The End Game

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.

Being an executor is more than just signing papers—it's a demanding, often emotional job that few fully understand. With the help of two certified estate professionals, we dive into the real workload, time commitment, and risks executors face; plus hear stories of when things got unexpectedly complicated. Learn the common pitfalls, how to handle conflicts of interest, and get practical tips for executors to protect themselves and keep family peace during a tough time. Joining ClearEstate CEO Davide Pisanu to discuss their challenging work are colleagues Carey Abma, TEP and Sara Hillier, TEP, MTI, Head of Estate Planning & Settlement Solutions at ClearEstate—Sara will add technical expertise and advice to our discussions throughout the series. For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

Think you know everything you own? Think again. Joining ClearEstate CEO Davide Pisanu is Doris Bonora, TEP​, KC—Partner, National Leader for Estates and Trusts at KPMG Law Canada. From forgotten bank accounts to digital assets you didn't realize mattered, we explore what people overlook in their estate plans and why it can cause big headaches later. Hear about the most surprising things ever left in a Will (yes, pets are on the list), how joint ownership and beneficiary designations can completely change who gets what, and the smartest way to organize your estate so your executor isn't left with a scavenger hunt. For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

No Will? Big mistake. Whether you own a house, have kids, or just a few keepsakes, you need one—and we'll explain why.  ClearEstate co-founder and CEO Davide Pisanu begins this discussion series by speaking with colleague, friend and fellow co-founder Alex Gauthier, whose personal estate horror stories inspired the creation of ClearEstate. Estate planning is one of the most underrated acts of empathy and goodwill toward your closest loved ones. We'll discover the must-haves and unexpected options that belong in your will, the most common DIY slip-ups, and how to keep family feuds from erupting. Subscribe to the ClearEstate Podcast for real-life stories, surprising lessons, and easy tips to get estate planning right—because your future shouldn't be left to chance. For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.

No one wants to think about death. Let alone talk about it. Or plan for it. But that's precisely what we'll be doing here on the ClearEstate Podcast. Join co-founder and CEO Davide Pisanu for a discussion series where we get real about estate planning and administration, and our efforts to disrupt old systems with new technology, and a good dose of empathy. In this introductory episode, Davide explains how the process of estate settlement hasn't fundamentally changed in centuries, with the roots of probate dating back to the Middle Ages. While being named as an estate's executor has historically been viewed as prestigious, modern bureaucracies make the experience a frustrating ordeal that drags on for one or two years under the best of circumstances. Founded five years ago this fall, ClearEstate was created to fill a critical gap in estate guidance. Our team is dedicated to modernizing the process, making it accessible, affordable and as stress-free as possible for families. For more guidance, insight and resources on estate planning and administration, visit www.clearestate.com.