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

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, deni...

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 Nig...

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 pla...

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 plan...

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 Amo...

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...

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 th...

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 h...

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...

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...

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 mo...

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…...

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: • Th...

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 p...

Estate planning is about more than wills and trusts. It’s about preserving your family’s legacy, protecting loved ones from probate chaos, and capturing the stories that define who you are. In this episode of Estate Planning Nightmares… and How to Avoid Them , Jon sits down with Pennsylvania estate planning attorney and Civil War historian John Benson to explore the powerful connection between his...

What if honoring a loved one didn’t stop at the cemetery… or even the ocean , but reached beyond Earth itself? In this powerful and inspiring episode of Estate Planning Nightmares… and How to Avoid Them , Jon sits down with Ryan Mitchell, founder of Ashes to Space , a groundbreaking company making it possible for everyday families to send a small portion of a loved one’s ashes into orbit. Ryan’s j...

What happens when estate planning is started.....but not finished? And what happens when a crisis hits and everything is already in place? In this episode of Estate Planning Nightmares… and How to Avoid Them , estate planning attorney Kelly Balamuth shares two real-life stories that reveal the stark difference between chaos and clarity. In the first , a mother created a trust but failed to properl...

In this unforgettable episode of Estate PlanningNightmares… and How to Avoid Them , Jon sits down with Attorney Ken Ventresca , a dual-licensed Pennsylvania and Florida estate planning expert who has seen just about everything — from museum-level art collections withzero documentation… to a home with rooms the size of two tennis courts full of taxidermy , to investors hiding physical stock certifi...

A $50,000 Venmo transfer. A generous father helping his son buy a house. And a single missing sentence that tore a family apart. In this episode of Estate Planning Nightmares… and How to Avoid Them , host Jon Braddock is joined by estate planning attorney Andrew M. Ayers to unpack one of the most modern (and preventable) estate disasters of our time, how a simple Venmo payment became the spark for...

He’s back — and this time, as an author! In this powerful new episode of Estate Planning Nightmares… and How to Avoid Them, host Jon Braddock welcomes returning guest Dean Eason-Williams , founder of NotaryCLT Signings and Apex Mentorship, and author of From Trust to Transfer: A Practical Guide for Notaries Conducting Estate Signings. Dean’s new book is quickly becoming an essential resource for n...

What happens when good intentions turn into estate planning nightmares? In this episode, Attorney Ivette Kuyateh, known as The Kingdom Shero Lawyer in Heels™️, joins host Jon Braddock to share how a former prosecutor became one of California’s most passionate advocates for family protection, financial empowerment, and legacy preservation. With years of courtroom experience and hundreds of trials b...

What happens when good intentions collide with bad advice? In this episode of Estate Planning Nightmares… and How to Avoid Them , Jon Braddock welcomes back Attorney Jolene Blackbourn the show’s very first guest from May 2023! Jolene shares a heartbreaking (and all too common) story about a 93-year-old father who tried to “simplify” his estate by adding his daughter to his accounts — leaving his s...

In this heartfelt and eye-opening episode of Estate Planning Nightmares… and How to Avoid Them , I sit down with Julie Ulrich—founder of Organized Legacy and creator of the WYNKfile™. Julie shares her unique expertise in helping families prepare for the inevitable—whether through legacy planning, decluttering, or after-loss support. Drawing from over 20 years of experience and the personal loss of...

In this episode of Estate Planning Nightmares...and How to Avoid Them , I sit down with Paul Yokabitus — a powerhouse estate planning attorney and entrepreneur based in Cary, North Carolina. Paul is the founder of Cary Estate Planning, one of the fastest-growing law firms in the country, as well as PlanWell Legal, Discovery Legal Marketing, and Elite Planner. We talk about his journey from Michiga...

In this episode of Estate Planning Nightmares… and How to Avoid Them, host Jon Braddock welcomes Holly Simpson — attorney, law firm founder, former therapist, and the driving force behind Simpson Law Firm in Fort Mill, South Carolina. What began as a solo journey just seven years ago has grown into a thriving estate planning practice with a team of 32 — built not through overnight success, but thr...