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The Wealthy Barber Podcast

Author: The Wealthy Barber Inc.

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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.

Dave Chilton has spent over 35 years demystifying personal finance, offering understandable, unbiased, and actionable advice that has empowered millions of Canadians to achieve their financial goals. Now, he’s bringing that same wisdom to your favourite podcasting platforms, with regular episodes designed to make personal finance simple, relatable, and yes, even entertaining.

Episodes of The Wealthy Barber Podcast features Dave in conversation with expert guests from across the spectrum of Canadian personal finance. From investing and real estate to taxes, RESPs, and even money psychology, no topic is off-limits. Plus, don’t miss our special “Office Hours” episodes, where Dave answers real questions from audience members, delivering informed, balanced, and sometimes downright funny advice.

Follow for Canadian personal finance made simple.
78 Episodes
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Our guest this episode is Julia Chung — CFP, FEA, TEP, Co-Founder and CEO of Spring Planning and Chair of the Financial Planning Association of Canada. Julia has worked in financial services since 1997 and has run an advice-only planning practice since 2011. She first joined Dave back on Episode #43 and returns for a second wide-ranging conversation. In this episode, Dave and Julia dive into women and money: why young women are so hungry for financial education, what the research actually shows about female investors and why fewer women are entering the financial profession. They also cover how differences in life expectancy between men and women should shape a financial plan, and why cash flow management and simple spending summaries remain the foundation of good planning. Julia also challenges some of the conventional thinking around the great wealth transfer. The conversation also explores what separates table-stakes service from what clients really need from an advisor, why Julia chose the advice-only model and how she is scaling that practice at Spring Planning. Along the way, Dave and Julia weigh in on whether affluent Canadians are leaving the country for tax reasons, why Dave adds 15% to insurance needs and whether a young planner can succeed without years of experience. Whether you're a financial professional, a longtime listener or someone trying to get a better handle on your own money, this episode is full of candid, practical insights you won't want to miss.   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Julia Chung (02:49) Why Julia Gives Back to the Financial Planning Industry (05:49) Why Young Women Are Hungry for Financial Education (11:01) What the Research Shows About Female Investors (14:23) Why Are Fewer Women Becoming Financial Professionals? (17:33) Life Expectancy Differences Between Men and Women (19:32) The Importance of Cash Flow Management & Spending Summaries (27:15) Rethinking the Great Wealth Transfer (32:49) Table Stakes vs. What Clients Really Need From Advisors (35:25) Why Julia Chose the Advice-Only Model (37:28) Scaling an Advice-Only Practice (39:48) Are Affluent Canadians Moving Away for Tax Reasons? (42:06) AI in Financial Planning & Confidentiality (45:07) Insurance Needs: Why Dave Adds 15% (50:55) Can a Young Planner Succeed Without Experience? (53:02) Spring Planning (54:09) Conclusion
Our guest this episode is Adam Chapman — Certified Financial Planner and founder of YESmoney, a London, Ontario practice built around helping Canadians spend with confidence in retirement. With nearly two decades in financial planning, Adam chairs the Estate Planners Council of London and is a founding member of the Financial Planning Association of Canada. He has spent his career helping retirees figure out what they actually want and start saying "yes" to their money. In this episode, Dave and Adam dive into the practical side of retirement income planning, from paying yourself first in retirement to managing cash flow once the paycheques stop. Adam walks through his three retirement planning checkpoints, the real costs of long-term care versus in-home care and why guaranteed income floors matter more than ever. They also break down annuities in detail, including copycat annuities, piggyback annuities and how pairing them with delayed government benefits can take the sting out of inflation fears. The conversation also explores the emotional side of money in later life, including the struggle many couples face when selling the family home and the psychology of spending in retirement, the subject of the book Adam is currently writing.  Whether you're approaching retirement or already there and wondering how to spend without worry, this episode is full of practical, grounded advice from a planner who spends every day helping Canadians make the shift from saving to spending.   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Adam Chapman (02:08) What East Side Mario's Taught Adam About Business (06:18) How to Pay Yourself First in Retirement (08:22) Living in the Woods in Forest City (09:37) Retirement Advice for Dave (11:32) The Real Costs of Long-Term Care vs. In-Home Care (13:06) Retirement Income Planning and Cash Flow Management (16:40) Adam's Three Retirement Planning Checkpoints (19:44) The Emotional Struggle of Selling the Family Home (23:39) Writing a Book on the Psychology of Spending Money in Retirement (27:28) Why Guaranteed Income Floors Matter More Than Ever (29:50) Copycat Annuities (32:31) Managing Inflation Fears with Annuities and Delayed Benefits (37:18) Piggyback Annuities and Financial Peace of Mind (39:55) Giving Living Legacies vs. Inheritances (45:56) Die With Zero and Turning Money into Memories (48:12) Conclusion
Our guest this episode is Daniel Foch — Chief Real Estate Officer at Valery, host of The Canadian Real Estate Investor Podcast and one of Canada's most-followed voices on housing data and market analysis. He first joined us back on Episode #35, and with so much having changed since then, we brought him back for a full update. In this episode, Dave and Daniel dive into the current state of Canadian real estate, starting with where prices and sales actually sit in Ontario and BC today. They break down the Toronto condo crash and the supply crisis it has created, why unrealistic sellers are keeping the market stuck and whether rents are going to keep falling. They also cover how tariffs and AI could push unemployment higher and what that would mean for housing. The conversation also explores the policy side of the picture, including CMHC's financing programs for rental developers, the government's housing incentives and why so many municipalities are now cutting development charges. Daniel explains why builders have stopped building small homes, lays out his concept of "houseflation" and shares his take on the biggest macroeconomic surprises of the year. Along the way, Dave and Daniel tackle whether downsizing baby boomers will flood the market, how immigration cuts are reshaping demand and how Daniel is using agentic AI to rebuild the way real estate businesses operate. Whether you're a homeowner, a renter trying to decide when to buy or simply trying to make sense of where Canadian housing goes from here, this episode is full of data-driven insights and candid analysis you won't want to miss.    Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Daniel Foch (03:35) The Current State of Real Estate in Ontario and BC (06:44) How Tariffs and AI Could Impact Unemployment (11:22) Why Unrealistic Sellers Are Hurting the Market (13:44) The Toronto Condo Market Crash and Supply Crisis (16:20) CMHC's Financing for Rental Developers (19:35) Are Rent Prices Going to Keep Falling? (20:18) The Impact of the Government's Housing Policy Incentives (22:53) Why Municipalities Are Cutting Development Charges (26:51) Why Builders Don't Build Small Homes Anymore (28:52) "Houseflation" (35:10) The Biggest Macroeconomic Surprises of the Year (38:53) Will Downsizing Baby Boomers Flood the Housing Market? (41:33) How Immigration Cuts Impact Canadian Real Estate (44:03) Using Agentic AI to Revolutionize Real Estate Businesses (48:52) Conclusion
Our guest this episode is Ted Cadsby — former President and CEO of CIBC Securities, bestselling author and one of Canada's earliest champions of index investing. Ted brought index funds to CIBC in the late 1990s, wrote "The Power of Index Funds" to make the case to everyday Canadians and has since turned his attention to how people think, with books including "Closing the Mind Gap" and "Hard to Be Human." In this episode, Dave and Ted dive into the case for index funds and the uphill battle Ted fought to bring them to the bank, including the clash with Wood Gundy brokers who saw indexing as a threat to their business. They break down why individual stocks are so hard to get right, how unknowable variables drive stock prices, whether "play money" accounts make sense and how Ted weights his own personal portfolio. The conversation also explores how to evaluate active money managers, how to separate luck from skill in investment performance and what to make of private equity pitches (plus Dave's due diligence approach from his Dragon's Den days). Along the way, Ted shares insights from his work on the psychology of decision making: the dangers of oversimplification and overconfidence, why active managers stay so sure of themselves and how financial biases can quietly affect our happiness. Whether you're a committed indexer or still wondering if you can beat the market, this episode offers a clear-eyed look at investing from someone who has seen both sides of the industry.    Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Ted Cadsby (02:16) A Disastrous Wealthy Barber Date (03:22) Bringing Index Funds to CIBC (05:52) The Clash With Wood Gundy Brokers (09:15) Individual Stocks vs. Index Funds (11:55) "Play Money" Accounts (12:55) The Impact of Unknowable Variables on Individual Stocks (15:34) Ted's Personal Portfolio Weights (17:28) How to Evaluate Active Money Managers (20:00) Luck vs. Skill in Investment Performance (21:26) Private Equity Pitches (24:36) Dave's Due Diligence Strategy on Dragon's Den (27:23) The Psychology of Decision Making (30:13) The Dangers of Oversimplification & Overconfidence (35:03) Why Active Managers Stay Overconfident (39:33) How Financial Biases Affect Happiness (40:40) Money Should Be a Means to an End (43:42) Conclusion
Our guest this episode is Jason Heath — Founder and Managing Director of Objective Financial Partners, one of Canada's largest advice-only financial planning firms. A Certified Financial Planner with more than 20 years in practice, Jason is a longtime personal finance columnist for the Financial Post and MoneySense and one of the country's most consistent voices for conflict-free financial advice. He last joined us on Episode #27 for Financial Planning 101, and this time the conversation looks ahead. In this episode, Dave and Jason dive into where financial planning is headed. They explore the role of technology in democratizing planning, from financial planning software to the future of AI in financial advice, including a look at The Wealthy Barber's own AI planning tool. Along the way, Jason shares how often a plan should be updated, why implementation matters as much as the plan itself, how tax optimization gets trickier with corporate assets and why even financial professionals need advice. They close with the chronic gap in life and disability insurance and the secret behind Jason's famously calm demeanour. Whether you're weighing the cost of an advice-only plan, curious how AI will change the way Canadians get financial guidance or simply want to make sure your retirement projections are realistic, this episode is full of clear, practical insights.    Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Jason Heath (02:49) Projected Rates of Return in Financial Planning (05:06) Are Retirees Taking on More Investment Risk? (06:10) The Danger of Forgetting Prolonged Market Downturns (07:24) The Rarity of Average Stock Market Returns (08:49) The Advice-Only Financial Industry (11:07) Conflicts of Interest and Biases in Wealth Management (13:50) The Evolution of Financial Planning (15:30) Democratizing Financial Planning with Technology (17:11) The True Cost and Value of an Advice-Only Financial Plan (18:18) How Often Should You Update Your Financial Plan? (21:00) Implementation and Financial Planning Through Conversation (22:57) Why You Need a Solid Plan Before Retirement (24:59) The Future of AI in Financial Advice (29:17) Conquest Financial Planning Software (32:06) Navigating Tax Optimization and Corporate Assets (33:32) Even Financial Professionals Need Advice (35:18) The Challenge of Asking AI the Right Financial Questions (37:58) The Wealthy Barber's AI Tool for Financial Planning (40:15) The Chronic Gap in Life and Disability Insurance (43:18) Jason's Calm Demeanour (45:45) Conclusion
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