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

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 behind her, Ivette now helps families stay out of court — by avoiding the very mistakes she once saw tear loved ones apart.

Together, Jon and Ivette unpack some of the most common (and costly) estate planning missteps:

• The danger of “set it and forget it” trusts

• Why leaving assets directly to minor children can backfire

• How “I love you” wills can create chaos instead of clarity

• And the critical updates every family should make before it’s too late

This is a conversation about faith, family, and the power of planning ahead — so your legacy becomes a gift, not a burden.

Estate Planning Nightmares… and How to Avoid Them!

Because some secrets shouldn’t be taken to the grave.

Contact Ivette Kuyateh

Kuyateh Law Group

7310 Miramar Road, Suite 450, San Diego, CA 92126

(619) 535-0066

Website:

https://www.kuyatehlawgroup.com

Email:

[email protected]

Follow on Social Media

LinkedIn:

https://www.linkedin.com/in/ivettekuyateh/

Facebook:

https://www.facebook.com/kingdomsherolawyerinheels

Instagram:

https://www.instagram.com/kingdomsherolawyerinheels/

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 special needs son dangerously unprotected.

Together, Jon and Jolene unpack five ways this plan can go wrong, how families unintentionally sabotage their loved ones’ futures, and what to do instead.

If you’ve ever thought, “It’ll be fine — I’ll just put my kid’s name on the account,” this episode is a must-listen.

🎧 Listen now and learn how to keep your good intentions from turning into a nightmare.

Contact Jolene at:

https://www.joleneblackbourn.com/

Follow Jolene on Instagram:

https://www.instagram.com/joleneestates/

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 her own parents, Julie brings compassion, clarity, and calm to some of life’s most overwhelming transitions.

We discuss:

• Why organizing now is one of the greatest gifts you can give your loved ones

• The emotional side of decluttering (and how to do it with grace)

• What most families forget to plan for—until it’s too late

• Practical tools and checklists to bring peace of mind to the planning process

• The power of after-loss support—and why it matters more than you think

Whether you're a professional in the estate planning space or simply someone who wants to make things easier for your family, this episode is packed with real talk, practical tips, and plenty of “why didn’t I think of that?” moments.

🎧 Tune in, take notes—and start organizing what matters most.

Connect with Julie:

Email:

[email protected]

Website:

https://organizedlegacy.com/home

LinkedIn:

https://www.linkedin.com/in/julie-ulrich/

Facebook:

https://www.facebook.com/organizedlegacy/#

Instagram:

https://www.instagram.com/organizedlegacy

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 Michigan to the Triangle, how he scaled a firm from scratch to 40+ team members, and the “nightmare scenarios” he helps families avoid every day.

You’ll hear:

• One of the biggest estate planning disasters Paul has ever seen (and how to prevent it)

• Why his firms operate with no upselling and no surprises

• How automation, client-first processes, and flat-fee transparency are changing the industry

• The one thing attorneys should stop doing if they want to grow their firm

Whether you're a family needing peace of mind or an attorney looking to better serve your clients, this conversation will leave you inspired — and ready to take action!

🔗 Learn more about Paul’s work:

www.caryestateplanning.com

www.planwell.legal

www.eliteplanner.com

⁠https://www.facebook.com/groups/2772280566257901/⁠

https://www.linkedin.com/in/paulyokabitus/

www.discoverylegalmarketing.com

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 through Holly’s powerful philosophy of improving just 1% every day in every corner of the business. From legal processes to client experience, that small-step mindset has been a game changer.

Holly shares how her background in therapy helps her connect with families on a deeper level, and how the firm’s Southern-style hospitality — which starts the moment you’re greeted by their receptionist — sets the tone for an experience that’s as warm and welcoming as it is professional.

We’ll explore:

• The biggest estate planning mistakes families make (and how to avoid them)

• Why Holly believes planning is just the beginning of the relationship

• What it takes to build a client-first culture in a law firm

• How one simple value — call clients back — became a differentiator

• And how 80s music, pickleball, mentoring teens, and being a “Grandma” all fit into her story

This episode is packed with real-life insight and inspiration for anyone looking to make estate planning more human — and more effective.

Connect with Holly Here:

Simpson Law Firm

Website:

https://simpsonestatelaw.com/

Facebook:

https://www.facebook.com/SimpsonLawFirmCarolina

Instagram:

https://www.instagram.com/simpsonlawfirm/

LinkedIn:

https://www.linkedin.com/company/simpsonlawfirm/about/

What do Gene Hackman and Jimmy Buffett have in common—aside from legendary careers? Sadly, both left behind estates that are reportedly causing legal headaches for their families.

In this powerful episode of Estate Planning Nightmares… and How to Avoid Them, Jon Braddock sits down with returning guest Laura Cowan, Esq., CPA—an award-winning estate planning attorney, entrepreneur, and author of the Amazon bestseller Lifestyle Lawyer Revolution.

Together, they unpack:

• The estate planning pitfalls that may beplaguing the Hackman and Buffett families

• The most common—and costly—mistakes Laura seesfamilies make
• How Laura built a seven-figure virtual law firmworking just a few hours a day
• What lawyers can do to escape the burnout grindand build a life-centered practice
• Why redefining success might be the smartestlegal strategy of all
• 
  

Whether you're an attorney, advisor, or someone who simply wants to protect their legacy—this episode is packed withreal talk, actionable tips, and a fresh perspective on estate planning.

🎧 Tune in now and learn how to avoid the nightmares… before it’s too late.

Get Laura's Book - "Lifestyle Lawyer Revolution"

https://www.amazon.com/Lifestyle-Lawyer-Revolution-Without-Leaving/dp/1966395809

Learn more about the 2-Hour Lifestyle Lawyer Program

https://www.2hourlifestylelawyer.com/Check Out Laura's Podcast:

https://open.spotify.com/show/5fc57BpEJJieud8m8636fSConnect with Laura on LinkedIn:https://www.linkedin.com/in/thelauracowan/

In this episode of Estate Planning Nightmares... and How to Avoid Them!, Jon Braddock sits down with attorney and author Nicole Harvey for a refreshingly funny and eye-opening conversation about estate planning.

Nicole is the author of I Hope You Die Laughing—a witty and wise guide that helps readers tackle the serious business of estate planning with grace, clarity, and even a few laughs along the way.

With years of experience in probate, trust administration, and more, Nicole shares stories, practical advice,and a unique perspective that reminds us: planning for the end is actually about living well now.

Whether you’ve been procrastinating your own plan or advising others on theirs, this episode will make you think—and maybe even chuckle—as you prepare for life’s final chapter.

🎙️ Tune in and discover how dying laughing might be the best legacy you can leave.

Get "I Hope You Die Laughing" here:https://ihopeyoudielaughing.com/

Or here:

https://www.amazon.com/Hope-You-Die-Laughing-Beginners/dp/B0D8F1ZYKL/

Contact Nicole at:

https://nevadacounsel.com/(775) 832-3012Follow Nicole:

https://www.facebook.com/IHYDL

https://www.instagram.com/i_hope_you_die_laughing/

https://www.linkedin.com/in/nicole-m-harvey-esq/