In this episode, Dave and Amber explore the world of investing and the ongoing debate between active and passive strategies. They discuss whether active managers can truly beat the market, whether retail investors should pay attention to the daily moves of the stock market and whether strategies like private equity are right for everyday Canadians.They also discuss why women remain underrepresented in finance, the differences in investing behaviour between men and women, and what lessons investors can learn from their mistakes.

It’s a wide-ranging conversation filled with thoughtful insights on investing, markets and the future of the economy.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Amber Kanwar

(04:08) How Amber’s First-Ever Article Become Front Page News at The Globe and Mail

(08:38) Leaving BNN Bloomberg to Start a Media Company

(13:45) The Debate: Active vs. Passive Investing

(19:38) Hard-Hitting Interviews and Past Performance Metrics

(21:05) Is Private Equity a Good Investment for Retail Investors?

(25:39) Learning From Investing Mistakes

(27:30) Why Are Women Underrepresented in Finance?

(28:30) Investing Differences Between Men and Women (on Average)

(32:38) The Difficulty of Investing Based on Macro Forecasts

(37:56) Outperformance in Small- and Mid-Cap Companies

(40:46) AI and the Impending Loss of Entry-Level Jobs

(43:04) Real Estate Trends

(45:14) Regulation and Business Formation in Canada

(48:14) Talent Retention Challenges for Canadian Businesses 

(50:00) Could Passive Investing Break the Market?

(54:58) Conclusion

In this conversation, Dave and Gary explore one of the most challenging topics families face: inheritances and how to talk about money with the people you love. They discuss why estate planning conversations are often avoided, how to add clarity and context to your will to prevent misunderstandings and strategies for navigating unequal inheritances, family cottages and potential hard feelings. Gary also shares insights from his new book, “Roots of Prosperity,” including how families can preserve not just wealth, but values and relationships across generations—and why open communication is the key to a lasting legacy.

If you’ve ever wondered how to start money conversations with your parents or children or want to avoid conflict around inheritances this episode is packed with thoughtful insights and practical advice.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Gary Teelucksingh

(02:09) Why Families Struggle to Talk About Money

(04:51) Why Estate Planning Conversations Are Considered Taboo

(06:22) Why You Need to Add Colour and Context to Your Will

(08:56) How to Avoid Hard Feelings with Inheritances

(12:30) Leaving Unequal Inheritances to Multiple Children

(14:26) The Challenges of Passing on a Cottage

(16:33) Why Gary Wrote “Roots of Prosperity”

(21:57) How to Talk with Aging Parents About Money

(23:37) The Inheritance Economy

(26:12) Creating the Impetus to Act

(28:07) Conclusion

In this conversation, Dave and Jon dive into Canada’s housing market, from how Jon correctly predicted the current downturn to where prices could be headed next. They explore the impact of interest rates, affordability challenges and even artificial intelligence on jobs and housing demand. The discussion also tackles controversial industry topics like realtor commissions, lead generation, double representation and the iPro scandal involving misappropriated trust funds. Jon shares insights on why many markets are stuck, the risks of overpricing in a declining market and why some speculative builds could be in serious trouble.

Whether you’re a homeowner, buyer, investor or just trying to make sense of Canada’s real estate headlines, this episode is packed with insights and practical perspective you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jon Flynn

(03:04) How Jon Predicted the Real Estate Crash 

(05:26) Where is the Real Estate Market Headed?

(08:57) The Impact of AI on Jobs and Real Estate

(11:16) Do Realtors Make Too Much Money?

(14:58) The Debate Over Double Representation

(17:05)  The iPro Scandal and Misappropriation of Trust Funds

(21:32) The Impact of the Cost of Living on Home Buyers

(25:05) “Lowball” Offers

(26:04) Real Estate Markets Around the Country

(28:35) The Dangers of Overpricing Your Home in a Down Market

(32:08)  The Market is Stuck Because of Negative Equity and an Inability to Move Up

(36:08) Speculative Country Home Builds Are in Trouble

(38:46) Conclusion

In this conversation, Dave and Meagan explore both the opportunities and challenges shaping the financial planning industry today. They dig into what a great financial plan actually is, why meaningful planning starts with deep, thoughtful questions and the strengths and weaknesses of the traditional Assets Under Management model. Meagan shares her perspective on the growing advice-only movement, fiduciary standards under the new RFP rules and whether products like cash value life insurance are being overused. They also tackle practical topics like disability insurance, insuring children and why there is so much misinformation around RRSPs.

Whether you work in financial planning, are seeking advice, or are simply curious about how the industry is evolving, this episode offers a thoughtful, insider look at where financial planning is headed.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Introduction to Meagan Balanski

(04:54) Meagan’s Recent Financial Planning Award and Flow State

(08:46) What is a Financial Plan? 

(10:09) Why Great Financial Planning Starts With Deep Questions

(12:29) The Assets Under Management Model

(15:30) Challenges of the Advice-Only Model and Implementation Gaps

(20:03) Reasons for Concern and Optimism About the Financial Planning Industry

(26:25) Fiduciary Responsibility and the New RFP Standard

(29:27) Is Cash Value Life Insurance Overused?

(34:15) Disability Insurance

(37:31) The Pros and Cons of Insurance on Children

(41:31) Is the Media Too Harsh on Financial Advisors?

(45:08) The Opportunity for Micro-Modular Financial Planning in Canada

(48:34) Debunking Misinformation About RRSPs

(50:42) Conclusion

In this episode, Dave and Julia explore what advice-only financial planning really means and why human-led planning matters more than ever. Their conversation ranges from the challenges of implementing financial plans to the rise of niche specialization in the industry and how retirees should think about the mosaic of retirement income. Julia also shares her insights on difficult but critical topics like planning for when one spouse passes away, choosing the right executor/POA and why adding kids as joint owners can be risky.

Whether you’re building a plan, managing a family business, or simply thinking more deeply about your financial future, this thoughtful and wide-ranging conversation is packed with insight.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Julia Chung

(03:38) What Advice-Only Financial Planning Really Means

(05:46) What Type of Clients Are Best Suited for Advice-Only Planning?

(09:30) Human-Led Financial Planning

(12:03) Cooperation in the Advice-Only Planning Community in Canada

(13:16) Challenges with Financial Plan Implementation

(17:25) The Growth of Niche Specialization in Financial Planning

(20:55) The Mosaic of Retirement Income

(24:09) Retirement Planning for When One Spouse Passes Away

(26:43) Julia’s Views on “Competitors” in the Financial Management Industry

(28:21) Choosing the Right Executor

(30:35) The Pros and Cons of Corporate Executors

(31:50) Beware of Adding Kids as Joint Owners

(34:57) The Critical Importance of Powers of Attorney

(37:17) Financial Institutions Are Resisting POA Documents More and More

(39:27) Qualities to Look for in Your POA for Personal Care

(41:46) Debunking RRSP Misinformation

(44:05) Why Disability Insurance is Underrated

(47: 31) Paying Off Your Mortgage or Investing

(49:34) The Evolution of Family Business Transitions

(53:42) Recommended Reading: “Designing Your Life”

(55:17) Financial Pet Peeves and Conclusion

In this conversation, Dave and Jason explore the financial advice landscape in Canada — from the differences between financial planners and advisors to which credentials actually matter and what it truly means to act as a fiduciary. They dig into how the CFP program has evolved, the pros and cons of advice-only planning, why the middle market is so underserved, and how revenue models shape client outcomes. Jason also shares his thoughts on broken insurance licensing, commission conflicts, specialization in planning and why communication and psychology are becoming just as important as technical expertise.

If you’ve ever wondered how financial advice really works in Canada (or where it needs to go next!) this episode is packed with thoughtful insights, practical perspectives and reasons for optimism about the future of the profession.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jason Watt

(03:14) Pro Bono Financial Planning

(04:27) Jason’s Background with Business Career College

(05:53) What is a Financial Planner vs. a Financial Advisor?

(08:47) What Credentials Actually Matter for Financial Advisors?

(10:52) What Does it Mean to Be a Fiduciary?

(12:46) How the CFP Program Has Evolved

(16:36) Different Revenue Models for Financial Advice

(18:49) Why the Middle Market is Underserved in Canada

(21:00) Advice-Only Planning: Strengths and Weaknesses

(23:29) Specialization and Niches in Financial Planning

(24:22) Financial Advisors are Focusing More on Communication and Psychology

(26:06) Why Insurance Licensing is Broken in Canada

(31:28) The Commission Conflict in Insurance Sales

(32:53) An Idea to Redesign Licensing: Certify by Complexity (Not Products)

(34:56) Cross-Border Financial Planning Gets Complicated Fast

(37:39) The Updated “The Wealthy Barber”

(39:33) Canada Has Some Great Financial Educators

(42:17) Should You Commute a Pension or Leave It?

(44:01) Reasons for Optimism in the Financial Advice Industry in Canada

(48:31) Gambling Worries 

(49:57) Housing Affordability and Expectations

(51:43) Conclusion

In this conversation, Dave and Chris dive into the world of side hustles and small entrepreneurship — how to turn skills and hobbies into income, why reselling is one of the easiest ways to start and why action always beats overplanning. Chris shares what successful side-hustlers have in common, how to find your first customers, why farmers’ markets are an underrated testing ground for business ideas, and how knowing when to quit can be just as important as knowing when to push forward.

Whether you’re thinking about starting a side hustle, testing a business idea, or just want a fresh perspective on work and time, this episode is full of practical insights and encouragement. Listen now on our website, YouTube, Apple Podcasts, Spotify and all major podcast platforms.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Chris Guillebeau

(02:05) Chris’s Unconventional Early Career

(05:03) The Why Behind Writing “The $100 Startup”

(08:06) Turning Skills and Hobbies Into Income

(11:04) Reselling is a Great Place to Start for Entrepreneurship

(11:56) Action Beats Overplanning

(13:06) How to Find Your First Customers

(14:45) What Do Successful Side-Hustlers Have in Common?

(21:12) The Impact of “The $100 Startup” 

(22:09) Knowing When to Quit is Vital

(23:40) Farmers’ Markets Are Great for Testing Business Ideas

(25:44) Why Enjoyment Matters More Than Scale for Side Hustles

(27:16) What is Time Anxiety?

(29:02) ADHD & Neurodiversity

(33:16) Conclusion

In this conversation, Dave sits down with Heather and Doug to explore how couples can navigate money as a team — from shifting income dynamics and caregiving to power, communication, and the invisible labour that often goes unrecognized. They share why they wrote Money Together and why strong financial partnerships aren’t built with spreadsheets, but with trust, curiosity, and shared values.

Whether you’re in a long-term relationship, newly partnered, or just want to understand how money and relationships intersect, this episode is packed with thoughtful insights and practical takeaways.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Heather & Doug Boneparth

(03:15) Why They Wrote “Money Together”

(07:22) How Power and Income Shift Relationship Dynamics

(09:13) Caregiving is a Real Economic Contribution

(14:26) The Breaking Point That Forced Change

(17:08) Division of Labour and How to Truly Create Space for Your Partner

(21:57) How to Talk About Money as a Team

(24:27) Start with Money Wins, Not with Spreadsheets

(27:42) Both Members of a Couple Need to Understand Their Finances

(29:04) Managing Your Finances Together is an Ongoing Activity

(30:12) Teaching Kids Values, Not Financial Math

(32:58) Money is Finite

(35:36) Money, Divorce and Difficult Conversations

(37:43) Growth Requires Discomfort & Curiosity

(39:02) Strong Couples Are Resilient to Whatever Life Throws at Them

(40:38) Conclusion

In this conversation, Dave and Shannon explore what real-world financial planning looks like for everyday Canadians. They dive into fee-only and modular financial planning, budgeting in real life, turning advice into action and how rising housing prices, down payments and “financial dysmorphia” are reshaping how Canadians think about money.

Whether you’re just getting started with your finances or feeling squeezed by today’s economic realities, this episode is full of perspective, practical advice and much-needed hope.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Shannon Lee Simmons

(02:22) Leaving Bay Street to Serve Everyday Canadians

(04:10) The Barter Babes Project

(08:01) Writing “Making Bank” for Teenagers

(11:59) What is Fee-Only Financial Planning?

(14:06) Modular Financial Planning for Real Life

(15:30) The Importance of Knowing How Much Money is Coming In and Going Out

(18:49) Who Typically Seeks Fee-Only Financial Planning?

(20:19) Turning Financial Advice Into Action

(22:26) Why Fee-Only Financial Planners Are Starting to Specialize

(25:58) Software vs. Spreadsheets

(26:55) Scaling a Fee-Only Practice

(28:43) Housing Prices are Squeezing Canada’s Middle Class

(32:15) More People Are Risking Their Own Retirement to Help Their Adult Children Financially

(34:33) Down Payments Squeeze All Other Savings

(36:20) Financial Dysmorphia and “Normal” Spending

(38:50) Hope is Your Biggest Asset 

(41:23) Real Estate Prices and Divorce

(43:03) Some Young People Are Still Doing Well Financially

(44:19) Retirement Planning is a Different Beast

(49:43) Reasons for Optimism and Hope

This is an amazing episode for anyone looking to better manage their money in 2026. In their conversation, Dave and Melissa explore the idea that money should support happiness, not compete with it. They dig into behavioural finance and simple “brain hacks” that can lead to better decisions, from the 24-hour rule for spending to the power of spending summaries. Melissa also shares insights on social media comparison, why experiences tend to bring more lasting happiness than stuff, the joy of anticipation, and why big purchases like cars so often fail to deliver long-term satisfaction.

The discussion also touches on generosity and happiness, valuing time over money, financial challenges women face, managing money as a couple, and practical ways to get started building healthier financial habits — without guilt or perfectionism.

Whether you’re trying to spend more intentionally in the new year, stress less about money, or align your finances with what actually makes you happy, this is a thoughtful and refreshing conversation you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Melissa Leong

(02:09) Melissa’s Path from Journalism to Money

(05:42) Behavioural Finance & Brain Hacks

(09:32) The 24-Hour Rule for Spending

(14:16) Social Media & The Pressures of Comparison

(16:41) Money Should Support Happiness, Not Compete With It

(18:56) Spending Now vs. Spending Later

(22:39) Experiences Create More Lasting Happiness Than Stuff

(24:12) The Joy of Anticipation

(30:29) Dave Doesn’t Have FOMO, He Has FOBI

(32:07) The Power of Spending Summaries

(36:16) Charity, Generosity & Joy

(39:17) Valuing Time Over Money

(40:31) Why Cars Rarely Deliver Lasting Happiness

(43:32) How Melissa Became a Regular on The Drew Barrymore Show

(45:11) Financial Challenges Women Face

(51:22) Managing Money as a Couple

(56:43) How to Get Started Managing Your Money Well

(59:01) Conclusion

In this conversation, Dave and Shaun explore what the research really says about money and happiness — from whether happier people make better financial decisions to why more money doesn’t always lead to more joy. They unpack concepts like hedonic adaptation, the “arrival fallacy” of wealth and the unconscious money scripts that quietly shape our spending, saving and relationships. Shaun also challenges the idea that financial success is purely about optimization, making the case for peace of mind, values-based decisions and “sailing to the right island” in life.

If you’ve ever wondered whether you’re chasing the wrong financial goals — or how to make money decisions that actually improve your well-being — this episode is full of thought-provoking insights and practical takeaways.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Shaun Maslyk

(03:39) Do Happier People Make Better Money Decisions?

(05:25) Research on Money, Happiness & Hedonic Adaptation

(11:45) The Arrival Fallacy of Wealth

(13:22) Money Stories & Unconscious Scripts

(16:17) How Money Scripts Affect Relationships

(20:51) Peace of Mind vs. Mathematical Optimization

(24:42) Do Walkers Have Better Financial Behaviour?

(26:57) Spending Summaries

(28:44) Make Sure You’re Sailing to the Right Island

(31:51) The Three Questions That Clarify Money Decisions

(35:43) Spending on Experiences vs. Possessions

(39:55) Too Much Luxury Can Reduce Joy

(41:02) What Would You Do If You Only Had 24 Hours to Live?

(43:10) Conclusion

In this conversation, Dave and Aravind walk through what great financial planning actually looks like in practice. They discuss the “financial quarterback” model, Aravind's four-step process for investing and why assessing true risk tolerance goes far beyond a simple questionnaire. Aravind explains how biology and financial stress affect investor behaviour, why unusually high returns are unlikely to last forever and how personal preferences should factor into a well-designed plan.

The episode also dives into estate and tax planning topics that are often overlooked—from common estate planning mistakes and the risks of joint accounts to when RRSPs should be left to an estate, how taxes work at death and traps grandparents can fall into with RESPs. The conversation wraps up with a practical comparison of TFSAs vs. RRSPs, a discussion on alternative investments and Aravind’s personal story about discovering The Wealthy Barber.

Whether you’re building your first financial plan or refining an existing one, this episode is packed with clear, thoughtful insights from one of Canada’s brightest young planners. 

Show Notes

(00:00) Intro and Disclaimer

(00:55) Intro to Aravind Sithamparapillai

(04:47) ​​The Financial “Quarterback” Model

(10:32) The Four-Step Investing Process

(14:38) How Do You Assess True Risk Tolerance?

(16:47) A Financial Planner’s Role in Changing Risk Tolerance

(19:04) Biology and Financial Stress

(21:38) 20% Returns (Probably) Won’t Go On Forever

(23:30) Personal Preferences & Maximizing Return

(25:05) Common Estate Planning Mistakes

(26:50) Reasons Why RRSPs Should Be Left to the Estate

(31:47) The Risks of Using Joint Accounts to Avoid Probate

(34:44) The Benefits of Leaving a Letter of Direction with Your Will

(36:43) What Happens Tax-Wise When You Die?

(38:26) The RESP Trap for Grandparents

(45:00) TFSA vs. RRSP

(49:09) The Risks of Alternative Investments

(56:13) Aravind’s Personal Story About The Wealthy Barber

(58:45) Conclusion

In this conversation, Dave and Daniel tackle the big questions facing the real estate market today. They discuss the Ontario government’s move to take over RECO, whether realtors should be able to represent both sides of a deal, and the evolving role of municipalities, development charges and zoning in housing affordability. Daniel shares his perspective on where the market goes from here, why most Canadians still want a detached home and what it will take to make those homes more affordable.

The conversation ranges far beyond prices, touching on the challenges of an aging population, mortgage stress tests and why older generations are staying “overhoused.” There’s also a fascinating discussion about the impact of AI, First Nations’ land claims and the rise in Powers of Sale.

If you’re interested in the state of Canadian real estate — from policy to affordability to where things might be headed — this episode is full of insights you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Daniel Foch

(05:06) Ontario Government Taking Over RECO

(07:57) Should Realtors Be Able to Represent Both Sides of a Deal?

(10:36) Housing Affordability and the Role of Government

(16:30) Should Municipalities Lower Their Development Charges?

(18:00) Where Does the Real Estate Market Go From Here?

(20:56) Most Canadians Still Want a Detached Home

(23:15) Owning vs. Renting

(26:25) How Do We Make Detached Homes More Affordable?

(28:40) Older Generations Are Overhoused But Not Downsizing

(34:07) Mortgage Stress Tests

(38:42) Daniel Thinks Municipal Governments Could Go Away

(40:13) The Potential Impact of AI on Societies

(41:54) First Nations’ Land Claims in Canada  

(44:31) Bill 60

(46:47) Valery AI

(50:15) Increasing Powers of Sale

(54:57) Conclusion

In this conversation, Dave and Morgan explore the timeless principles that shape how we think about money, happiness and decision-making. Morgan shares the story behind writing “The Psychology of Money,” why earning more didn’t change his life as much as he expected and why he believes money is “the greatest show on Earth.” They dig into core ideas like why firsthand experiences are more persuasive than data, why “no one’s crazy” and how comfort (not speed) is often the real goal in personal finance.

The discussion also covers the emotional side of money — from spending mistakes and regrets to what Morgan actually enjoys spending on — along with big-picture themes like luck, independence, volatility and how to think in terms of what’s reasonable rather than purely rational.

If you’re fascinated by human behaviour, personal finance or simply want to make better decisions with your money, this episode is packed with thoughtful insights and memorable lessons from one of today’s most influential financial thinkers. 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Morgan Housel

(03:01) The Story of Writing “The Psychology of Money”

(07:37) How Making More Money Changed Morgan’s Life (Spoiler: Not Much)

(09:56) Why Morgan Calls Money "The Greatest Show on Earth"

(11:25) Nothing is More Persuasive Than What You’ve Experienced Firsthand

(13:42) “No One’s Crazy”

(17:16) You Can Either Make the Train Twice as Fast or Twice as Comfortable

(19:33) Was There Pressure Writing a Follow-Up Book?

(21:26) Nobody is Paying as Much Attention to You as You Are

(23:32) Volatility is the Price of Admission in Investing

(26:05) Buying Independence vs. Buying Expensive Things

(29:12) Spending Mistakes vs. Regrets

(32:17) What Does Morgan Like to Spend Money On? 

(35:08) The Role of Luck in Our Lives

(40:33) Reasonable vs. Rational in Personal Finance

(43:21) The Most Overrated Financial Advice 

(44:48) Conclusion

John’s newest book, “Fixed: Why Personal Finance Is Broken and How to Make It Work for Everyone,” makes a compelling case that the financial system — while vital — is failing ordinary people. Between unnecessary complexity, steep fees, confusing products and poor incentives, most households are left navigating a system that isn’t built with their best interests in mind. John draws on decades of research to explain what’s gone wrong and how better product design, smarter regulation and clearer advice could dramatically improve financial outcomes.

In this episode, Dave and John explore how the system can be fixed — from mandatory universal retirement accounts to simpler, standardized financial products, to improving disclosures on credit cards. They also discuss the pitfalls of active mutual funds, the challenges of financial advice models, the role of technology in impulse spending and the rise of gambling and meme-stock behaviour. It’s a wide-ranging and accessible conversation with one of the world’s top financial thinkers.

If you care about personal finance, financial policy or simply understanding why the system feels so confusing this episode is a must-listen.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to John Campbell and His Book “Fixed”

(05:14) How Should the Financial Industry be Fixed?

(09:30) Mandatory Universal Retirement Accounts

(12:52) Active Mutual Funds Have Costly Fees 

(15:48) The Different Models for Financial Advice

(18:37) How Standardized Financial Products Could Help

(21:07) Life Insurance and Complexity

(24:57) Two Thoughts on Debt

(26:21) Technology and Impulse Spending

(29:24) Gambling & Meme Stocks

(31:19) Policy Ideas to Fix the Financial System

(36:21) How Disclosures on Credit Cards Could Be Improved

(38:33) Conclusion

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

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

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

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

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

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

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 (32:40) Most People Still Want a Detached Home

(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

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

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

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

In this conversation, Brian joins Dave to share the story behind his entrepreneurial journey—from naming the company after a phone number to franchising it internationally to turning “ordinary” home services into premium, trusted brands. They dive into the lessons Brian learned while building the business, why he believes anyone can be an entrepreneur and how his grandfather’s advice on kindness continues to shape his leadership style. 

Whether you’re a budding entrepreneur or just curious how a scrappy Canadian startup turned into a household name, this episode is packed with insights and inspiration.

Show Notes

(00:00) Intro & Disclaimer

(00:57) Intro to Brian Scuadmore

(02:47) How Brian’s Grandparents Taught Him to Treat People Kindly

(04:23) 1-800-GOT-JUNK Today

(08:10) Brian’s New Brands

(09:26) Business Differences in Canada vs. the U.S.

(11:23) How Brian Started 1-800-GOT-JUNK

(13:54) Naming the Business a Phone Number

(15:32) Keys to Success in Home Services

(19:23) Successes and Failures of Growing Internationally 

(20:56) The Franchise Model

(23:54) Premium Pricing in the Service Industry

(26:55) Finding $400k in the Floorboards

(28:13) Business Formation in Canada

(30:31) Starting New Home Service Brands

(37:54) Dragons’ Den

(41:54) Anyone Can Be an Entrepreneur 

(42:45) The Future of Brian’s Businesses

(44:39) The Impact of Dragons’ Den

(47:52) Conclusion

From the condo market crash to vacancy rates for rentals to the role of HELOCs and immigration policy, Ben explains how we got here, what’s coming next and what it all means for affordability in this country. He also shares the story of catching Fortress as a fraud and offers a candid take on whether Canada is too soft on white-collar crime.

If you care about housing, affordability or the future of Canada’s economy, this episode is a must-listen.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Ben Rabidoux

(02:19) Catching Fortress as a Fraud

(09:26) Is Canada Too Soft on White-Collar Crime?

(11:56) Are Rents Going to Come Down in Canada?

(15:12) How Much Do Home Prices Need to Drop to Become Affordable Again?

(16:33) The Condo Market is Hyper-Cyclical

(17:58) The Condo Market Crash

(24:34) Who Was Buying These Pre-Sale Condos?

(25:27) Where is This Condo Crisis Headed?

(28:18) The Impact HELOCs Have on Canada’s Economy

(32:51) Immigration and Its Impact on Canadian Real Estate

(38:47) A Challenge Our Government Faces Over Immigration

(41:01) The Impact of AI on Immigration Levels

(44:46) How Does Canada Fix Its Affordability Challenges?

(48:09) Conclusion

In this conversation, Dave and Adam dive deep into the world of retirement planning—from understanding the “Go-Go, Slow-Go, and No-Go” phases of retirement to managing taxes through RRSP meltdowns to whether you really need $1 million to retire. Adam shares why retirees need a financial plan, common mistakes people make and how strategies like delaying CPP, TFSAs and even reverse mortgages can play a role in a well-structured retirement.

If you’re planning for retirement—or even just starting to think about it—this episode is packed with insights, myths debunked and practical advice tailored to Canadian listeners.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Adam Bornn

(03:35) Why Did Adam Specialize in Retirement Planning?

(05:23) Why Retirees Need a Financial Plan

(10:45) The Go-Go, Slow-Go and No-Go Phases of Retirement

(11:57) What is an RRSP Meltdown?

(13:16)  Your Average Tax Rate Should Be Consistent Through Retirement

(14:38) OAS Clawback

(16:07) Do Reverse Mortgages Fit Into Retirement Plans?

(17:08) Annuities

(18:03) The “Die With Zero” Concept

(19:11) Building Generational Wealth

(20:44) People Underestimate How Long They’re Going to Live

(22:44) Single Retirees Are at a Massive Disadvantage

(23:57) When Does Whole Life Insurance Make Sense?

(25:57) Most Retirees Need Stocks in Their Portfolios

(27:33) Should You Plan for Large Late-Life Healthcare Costs?

(29:41) Pre-Retirees Should Do Their Research

(31:28) The Biggest Mistakes Adam Sees Retirees Make

(32:20) Myth: You Need $X Number to Retire

(33:01) TFSAs Add Flexibility for Retirees

(34:56) Conclusion

In this episode, Dave and Amanda dive into the state of Canada’s economy from our productivity struggles and housing crisis to the US tariffs to whether the capital gains tax on real estate needs to change. They also unpack the profound impacts artificial intelligence is already having on the job market, the economy and business formation.

It’s a wide-ranging and thought-provoking episode you won’t want to miss!

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Amanda Lang

(02:48) Lang & O’Leary

(06:12) Canadian Productivity Growth & Losing Top Talent

(09:38) How Can We Solve Canada’s Housing Crisis?

(12:02) Should We Change the Capital Gains Tax on Real Estate?

(15:40) How AI is Going to Change Our Economy

(20:01) The Dangers of New Technology Being Used for Evil

(25:11) Professions at Risk From AI

(27:52) US Tariffs 

(30:32) Dave’s Biggest Worry: The US Debt

(36:39) Fewer Young People Are Starting Businesses

(42:16) The Changing Media Landscape

(44:30) Dave Has Only Been to ONE Concert in His Life

(46:24) Worried For Young People Today

(48:44) Can We Get Big Projects Done in Canada?

(51:36) Conclusion

In this episode, Bruce joins Dave to talk about the growing debt problem in Canada and the personal stories behind it. They dig into everything from credit scores to the rising cost of kids’ sports to the impact of divorce on your finances. Bruce also shares his own unique journey—leaving a corporate job to become a business journalist and help launch BNN, before becoming a financial educator with a bestselling book and podcast “Moolala.”

If you’ve ever felt overwhelmed by debt or just want to understand how credit counselling really works, this is a candid, insightful and engaging conversation you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Bruce Sellery

(03:37) Leaving a Corporate Career to Be a TV Reporter and Help Launch BNN

(07:06) Personal Finance vs. Business/Investing News

(09:05) How Bruce Developed His Communication Skills

(12:17) The Grace of a Well-Lived Life

(13:44) The Affordability Crisis in Canada

(16:04) What is Credit Canada?

(17:52) Credit Canada’s Non-Profit Structure

(22:12) What Happens if You Need to Claim Bankruptcy?

(23:30) How Do People Get Into Trouble with Debt?

(29:50) What Impacts Your Credit Score?

(32:28) The Housing-Affordability Crisis’s Impact on Debt Levels

(37:42) Divorce and Debt

(39:30) Kids’ Sports Have Become CRAZY Expensive

(43:56) Conclusion

In this episode, Dave and Jim cover a wide range of investing topics—from how Jim first got into real estate investing to whether it still makes sense today. They dig into Jim’s philosophy on using leverage, his take on individual stocks vs. ETFs, and why he prefers US-only investing over global diversification. Jim also shares what motivates him to create content and how he approaches simplifying complex financial ideas for everyday Canadians.

If you’re curious about real estate, passive investing or just want to hear from someone who’s built a personal finance brand from scratch—this episode is packed with practical insights. 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jim Chuong

(01:44) How Jim Learned About Personal Finance

(06:52) Jim’s Early Investing Approach

(09:49) Getting Started with Real Estate Investing

(15:54) Is Real Estate Investing Still Attractive Today?

(20:34) The Toronto Real Estate Market

(22:12) Is Crypto An Investment?

(23:57) Jim’s Philosophy on Leverage and Investing

(25:49) Canada is a Wonderful Country 

(27:43) Parenting Teenagers

(29:12) Why Does Jim Make Content Online?

(33:15) US-Only Investing Versus Global Diversification

(36:43) Investing in Individual Stocks vs. Broad-Market ETFs

(39:56) Why Private-Market Investing Isn’t Well Suited for the Average Investor

(42:05) Conclusion

In this episode, Dave sits down with Kelley to unpack some of the most pressing financial challenges people face today. From the emotional weight of debt to the psychological traps that make it so easy to overspend, Kelley brings both empathy and expertise to the table. They dive into why debt happens in the first place, practical strategies to get out of it and how to avoid the subtle (and not-so-subtle) pressures that push people to spend more than they should. Kelley also shares crucial tips on how to spot and prevent financial fraud in a world where scams are becoming increasingly sophisticated.

Whether you’re struggling with debt, trying to get a better handle on your spending or simply want to protect yourself from financial fraud, this episode is full of valuable insights.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Kelley Keehn

(03:57) The Crushing Weight of Debt 

(06:10) Strategies to Get Out of Debt

(08:31) Snowball vs. Avalanche Method

(10:41) Why Do People Get Into Debt?

(12:01) It’s So Easy to Spend Today

(14:23) Everybody Wants You to Spend

(17:24) Spending Summaries

(20:32) How Taking a Timeout Can Help You to Spend Purposely

(21:59) Credit Scores

(25:48) Pay Yourself First, But Revisit the Amount

(27:39) Are FHSAs Always Best?

(29:05) Don’t Chase Discounts on Things You Don’t Need

(32:39) Buying Used Can Come With Opportunity Costs

(34:17) How to Prevent Financial Fraud

(43:45) What’s The Worst Investment Kelley Has Ever Made?

(44:17) What’s The Smartest Investment Kelley Has Ever Made?

(45:39) Conclusion

In this 15ish minute episode, Gerry sits down with Dave to talk about the lessons he learned during his early career as a teacher, his leap into stand-up comedy, his big break with “Mr. D” and how all of those experiences shaped how he thinks about money.

Tune in for laughs, insights and a fun dose of nostalgia! 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Gerry Dee

(02:14) Gerry’s Early Life

(04:20) Gerry’s Career as a Comedian & Entrepreneur

(07:56) Lessons Learned From Gerry’s Athletic Background

(12:16) When Gerry’s Career Took Off

(13:43) The Story of Mr. D

(14:33) Gerry’s Investing Approach

(17:41) The Best Investment Gerry Ever Made

(18:17)  Does Gerry Follow The Wealthy Barber Principles?

(20:08) Conclusion

From coast to coast, listeners asked about everything from budgeting for big home repairs to whether “Pay Yourself First” applies to before- or after-tax income to investing tips for those who got a later start and much, much more. No jargon, no fluff—just honest, helpful education from one of Canada’s most trusted voices in personal finance.

Don’t miss this candid, fast-paced and surprisingly fun Q&A session. Got a question of your own? Submit it through our website’s contact form or DM us on social media and you might be featured in the next “Office Hours” episode!

FILMED: April 1, 2025

Show Notes

(00:00) Intro & Disclaimer

(00:48) Best Investments for the Short-Term?

(03:18) Which Index Funds to Pick as a Passive Investor?

(06:47) Advice if You Started Investing Later in Life?

(11:13) Is “Pay Yourself First” Before or After Tax?

(14:26) How to Budget for Major Home Expenses?

(16:56) What Should You Look For in a Financial Advisor?

(19:58) Lump Sum vs. Dollar-Cost Averaging

(23:51) Is the 4% Rule Still Valid Today?

(28:51) Send Us Your Questions!

In this 15ish minute episode, Dave and Mark chat about Mark’s experience playing the NHL, what he likes to spend his money on, his approach to investing and, most importantly, Mark’s role on Dave’s fantasy hockey team.

Enjoy this quick episode with NHL star Mark Scheifele!

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Mark Scheifele

(01:26)  Mark and the Winnipeg Jets' Great Year

(04:01)  Dave's Fantasy Hockey Team

(04:41)  When Mark First Read "The Wealthy Barber”

(06:00)  What Does Mark Like to Spend Money On?

(07:10)  The Parallels Between Hockey and Golf

(09:45)  How Exciting Would it Be to Win the Stanley Cup in Winnipeg?

(10:25)  Mark's Investing Approach

(11:59)  Playing and Living in Winnipeg

(13:04) Conclusion

In this podcast, Mark and Dave break down key points including why RRSPs get a bad rap (but shouldn’t), how RRSP withdrawals can actually be tax-efficient and why a TFSA’s flexibility isn’t always an advantage. All that, and more, in a fast-paced, insight-packed episode.

Don’t miss this one—20 minutes could save you thousands in retirement savings! 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Mark McGrath

(02:27) TFSAs vs. RRSPs

(05:19) Comparing Tax on TFSAs vs. RRSPs

(09:09)  Why RRSP Withdrawals Can Often Be At a Lower Tax Rate

(14:53)  What if The Government Raises Taxes in the Future?

(17:31)  How the Canada Child Benefit (CCB) Changes the Math

(18:40)  TFSAs Are More Flexible—A Double-Edged Sword

(20:47) Conclusion

In this podcast, Dave and Robb discuss navigating retirement and the world of advice-only financial planning—what it is, why it’s not as common in Canada and Robb’s unconventional career path in finance. Much of the conversation has Robb sharing his expertise on retirement planning, covering everything from when to take your CPP to safe withdrawal rates to planning for big expenses and much more.

Whether you’re nearing retirement or just curious about fee-only financial planning, this episode is packed with insights you won’t want to miss!

Show Notes 

(00:00:00) Intro & Disclaimer

(00:00:55) Intro to Robb Engen

(00:06:39) What is Advice-Only Financial Planning

(00:12:26)  What Type of Clients Are Best for Advice-Only Planning

(00:17:09)  Why Isn't Advice-Only Planning More Popular in Canada

(00:19:17) Upsizing in Retirement

(00:21:04)  When Should You Take Your CPP?

(00:25:11) Spending in Retirement

(00:29:29) ​​ All-in-One ETFs

(00:30:56) Robo-Advisors Turning Into Speculative Investment Platforms

(00:35:01)  Safe Withdrawal Rates in Retirement

(00:37:47)  Planning for Large One-Time Expenses in Retirement

(00:42:57)  Giving Kids Money for a Down Payment

(00:44:02)  Housing Prices Are Unfair For The Younger Generation

(00:45:49) Postnups

(00:46:55)  Options for Accessing Your Home Equity in Retirement

(00:50:43)  Giving Money Away if You Have Enough for Retirement

(00:53:58) Life Insurance

(00:55:43) Grandparents Helping to Fund RESPs

(00:57:28) Robb’s Big Three Takeaways

(00:59:51)  You Just Retired… Now What?

(01:02:40)  Dave's Dad's "Solution" to Financial Planning

(01:03:46) Die With Zero

(01:04:48) Conclusion

In this episode, Dave and Arlene reminisce about their time on "Dragons’ Den" together and chat about everything from Arlene’s early career struggles to the potential US tariffs to the current economic climate for Canadian entrepreneurs and much, much more.

Don’t miss this fantastic episode! 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Arlene Dickenson

(02:46) Dragons’ Den

(04:26)  Handling Online Criticism

(08:21) Arlene’s Early Career Struggles

(16:13) How Did Arlene Become a Dragon?

(19:46) Reflecting on the Impact of Dragons’ Den 

(22:14)  Two Lessons Arlene Taught Dave

(24:24)  The Time Arlene Accidentally Got Drunk on Dragons' Den

(25:53) The Current Economic Climate for Canadian Entrepreneurs

(30:03) Potential US Tariffs

(33:48) Younger Canadians Are Frustrated

(36:08) Taxes & Government Spending in Canada

(37:56)  How Do We Build Up the Canadian Entrepreneur Ecosystem?

(42:46) The Impact of AI

(47:12)  Arlene's Closing Message for the Audience

In this episode, Dan and Dave dive deep into index investing, covering everything from active vs. passive investing styles to tips for DIY investors, asset allocation strategies, the pros and cons of all-in-one ETFs in Canada and much more. There’s a lot to unpack, but Dan and Dave make it all easy to understand.

This episode is a must-listen for anyone serious about DIY investing—tune in now!

Show Notes

(00:00:00) Intro & Disclaimer

(00:00:55) Intro to Dan Bortolotti

(00:02:04) The Origins of the “Canadian Couch Potato”

(00:06:56) What is an Index Fund

(00:08:52) Why Don't Most Active Managers Outperform the Market?

(00:15:12) How Dave's Dad Can Beat Professional Money Managers

(00:16:57) Group Retirement Plans

(00:19:25) Mutual Fund Underperformance

(00:22:42) Should People Speculate with 5-10% of Their Portfolio?

(00:26:31) The Financial-Planning-First Model

(00:33:42) How to Construct An Index-Fund Portfolio

(00:35:52) Risk Tolerance and Asset Allocation

(00:42:50) When Stocks & Bonds Both Went Down

(00:44:56) What Goes Into a Financial Plan?

(00:46:34) Get Life Insurance!

(00:47:59) There is No "Optimal" Financial Plan

(00:49:52) When to Take CPP

(00:51:21) The Risks of Helping Kids/Grandkids with Down Payments

(00:53:52) All-in-One ETFs

(00:58:16) Withholding Taxes on US Stocks

(01:02:27) Online Investment Platform Recommendations

(01:04:26) Conclusion

In this episode, Dave and Ron discuss all things real estate including the pros/cons of using a mortgage broker, where they think interest rates are headed, whether people should use fixed- or variable-rate mortgages and much, much more. 

Enjoy this entertaining and insightful episode.

Show Notes

00:00 – Intro & Disclaimer

00:57 – Intro to Ron Butler

03:20 – Pros/Cons of Using a Mortgage Broker

05:29 – Canada vs. USA Use of Mortgage Brokers

08:19 –  Where Ron Thinks Interest Rates Are Headed

09:47 –  Divergence Between Haves vs. Have-Not

11:48 – Fixed vs. Variable Mortgage Rates

13:54 – Parents Helping with Down Payments

18:02 –  The Financialization of Housing

20:07 – Where Are Housing Prices Headed?

25:51 – The Small-Condo Market

30:09 – 30-Year Amortizations

32:10 – High Transaction Costs in Real Estate

34:46 – Renovations

39:37 – Big vs. Small Homes

43:23 – High Housing Costs Causing People to Leave Canada

46:10 –  The Housing-Affordability Crisis

51:42 – Rapid-Fire Questions

57:16 – An F-Bomb-Filled Ron Rant

59:03 – Conclusion

In this episode, Dave and Richard discuss the rise of "Finfluencers" in today’s social-media-driven world and explore the fascinating landscape of behavioural finance. They cover everything from the origins of “The Plain Bagel,” to the pros and cons of getting financial advice online, to the biases that affect us all and much, much more. 

Enjoy this fantastic episode featuring two of Canada’s top financial educators.

Show Notes

00:00:00 – Intro & Disclaimer

00:00:55 – Intro to Richard Coffin

00:03:28 – Origin of “The Plain Bagel”

00:08:13 – Richard’s Work & Educational Background

00:12:13 – The Rise of Finfluencers

00:16:34 –   The Laws Around Giving Financial Advice Online

00:20:14 –  How to Evaluate Online Financial Advice

00:21:24 – Trusting Finfluencers More than Wall Street

00:25:20 – The “Beginner” Finfluencer

00:28:58 – Investing Courses

00:38:42 – Trustworthy Canadian Finfluencers

00:44:41 – It’s Easy to Fake Wealth Online

00:47:57 –  YouTubers Being Paid to Promote Stocks

00:55:27 – Behavioural Finance & Loss Aversion

01:02:56 – Confirmation Bias

01:06:35 –  The Skills Behind Creating Content People Enjoy Watching

01:08:46 – Recency Bias

01:13:41 – Framing Bias

01:19:02 – Conclusion

In this episode Dave asks Barry everything Canadians need to know about credit card points and loyalty programs including which programs offer the most lucrative sign-up bonuses, tips for how to maximize the value of your points, which card is best for travel and much, much more. 

This is a highly informative episode and you’ll be sure to take away a few valuable tips by listening.

Show Notes

00:00 – Intro & Disclaimer

00:56 – Intro to Barry Choi

03:02 – Loyalty Programs and Data

06:35 – Learn a Few Programs Inside Out

08:51 – Transferring Points to Increase Value

10:47 – Credit Card Points as an Employee Benefit

12:04 – Tips to Maximize Points

14:39 – How to Optimize Points for Travel

17:12 – Which Credit Card is Right for You

18:56 – Sign-Up Bonuses

22:16 – Dave’s Reservations About Credit Cards

25:32 – High-Income Canadians with Credit-Card Balances

28:01 – Barry’s Spending

30:02 – When Barry Took His Family to Hong Kong

34:09 – American Express

37:37 – Dave Doesn't Use Airport Lounges

38:26 – Non-Point Benefits

41:20 – The Lifecycle of a Fintech Company

42:25 – Consumerism & Stuff

45:49 – Donating Loyalty Points

46:58 – Fraud with Loyalty Points

48:37 – Conclusion

In this episode Dave and Ben dive deeply into the world of investing. They cover everything from active versus passive styles to why CPP is a one-of-a-kind asset to why people underperform so badly in mutual funds and much, much more. 

This is a must-listen episode featuring two of Canada’s top financial educators.

Show Notes:

00:00:00 – Intro & Disclaimer

00:00:55 – Intro to Ben Felix

00:04:25 – Ben’s New Hair

00:05:50 – Why Is It So Difficult to Beat the Market?

00:08:02 – Why It's Hard for Active Managers to Consistently Outperform

00:11:42 – “Buy the Haystack” (Passive Investing)

00:13:55 – The Market is Forward Looking

00:17:45 – Why Dave & Ben Don't Listen to Market Forecasts

00:21:46 – Dave's Only Market-Timing Story (Gone Wrong)

00:25:22 – Performance Gaps for Individual vs. Fund Performance

00:29:55 – Lump Sum vs. Dollar-Cost Averaging

00:35:18 – Everyone's Risk Tolerance is Different

00:36:56 – Countries With High Economic Growth ≠ High Stock Returns

00:41:35 – Beware of High Growth Industries & Thematic ETFs

00:46:00 – The Difference Between Investment Planning & Financial Planning

00:51:20 – How Can Everyday Canadians Get Good Financial Advice?

00:55:44 – Trust is Key in Financial Planning

00:57:26 – Why a 2% Mutual Fund Fee Is So Costly

00:59:11 – Canadian Banks

01:01:19 – Keep it Simple! Complexity Underperforms

01:04:09 – Venture Capital

01:05:42 – Can the US Market Continue to Outperform?

01:13:36 – Robo-Advisors

01:17:44 – Would Ben Ever Be a Landlord?

01:20:00 – CPP – Four Reasons Why You Should Wait to Take It

01:26:11 – Conclusion

In this episode Dave and Jessica discuss how our emotions and past experiences affect our relationship with money including bad financial habits people learn from their parents, biases that get in our way, why the financial industry benefits from making it seem more complicated than it is and much, much more.

Don’t miss this engaging discussion with Jessica Moorhouse.

Show Notes 00:00 – Introduction 00:56 – Jessica's Background 03:21 – How Jessica's Podcast Started 05:51 – Jessica's Upcoming Book 11:43 – Bad Money Habits We Learn From Our Parents 15:34 – Money and Shame 17:18 – How to Take Control of Your Relationship with Money 19:07 – Status Quo Bias 22:15 – Anyone Can Learn to be Good With Money 24:33 – Overconfidence Bias in Young Men 27:02 – Women and Investing 29:02 – Emotions and Investing 31:51 – Index Investing & Fintech 33:51 – Focus on What You Can Control and Don't Give Up Hope 38:10 – Living in Toronto 40:37 – The Best Financial Educators Are Truly Trying to Help 43:55 – Happiness and Financial Planning 46:39 – COVID 49:18 – Where to Get Jessica’s Book

In this episode Dave and Rob discuss how personal finance in Canada has changed over the last 35 years including how more parents are helping their adult-age children financially, how social media is increasing the pressure to spend, why FHSAs are the ultimate no-brainer and much, much more.

You'll enjoy this discussion with Rob Carrick.

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The Wealthy Barber Podcast is Canada’s go-to source for approachable, entertaining, and free financial education. Hosted by none other than David Chilton—former Dragon on CBC’s ”Dragons’ Den” and the best-selling author of ”The Wealthy Barber” and ”The Wealthy Barber Returns”—this podcast is here to help Canadians manage their money better. Much better.

Find all episodes and more Canadian personal finance content at https://thewealthybarber.com.

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Show Notes: (00:00:00) – Introduction (00:03:30) – It's More Expensive to Have Kids Today (00:06:01) – Pressure to Spend (00:07:24) – Crazy What People Spend on Cars (00:09:24) – Spending & Lines of Credit (00:12:27) – What Dave is Seeing From People's Spending Summaries (00:13:47) – It’s Financially Difficult to be Single (00:15:12) – Costs Are Rising for Seniors (00:19:06) – More Parents Are Helping Their Kids Financially (00:22:09) – People Need Help with Retirement Planning (00:27:05) – Fee-Only Financial Planning (00:31:19) – Divorce Rates Going Down (00:32:18) – People Are Having Fewer Kids (00:33:13) – Boomers Had It Easier (00:36:18) – Pensions Are Making a Comeback (00:38:18) – Counting on Inheritances (00:39:05) – Some Young People Are Giving Up (00:40:16) – Anyone Can Manage Their Money Well (00:41:24)  – Is Personal Finance Harder Today? (00:42:17) – Pets Are More Expensive Than You Expect (00:44:30) – You Have to Make Spending Tradeoffs (00:46:16) – You Feel Better When You’re On Top of Your Finances (00:48:44) – Debit vs. Credit Cards (00:50:54) – Should Couples Manage Their Money Together? (00:54:01) – FHSAs (00:55:08) – TFSAs (00:58:11) – The Problem with the Bank-Branch System in Canada (01:00:23) – FHSAs Are a No-Brainer (01:03:39)  – Why Hasn’t Canada Embraced Passive Investing Like the US? (01:05:38) – The Wrong Way to Use ETFs (01:08:26) – Men vs. Women Investing (01:12:19) – Why Don’t Canadians Use Mortgage Brokers? (01:14:08) – RRSPs are Still Great (01:16:48) – Conclusion

In this episode we discuss all things parents should know when teaching their kids about money, from allowances, to piggy banks, to how much kids should save, and much more. You'll enjoy this discussion with Robin Taub.

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The Wealthy Barber Podcast is Canada’s go-to source for approachable, entertaining, and free financial education. Hosted by none other than David Chilton—former Dragon on CBC’s ”Dragons’ Den” and the best-selling author of ”The Wealthy Barber” and ”The Wealthy Barber Returns”—this podcast is here to help Canadians manage their money better. Much better.

Find all episodes and more Canadian personal finance content at https://thewealthybarber.com.

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Show Notes:

(00:00:00) Introduction

(00:01:11) How Do You Teach Kids About Money?

(00:07:38) Allowances

(00:11:41) Robin's Book & Framework

(00:15:52) Teaching Kids About Investing 

(00:18:55) People Are Having Fewer Kids 

(00:20:00) Young People More Affected by Inflation 

(00:22:42) Piggy Banks 

(00:24:04) Spending in the Digital Era 

(00:26:01) "Cooling-Off" Periods

(00:27:25) How Much Kids Should Save

(00:28:59) Grandparents More Financially Involved Now 

(00:31:58) Biggest Money Mistakes Parents Make

(00:35:08) Money Stress is the Worst Stress

(00:37:14) The Importance of Sharing

(00:41:09) Dave & Robin's Kids 

(00:45:01) Other Resources for Parents

(00:47:08) Conclusion

Our first guest is Preet Banerjee—one of the top financial educators in Canada, having been a regular for years on CBC's The National, renowned speaker and author of the bestselling book, “Stop Overthinking Your Money.” Recently, Preet completed a doctorate with his research focusing on the value of financial advice to Canadian households and how to improve the outcomes for the mass market. 

In this episode, we discuss what Preet learned from his research and all things Canadian personal finance, from RRSPs versus TFSAs, to active versus passive investing, to whether investing in Canadian rental real estate still makes sense, to who has the better hair and much, much more. You'll enjoy this discussion with Preet Banerjee, a great communicator and a truly great guy.

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The Wealthy Barber Podcast is Canada’s go-to source for approachable, entertaining, and free financial education. Hosted by none other than David Chilton—former Dragon on CBC’s ”Dragons’ Den” and the best-selling author of ”The Wealthy Barber” and ”The Wealthy Barber Returns”—this podcast is here to help Canadians manage their money better. Much better.

Find all episodes and more Canadian personal finance content at https://thewealthybarber.com.

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Show Notes:

(00:00:00) Introduction

(00:01:59) Preet’s Research

(00:06:16) Biggest Problem Young Canadians Face Today

(00:10:32) RRSP vs. TFSA

(00:13:06) FHSAs

(00:14:38) Active vs. Passive

(00:20:40) Men vs. Women Investing

(00:23:52) Inflation

(00:29:14) Who has better hair?

(00:29:47) Giving Advice to the Masses

(00:32:36) Group RRSP Matching

(00:34:58) Investing in Rental Real Estate in Canada

(00:37:41) Getting Help From Parents

(00:40:19) Emergency Funds

(00:43:08) Has the Pendulum Swung Too Far

(00:45:23) Other Personal Finance Creators

(00:48:02) An Experience That Changed Preet’s Perspective on Life

(00:51:35) Conclusion