About Estate Planning Nightmares
.....and how to avoid them!
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!
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/ (https://www.lifeclaim.com/)
stephanie.prestridge@lifeclaim.com (stephanie.prestridge@lifeclaim.com)
888-615-3270
LinkedIn:
https://www.linkedin.com/in/stephanie-prestridge-69803926/ (https://www.linkedin.com/in/stephanie-prestridge-69803926/)
Instagram:
https://www.instagram.com/lifeclaimwins/ (https://www.instagram.com/lifeclaimwins/)
Facebook:
https://www.facebook.com/lifeclaimwins (https://www.facebook.com/lifeclaimwins)
15 Sept 2026
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 (https://www.youtube.com/@CabanaJohn702)
And Website:
https://www.cabanajohn.com/ (https://www.cabanajohn.com/)
2 Sept 2026
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/ (https://rootsep.com/)
Follow on Facebook:
https://www.facebook.com/rootslaw (https://www.facebook.com/rootslaw)
Connect on LinkedIn:
https://www.linkedin.com/in/rileykern/ (https://www.linkedin.com/in/rileykern/)
Who has been a guest on Estate Planning Nightmares
.....and how to avoid them!
Names identified in recent episode analyses. Showing up to five guests.
Paul Yokabitus
Holly Simpson
Laura Cowan
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
4,118
Score snapshot 15 Sept 2025
Apple Podcasts (US)
4.5 / 5
4 ratings
Spotify
5.0 / 5
2 ratings
Podcast Authority Score: 66 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
89
Social presence
0
YouTube
74
Engagement
32
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.....and how to avoid them!
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