Estate & Legacy

Tim Hewson, CEO of LegalWills, discusses why so many Canadians still have no will and what happens when someone dies without one. Listeners learn how online platforms have made compliant wills simpler and cheaper, when a will needs updating, and how it interacts with succession and corporate structure for owners.

Sandy Pollack, author of Don't Leave a Mess, frames estate planning as more than documents: leaving affairs organized so loved ones are not left untangling them. The episode distinguishes financial thinking from financial planning and covers what clear records, a named executor, and communicated wishes accomplish.

David Edey, certified executor advisor and author of Executor Help, explains what it takes to administer an estate well. The episode covers an executor's role and responsibilities, how preparation sets an estate up for success, and why taxes and debts get settled before any cash goes out.

What happens to digital assets when someone dies? Betsy Ehrenberg, founder of Legacy Concierge, describes the scope of a person's digital footprint, why an inventory of accounts grows more important with age, and how software can freeze, delete, or transfer online accounts after death.

Susan O'Brien, founder of Net Worth Thinking, talks about raising money-smart kids. Listeners will hear at what age money coaching can begin, practical ways to encourage children to save, and why teaching kids about the needs of others matters as much as their own.

Melissa Best, founder of QuickEstate, outlines what it takes to be an effective executor. Listeners will learn the full scope of an executor's responsibilities, why so many executors start out unprepared, and why assets like the family cottage are often the hardest to settle.

Dr. Daren Heyland, a former critical care physician, discusses planning ahead for serious illness. The conversation covers why appointing a decision-maker early reduces stress, how the Plan Well Guide helps people clarify their values and treatment preferences, and where powers of attorney fit in.

Denise Fernandes of Diabetes Canada explains how planned giving works alongside financial advice. Listeners will hear how charities coordinate with donors' advisors, why Ontario's charitable credit rate is the lowest in Canada, and when charities get involved in estate planning.

Dane ZoBell of Felesky Flynn discusses succession and tax planning for the family farm. Topics include which assets can qualify for the capital gains deduction, why rising land values have outpaced that shelter, and how gifted property affects the next generation's tax options.

Christine Brunsden of Trusted Legacy discusses planning for how you want to be remembered, not just your finances. The conversation covers why people put off legacy and estate planning and how tools like alter ego and joint partner trusts fit into the picture in Ontario.

Estate planner Harris Jones shares how estate plans go wrong and how disasters can be avoided. Listeners will hear why grief clouds decision-making, why no product actually eliminates estate taxes, and how planning can instead help cover those taxes when they come due.

Rachel Blumenfeld of Aird & Berlis walks through estate planning for business owners. Topics include why dual wills are used to reduce probate costs, how joint accounts can trigger estate litigation, and what changes when an American citizen is part of a Canadian estate plan.

In a role reversal, Guy Anderson interviews host Jason Pereira on the basics of estate planning for business owners. The episode explains where money can go after death, why having your own plan beats leaving it to government default rules, and the three scenarios every will has to address.

Heather Hansen, Partner at Martha McCarthy & Company, joins Jason to explain how family law affects business owners. Listeners will learn the legal ramifications of marriage and separation, how a business's value factors into property division and support, and common myths worth questioning.

Lee Fernandes, Senior Wealth Consultant at Cidel, gives Jason a general education on trusts. Listeners will learn the three certainties a trust must meet, common use cases for wealth protection and control, and how trusts are taxed in Canada.

Jason and Trevor Parry of TRP Strategy Group dig into post-mortem planning for holding companies. Listeners will learn what happens to corporate investments after an owner passes away, how deemed dividends are taxed, and the roles of loss carrybacks, share redemptions, pipeline transactions, and life insurance.

Dr. Tom Deans, author of Every Family's Business, joins Jason to talk about exit planning when family succession is on the table. The conversation covers why a willing buyer matters as much as a willing seller, why a smooth transition rests on the owner rather than the children, and how treating kids like valued employees shapes long-term outcomes.