies, what is submitted during an appeal can severely limit what evidence and arguments can later be considered. We also discuss beneficiary disputes, employer-provided life insurance, what estate-planning attorneys should be reviewing with clients, and why simply having a policy isn't enough. As Jon puts it during the conversation: A life insurance policy is only useful to your family if someone knows it exists. This episode isn't about being afraid of life insurance. In fact, Stephie remains a strong believer in it. It's about understanding what can happen when the unexpected happens—and making sure the people you love know what to do next. Because confusion creates conflict. Clarity creates peace. 🎧 In This Episode - Why life-insurance claims can be denied even when premiums were paid - What the two-year contestability period means - “Guaranteed coverage” vs. guaranteed payout - What insurers may investigate after someone dies - Why beneficiaries should be careful during post-death phone calls - What to do when a claim is delayed - Why a DIY appeal can create serious problems - How beneficiary designations can be challenged - Special considerations with employer-sponsored policies - What estate-planning attorneys should discuss with clients - Why families need to know where the policy is and what to do when the insured dies Connect with Stephie at LifeClaim: https://www.lifeclaim.com/ stephanie.prestridge@lifeclaim.com 888-615-3270 LinkedIn: https://www.linkedin.com/in/stephanie-prestridge-69803926/ Instagram: https://www.instagram.com/lifeclaimwins/ Facebook: https://www.facebook.com/lifeclaimwins

  2. Sep 15

    Stop Waiting for Someday: How to Live Your Next Chapter

    What if one of the biggest mistakes we make in planning for the future is assuming we're actually going to get there? We spend decades building careers, businesses, wealth and reputations. We tell ourselves we'll take the trip, call the old friend, slow down, try something new and finally start enjoying life...someday. But someday isn't promised. In this episode of Estate Planning Nightmares...and How to Avoid Them, Jon Braddock welcomes back former probate attorney John Palley, but this time he's not here as the attorney Jon interviewed two years ago. He's here as Cabana John! After more than 25 years building a successful legal career, John is now 99% retired and embracing an entirely different chapter built around travel, experiences, friendships, community and a willingness to say yes. The conversation takes an emotional turn when John shares the story of a healthy woman in her 60s who was unexpectedly told she had two to three weeks to live. She didn't have two to three weeks. She had only days! That story becomes the backdrop for a much bigger conversation about the dangerous assumption that life will follow the timeline we've created for it. Jon and John talk candidly about the “one more year” trap that keeps successful professionals working long after they may need to, the identity shift that comes with leaving a career, why retirement requires more than financial preparation, and why having something to retire to may matter as much as having enough money to retire. They also explore John's philosophy of saying yes, including the time saying no cost him the chance to meet Muhammad Ali, why becoming a stadium usher after a successful legal career changed his perspective on status, and why he traveled all the way to Africa...only to skip a safari. Because sometimes living fully means saying yes to the adventure. And sometimes it means saying yes to yourself. Perhaps most importantly, John explains why golf isn't really about golf, Starbucks isn't really about coffee, and the activities we choose later in life can become the vehicles through which we build friendship, purpose and belonging. This isn't really an episode about retirement. It's an episode about living. Because preparing for what happens after you die matters. But so does making damn sure you actually live before your estate plan becomes relevant. Stop waiting for someday. Live your next chapter. Be sure to check out Cabana John's YouTube Channel: https://www.youtube.com/@CabanaJohn702 And Website: https://www.cabanajohn.com/

  3. Sep 2

    Good Grief: Why Your Family Needs More Than an Estate Plan | Riley Kern

    What if a good estate plan isn't just about preparing for death, but helping the people you love grieve well when that day comes? In this episode of Estate Planning Nightmares and How to Avoid Them, Jon Braddock sits down with Riley Kern, estate planning attorney and founder of Roots Law, for a conversation that goes far beyond wills, trusts and legal documents. Riley calls a good estate plan “the practice of good grief.” Grief is unavoidable. But confusion, suspicion, unnecessary anxiety and family conflict often aren't. Riley shares his unconventional journey from small-town Oklahoma and vocational ministry to touring as a musician, working with chimpanzees, researching wild bees, attending law school and building an estate planning practice. And most recently, returning to the stage as Ike Skidmore in Oklahoma! at the Tulsa Performing Arts Center. That remarkable journey has helped shape Riley's philosophy: Estate planning should be about people, not paperwork. Jon and Riley explore why families need to understand not only what an estate plan says, but why those decisions were made. Without that explanation, even a well-designed trust can create questions, hurt feelings and unintended conflict. They also discuss legacy letters, recorded videos and creative ways to preserve the stories and memories that legal documents simply can't capture. Then Riley shares an unforgettable estate planning nightmare. A couple created a thorough estate plan. Their trust was funded. Their assets were properly handled. Then they placed their original documents and electronic copies inside a safe-deposit box they owned individually. When they died, their family couldn't access it. They had to open probate just to retrieve the estate planning documents designed to help them avoid probate. It's a powerful example of why Riley says: “Estate planning is a verb, not a noun.” Jon and Riley also discuss proactive estate-plan maintenance, the limitations of “sign it and shelve it” planning, and how becoming a father changed Riley's understanding of his own legacy. Because someday, our families probably won't remember how many documents we signed. They'll remember us. Confusion creates conflict. Clarity creates peace. And don't spend so much time preparing for someday that you forget to live today. Play the guitar. Get back onstage. Create some memories worth leaving behind. Contact Riley: https://rootsep.com/ Follow on Facebook: https://www.facebook.com/rootslaw Connect on LinkedIn: https://www.linkedin.com/in/rileykern/

  4. Aug 31

    Your Family Will Inherit Your Preparation...or Your Procrastination

    What do being an Army Ranger, working inside the IRS, and helping families prepare for death have in common? Preparation. In this episode of Estate Planning Nightmares...and How to Avoid Them, Jon Braddock sits down with Charles R. Frazier, founder of Frazier Law, whose remarkable journey took him from Army Ranger training to serving as an IRS Revenue Agent and ultimately becoming an estate planning and tax attorney. And Charles has seen what happens when people prepare...and what happens when they don't. Charles shares the unforgettable story of entering Ranger training without knowing how to swim and refusing to quit, along with the lessons the military taught him about planning for Plan A, Plan B, Plan C...and what happens when things don't go according to plan. Those lessons followed him into tax law and estate planning. In this conversation, Jon and Charles explore: • What working inside the IRS taught Charles about fear, avoidance and procrastination• Why the IRS may not be quite as terrifying as people think• What can happen when someone waits too long to create an estate plan• The $200,000 account oversight that forced a surviving spouse into probate• Why DIY estate planning often fails to ask the two most important words: "What if?"• How family fights can erupt over Grandma's Bible, a family cookbook or an heirloom clock rather than money• Why an estate plan should never be "set it and forget it"• What Army Ranger mission planning can teach families about preparing for incapacity and death But the conversation eventually moves beyond wills, trusts, taxes and probate to something even more important: Legacy. Charles shares a lesson his great-grandfather gave him when he was young: "It's not what you make. It's what you keep." It took years for Charles to fully understand what those words meant. Today, he believes true legacy isn't simply the property or money we leave behind. It's the knowledge, lessons, stories and wisdom we pass to the generations that follow us. Because someday, your family will inherit one of two things: Your preparation...or your procrastination. Make sure it's the former. Contact Charles: https://www.frazier.law/ Connect on LinkedIn: https://www.linkedin.com/in/crfraziertaxpro/

  5. 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/

  6. 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/

  7. 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/

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!

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