The Wealthy Barber Podcast

Epizode

• #59 — Benjamin Tal: The State of Canada’s Economy and Housing Market in 2026 02.06.2026 27min

  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
• #58 — Robb Engen (Returns): Retirement Advice for Regular Canadians 26.05.2026 51min

  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
• #57 — Daniel Crosby: How to Overcome Your Financial Biases 19.05.2026 44min

  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
• #56 — Daniel Glazier: Appraisals & How to Avoid Family Conflict Over Your Estate 12.05.2026 34min

  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
• #55 — Mark McGrath: All-in-One ETFs, Rent vs. Buy and Financial Trade-Offs 05.05.2026 56min

  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
• #54 — Frederick Vettese: Retirement Planning Advice on CPP, Annuities and More 28.04.2026 42min

  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
• #53 — Brian Orlando: The Case for Keeping Your Finances Simple 21.04.2026 54min

  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
• #52 — Moira Rose Váně: RESPs & How to Save for Your Kids’ Education 14.04.2026 45min

  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
• #51 — Doug Hoyes: Bankruptcy, Consumer Proposals and the State of the Canadian Consumer 07.04.2026 42min

  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
• #50 — Ben Felix (Returns): Investing Insights and Rapid-Fire Q&A 31.03.2026 54min

  Our guest this episode is Ben Felix — Chief Investment Officer at PWL Capital, co-host of the Rational Reminder podcast and creator of one of the most respected investing YouTube channels, @BenFelixCSI. Ben is a returning guest from Episode #5, one of our most popular episodes to date. In this episode, Dave and Ben go through a rapid-fire Q&A on some of the most important (and misunderstood) topics in investing. They cover everything from the biggest mistakes investors make to the difference between investing and gambling to why professional investors struggle to beat the market and common misconceptions about dividends. Ben and Dave also break down the flaws with covered call funds, market timing, and touch on other topics like annuities, crypto, homeownership, life insurance and all-in-one ETFs. If you want clear, evidence-based answers to your biggest investing questions this is an episode you won’t want to miss. Tune in now on our website, YouTube, Apple Podcasts, Spotify and all other podcasting platforms!   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Ben Felix (04:22) A Huge Investor Mistake: Not Owning Enough Equities  (06:04) The Difference Between Investing and Gambling (07:33) Increasing Your Income is One of the Best Things You Can Do for Your Personal Finances (08:55) Dave and Ben’s Advice: Don’t Trade Options (09:40) Why Professional Investors Struggle to Beat the Market (13:40) Misunderstandings About Dividends (16:11) Why Covered Call Funds Underperform Over the Long Run (20:17) Even Experts Can’t Effectively Time the Market (23:18) High Valuations and Expected Returns (25:12) Behavioural Traps: Overconfidence and Pessimism (27:31) The Role of Annuities in Retirement Planning (32:03) Crypto and Prediction Markets (35:21) Renting vs. Owning a Home (38:56) The True Maintenance Costs of Home Ownership and “While We’re At It” (40:46) Is Life Insurance a Good Investment Product? (45:03) How Often Should You Check Your Portfolio? (46:30) The Benefits of All-in-One Asset Allocation ETFs (48:12) The Behaviour Gap in Investing (48:53) The Positive Evolution of the Financial Advice Industry (54:15) Conclusion
• #49: Ron Butler (Returns): Mortgages & Real Estate in 2026 24.03.2026 45min

  Our guest this episode is Ron Butler — owner of Butler Mortgage and a 30-year veteran of the Canadian mortgage brokerage industry. Ron returns as a repeat guest after being a fan favourite when he first joined us back in episode #8. He’s widely known for his blunt takes on the housing market through social media and the Angry Mortgage Podcast. In this conversation, Dave and Ron tackle the current state of Canada’s housing and mortgage markets — from what Ron calls “the Ontario real estate disaster” to his outlook for real estate in 2026. They discuss the looming shortage of new single-family construction, whether municipalities will have to cut development fees and why housing prices remain so high relative to incomes. Ron also explains mortgage basics, why using a mortgage broker can matter, the hidden risks of co-signing a mortgage and the growing issue of homeowners sitting on mortgages with little or no equity. They also explore several major trends shaping the market right now, including the huge wave of mortgage renewals coming in 2026, the rise of extended amortizations, questionable behaviour in the private mortgage market and why moving homes is often far more expensive than people realize. Along the way, Ron and Dave discuss their thoughts on inflation, job security, the future of real estate investors and even how AI could begin affecting white-collar employment. If you want a candid, big-picture look at where Canada’s housing market might be headed, this episode is packed with insight, strong opinions and practical perspective.   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Ron Butler (02:32) Real Estate Market Update: The Ontario Disaster (03:36) Is a Real Estate Crash Good for Young Canadians? (04:42) 2026 Real Estate Forecast (05:36) The Looming Crisis of No New Single-Family Construction (09:03) Do Municipalities Have to Cut Their Development Fees? (11:45) Mortgage Basics (13:17) The Impact of the War in the Middle East on Mortgage Rates (15:51) Housing is Still Expensive Relative to Incomes (18:25) Inflation and Its Impact on the Bottom 50% of Income Earners (23:55) The Hidden Dangers of Co-Signing a Mortgage (25:23) Underwater Mortgages With No Equity (26:22) Why Should Someone Use a Mortgage Broker? (28:40) 2026 Will Be the Biggest Year for Mortgage Renewals in Canadian History (30:04) Are Many Canadians Extending Their Amortization (31:24) The Vanishing Starter Home: Why We Only Build Big (33:47) Private Mortgage Misbehaviour (35:20) Moving is Way More Expensive Than People Realize (37:03)  The Collapse of Rural Real Estate as Offices Call People Back (38:47) Are Lenders Concerned About Job Security? (39:52) Are Real Estate Investors Going to Come Back to the Market? (42:37) How AI Is Already Cutting White Collar Hiring (44:03) Conclusion
• #48 — Rob Carrick (Returns): Retirement, the Value of Financial Advice and the Canadian Economy 17.03.2026 50min

  Our guest this episode is Rob Carrick — longtime personal finance columnist at The Globe and Mail and one of Canada’s most respected voices on money. Rob returns as our first-ever repeat guest after being a fan favourite back in episode #3! For 27 years, Rob helped Canadians make sense of investing, housing, debt and retirement through his widely read column at The Globe. He semi-retired in the spring of 2025 and now writes a Substack newsletter, does public speaking and contributes biweekly columns to The Globe. In this episode, Dave and Rob cover a wide range of timely topics — from Rob’s transition into semi-retirement and how people can successfully navigate retirement themselves, to the growing role of advice-only financial planners and why the quality of financial advice in Canada has improved dramatically. They also dive into broader economic issues affecting Canadians today, including inflation, mortgage renewals, household debt levels, the true cost of home ownership and whether Canadians should be counting on their homes to fund retirement. It’s a thoughtful, wide-ranging conversation with one of Canada’s most experienced personal finance journalists — packed with practical insights and big-picture perspectives on money in Canada today.   Rob Carrick's Substack: https://robcarrickpf.substack.com/   Show Notes: (00:00) Intro & Disclaimer (00:55) Intro to Rob Carrick (02:18) Rob’s Retirement From The Globe and Mail (04:47) The Power of Reader Feedback (06:39) Rob’s Impact on Readers (08:06) How to Successfully Transition to Retirement (11:05) Finding Purpose in Retirement in Key (13:27) The Rise of Advice-Only Financial Planners (17:25) The Quality of Financial Advisors Has Increased Dramatically (22:55) Why Almost Everyone Needs a Financial Advisor Near Retirement (25:41) Pros and Cons of Advice Only Financial Planners (28:30) The Power of Paying Yourself First (29:17) Should You Ask ChatGPT Your Financial Questions? (33:37) Inflation and Economic Worries (35:02) Does CPI Accurately Reflect Inflation? (36:43) Mortgage Renewals and Financial Strain (37:59) Canada’s Dangerous Debt Levels (39:41) The K-Shaped Economy (41:09) The True Cost of Owning a Home (44:53)  Counting on Your Home for Retirement and the Realities of Downsizing (48:30) The High Costs of Aging in Place (50:09) Conclusion
• #47 — Amber Kanwar: Investing and the Active vs. Passive Debate 10.03.2026 55min

  Our guest this episode is Amber Kanwar, host of the “In the Money” Podcast and former BNN Bloomberg anchor who has spent over a decade covering financial markets and interviewing hundreds of portfolio managers, CEOs, political leaders and major newsmakers across North America. In this episode, Dave and Amber explore the world of investing and the ongoing debate between active and passive strategies. They discuss whether active managers can truly beat the market, whether retail investors should pay attention to the daily moves of the stock market and whether strategies like private equity are right for everyday Canadians.They also discuss why women remain underrepresented in finance, the differences in investing behaviour between men and women, and what lessons investors can learn from their mistakes. It’s a wide-ranging conversation filled with thoughtful insights on investing, markets and the future of the economy.   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Amber Kanwar (04:08) How Amber’s First-Ever Article Become Front Page News at The Globe and Mail (08:38) Leaving BNN Bloomberg to Start a Media Company (13:45) The Debate: Active vs. Passive Investing (19:38) Hard-Hitting Interviews and Past Performance Metrics (21:05) Is Private Equity a Good Investment for Retail Investors? (25:39) Learning From Investing Mistakes (27:30) Why Are Women Underrepresented in Finance? (28:30) Investing Differences Between Men and Women (on Average) (32:38) The Difficulty of Investing Based on Macro Forecasts (37:56) Outperformance in Small- and Mid-Cap Companies (40:46) AI and the Impending Loss of Entry-Level Jobs (43:04) Real Estate Trends (45:14) Regulation and Business Formation in Canada (48:14) Talent Retention Challenges for Canadian Businesses  (50:00) Could Passive Investing Break the Market? (54:58) Conclusion
• #46 — Gary Teelucksingh: Inheritances & How to Talk to Your Family About Legacy 03.03.2026 28min

  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
• #45 — Jon Flynn: Wow, The Canadian Housing Market Is Leaking And It Won't Stop Raining 24.02.2026 40min

  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
• #44 — Meagan Balaneski: Opportunities and Challenges in the Financial Planning Industry 17.02.2026 52min

  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
• #43 — Julia Chung: Human-Led Financial Planning 10.02.2026 58min

  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
• #42 — Jason Watt: The Financial Advice Landscape in Canada 03.02.2026 52min

  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
• #41 — Chris Guillebeau: How to Start a Side Hustle 27.01.2026 34min

  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
• #40 — Heather & Doug Boneparth: Managing Money Together in a Relationship 20.01.2026 42min

  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