Episode #32 is out now! Our guest this episode is Leanne Kaufman — President and CEO of RBC Royal Trust, the division of RBC that helps Canadians with estate, trust and incapacity planning/professional administration. Leanne is a lawyer by training and is extremely knowledgeable about all things estate planning in Canada.

In this conversation, Dave and Leanne dive deep into the fundamentals of estate planning — why every Canadian needs a will, the real cost of getting one and what qualities make for an ideal executor. They explore tricky questions like whether you should choose a family member as your executor, if co-executors are ever a good idea and why keeping a “When I Die” binder can spare your loved ones a world of stress.

From corporate executors to cottages (and the conflict they often create) to the risks of joint ownership and the scenarios where trusts actually make sense, this episode covers the most common estate-planning pitfalls Canadians face—and how to avoid them.

Whether you’re creating your first will or updating your entire estate plan, this episode is packed with practical advice, clear explanations and guidance every Canadian should hear.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Leanne Kaufman

(02:34) Why Everyone Needs a Will

(05:01) How Much Does it Cost to Get a Will?

(07:29) What Qualities Does an Ideal Executor Have?

(13:28) Should You Choose a Family Member as Your Executor?

(15:46) Co-Executors: Yay or Nay?

(18:06) The Importance of a “When I Die” Binder

(20:33) Should You Keep Old Wills?

(22:05) What is a Power of Attorney?

(26:52) Why Dave Doesn’t Like Co-Powers of Attorney for Personal Care

(28:39) When Do POAs Take Effect?

(30:56) Name Alternate Executors & POAs

(32:41) How to Make Sure Your POA Will Be Accepted

(34:46) Corporate Executors

(40:50) Cottages and Family Conflict

(44:26) Use Cases for Trusts

(47:28) The Dangers of Joint Ownership in Estate Planning

(50:39) Estate Planning is a Holistic Exercise

(54:00) Conclusion

Our guest this episode is Andrew Hallam—bestselling author of “Millionaire Teacher,” “Millionaire Expat” and “Balance.”

Andrew’s journey into personal finance started in an unlikely place: at 19 years old, he met a millionaire mechanic who taught him that building wealth isn’t about earning a high salary — it’s about making your money work harder than you do. Since then, Andrew has become one of the most respected voices in financial literacy, known for his practical and globally minded approach to investing and life.

In this conversation, Dave and Andrew discuss everything from the timeless principles of index investing and global diversification to the rise of robo-advisors and the pros and cons of real estate investing. Andrew also opens up about his nomadic lifestyle and shares lessons from his book Balance — on finding happiness, health, and purpose beyond the pursuit of money.

It’s an inspiring and insightful episode for anyone looking to build wealth and a better life.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Andrew Hallam

(01:30) How Andrew First Learned About Finance

(03:13) How a Teacher Became a Bestselling Personal-Finance Author

(11:59) How one Key Review Led to Massive Sales

(15:16) Does the Millionaire Teacher Still Believe in Index Investing?

(17:57) All-in-One Asset-Allocation ETFs

(19:27) Chasing Active Outperformance

(23:27) Robo-Advisors vs. Asset-Allocation ETFs

(25:48) The Importance of Global Diversification

(29:29) Real Estate Investing

(32:23) Andrew’s Nomadic Lifestyle

(36:26) Finding Balance in Life

(42:17) What Changes Are Needed to The Financial Industry?

(47:28) Conclusion

SPECIAL EPISODE: To commemorate the launch of the fully updated “The Wealthy Barber,” we’re doing a very special episode this week where Dave is the guest on his own podcast!

We brought back fan favourite and financial-educator extraordinaire, Preet Banerjee, to host the conversation and turn the tables on Dave. Together, they dive into the stories behind “The Wealthy Barber” — from why Dave first wrote the book and how it was tested, to his early days shipping copies with his mom and the moment he realized his life was about to change forever.

They also touch on his time on “Dragons’ Den,” the pressure (and fun) of updating the book for a new generation, the behind-the-scenes team that helped make it happen, and even a few lighter topics — like Dave’s love of A&W, black nibs and eating every meal out.

It’s a funny, nostalgic and inspiring look at one of Canada’s most beloved financial voices and the incredible journey behind one of the bestselling books in Canadian history.

Show Notes

(00:00) Intro & Disclaimer

(00:55) A Special Episode

(03:23) Why Dave Wrote the Original “The Wealthy Barber”

(06:11) How Important Testing is For Dave’s Books

(10:32) Dave’s Goal Was to Sell 10,000 Copies 

(12:31) Dave’s Life in 1989

(14:15) Dave and His Mom Fulfilled Orders at First

(17:49) When Dave Realized His Life Was Going to Change Forever

(20:52) Becoming a Reluctant Publishing Consultant

(24:16) Dragons’ Den

(30:16) The Pressure of Updating “The Wealthy Barber”

(33:19) Preet’s Review of the New Book

(35:57) The Team Behind The Wealthy Barber Podcast and Socials

(39:30) Who is The Wealthy Barber’s Barber?

(40:25) Benefitting From Having Kids in the Book’s Target Market 

(41:38) Dave Eats Every Meal Out 

(45:36) Dave’s Love of A&W and Black Nibs

(47:11) A Day in the Life of The Wealthy Barber

(48:27) Who is the Updated “The Wealthy Barber” For?

(51:55) Conclusion

Our guest this episode is Jason Pereira — Senior Partner & Financial Planner at Woodgate Financial and one of Canada’s most prolific voices in the financial planning industry.

Jason has spent over two decades immersed in the world of financial planning — earning nine professional designations, contributing to hundreds of articles and podcasts and becoming a trusted expert on everything from practice management to fintech to insurance strategy.

In this wide-ranging conversation, Dave and Jason explore the evolution of financial advice in Canada including how it compares globally, why many Canadians still have blind trust in big institutions and what younger advisors are doing differently. They also dig into some of the thorniest financial planning topics: over- and under-insurance, capital gains at death, intergenerational wealth transfers, life insurance for children, rental real estate in 2025 and much, much more.

Jason doesn’t hold back — sharing candid insights on the gaps in Canada’s advisory landscape and how consumers can better navigate the system. Whether you’re a new investor or just someone trying to make smart decisions with your money, this episode is packed with thought-provoking ideas and practical takeaways.

Show Notes

(00:00:00) Intro & Disclaimer

(00:00:55) Intro to Jason Pereira

(00:02:13) The Different Ways to Pay for Financial Advice

(00:05:26) How Does Canada’s Financial Advisory Industry Compare to Other Parts of the World?

(00:10:52) Young Advisors Want To Do More Financial Planning

(00:12:57) Canadians Have Misguided Trust in Large Financial Institutions

(00:16:17) Jason Thinks People Are Being Sold Too Much Insurance They Don’t Need

(00:19:06) Term vs. Cash Value Insurance

(00:21:27) Using Insurance to Cover Large Capital Gains Taxes

(00:25:25) Passing On Cottages Can Cause Much Family Friction

(00:26:45) Corporate Executors

(00:29:37) Many Young Canadians Don’t Have Enough Life Insurance

(00:34:50) How Much Life Insurance Do You Need?

(00:41:20) Buying Life Insurance on Young Children

(00:44:54) It’s So Hard to Max Out All of Your Registered Accounts

(00:46:23) AI and Financial Planning

(00:52:59) Rental Real Estate in 2025

(00:55:32) Any Risks with the Rise of Passive Investing?

(00:58:13) Parents Are Gifting More Money

(01:00:39) When Financial Advisor Fees Are Worth It

(01:04:10) Conclusion

We’re doing something a little different this week! Instead of posting one of our usual episodes, we’re sharing a recent conversation Dave had on "The Rational Reminder Podcast" — one that resonated deeply with listeners.

The feedback on this episode was overwhelmingly positive, with many saying it offered timeless insights, humour and refreshingly practical advice. So, we wanted to make sure our audience didn’t miss it.

Enjoy this special replay of “The Rational Reminder Podcast” featuring Dave Chilton, and we’ll be back next week with a brand-new regular episode.

Show Notes

(00:00:00) Intro

(00:03:50) Introducing Dave Chilton

(00:06:16) What wisdom from the first print of Dave's book, The Wealthy Barber, still holds true today

(00:08:50) If someone read that first print today, the advice Dave would tell them to ignore

(00:12:10) How the success of that first book changed Dave's life

(00:17:55) The sections or topics in Dave's forthcoming book that he is most excited to share with the world

(00:21:29) How (and why) is Dave using other media like videos and podcasts to connect with his audience

(00:27:14) How often individual investors send Dave their portfolios looking for feedback

(00:34:48) How Dave thinks investors should decide between lump sum vs. dollar cost averaging when someone has a big pile of cash to invest

(00:39:50) How Dave tells people to think through whether it makes sense to invest or pay off debt

(00:41:53) The role Dave sees for financial advisors in people's lives

(00:45:28) The number of people who have shared the full details of their home purchases, ongoing costs, and eventual sales with Dave

(00:52:59) The biggest mistakes people make with respect to homeownership

(00:55:51) How Dave thinks people should approach repaying their Home Buyer’s Plan RRSP withdrawals

(01:02:18) What people can do to save more

(01:06:15) The spending categories Dave finds people are most surprised by when they tabulate their spending

(01:11:18) What “good savers” splurge on, based on Dave's experience reviewing people's budgets

(01:19:49) How people can avoid the effects of upward social comparison making them want perpetually more stuff

(01:24:31) Dave's biggest lessons learned from being a Dragon on Dragon's Den

(01:31:12) Dave defines success in his life

Our guest this episode is Jason Heath—Managing Director at Objective Financial Partners and one of Canada’s most respected fee-only/advice-only financial planners.

In this episode, Dave and Jason cover the foundations of financial planning in Canada, tackling hot-button topics like RRSPs vs. TFSAs, reverse mortgages, annuities, CPP/OAS timing, insurance planning, estate-planning pitfalls and more. They also discuss how to prioritize financial goals, avoid common mistakes and build a plan that actually works in the real world.

Whether you’re planning for retirement, building your financial future or just want a clearer understanding of how all the pieces fit together, this episode is a masterclass in financial planning.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jason Heath

(03:00) The Rising Cost of Living in Canada

(05:00) The Pros and Cons of Getting Financial Information from Finfluencers

(10:06) Investing vs. Financial Planning

(12:47) Objective Financial Partner’s Clients and Services

(15:10) Estate Planning

(18:41) Reverse Mortgages Get a Bad Rap

(21:04) Use Cases for Annuities

(24:24) People Don’t Want to Listen to the Experts and Defer CPP and OAS

(25:31) TFSAs vs. RRSPs

(27:54) Decumulation Planning for Retirees

(33:01) Disability Insurance

(35:29) Life Insurance

(40:04) Gifting Money to Kids

(41:52) Estate Planning Mistakes

(44:24) The Importance of Prioritization in Financial Planning

(49:34) Financial Education and Finding Balance

Our guest this episode is Steve Saretsky—a top 1% realtor in Vancouver and the host of one of Canada’s most popular real estate YouTube channels and the podcast “The Loonie Hour.” 

In this wide-ranging conversation, Dave and Steve explore the current state and uncertain future of Canada’s real estate market. They talk about the collapse of the condo market, cancelled development projects, rising risk for lenders and whether sellers are finally starting to accept reality. Steve also shares his insights on affordability challenges, the impact of immigration, which markets still offer value and why detached homes remain the dream for many Canadians.

If you’re trying to make sense of the Canadian housing market—whether you’re a buyer, seller, investor, or just a curious observer—this episode offers a candid, data-driven and often surprising look at where things stand.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Steve Saretsky

(03:06) The Collapse of Canada’s Condo Market

(06:45) Where Are Real Estate Prices Headed?

(10:08) Are Real Estate Developers and Lenders in Trouble?

(14:38) Layoffs at Real Estate Development Companies

(17:01) Lend and Pretend

(19:00) Cancelled Development Project in Vancouver

(21:15) What Caused the Crazy Real Estate Market in 2021?

(24:46) Are Sellers Being Too Stubborn?

(26:50) First-Time Homebuyers Can’t Move Up

(30:49) The Impact of Immigration on the Real Estate Market

(39:02) Which Markets Are Still Affordable in Canada?

(41:44) Landlord Challenges & Investing Across Provinces

(48:49) The Cottage Real Estate Market

(50:56) Policy Changes to Fix the Canadian Real Estate Market

(53:45) Land Costs Drive All Prices Up

(56:01) Conclusion

Our guest this episode is Joyee Yang—a “finfluencer” with over 300,000 followers across Instagram, TikTok, YouTube and more. Joyee has built an audience by taking the intimidation out of investing and teaching the basics in a clear, relatable way.

In this episode, Dave and Joyee dive into her journey: from getting kicked out at 19, to working three jobs to pay off student debt and buy a condo, to becoming one of Canada’s most-followed finfluencers. They discuss the rise of all-in-one ETFs, the pros and cons of individual stocks vs broad-market index funds and how apps like Blossom are helping investors to learn and share their portfolios. 

Whether you’re brand new to investing or curious about the finfluencer landscape in Canada, this episode is packed with stories and beginner-friendly advice.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Joyee Yang

(03:17) How Joyee Became a Finfluencer

(04:44) Working Three Jobs to Pay Off Student Debt and Buy a Condo

(08:05) Individual Stocks Versus Broad-Market ETFs

(11:45) Teaching the Basics and How to Open Accounts

(16:21) Blossom Social Investing App

(18:21) Cooperation Amongst Canadian Finfluencers

(21:58) Joyee’s Desire to Help the Younger Generation

(23:05) All-in-One ETFs

(23:58) Learning About Volatility in the Stock Market

(25:44) Conclusion

Our guest this episode is Jamie Golombek—Managing Director of Tax & Estate Planning at CIBC and a widely respected voice in the Canadian financial industry. Jamie is a frequent guest on BNN, CTV and CBC’s The National, and in 2023 was awarded the prestigious CPA Fellow designation.

In this episode, Dave and Jamie dive deep into the world of tax and estate planning in Canada. They cover everything from RRSPs and FHSAs to the most tax-efficient ways to donate to charity. Jamie shares practical advice on how to think about your tax return (hint: a big refund isn’t a good thing), how to avoid common estate planning mistakes and why keeping a net worth statement with your will might be one of the smartest moves you can make.

Whether you’re saving for retirement, thinking about gifting an early inheritance or just want to better understand Canada’s tax system, this episode is filled with insights, tips and examples every Canadian can learn from.

Show Notes

(00:00:00) Intro & Disclaimer

(00:00:55) Intro to Jamie Golombek

(00:03:43) What is Tax Planning and Estate Planning?

(00:08:17) You Shouldn’t Want a Large Tax Refund

(00:13:53) Employer Matching is a Fantastic Deal

(00:17:49) Registered Accounts in Canada 

(00:22:32) FHSAs are Incredible

(00:24:26) RRSPs and the Advantages of Tax-Free Investing

(00:27:00) Tax on RRSPs and Investments

(00:31:02) Our Tax System is Unfair for Single People

(00:33:25) The Most Tax-Efficient Way to Donate to Charity

(00:39:25) Tax Deductions if You Work From Home

(00:41:37) Changing the Principal Residence Exemption in Canada

(00:45:21) Joint Powers of Attorney for Personal Care

(00:48:01) Cottages and Estate Planning

(00:49:32) The Importance of Keeping a Net Worth Statement with Your Will

(00:52:02) Would Dave or Jamie Ever Be an Executor?

(00:53:18) Corporate Executors 

(00:55:42) How to Avoid Family Fights with The Estate Items

(00:59:38) Early Inheritance Gifts

(01:02:58) Probate Fees

(01:06:01) Beware of Joint Ownership with Your Kids

(01:08:20) Conclusion

Our guest this episode is Aaron Hector—Founding Partner of TIER Wealth, President of the Institute of Advanced Financial Planners and a fellow personal-finance nerd like Dave.

In this episode, Dave and Aaron explore some of the most overlooked opportunities in Canadian financial and estate planning. From optimizing RESP withdrawals to gifting tax deductions to your kids, Aaron shares smart, actionable strategies that can help families build and preserve wealth more effectively. They also cover timely topics like when to defer RRSP or FHSA deductions, how to handle joint accounts, why every Canadian needs a will and the difference between a beneficiary and a successor holder.

Whether you’re just building your financial plan or revisiting it with an eye for tax efficiency, this episode is full of practical tips and clear explanations you can put to use.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Aaron Hector & TIER Wealth

(04:23) Detailed Optimizations in Financial Planning

(07:22) When Should You Defer FHSA or RRSP Tax Deductions?

(10:41) A FREE Strategy for Parents to Help Their Kids Buy a Home (Gifting a Tax Deduction)

(15:22) TFSA vs. RRSP

(17:13) RESP Lump-Sum vs. Gradual Contributions

(20:34) Optimal RESP Withdrawal Strategies

(26:45) A Simple—But Powerful—Estate Planning Exercise

(30:17) Joint Tenancy on Non-Registered Accounts

(32:01) Get a Will!

(34:44) What’s the Difference Between a Beneficiary and a Successor Holder?

(37:23) The Importance of Estate Planning

(39:10) Corporate Executors

(42:24) Tax Opportunities When the Stock Market Pulls Back

(44:49) Are More Grandparents Giving Money to Their Grandchildren?

(46:24) Conclusion