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

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

Hosted by Jonathan Braddock

BusinessInterviews guests

Episodes

81

Latest episode

Aug 2026

Language

EN-US

About the show

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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60 recent
August 12, 2026Episode 8147 min

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/

June 30, 2026Episode 8047 min

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/

June 10, 2026Episode 7941 min

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/

June 3, 2026Episode 7848 min

The Final Gift: How Clarity Replaced Guilt and Conflict

What if the greatest gift you leave your family isn't money, but clarity? In this episode, estate planning attorney Sabrina Winters shares the personal experience that shaped her career after watching her family struggle through the consequences of having no plan in place. When her uncle passed away without proper directives and planning, the family was left with conflict, uncertainty, and a haunting question: "Did we do the right thing?" Years later, when her own father passed away with clear instructions and open family communication, the experience was completely different. Join Jon Braddock and Sabrina as they explore the difference between chaos and peace, guilt and confidence, and why estate planning is ultimately about protecting the people you love. This is a conversation every family needs to hear. Connect with Sabrina Website: https://ncestateplanninginfo.com/ Facebook: https://www.facebook.com/SabrinaWintersAttorneyatLawPLLC Instagram: https://www.instagram.com/estatelawyernc/?hl=en LinkedIn: https://www.linkedin.com/in/sabrinawinterslaw/

April 21, 2026Episode 7740 min

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

April 15, 2026Episode 7645 min

Your Estate Plan Needs a Lifeguard (Here’s Why Most Plans Fail Anyway)

Most people think estate planning is about documents. Wills. Trusts. Paperwork. But what if that’s not what actually protects your family? In this episode of Estate Planning Nightmares… and How to Avoid Them, Jon Braddock sits down with returning guest and estate planning attorney Heidi Thompson—founder of Lifeguarding Legacies and author of Lifeguard Your Legacy. Together, they explore a powerful analogy: A great estate plan should function like a lifeguard. Because when everything is calm, you don’t notice it. But when something goes wrong—when emotions are high, decisions are unclear, and families are overwhelmed… That’s when it matters most. Inside this episode: • Why estate plans don’t fail on paper—they fail with people • How the “lifeguard mindset” changes the way you plan • The hidden risks of having documents without clarity • How to guide your family when you’re no longer there to explain things • Why communication and structure matter more than most people realize This isn’t about having a plan. It’s about having a plan that actually works when your family needs it. If you’re still breathing… you still have time to get this right. Contact Information: Heidi J. Thompson, Ed.M., JD Website: https://lifeguardinglegacies.com/ Get Heidi’s Book, “Lifeguard Your Legacy” here: https://www.amazon.com/dp/B0GSNFVJ4T

April 7, 2026Episode 7542 min

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

April 2, 2026Episode 7433 min

The Estate Plan Killer No One Talks About: Why Long-Term Care Changes Everything

Most estate plans don’t fail because of bad documents… They fail because of what happens before death. In this episode of Estate Planning Nightmares… and How to Avoid Them , Jon sits down with long-term care expert Raymond Lavine to unpack one of the biggest blind spots in financial and estate planning today. Because here’s the reality: You can have a perfectly drafted will… a fully funded trust… and still watch everything unravel when a long-term care event hits. Raymond brings both professional expertise and deeply personal experience to this conversation—having walked through long-term care with his own family. What he shares isn’t theory… it’s what actually happens when planning meets reality. Together, they break down: • Why long-term care is the missing piece in most estate plans • How even wealthy families get financially and emotionally blindsided • The hidden costs of caregiving that no one prepares for • Why “I’ll just self-insure” is often a dangerous assumption • How long-term care planning protects not just assets… but relationships • What a real plan looks like—and how to start If you think your estate plan has you covered…this episode may change your mind. Connect with Raymond Lavine: Website: https://www.lavineltcins.com/ LinkedIn: https://www.linkedin.com/in/ltc-benefits/ Phone: 253-275-6091

March 1, 2026Episode 7335 min

Married 60 Years… But the Law Kept Them Apart

An elderly couple married for 60 years were separated during COVID. Not because they wanted to be. Because they didn’t have the right legal documents in place. In this powerful episode of Estate Planning Nightmares… and How to Avoid Them , I sit down with Attorney Karnina “Nina” Deane , founder of K. Deane Law, to discuss the real-life consequences of missing incapacity planning. Nina shares: • The heartbreaking story of a husband who couldn’t make medical decisions for his wife • Why marriage alone does NOT give automatic authority • The Louisiana case where five previously unknown half-siblings inherited part of an estate • Why intestacy laws prioritize biology over relationship • The myths millennials believe about wills and probate • Why everyone over 18 needs a financial and healthcare power of attorney After losing her mother at age six without an estate plan in place, Nina made it her mission to make estate planning REAL — Relatable, Easy to Understand, Accessible, and Legacy Building . This episode is about more than legal documents. It’s about protecting love. It’s about avoiding chaos. It’s about making sure the state doesn’t write your will for you. Listen now — and share it with someone you care about. Contact Info: Karnina Deane Your Legacy Building Advocate https://www.yourlba.com/ Facebook https://www.facebook.com/YourLegacyBuildingAdvocate Instagram https://www.instagram.com/yourlba/ LinkedIn https://www.linkedin.com/in/karninadeane/

February 24, 2026Episode 7234 min

“I Survived a Heart Attack — And My Estate Plan Saved My Family From Chaos”

What would happen to your family if something unexpected happened tomorrow? In this powerful episode of Estate Planning Nightmares… and How to Avoid Them! , Jon sits down with Andrew G. Rosenberg , founder of the Rosenberg Law Firm , to discuss what 30 years in estate planning has taught him about crisis, preparation, and peace of mind. But this conversation goes beyond theory. Andrew shares his personal story of surviving a massive heart attack — and how having his own estate plan organized brought clarity and calm during one of the most uncertain moments of his life. In this episode, you’ll learn: • Why having a will alone guarantees probate • The difference between estate taxes and probate (and why people confuse them) • Why incapacity planning is often more important than planning for death • How durable powers of attorney can prevent guardianship court • Why estate planning is not just for the wealthy • The most dangerous misconception families have about “getting around to it someday” Andrew also shares his philosophy of radical accessibility — giving clients direct access to him via cell phone, email, Zoom, and monthly office hours — because estate planning isn’t a transaction. It’s a relationship. If you’ve been delaying your planning, this episode may change your perspective. Because life is unpredictable. And peace of mind isn’t accidental. It’s designed. Connect with Andy: Andrew G. Rosenberg Rosenberg Law Firm 5421 N University Dr # 101 Coral Springs, FL 33067 (954) 755-7803 andrew@rosenberglawfirm.net Andy’s Book, “If You Don’t Plan, You’re Stupid!” https://www.amazon.com/You-Dont-Plan-Youre-Stupid/dp/B0FXSG1V53/ LinkedIn https://www.linkedin.com/in/andrew-rosenberg-652243139/ Facebook https://www.facebook.com/AndrewRosenbergLawFirm

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