The Wealthy Barber Podcast

The Wealthy Barber Inc.

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.

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#71
September 1 · 55 min
#70 — Chad Wiebe: Retirement Planning 101
Our guest this episode is Chad Wiebe — Certified Financial Planner and Founder of Pathway Wealth, a virtual, advice-only financial planning firm based in Winnipeg serving clients across Canada. In this episode, Dave and Chad take a deep dive into the fundamentals of retirement planning. They explore why so many retirees struggle to give themselves permission to spend, how to build a financial plan that accounts for spending shocks, and the massive potential costs of long-term care. Chad also breaks down the hidden benefits of downsizing your home, the factors to weigh when deciding how many more years to work, and the delicate task of telling a client they can't retire just yet. The conversation also covers plenty of nuts-and-bolts strategy, including strategic RRIF withdrawals to smooth out your average tax rate, why the RRSP is still an outstanding vehicle for most people, whether everyone should delay CPP, and the tax disadvantages facing single seniors. Along the way, Chad shares his perspective on giving early inheritances to children, the assets you should consider selling before retiring, and the complexities of retiring with a corporate account. Whether retirement is decades away or right around the corner, this episode is full of practical guidance to help you plan with confidence. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Chad Wiebe (02:44) Why Chad Left K4 Financial to Start His Own Firm (04:43) Scaling an Advice-Only Financial Planning Business (06:06) The Value of Advice-Only Financial Planning (07:16) Specializing in Deaccumulation and Retirement Planning (10:00) Common Pre-Retirement Mistake: No TFSA (12:05) The Permission Problem in Retirement (14:15) Creating a Financial Plan with Spending Shocks (19:22) Planning for the Massive Costs of Long-Term Care (22:29) The Hidden Benefits of Downsizing Your Home in Retirement (25:50) The Factors When Deciding How Many More Years to Work Before Retirement (29:51) How to Tell a Client They Cannot Retire Yet (31:49) The Risks and Rewards of Giving Early Inheritances to Children (34:35) Strategic RRIF Withdrawals to Smooth Out Your Average Tax Rate (39:09) Why the RRSP is Still an Outstanding Vehicle for Most People (40:53) The Tax Disadvantages for Single Seniors (43:24) Should Everyone Delay CPP? (48:41) Assets You Should Sell Before Retiring (50:32) The Complexities of Retiring with a Corporate Account (53:10) Growing a YouTube Channel (54:21) Conclusion
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#70
August 25 · 46 min
#69: Mike Lipkin: How to Find Purpose in Life and Retirement
Our guest this episode is Mike Lipkin — motivational speaker, executive coach and founder of Environics/Lipkin, a Toronto-based research and motivation company. Mike has spoken to more than a million people across 43 countries, authored 18 books on leadership and high performance, and has built his career around helping people play at their best. In this episode, Dave and Mike dive into what it takes to build a life of purpose in retirement, starting with the sobering statistics linking retirement and depression and why so many men in particular struggle once they stop working. They cover the habits that keep you energetic and fit as you age, including six daily practices that can extend your life span, the case for mini home workouts and the neuroscience behind why personal growth matters more than ever in your later years. The conversation also gets personal. Mike opens up about his own battle with severe depression and how he rebuilt his life, shares inspiring stories of lifelong learning and choosing impact over comfort, and warns about the atrophy that can set in early in retirement if you don't stay involved. He also reflects on balancing travel and independence in marriage, his spectacular success investing in tech stocks, lessons from 44 years of marriage and a preview of his upcoming book. Whether you're approaching retirement, already there or simply want to age with more energy and purpose, this episode is full of practical wisdom you can put to work right away. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Mike Lipkin (04:08) Retirement and Depression Statistics (07:45) Staying High Energy and Fit as You Age (09:39) Six Daily Habits to Extend Your Life Span (12:08) The Benefits of Mini Home Workouts (14:09) Mike's Story About Overcoming Depression and Rebuilding (17:03) Why Men Struggle with Purpose in Retirement (18:59) The Neuroscience of the Importance of Personal Growth in Retirement (21:23) Staying in Shape as You Age (23:29) Inspiring Stories of Lifelong Learning (26:17) Impact Over Comfort (28:06) The Danger of Atrophy in Early Retirement if You Don't Stay Involved (31:44) Balancing Travel and Independence in Marriage (33:53) Mike's Spectacular Success Investing in Tech Stocks (39:51) Lessons From 44 Years of Marriage (42:35) Mike's Upcoming Book (45:21) Conclusion
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#69
August 18 · 44 min
#68 — Brian Portnoy: A Behavioural Finance Expert on How to Shape a Life of Money and Meaning
Our guest this episode is Brian Portnoy — behavioural finance expert, founder and CEO of Shaping Wealth and author of "The Geometry of Wealth" and "The Investor's Paradox." Brian holds a PhD from the University of Chicago, is a CFA charterholder and spent more than two decades in the financial industry. His mission is helping people use their money to underwrite a meaningful life. In this episode, Dave and Brian dive into behavioural finance and the fast-changing world of financial advice. They explore the challenges of building an AI coach that's genuinely helpful, the lessons Brian took from Morningstar and the hedge fund industry, and why "simplicity on the far side of complexity" is worth striving for. They also break down the investor's paradox, choice overload and how thoughtful choice architecture can combat decision fatigue. The conversation also traces the 50-year arc of financial advice, from product-pushing to planning to the human side of money, and why good financial planning can sometimes feel like marriage counselling. Along the way, Brian shares the difference between being rich and being wealthy, the impact of his "funded contentment" concept and his perspective on growth, hope and defining "enough." Whether you're an investor, an advisor or simply someone trying to figure out what money is actually for, this episode is packed with thoughtful insights you won't want to miss. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Brian Portnoy (03:52) Shaping Wealth and the Lydia AI Innovation (06:43) The Challenges of Building an AI Coach (08:50) Partnering with Conquest Planning Software (13:15) Lessons from Morningstar and the Hedge Fund Industry (15:53) Simplicity on the Far Side of Complexity (20:33) The Investor's Paradox and Choice Overload (24:04) Decision Fatigue & Choice Architecture (29:03) The 50-Year Arc of Financial Advice (33:25) Financial Planning Can Be Like Marriage Counselling (35:35) The Difference Between Being Rich and Being Wealthy (40:53) The Impact of the Funded Contentment Concept (42:03) Growth, Hope, and Defining Enough (44:08) Conclusion
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#68
August 11 · 48 min
#67 — Alexandra Macqueen: How Retirement Planning Has Changed Over the Years
Our guest this episode is Alexandra Macqueen — CFP professional, Vice President of Learning, Development and Professional Practice at FP Canada and one of Canada's leading voices on retirement income planning. Alexandra has been a practicing financial planner since 2005, taught personal finance at York University's Schulich School of Business and co-authored the bestselling book "Pensionize Your Nest Egg." In this episode, Dave and Alexandra dive into how retirement planning has changed over the years, from the way rising longevity has reshaped Canadians' awareness of retirement risks to the assumptions that underpin every retirement plan. They cover why financial planning has become harder, when professional advice can pay off for retirees, and the roles FP Canada and the QAFP designation play in raising the standard of advice. Alexandra also breaks down the factors to weigh when deciding whether to commute a defined benefit pension and makes the case for annuities as a retirement planning tool. The conversation also explores reverse mortgages and how they compare to HELOCs, the "Die With Zero" legacy approach, lessons from "The Millionaire Next Door" and why the timing of CPP and OAS is different for everyone. Whether you're nearing retirement or simply want to understand the decisions that will shape it, this episode is packed with practical insights from one of Canada's most respected retirement planning experts. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Alexandra Macqueen (03:07) Why Alexandra Specialized in Retirement Income Planning (04:32) Why Longevity Has Changed the Awareness of Retirement Planning (06:56) Assumptions in Retirement Planning (10:14) Financial Planning Has Become Harder (12:55) Why Professional Financial Advice Can Pay Off for Retirees (13:51) What Is FP Canada? (15:23) What Is the QAFP Designation? (17:45) The Factors When Deciding to Commute a Defined Benefit Pension or Not (22:15) Annuities as a Retirement Planning Tool (25:13) Are Reverse Mortgages an Underappreciated Financial Tool? (26:30) Reverse Mortgages vs. HELOCs: Which Makes More Sense? (28:08) Evaluating the Die With Zero Legacy Approach (29:17) Lessons from "The Millionaire Next Door" (32:01) It's Harder to Navigate Financial Planning Today (36:17) The Value of an Outside Voice in Financial Planning for Spouses (37:54) The Role of Active vs. Passive Investing Strategies (39:23) When to Take CPP and OAS Is Different for Everyone (41:20) The Increasing Costs of Assisted Living (42:44) Teaching Financial Planners the Psychological Aspects of Working with Clients (45:18) The Reality of Family Adjustments After Retirement (46:03) The Improvement of the Financial Advice Industry (47:54) Conclusion
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#67
July 28 · 41 min
#66 — Brenda Hiscock: A Remarkable Story About Overcoming Hardships and Finding Fulfillment as a Financial Planner
Our guest this episode is Brenda Hiscock, a CFP with Objective Financial Partners, one of Canada's leading advice-only planning firms. Brenda's route to financial planning was anything but easy. She lost her mother as a teenager, faced homelessness, battled addiction and overcame a cancer diagnosis, all while building a decades-long career in Canadian financial services. Today, she draws on those experiences to help clients navigate both the numbers and the emotions of money. In this episode, Dave and Brenda dive into her remarkable life story: the childhood hardship and early family loss that shaped her, and the turning point that came through therapy, mentorship and self-forgiveness. The conversation also explores a wide range of retirement topics, including practical tips for people who start their financial planning later in life, retiring abroad, planning for the potential costs of long-term care and the psychology of actually spending your savings later in life. Brenda shares her thinking on protecting parents' retirements before making gifts to their kids, using trusts to protect generational wealth, RRSP meltdowns, delaying CPP and OAS, and facing retirement with a mortgage. This episode is packed with practical insights and an inspiring story you won't want to miss. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Brenda Hiscock (02:09) Brenda's Childhood Hardship and Early Family Loss (05:41) The Trauma of Eviction and Developing an Addiction (07:31) The Turning Point: Therapy, Mentorship and Self-Forgiveness (10:54) Overcoming a Cancer Diagnosis and Rebuilding Confidence (11:54) Tips if You Start Financial Planning Later in Life (14:10) How Brenda's Life Experiences Have Informed Her Views on Insurance (16:00) Retiring Abroad (18:29) Managing Client Fears About the Stock Market (20:54) Planning for the Looming Potential Costs of Long-Term Care (22:40) The Psychology of Spending Your Savings Later in Life (25:08) Protecting Parents' Retirement Before Making Gifts to Their Kids (27:39) Using Trusts to Protect Generational Wealth (28:29) RRSP Meltdowns and Delaying CPP/OAS (30:04) Who Seeks Advice-Only Financial Planning? (31:01) The Impact of "Millionaire Teacher" (32:00) Raising the Standards in the Canadian Financial Planning Industry (35:00) Facing Retirement with a Mortgage (37:23) Embracing Your Authentic Life Story (39:50) Conclusion
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#66
July 21 · 48 min
#65 — Michael J. Wiener: Answers to the Money Questions That Matter
Our guest this episode is Michael J. Wiener — retired cryptologist and the writer behind the long-running Canadian personal finance blog "Michael James on Money." After a high-tech career in cryptography that produced roughly 20 patents, Michael has spent nearly two decades applying an engineer's rigour to investing and retirement math, helping everyday Canadians make clearer, lower-fee, evidence-based decisions with their money. In this episode, Dave and Michael dive into the real cost of investment fees, from high-fee group RRSPs to how seemingly small percentages quietly erode a portfolio over decades. They cover the evidence for passive investing over active management, how to optimize RESP contributions, strategies for smoothing taxes on retirement income and whether it makes sense to delay taking CPP and OAS. The conversation also explores how Michael uses the CAPE ratio to adjust his asset allocation, planning ahead for cognitive decline, the debt paydown vs. investing question and why he's skeptical of Dalbar's famous mutual fund underperformance data. Along the way, Michael shares his takes on real estate investing, reverse mortgages, budgeting for healthcare and long-term care costs, and estate planning essentials. If you want clear, math-driven thinking on investing and retirement from someone with no product to sell, this episode is packed with insights you won't want to miss. Show Notes (00:00) Intro & Disclaimer (00:57) Intro to Michael J. Wiener (03:09) The Impact of High Fees in Group RRSPs (05:23) The Big Impact of Seemingly Small Investment Fees (07:09) Active Management vs. Passive Investing (08:46) Optimizing RESP Contributions: Lump Sum vs. Ongoing (12:02) Smooth Taxation Strategies for Retirement Income Planning (14:49) Should You Delay Taking OAS and CPP? (17:02) How Michael Uses the CAPE Ratio to Adjust His Asset Allocation (20:40) Addressing Cognitive Decline and Managing Your Investments (22:25) Balancing Debt Paydown vs. Investing (24:21) RRSP vs. TFSA Debate (25:55) Is a 100% Equity Portfolio Right for Young Investors? (27:19) Evaluating Dalbar's Mutual Fund Underperformance Data (30:34) The Realities and Hassles of Real Estate Investing (33:28) The Hidden Risks and Rules of Reverse Mortgages (35:01) Common Financial Mistakes Savers Make in Retirement (36:38) Budgeting for Healthcare and Long-Term Care Costs (39:47) Cash Value Insurance vs. Term Insurance for Canadians (41:24) Essential Estate Planning and Power of Attorney Tips (42:15) The Importance of Decluttering for the Next Generation (44:07) Engineering, Cryptography, and Quantum Computing Threats (45:01) The Story Behind Michael's Pseudonym (45:49) Finding an Initial Audience and Blogging Success (46:34) Conclusion
- Chapters
#65
July 14 · 38 min
#64 — Hanif Bayat: Macroeconomics and Entrepreneurship in Canada
Our guest this episode is Hanif Bayat — founder and CEO of WOWA.ca, one of Canada's largest personal finance platforms. A former quantitative analyst at BMO and RBC with a Ph.D. in theoretical chemical physics from the University of Toronto, Hanif left banking in 2018 to build WOWA into a resource of over 1,000 calculators, guides and market reports now used by millions of Canadians every year. In this episode, Dave and Hanif dive into the state of the Canadian economy, starting with the story behind WOWA and how it grew into a platform reaching millions of page views. They explore the drivers of Canada's housing affordability crisis, why asset prices have climbed so far beyond the Consumer Price Index, and how loose monetary policy has reshaped what Canadians can actually afford. Along the way, Hanif shares his perspective on policy solutions for Canada's real estate market, the looming US debt, the lack of financial knowledge among consumers, and where the mortgage industry stands today. Whether you're trying to make sense of Canada's housing market or curious about the bigger economic forces shaping your finances, this episode is packed with sharp analysis and practical perspective you won't want to miss. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Hanif Bayat (06:44) What is the WOWA Platform? (07:35) Reaching One Million Page Views (09:16) The Origin of WOWA (11:37) How AI Could Threaten Content Businesses (15:09) Drivers of Canada's Housing Affordability Crisis (18:44) Asset Prices vs. the Consumer Price Index (CPI) (21:51) Competitive Realities of the Modern Job Market (23:20) The K-Shaped Economy and the Impact of Asset Prices on Entrepreneurship (25:55) Policy Solutions for Canada's Real Estate Market (29:34) The Looming US Debt (32:07) Addressing the Lack of Financial Knowledge Among Consumers (35:05) Mortgage Industry Dynamics Today (36:49) Conclusion
- Chapters
#64
July 7 · 48 min
#63 — Sandi Martin: Financial Lessons from One of Canada’s First Advice-Only Planners
Our guest this episode is Sandi Martin — one of Canada's first advice-only financial planners and a Certified Financial Planner who left retail banking to build a practice built around her values. Sandi co-founded the Financial Planning Association of Canada, co-hosted the Because Money podcast and has spent over a decade championing a simple idea: helping everyday Canadians figure out what "enough" really looks like. In this episode, Dave and Sandi dive into the advice-only model and why she walked away from the bank to build it. They unpack the CBC Marketplace exposé on the Canadian banking industry, the aggressive marketing of lines of credit and what really happens behind the sales culture most Canadians never see. Sandi also explains her transition into the advice-only space, the early strategies she used to find clients and why she has chosen to run a solo operation rather than scale. The conversation also explores the everyday planning questions that trip people up, from the emergency fund debate (cash savings versus lines of credit) to the RRSP versus TFSA decision and why accounts are best understood as tools rather than goals. Sandi shares her perspective on the financial nuances of divorce and partnerships, the essential role planners play in building retirement income, the often-overlooked costs of late-life healthcare and assisted living, and why high-fee mutual funds still dominate in Canada. Whether you're rethinking who you take financial advice from or simply want a clearer, no-nonsense view of how planning actually works, this episode is packed with practical takeaways you can implement right away. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Sandi Martin (03:24) The CBC Marketplace Exposé on the Canadian Banking Industry (09:52) The Problem with Aggressive Marketing of Lines of Credit (12:00) Sandi's Transition into the Canadian Advice-Only Space (14:25) Early Marketing Strategies for Getting Advice-Only Clients (17:37) Why Sandi Runs a Solo Operation (19:49) Financial Planning Nuances in Divorce and Partnerships (24:08) Maintaining Autonomy and Control Over Your Work Schedule (25:55) Emergency Funds Debate: Cash Savings vs. Lines of Credit (29:14) The RRSP vs. TFSA Debate and Viewing Accounts as Tools (34:05) The Essential Role of Planners in Retirement Income Strategies (38:45) Factoring Late-Life Healthcare and Assisted Living Costs into Your Financial Plan (42:40) The Dominance of High-Fee Mutual Funds in Canada (47:08) The Benefits of Talking Openly About Money (49:37) Conclusion
- Chapters
#63
June 23 · 50 min
#62 — Ben Rabidoux (Returns): Canada’s Real Estate Outlook in 2026
Our guest this episode is Ben Rabidoux — founder of North Cove Advisors and Edge Realty Analytics, and one of Canada's most closely followed housing and macroeconomic analysts. Ben's data-first research is relied on by institutional investors and real estate professionals across the country, and he returns to the show to break down where Canada's real estate market is headed in 2026. In this episode, Dave and Ben dive into the state of the Canadian economy and what it means for housing. They unpack the disconnect between strong bank earnings and a weakening economy, the rising power of sales, and what corporate results from companies like Tim Hortons and Pizza Pizza reveal about the health of the consumer. Ben also explains why new rents may be poised for a trend reversal and what the latest data signals for the months ahead. The conversation also explores the pressures facing real estate agents, whether a coming wave of baby boomer property sales could suppress prices, and early signs of life in the GTA condo market. Ben also weighs in on government tax changes and development fees, blanket appraisals in the condo market, and what next year's mortgage renewal environment could look like. Whether you're a homeowner, an investor or simply trying to make sense of where Canadian real estate is heading, this episode is packed with data-driven insights you won't want to miss. Ben’s Real Estate and Mortgage Intelligence Reports: http://www.edgeanalytics.ca/ Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Ben Rabidoux (02:36) Explaining the Disconnect Between Bank Earnings and the Economy (04:11) What is Driving the Increasing Power of Sales? (06:34) Reconciling Weak Economic Data with Packed Restaurants (10:22) What Tim Hortons' and Pizza Pizza's Earnings Tell You About the Economy (11:13) Predicting the Trend Reversal in New Rents (17:17) How Having Fewer International Students is Affecting Certain Markets (19:55) Alternative Ways to Measure Population Growth (22:09) Temporary Foreign Workers Program (23:59) North Cove Advisors and Edge Analytics (27:42) Real Estate Agents are Facing Pressures (30:11) Where Are Canadian Housing Prices Headed? (34:47) Will the Future Wave of Baby Boomer Property Sales Suppress Housing Prices? (38:00) GTA Condo Market Showing Signs of Life (38:54) Evaluating Government Tax Changes & Development Fees (41:34) Blanket Appraisals in the Condo Market (47:36) Forecasting Next Year's Mortgage Renewal Environment (50:17) Conclusion
- Chapters
#62
June 16 · 52 min
#61 — Andrea Thompson: The Growth of Advice-Only Planning & Cross-Border Tips
Our guest this episode is Andrea Thompson — Founder and lead financial planner of Modern Cents, a virtual, advice-only firm she launched in 2022 after more than 16 years in the financial industry. A CFP who also writes and marks the national CFP exam for FP Canada, Andrea built her practice to serve Canadians who have cash flow instead of assets, making quality financial advice accessible to younger people and those below traditional asset minimums. In this episode, Dave and Andrea dive into the rise of advice-only financial planning in Canada. They explore why she walked away from the traditional model to build Modern Cents, the factors fueling the model's growth, how advice-only planners find clients and where the pricing sweet spot lands. They also break down one of the model's biggest hurdles, the implementation gap between receiving a plan and actually executing it, along with the question of whether financial planners and investment advisors should stay in their respective lanes. The conversation also explores Andrea's specialty in cross-border financial planning, including the common mistakes Canadian residents make with their US 401(k) accounts. They discuss the overlooked psychological and financial value of annuities and why so many people resist them, how young adults should balance saving for a down payment against retirement, and the case for term insurance over permanent cash value policies. Whether you're curious about the advice-only model, weighing the value of professional financial advice or navigating the complexities of cross-border planning, this episode is full of practical takeaways you can put to use right away. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Andrea Thompson (02:43) Why Andrea Started Her Advice-Only Firm (06:43) Factors Fueling the Growth of Advice-Only Planning in Canada (07:55) Lead Generation for Advice-Only Planners (09:25) How CFP Education Has Improved Over the Years (11:55) Community and Collaboration Within Canada's Financial Planning Industry (13:55) Overcoming the Implementation Challenge in Advice-Only Financial Planning (21:23) Navigating Investment Execution for Advice-Only Clients (23:47) Should Investment Advisors and Financial Planners Stay in Their Respective Lanes? (28:03) Should You DIY Your Retirement Plan? (29:52) What's the Pricing Sweet Spot for Advice-Only Planners? (32:27) Cross-Border Financial Planning Challenges (35:35) Common Mistakes with US 401(k) Accounts for Canadian Residents (36:53) The Psychological and Financial Value of Annuities (40:41) Why Don't People Like Annuities? (43:34) Balancing Down Payments and Retirement Savings for Young Adults (47:43) Childhood Money Lessons from an Actuary Father (48:29) Term Insurance vs. Permanent Cash Value Insurance (50:07) The Critical Importance of Disability Insurance (51:29) Conclusion
- Chapters
#61
June 9 · 46 min
#60 — Adam Bornn (Returns): Retirement Planning Tips & Common Mistakes to Avoid
Our guest this episode is Adam Bornn — founder of Parallel Wealth Financial Group and the creator of the Parallel Wealth YouTube channel, one of Canada's largest channels devoted to retirement planning. Adam returns to the show to focus on a single, high-stakes subject: how Canadians can build a retirement plan that actually works, and the common mistakes that quietly derail one. In this episode, Dave and Adam dive into the realities of the retirement transition, from the most common mistakes people make to how to balance spending early with the cost of care later in life. They break down the "go-go, slow-go and no-go" years, why health and finding joy matter as much as the numbers, and when the ideal time to start planning really is. Adam also explains when it makes sense to convert an RRSP to a RRIF and how a TFSA can act as a flexible lever account inside a broader plan. The conversation also explores the issues that complicate real-world retirement, including the squeeze on the sandwich generation, why more retirees are helping their adult kids financially, and how to plan around large age gaps or being single. Adam digs into some of the costliest missteps too, from taking CPP early when you don't need to, to letting registered accounts grow tax-deferred for too long and running into the OAS clawback. Along the way, they cover tax planning when liquidating cottages and rental properties, the limited role of reverse mortgages and HELOCs, and how to think about high market valuations and cash wedges in retirement. Whether you're years away from retirement or already making the transition, this episode is packed with practical, tax-smart insights to help you avoid the mistakes that cost retirees the most. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Adam Bornn (01:30) Common Retirement Transition Mistakes (03:22) Balancing Early Spending & Late-Life Care (05:25) Go-Go, Slow-Go & No-Go Years (07:37) Finding Joy and the Importance of Health in Retirement (10:56) Adam's YouTube Channel and Focus on Retirement Planning (13:35) When Is the Ideal Time to Start Retirement Planning? (15:40) When to Convert an RRSP to a RRIF (17:35) The Power and Flexibility of a TFSA Lever Account (19:23) Factoring in Lump-Sum Obligations to Your Retirement Plan (21:36) Careless Tax Mistakes Can Cost You Huge Money (23:18) The Sandwich Generation (25:00) Why Some Retirees Are Helping Their Kids Financially (28:14) Navigating Retirement Planning with Large Age Gaps (30:07) The Disadvantages of Retirement Planning for Single People (31:57) The Biggest Retirement Mistake: Taking CPP Early if You Don't Need To (34:16) Avoid the Trap of Growing Registered Accounts Tax-Deferred For Too Long (36:18) Optimizing to Avoid the OAS Clawback (37:55) Tax Planning When Liquidating Cottages and Rental Properties (40:53) The Limited Use of Reverse Mortgages and HELOCs (41:40) High Market Valuations, Equities & Cash Wedges in Retirement (44:38) Conclusion
- Chapters
#60
June 2 · 26 min
#59 — Benjamin Tal: The State of Canada’s Economy and Housing Market in 2026
Our guest this episode is Benjamin Tal — Managing Director and Deputy Chief Economist at CIBC Capital Markets. Benjamin has spent over two decades publishing CIBC's influential "In Focus" research, has been recognized by the International Monetary Fund as a leading expert on Canada's real estate market and has testified before Parliamentary committees on the country's most pressing economic issues. In this episode, Dave and Benjamin dive into the state of Canada's economy heading into 2026. They break down what's gone wrong with Canada's real estate market, evaluate recent central bank decisions and unpack the impact of HST/GST relief and development charges on housing supply. Benjamin also explains the structural shift toward a rental culture in Canada and why rent control has been so disastrous for affordability. The conversation also explores the widening productivity gap between Canada and the U.S. in the AI era and the possibility of universal income guarantees on the horizon. Along the way, Benjamin shares his perspective on monopolies and limited competition in Canadian industry, the overwhelming red tape facing small businesses, the real effects of immigration on the market and why CPI calculations may be understating the true cost of living. Whether you're a homeowner, an investor or simply trying to make sense of where Canada's economy is heading, this episode is packed with sharp, data-driven insights from one of the country's most trusted economists. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Benjamin Tal (02:32) Why It's Important to Connect Macroeconomics to Personal Finance (03:15) Understanding Canada's Broken Real Estate Market (07:23) Evaluating Central Bank Decisions and Interest Rates (08:05) Impact of HST/GST Relief and Development Charges (09:48) A Shift Toward a Rental Culture in Canada (11:38) The Disastrous Impact of Rent Control (13:22) How the Condo Market and Developer Landscape Is Changing (16:18) Canada Versus U.S.A. Productivity & The AI Revolution (20:56) Are We Headed Towards Universal Income Guarantees? (21:45) Monopolies and Limited Competition in Canadian Industry (22:23) Overwhelming Regulations and Red Tape for Small Businesses (24:25) The Current Immigration Situation and its Market Effects (25:52) Inaccuracies in CPI Calculations and the Real Cost of Living (26:29) Conclusion
- Chapters
#59
May 26 · 51 min
#58 — Robb Engen (Returns): Retirement Advice for Regular Canadians
Our guest this episode is Robb Engen — a Qualified Associate Financial Planner (QAFP), advice-only financial planner and the longtime voice behind Boomer & Echo, one of Canada's most-read personal finance blogs. Robb returns to the show to share what he's learned helping regular Canadians plan, save and spend through retirement with confidence. In this episode, Dave and Robb take a deep dive into one of the biggest paradoxes in retirement planning: why so many Canadians who have done everything right are still afraid to spend their savings. They break down the "golden tax planning windows" in your sixties, the trade-offs between RRSP and TFSA withdrawals and why DIY retirement income planning is much harder than the accumulation years that came before it. Robb also explains how to budget for lumpy, one-time retirement expenses and why the current RRIF minimum withdrawal rules deserve a rethink, especially for single retirees. Whether you're approaching retirement, already there or just trying to think more clearly about decumulation, this episode is packed with practical, no-nonsense insights from one of Canada's most trusted personal finance voices. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Robb Engen (03:15) The Longevity of Robb's Blog Boomer & Echo (05:56) Why Robb Focuses on "Regular Canadians" (09:12) The QAFP Designation (11:19) RRSP vs. TFSA: Retirement Tax Brackets & Delaying CPP (14:21) The Ideal Age to Start Retirement Planning (15:31) Why It's Hard to DIY Retirement Income Planning (17:28) Golden Tax Planning Windows in Your Sixties (19:17) Budgeting for Lumpy and One-Time Retirement Expenses (20:30) Rethinking RRIF Minimum Withdrawal Rules for Singles (23:22) Many Retirees Are Hesitant to Spend (25:13) How to Get Retirees to Safely Spend More (27:56) Countering Retirees' Fears of Overspending (29:25) Unlocking the Tax-Free Compounding Power of TFSAs (32:05) Is It Wise to Plan Around Worst-Case Monte Carlo Simulations? (33:55) Robb's Advice-Only Model (37:36) Will the AUM Model Come Under Pressure? (39:44) The Value of Advisory Continuity and Turnover Realities (41:15) Robb's Worries: Navigating Media Anxiety and Alternative Investments (43:51) Dave's Thoughts on Alternative Investments (46:05) "One More Year" Syndrome (48:00) Employer RRSP Matches (49:50) Conclusion
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#58
May 19 · 44 min
#57 — Daniel Crosby: How to Overcome Your Financial Biases
Our guest this episode is Dr. Daniel Crosby — psychologist, behavioral finance expert and Chief Behavioral Officer at Orion Advisor Solutions. Daniel is the bestselling author of several books on the psychology of money, including "The Behavioral Investor" and "The Soul of Wealth," and is the host of the popular podcast "Standard Deviations." His mission is to help investors and advisors understand how psychology shapes financial decisions and what true wealth really means. In this episode, Dave and Daniel dive into the psychology behind investing and the behavioral biases that quietly sabotage even the smartest investors. They break down the four major investor biases, why overconfidence is the most damaging of the bunch and Daniel's "Three E's" framework for overcoming them. They also explore why money is emotional rather than purely mathematical and the role behavioral fintech design can play in helping people make better long-term decisions. The conversation also explores the rise of the "gamblification" of investing, the impact of social media on young investors and why personal benchmarking tends to serve people far better than chasing the S&P 500. Along the way, Daniel shares his framework of believing, belonging and becoming as the keys to a good life, his perspective on managing anxiety in uncertain times and why so many investors still fall into the trap of buying high and selling low. Whether you're a seasoned investor or just starting to think about your relationship with money, this episode is packed with insights that will help you understand yourself as much as the markets. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Daniel Crosby (03:02) Daniel's Path From Psychology to Finance (05:21) Statistics on Reading (06:48) The Four Major Investor Biases (13:12) The Three E's to Overcome Biases (18:25) Why Overconfidence Is the Most Damaging Bias in Investing (19:02) Money Is Emotional, Not Just Mathematical (22:50) Daniel's Role at Orion & Behavioral Fintech Design (24:56) Personal Benchmarking vs. Chasing the S&P 500 (25:45) Mental Accounting & The House Money Effect (26:50) The Gamblification of Investing & Young Men (30:36) Social Media's Damage to Young Investors (33:51) Believing, Belonging & Becoming: Keys to a Good Life (38:56) Managing Anxiety in Uncertain Times (42:05) Why We Buy High & Sell Low (44:19) Conclusion
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#57
May 12 · 34 min
#56 — Daniel Glazier: Appraisals & How to Avoid Family Conflict Over Your Estate
Our guest this episode is Daniel Glazier — a Certified Personal Property Appraiser (CPPA) with more than 25 years in the designation. Daniel spent decades in the used furniture and antiques trade before moving into appraisals full-time and has now completed over 1,000 appraisal reports for families, executors, lawyers and financial institutions across Southern Ontario. In this episode, Dave and Daniel dive into the often-overlooked world of personal property appraisals and why so many family fights after a death have nothing to do with money and everything to do with stuff. They cover the endowment effect, Daniel's "VHS system" for identifying the items most likely to cause conflict, how to resolve disputes over contested belongings and why making a plan ahead of time is one of the most important and overlooked parts of estate planning. Whether you're working on your own estate plan, helping a parent downsize or settling an estate as an executor, this episode is packed with practical insights that could save your family real money and a lot of unnecessary conflict. Show Notes (00:00) Intro & Disclaimer (01:44) Intro to Daniel Glazier (03:42) Daniel's Origin Story: Used Furniture & Strip Joints (06:06) The Endowment Effect & The Used Furniture Market (07:53) The VHS System for Identifying Items That Could Cause Family Conflict (11:16) Resolving Conflicts Over Contested Items by Selling Them (13:26) Make a Plan Ahead of Time to Avoid Family Conflict (16:15) The Research on Sentimental Items (17:34) A Solution to the Wedding Ring Dilemma (18:52) Handling Non-Monetary Heirlooms (20:50) The Appraiser's Role in Estate Planning (23:24) The $5,000 Lamp Nobody Noticed (25:22) Will AI Replace Personal Property Appraisers? (26:55) Getting the Appraiser Involved Early (28:02) How Clients Find Daniel (29:41) Why Sold Prices Beat Asking Prices (31:10) Location & Charitable Auctions Skewing Values (33:11) Conclusion
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#56
May 5 · 56 min
#55 — Mark McGrath: All-in-One ETFs, Rent vs. Buy and Financial Trade-Offs
Our guest this episode is Mark McGrath — one of Canada's top voices on evidence-based personal finance and a returning guest from episode #12. Mark recently came out of semi-retirement to launch his own advice-only practice called Phynance which focuses on helping physicians with financial planning. He is also co-author of "Wealthier: The Investing Field Guide for Canadian Millennials." In this episode, Dave and Mark dive into all-in-one ETFs and why simplicity often beats last-mile portfolio optimization for the typical Canadian. They also discuss the renting vs. buying debate as Mark’s family has recently decided to sell their house and become renters. The conversation also explores the limits of the 4% rule, how safe withdrawal rates differ across countries, and whether retirees are more comfortable holding stocks today than they used to be. Along the way, Mark talks about calling out charlatans on Twitter and shares which personal finance opinions he has changed his mind on over the years. Whether you're a DIY investor, a homeowner weighing your options, or anyone trying to cut through the noise of online personal finance commentary, this episode is packed with practical, evidence-based perspective from one of Canada's most trusted financial voices. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Mark McGrath (02:28) Mark's Semi-Retirement and His New Firm Phynance (06:01) The Evolution of the Financial Planning Industry (09:27) All-in-One ETFs Explained (12:32) Simplicity Over Last-Mile Optimization (15:39) The Case for a Home-Country Investing Bias (19:27) Why Mark's Family Decided to Sell Their House & Become Renters (23:44) Renting With Young Kids & Schools (25:58) Why Mark Didn't Like Being a Landlord (27:07) Homeowners Are Often Out of Touch With Costs (29:44) What The 4% Rule Leaves Out (34:05) Safe Withdrawal Rates Across Countries (36:09) Are Retirees More Comfortable Holding Stocks Now Than in the Past? (37:37) Voices Mark and Dave Respect in the Financial Industry (40:54) Getting Assessed for ADHD (41:54) Wife's Take on Personal Finance (42:42) Calling Out Charlatans on Twitter (45:03) Why Market Forecasters Keep Getting Booked (45:55) Why Mark Stepped Away from Twitter (48:32) What Personal Finance Opinions Has Mark Changed His Mind On (53:02) Phynance Already Has a Waitlist (55:52) Conclusion
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#55
April 28 · 42 min
#54 — Frederick Vettese: Retirement Planning Advice on CPP, Annuities and More
Our guest this episode is Frederick Vettese — former Chief Actuary at Morneau Shepell (now Telus Health), longtime Globe & Mail columnist and one of Canada’s leading voices on retirement planning. Fred is also the author of four books on retirement, including the bestselling “Retirement Income for Life.” In this episode, Dave and Frederick cover a wide range of retirement topics from why many Canadians may be more prepared than they think to how annuities can fit into a retirement income plan. They also discuss reverse mortgages, whether it makes sense to delay OAS, RRSP meltdown strategies and how thinking around withdrawals has evolved over time. Along the way, Frederick shares thoughtful perspectives on carrying a mortgage into retirement, gifting to adult children, universal life insurance and his own estate planning approach. Whether you’re approaching retirement or simply want to better understand the key decisions that shape it, this episode is packed with practical insights and real-world advice from one of Canada’s top experts. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Fred Vettese (02:21) How Fred Comes Up With Writing Topics for The Globe & Mail (04:30) Fred’s Career as an Actuary & Author (06:45) Why Many Canadians Are Better Prepared for Retirement Than They Think (10:31) Longevity Risk & the Case for Delaying CPP to 70 (12:15) The Role of Annuities in Retirement Income (14:29) When Reverse Mortgages Make Sense (16:32) Delaying CPP: Why Canadians Are Finally Coming Around (18:47) Should You Also Delay OAS to Age 70? (21:10) RRSP Meltdown Strategy & Income Smoothing (23:20) How the Industry Shifted on RRSP Withdrawal Thinking (25:27) Will People Get Married for the Financial Benefits in Retirement? (27:12) Insurance Products: Universal Life & When They Make Sense (29:38) Carrying a Mortgage Into Retirement (31:13) Gifting Money to Adult Children & The Risk to Your Own Retirement (34:02) Fred’s Own Estate Planning & Will Strategy (35:43) Fred’s Personal Investment Mistakes & Lessons (39:31) How the Financial Advice Industry Has Improved (41:10) Some Grandparents are Upsizing (42:14) Conclusion
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#54
April 21 · 54 min
#53 — Brian Orlando: The Case for Keeping Your Finances Simple
Our guest this episode is Brian Orlando — CPA and creator of the fast-growing Canadian personal finance account @CalmMoneyCoach. Brian has over 15 years of experience across accounting, finance and tech, before recently leaving the corporate world to pursue financial coaching full time. His mission is simple: reduce money stress and help people build plans they can actually stick to. In this conversation, Dave and Brian explore why simplicity is often the most powerful strategy in personal finance — from automating savings and avoiding high-fee products to cutting through common misconceptions around RRSPs and investing. They also dive into real-world challenges Canadians are facing today, including the rising cost of living, lifestyle inflation and the pressure to “keep up.” Along the way, Brian shares practical insights on everything from the Smith Maneuver to employer RRSP matching, renting vs. buying, insurance decisions and how to make smarter financial choices in your 30s and beyond. If you’re looking for straightforward, no-nonsense financial advice that actually works in the real world, this episode is packed with practical takeaways you can implement right away. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Brian Orlando (The Calm Money Coach) (02:26) Brian’s Background & Career Path (05:37) How Brian Grew His Audience for Calm Money Coach (07:55) Why Simplicity Beats Complexity in Investing (11:03) Automating Savings & Paying Yourself First (11:54) The Downside of Fintech Platforms & Expensive Investment Products (13:52) The Rising Cost of Living & Financial Desperation (16:10) The Smith Maneuver Explained (23:08) Financial Advice for Canadians in Their 30s (27:55) Canada is Lucky to Have Great Financial Educators (29:59) RRSP Misconceptions & Tax Efficiency (32:59) Getting Good Advice for Retirement is Financially and Emotionally Beneficial (36:30) Will People Get Married in Retirement for the Tax Advantages? (37:50) Rent vs. Buying a Home (43:45) The FHSA & Its Triple Tax Advantage (44:21) Term vs. Whole Life Insurance (47:10) Employer Matching on Group RRSP & Fees (49:46) Overspending on Cars & Lifestyle Inflation (52:32) Conclusion
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#52
April 14 · 45 min
#52 — Moira Rose Váně: RESPs & How to Save for Your Kids’ Education
Our guest this episode is Moira Rose Váně — a full-time lawyer and Qualified Associate Financial Planner® who specializes in helping Canadian families save for their kids’ education through RESPs. In this conversation, Dave and Moira take a deep dive into everything you need to know about RESPs — from how they work to how to invest inside them to the often-overlooked pitfalls like high fees and estate planning risks when grandparents are involved. They also break down strategies for maximizing government grants, optimizing withdrawals and why family RESPs can be such a powerful tool. Along the way, Moira shares her perspective on passive investing, her unique career path as both a lawyer and financial planner and the financial planning challenges that disproportionately impact women. Whether you’re a parent, grandparent or planning to have kids in the future, this episode is packed with clear, practical advice to help you make the most of RESPs and avoid costly mistakes. Show Notes (00:00) Intro & Disclaimer (00:55) Intro Moira Rose Váně (02:10) Being a Lawyer and a Financial Planner (04:28) Why Moira is Focusing on RESPs (07:27) RESP Basics: What Is It & How It Works (10:33) How to Invest Inside Your RESP (14:06) Index Funds & The Evidence for Passive Investing (15:38) The Problem With Group RESPs (16:43) Best Platforms for Self-Directed RESPs (19:37) Getting Grandparents Involved in RESPs (21:14) The Impact of Fees on RESPs (22:19) Estate Planning Risks When Grandparents Are Subscribers (24:19) How Taxes Work With RESPs (27:35) Why Dave and Moira Like Family RESPs (30:04) Withdrawing from Your RESP: Strategies & Common Mistakes (32:21) Financial Planning Challenges Unique to Women (38:26) Moira’s 12-Month Implementation Advice Model (43:29) Conclusion
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#51
April 7 · 42 min
#51 — Doug Hoyes: Bankruptcy, Consumer Proposals and the State of the Canadian Consumer
Our guest this episode is Doug Hoyes — Co-Founder of Hoyes Michalos, Licensed Insolvency Trustee and one of Canada’s leading experts on debt and personal insolvency. Doug has spent decades helping Canadians navigate financial hardship and is a passionate advocate for ensuring people understand their options and find the right path forward. In this episode, Dave and Doug dive into the world of debt, bankruptcy and consumer proposals — what they are, how they work and when each option might make sense. They break down how Licensed Insolvency Trustees operate, how consumer proposals are negotiated and what actually happens if you file for bankruptcy (what you keep, what you lose and who typically ends up choosing each path). Doug also shares insights into why so many Canadians are struggling with debt today, from inflation and the “K-shaped” economy to mortgage renewals, rising vehicle costs and the financial impact of divorce. The conversation also explores some of the lesser-discussed drivers of debt including gambling, travel spending and lifestyle creep, along with practical advice on when to seek help and why early action can make a significant difference. Doug brings decades of real-world experience to highlight common mistakes and what people can do to avoid them. If you want a clear, practical understanding of debt and insight into the Canadian economy from someone with boots on the ground, this episode is packed with insights you won’t want to miss. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Doug Hoyes (01:51) Why Debt Education is So Important (03:11) Inflation and the K-Shaped Economy (07:29) Consumer Proposal vs. Bankruptcy Explained (09:18) How the Trustee Negotiates Consumer Proposals (10:37) Who Ends Up Filing Bankruptcy vs. Consumer Proposal? (12:34) Who Should Talk to a Licensed Insolvency Trustee and When? (17:03) If You Claim Bankruptcy, What Do You Lose vs. Keep? (19:48) How Do People Get Into Trouble with Debt? (24:02) Gambling's Role in Insolvency (25:38) Historical Homeownership Rates Among Insolvency Clients (27:02) Mortgage Resets and the Condo Crash (29:56) Vehicles Can Be a Major Financial Trap (32:54) Divorce and the Financial Cost of Separation (34:53) Travel and Debt (36:38) No One Cares About Your Money More Than You Do (38:20) Rapid Fire Questions (40:43) Conclusion
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