No two families are the same, and no one conversation can unlock all the benefits of proper estate planning.

It is an ongoing process, and this episode offers a wide range of practical ideas for getting started. Marc Seguin, who specializes in the family estate meeting, joins Davide and Sara for a wide-ranging discussion on what can actually trigger that first conversation, and why the first step is often less about paperwork and more about timing, trust and emotional intelligence.

Marc's interview took place on the eve of his fifth family estate meeting, and he shares some surprising lessons from that experience, including the value of creativity, scenario planning and even role-play to help people engage with difficult realities.

ClearEstate experts Kim Nelson and Mike Love then widen the lens with a more tactical look at what family meetings can accomplish, where they can go wrong, and when family dynamics may call for a facilitator or professional executor. The result is a candid brainstorm on how to begin one of the most important conversations a family can have together.

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

What does it mean to think like a CEO, or even a monarch, about the future of your business and estate?

Davide and Sara are joined by Karl Moore, professor at McGill University's Desautels Faculty of Management, Forbes contributor and longtime host of the CEO Series podcast, for a wide-ranging conversation about leadership, succession and the difference between building a business for the quarter and building one for generations.

Honoured in the Canadian Senate last month for having "enriched public discourse... translating rigorous research into accessible insight", Karl explains why the strongest business legacies are shaped by disciplined succession planning and a serious commitment to developing younger leaders. Drawing on decades of conversations with senior executives, he reflects on why family businesses often outperform, what other CEOs can learn from that model, and why organizations should be planning not just for the next leader, but for the layers of leadership that follow.

The conversation also explores reverse mentorship, the changing definition of success for younger generations, and the growing pressure on leaders to respond to AI, climate concerns and a more volatile economy.

Karl's latest book is We Are All Ambiverts Now: Introverts, Ambiverts, and Extroverts in the C-Suite.

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com

If you had to explain the difference between a will and an estate plan in a sentence, could you?

In this ​special 'Estates 101' discussion, Sara chats with ClearEstate co-founder Alex Gauthier to ​make one very important point​, and explain ​why it matters so much in real life​. As Davide observes, "the simplicity of the distinction also hides the​ complexity of the process"​.

You can also read Alex's blog at clearestate.com/blog for a detailed breakdown of the distinction and tons of practical advice.

​Spoiler: A will is a legal document​ and part of an estate plan​, which itself is closer to an operating system​ or collection of various documents​ related to estate administration. Alex and Sara walk through ​​what belongs in the plan, including details on assets and liabilities, ​powers of attorney, healthcare directives and other critical information necessary to avoid painful paperwork or family conflict.

They also explain why th​e will vs. estate plan distinction is crucial for financial advisors and other professionals on the periphery of estate ​administration. If you've spent years helping clients build wealth, ​Alex notes, you don't want to see it diluted​ or torn apart​.

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com​.

Families rarely plan senior transitions. They are usually forced into them.

The catalyst most often comes in the form of bad news, like a fall, hospitalization or caregiver burnout. It doesn't have to be this way. Joining Davide and Sara is senior living expert Matt Del Vecchio, a Certified Professional Consultant on Aging (CPCA) and Life Unrehearsed podcaster, who runs a free brokerage service offering solutions to seniors. Staying at home as long as possible is a question of values, while Matt helps families perform a more neutral cost-benefit analysis.

"The vast majority of Canadians want to age in place," Matt said, but "our healthcare system is letting us down."

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

If you had unlimited resources and influence, how would you approach estate planning?

As Davide Pisanu and co-host Sara Hillier begin exploring more in-depth conversations on The End Game, they speak with New York–based podcaster and estate lawyer David Lenok, who since 2019 has been unpacking high-profile horror stories—and the occasional planning and settlement success—on Celebrity Estates: Wills of the Rich and Famous, including cases like the Armani empire.

The best-planned estates prioritize two things, flexibility and communication, David argues. And while HNW families operate at a different scale, he notes their estates often face the same issues as everyday families, just "with the volume turned up."

Davide also reflects on his time at Cirque du Soleil, negotiating with representatives of artists' estates like The Beatles and Michael Jackson. One takeaway: more people are invested in your legacy than you may think.

⚠ Content warning: This episode includes frank discussion of death and end-of-life matters. Listener discretion is advised.

Settling an estate is certainly a lot of paperwork but there is also the emotional journey for families coping with death; and professional help is available for both.

In this episode, we explore how thoughtful end-of-life planning can include the role of a death doula, a non-medical expert providing support for individuals and families. ClearEstate's own Kim Nelson, an estate planning advisor by day, shares her unique journey from tax lawyer to death doula (with Hollywood acting gigs along the way). She explains the nature of the work, how it fits into an advanced care plan, and what doulas can do to make life easier for families in especially tense situations.

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

We all plan for the future, but what happens if you can't make decisions for yourself?

Joining Davide and Sara is Dr. Daren Heyland, founder of the Plan Well Guide and Professor of Medicine and Epidemiology at Queen's University. The emergency care physician, and advocate for medical care plans that cover serious injury or illness, speaks about the tough reality of incapacity, common mistakes, and why so many put off this crucial part of planning. We cover important scenarios you might not expect—including how Medical Assistance in Dying (MAID) fits into the picture.

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

When estate matters get complex, emotions run high, or family dynamics get tricky, a professional executor can be a game changer.

Joining host and ClearEstate CEO Davide Pisanu is Christine Van Cauwenberghe, one of Canada's foremost experts on such matters and the co-author, with Blair Evans, of Wealth Planning Strategies for Canadians, which will soon print its 20th edition. Christine is the head of Financial Planning for IG Wealth Management.

We break down what a professional executor does, when it's worth bringing one on board, and how they handle tough situations with expertise and fairness. Plus, we tackle costs, common misconceptions, and whether a pro can also serve as your Power of Attorney.

For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.