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

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: [email protected] 

Take the Free Financial Literacy Quiz

 https://financialliteracyindex.com/skuyateh/quiz

Get the Money Books  (also free)

 https://howmoneyworks.com/skuyateh/books

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

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/

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

[email protected]

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

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 history, legacy planning, and the consequences of waiting too long.

John shares:

History teaches us that decisions—and indecision—have lasting consequences.

The same is true in estate planning.

If you’ve been putting off updating your will, creating a trust, organizing your important documents, or having difficult conversations with loved ones, this episode will challenge you to rethink the cost of waiting.

Because estate planning isn’t just financial preparation.

It’s legacy preservation.

Listen now and take the first step toward clarity for your family.

Contact John Benson

Website

https://www.penglaseandbenson.com/

LinkedIn

https://www.linkedin.com/in/john-benson-esquire-2892179/

Facebook

https://www.facebook.com/penglaseandbenson/

GET TO KNOW YOUR FAMILY

https://www.mylifeandwishes.com/checklists/

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 journey is as compelling as the service itself. With a background in aerospace engineering, including work on the Space Shuttle program with NASA and at Blue Origin, Ryan combines deep technical expertise with a profoundly human mission born from personal loss. After scattering ashes at sea and later gazing at satellites crossing a dark night sky, a question took hold:

What if space could be accessible… even for remembrance?

In this conversation, Jon and Ryan explore:

• How Ashes to Space works, from ordering online to tracking a loved one’s journey via satellite

• Why only a symbolic amount of ashes is sent, and what happens during re-entry

• How Ryan made a space memorial affordable at just $249

• The emotional impact families experience when they can literally look up and track their loved one in orbit

• Why this isn’t about novelty, but meaning, intention, and expanding how we think about legacy

This episode isn’t about science fiction.

It’s about human connection, remembrance, and redefining what’s possible.

If you’ve ever looked at the stars and felt something bigger… this episode is for you.

Guest: Ryan Mitchell

Founder, Space Beyond and creator of the Ashes to Space Program

Website: https://ashestospace.com

LinkedIn: https://www.linkedin.com/in/ryan-nick-mitchell/

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 properly fund it, leaving her children scrambling to locate assets after her death. Before the trust administration was even completed, one of her adult children died without an estate plan of his own, triggering probate, court involvement, and a judge-controlled trust for his minor children. The result: compounded legal complexity, emotional stress, and outcomes no one intended.

In the second story, Kelly shares how proper planning didn’t prevent a medical crisis, but it did prevent confusion. When a client became critically ill while traveling, his legally prepared and accessible documents allowed loved ones to act immediately, make decisions confidently, and focus on care instead of chaos.

This episode is a powerful reminder that estate planning isn’t about predicting tragedy, it’s about protecting the people you love when life takes an unexpected turn.

Contact Information:

Kelly Balamuth

California Trust & Legacy

(925) 254-1234

https://californiatrustandlegacy.com/

In California…Book A Free 15-Minute Consultation

https://californiatrustandlegacy.com/book-a-call/

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 certificates in strong boxes all over the house.

These real-world stories expose the same problem:
Most families don’t organize their lives in a way that makes sense to anyone but them.

Ken breaks down what went wrong in each case, what couldhave prevented the chaos, and why proper documentation, updated instructions, and clear digital organization are just as important as having a will or trust in place.

If you work with families, business owners, snowbirds, oranyone with assets in multiple states or if you simply want peace of mind for your own family, this episode is packed with insight, wisdom, and “never again” moments you’ll be talking about long after the show ends.

Contact Ken:

In Pennsylvania: (724) 220-4052

In SW Florida: (239) 331-5100

Website:

https://www.ventrescalaw.net/

Follow On LinkedIn:https://www.linkedin.com/in/kenneth-ventresca-b676806/

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 a bitter, $35,000 legal battle between siblings.

Because in today’s world, your legacy isn’t just what’s in your will it’s what’s written (or not written) in your transaction history.

Connect with Andrew

Website:

https://www.andrewmayers.com/

Social Media:

LinkedIn: https://www.linkedin.com/in/ayerslaw/
YouTube: https://www.youtube.com/@ayerslaw

Instagram: https://www.instagram.com/ayerslaw

Facebook: https://www.facebook.com/ayerslaw/

X: https://x.com/ayerslaw

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 notaries and estate planning professionals alike. Together, Jon and Dean dive into the dos and don’ts of trust signings, red flags every notary should recognize, and why estate planning attorneys should take notice of the critical role trained, confident notaries play in protecting their clients and their firm’sreputation.

Whether you’re a notary looking to elevate your professionalism, or an attorney seeking trusted partners for client signings, this episode is packed with insight, empathy, and real-world experience.

Contact Dean Eason-Williams

Website:

https://notaryclt.com/

Get Dean's Book:

https://www.amazon.com/Trust-Transfer-Practical-Notaries-Conducting/dp/B0FKMLFR8P/

Learn About Apex Mentorship Program:

https://www.skool.com/notarycltapex