The Wealthy Barber Podcast

Our guest this episode is Gary Teelucksingh, author of “Roots of Prosperity” which is a guide to preserving wealth, values and family unity across generations. Gary is also a seasoned financial services expert and consultant with over two decades of experience spanning operations, technology and strategic transformation across North America and beyond. 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

Our guest this episode is Jon Flynn — Broker of Record at Flynn Real Estate Inc. and a well-respected Realtor with more than 15 years of experience. Jon is also the creator of the popular YouTube channel “Jon Flynn Real Estate Stats” where he analyzes Canadian housing trends and market data to help consumers better understand what’s happening in real estate. 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

Our guest this episode is Meagan Balaneski — Portfolio Manager and Certified Financial Planner® with Aligned Capital Partners in Vermilion, Alberta. Meagan earned a place on the CFP® President’s List for top exam performance in 2013 and recently won the FPAC 2025 Financial Planning Award. 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

Our guest this week is Julia Chung, CFP®, FEA, TEP — CEO of Spring Planning, President of FPAC and a Financial Planning & Family Enterprise Consultant with over 25 years of experience helping people navigate complex financial decisions. 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

Our guest this episode is Jason Watt — a Canadian financial education leader and long-time contributor to the professional training and development of financial planners, advisors, and insurance professionals across the country. Jason has spent years helping shape how financial advice is taught in Canada, including previously serving as the lead instructor at Business Career College, where he developed curriculum and continuing education for industry professionals. 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

Episode #41 is out now! Our guest this episode is Chris Guillebeau — author, entrepreneur, blogger and speaker best known for “The $100 Startup,” “Side Hustle,” and his latest book, “Time Anxiety.” Chris first rose to prominence through his blog “The Art of Non-Conformity,” where he shared stories of unconventional work, travel and building income on your own terms. 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

Our guests this episode are Heather and Doug Boneparth — co-authors of the book Money Together: How to find fairness in your relationship and become an unstoppable financial team. Doug is the founder of Bone Fide Wealth in New York City and serves on the advisory councils for CNBC and Investopedia. Heather is a lawyer-turned-financial-writer, Bone Fide Wealth’s Director of Business and Legal Affairs and a rising voice at the intersection of love, money and family. 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

Our guest this episode is Shannon Lee Simmons — Certified Financial Planner®, Chartered Investment Manager®, bestselling author, media personality and founder of the New School of Finance™. Shannon is widely recognized as a trailblazer in Canada’s fee-only financial planning movement and her latest book is “Making Bank,” a financial guide for teens.  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

Our guest this episode is Melissa Leong — national media personality, a sought-after speaker and award-winning author of the feel-good finance guide “Happy Go Money.” Melissa has been the resident money expert on Canada’s leading daytime talk show “The Social” for 14 years and is also a repeat guest on “The Drew Barrymore Show” on CBS. 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

Our guest this episode is Shaun Maslyk — a practicing Certified Financial Planner® and Certified Financial Behavior Specialist® who blends financial planning with positive psychology to help people understand their money stories and flourish beyond their finances. Shaun holds a master’s degree in positive psychology from the University of East London, where his research focused on the relationship between money, behaviour change and human happiness. 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

Our guest this episode is Aravind Sithamparapillai, a financial planner at Ironwood Wealth Management Group. Earlier this year, Aravind earned his CFP® designation with the highest exam score in the country, placing him at the top of the CFP® Exam President’s List, and was also selected for FP Canada’s Emerging Leader’s Award. 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

Our guest this episode is Daniel Foch, a Canadian real estate broker, co-host of “The Canadian Real Estate Investor” podcast and Chief Real Estate Officer at Valery.ca. Daniel creates widely-followed content at the intersection of data, news and insights for the Canadian housing market. 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

Our guest this episode is Morgan Housel, international bestselling author of “The Psychology of Money,” “Same as Ever” and his newest book, “The Art of Spending Money.” 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

Our guest this week is John Y. Campbell — a globally respected Harvard economist and one of the most influential voices in academic financial economics. Over his career, John has published more than 100 academic papers spanning fixed-income markets, equity valuation, portfolio theory and household finance.   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

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