The Wealthy Barber Podcast

Our guest this episode is Brian Orlando — Halifax-based CPA and founder of Calm Money Coach, one of Canada's fastest-growing advice-only personal finance platforms. Brian first joined us on Episode #53 to make the case for keeping your finances simple, and he returns this time to tackle one of the most generous and least-used accounts in the country, the RDSP. In this episode, Dave and Brian take a deep dive into the Registered Disability Savings Plan (RDSP): who qualifies, how the government matching rules work, what the Canada Disability Savings Bond provides for lower-income families and how the 10-year look-back rule can unlock years of retroactive grants. They break down why an RDSP can be worth up to $90,000 in government grants and bonds, how to invest inside the plan and why it often deserves priority over an RRSP or TFSA. The conversation also explores how the RDSP interacts with other government benefits, how withdrawals are taxed, the widely misunderstood 10-year clawback rule and the costly…

Our guest this episode is Julia Chung — CFP, FEA, TEP, Co-Founder and CEO of Spring Planning and Chair of the Financial Planning Association of Canada. Julia has worked in financial services since 1997 and has run an advice-only planning practice since 2011. She first joined Dave back on Episode #43 and returns for a second wide-ranging conversation. In this episode, Dave and Julia dive into women and money: why young women are so hungry for financial education, what the research actually shows about female investors and why fewer women are entering the financial profession. They also cover how differences in life expectancy between men and women should shape a financial plan, and why cash flow management and simple spending summaries remain the foundation of good planning. Julia also challenges some of the conventional thinking around the great wealth transfer. The conversation also explores what separates table-stakes service from what clients really need from an advisor, why Julia chose the advice-only…

Our guest this episode is Adam Chapman — Certified Financial Planner and founder of YESmoney, a London, Ontario practice built around helping Canadians spend with confidence in retirement. With nearly two decades in financial planning, Adam chairs the Estate Planners Council of London and is a founding member of the Financial Planning Association of Canada. He has spent his career helping retirees figure out what they actually want and start saying "yes" to their money. In this episode, Dave and Adam dive into the practical side of retirement income planning, from paying yourself first in retirement to managing cash flow once the paycheques stop. Adam walks through his three retirement planning checkpoints, the real costs of long-term care versus in-home care and why guaranteed income floors matter more than ever. They also break down annuities in detail, including copycat annuities, piggyback annuities and how pairing them with delayed government benefits can take the sting out of inflation fears. The…

Our guest this episode is Daniel Foch — Chief Real Estate Officer at Valery, host of The Canadian Real Estate Investor Podcast and one of Canada's most-followed voices on housing data and market analysis. He first joined us back on Episode #35, and with so much having changed since then, we brought him back for a full update. In this episode, Dave and Daniel dive into the current state of Canadian real estate, starting with where prices and sales actually sit in Ontario and BC today. They break down the Toronto condo crash and the supply crisis it has created, why unrealistic sellers are keeping the market stuck and whether rents are going to keep falling. They also cover how tariffs and AI could push unemployment higher and what that would mean for housing. The conversation also explores the policy side of the picture, including CMHC's financing programs for rental developers, the government's housing incentives and why so many municipalities are now cutting development charges. Daniel explains why builders…

Our guest this episode is Ted Cadsby — former President and CEO of CIBC Securities, bestselling author and one of Canada's earliest champions of index investing. Ted brought index funds to CIBC in the late 1990s, wrote "The Power of Index Funds" to make the case to everyday Canadians and has since turned his attention to how people think, with books including "Closing the Mind Gap" and "Hard to Be Human." In this episode, Dave and Ted dive into the case for index funds and the uphill battle Ted fought to bring them to the bank, including the clash with Wood Gundy brokers who saw indexing as a threat to their business. They break down why individual stocks are so hard to get right, how unknowable variables drive stock prices, whether "play money" accounts make sense and how Ted weights his own personal portfolio. The conversation also explores how to evaluate active money managers, how to separate luck from skill in investment performance and what to make of private equity pitches (plus Dave's due diligence…

Our guest this episode is Jason Heath — Founder and Managing Director of Objective Financial Partners, one of Canada's largest advice-only financial planning firms. A Certified Financial Planner with more than 20 years in practice, Jason is a longtime personal finance columnist for the Financial Post and MoneySense and one of the country's most consistent voices for conflict-free financial advice. He last joined us on Episode #27 for Financial Planning 101, and this time the conversation looks ahead. In this episode, Dave and Jason dive into where financial planning is headed. They explore the role of technology in democratizing planning, from financial planning software to the future of AI in financial advice, including a look at The Wealthy Barber's own AI planning tool. Along the way, Jason shares how often a plan should be updated, why implementation matters as much as the plan itself, how tax optimization gets trickier with corporate assets and why even financial professionals need advice. They close…

Our guest this episode is Leanne Kaufman — President and CEO of RBC Royal Trust and one of Canada's leading voices on trust and estate planning. A lawyer by training, Leanne joined RBC Royal Trust in 1999 and has spent more than two decades helping Canadian families protect and transfer their wealth. She returns to the show after first joining us back in episode #32. In this episode, Dave and Leanne dive into the estate planning issues that trip up Canadian families most often. They break down what probate actually is, and the risks of using joint accounts and gifting to avoid it. Leanne also explains how regular-income Canadians can use trusts, covering formal vs. informal trusts, multi-generational planning, the tax disadvantages, the 21-year rule and the legal duties that come with being a trustee. The conversation also explores the practical side of getting your affairs in order, from what to do before naming someone as your executor to thinking through your beneficiary designations and building a "When…

Our guest this episode is Jonathan Chevreau — veteran personal finance journalist, author and founder of the Financial Independence Hub. Jonathan spent nearly two decades as the National Post's personal finance columnist, served as Editor-in-Chief of MoneySense and still writes the magazine's Retired Money column. In this episode, Dave and Jonathan dive into the lessons of a career spent covering Canadian money, from Jonathan's early years sounding the alarm on mutual fund fees to the discipline of filing a story a day for a national newspaper. They explore why Jonathan sees a paid-off house as the foundation of financial independence, what the "12 good years" of retirement are, and what it looks like to keep working on your own terms well past the traditional finish line. Whether you're planning your own path to financial independence or already living it, this episode offers a hard-won perspective from one of the most experienced voices in Canadian personal finance. Show Notes (00:00) Intro & Disclaimer…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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"…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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…

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,…

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…

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…

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…

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…

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…

Our guest this episode is Shannon Lee Simmons — Certified Financial Planner®, Chartered Investment Manager®, bestselling author, media personality and founder of the New School of Finance™. Shannon is widely recognized as a trailblazer in Canada’s fee-only financial planning movement and her latest book is “Making Bank,” a financial guide for teens. In this conversation, Dave and Shannon explore what real-world financial planning looks like for everyday Canadians. They dive into fee-only and modular financial planning, budgeting in real life, turning advice into action and how rising housing prices, down payments and “financial dysmorphia” are reshaping how Canadians think about money. Whether you’re just getting started with your finances or feeling squeezed by today’s economic realities, this episode is full of perspective, practical advice and much-needed hope. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Shannon Lee Simmons (02:22) Leaving Bay Street to Serve Everyday Canadians (04:10) The…

Our guest this episode is Melissa Leong — national media personality, a sought-after speaker and award-winning author of the feel-good finance guide “Happy Go Money.” Melissa has been the resident money expert on Canada’s leading daytime talk show “The Social” for 14 years and is also a repeat guest on “The Drew Barrymore Show” on CBS. This is an amazing episode for anyone looking to better manage their money in 2026. In their conversation, Dave and Melissa explore the idea that money should support happiness, not compete with it. They dig into behavioural finance and simple “brain hacks” that can lead to better decisions, from the 24-hour rule for spending to the power of spending summaries. Melissa also shares insights on social media comparison, why experiences tend to bring more lasting happiness than stuff, the joy of anticipation, and why big purchases like cars so often fail to deliver long-term satisfaction. The discussion also touches on generosity and happiness, valuing time over money, financial…

Our guest this episode is Shaun Maslyk — a practicing Certified Financial Planner® and Certified Financial Behavior Specialist® who blends financial planning with positive psychology to help people understand their money stories and flourish beyond their finances. Shaun holds a master’s degree in positive psychology from the University of East London, where his research focused on the relationship between money, behaviour change and human happiness. In this conversation, Dave and Shaun explore what the research really says about money and happiness — from whether happier people make better financial decisions to why more money doesn’t always lead to more joy. They unpack concepts like hedonic adaptation, the “arrival fallacy” of wealth and the unconscious money scripts that quietly shape our spending, saving and relationships. Shaun also challenges the idea that financial success is purely about optimization, making the case for peace of mind, values-based decisions and “sailing to the right island” in life.…

Our guest this episode is Aravind Sithamparapillai, a financial planner at Ironwood Wealth Management Group. Earlier this year, Aravind earned his CFP® designation with the highest exam score in the country, placing him at the top of the CFP® Exam President’s List, and was also selected for FP Canada’s Emerging Leader’s Award. In this conversation, Dave and Aravind walk through what great financial planning actually looks like in practice. They discuss the “financial quarterback” model, Aravind's four-step process for investing and why assessing true risk tolerance goes far beyond a simple questionnaire. Aravind explains how biology and financial stress affect investor behaviour, why unusually high returns are unlikely to last forever and how personal preferences should factor into a well-designed plan. The episode also dives into estate and tax planning topics that are often overlooked—from common estate planning mistakes and the risks of joint accounts to when RRSPs should be left to an estate, how taxes…

Our guest this episode is Daniel Foch, a Canadian real estate broker, co-host of “The Canadian Real Estate Investor” podcast and Chief Real Estate Officer at Valery.ca. Daniel creates widely-followed content at the intersection of data, news and insights for the Canadian housing market. In this conversation, Dave and Daniel tackle the big questions facing the real estate market today. They discuss the Ontario government’s move to take over RECO, whether realtors should be able to represent both sides of a deal, and the evolving role of municipalities, development charges and zoning in housing affordability. Daniel shares his perspective on where the market goes from here, why most Canadians still want a detached home and what it will take to make those homes more affordable. The conversation ranges far beyond prices, touching on the challenges of an aging population, mortgage stress tests and why older generations are staying “overhoused.” There’s also a fascinating discussion about the impact of AI, First…

Our guest this episode is Morgan Housel, international bestselling author of “The Psychology of Money,” “Same as Ever” and his newest book, “The Art of Spending Money.” In this conversation, Dave and Morgan explore the timeless principles that shape how we think about money, happiness and decision-making. Morgan shares the story behind writing “The Psychology of Money,” why earning more didn’t change his life as much as he expected and why he believes money is “the greatest show on Earth.” They dig into core ideas like why firsthand experiences are more persuasive than data, why “no one’s crazy” and how comfort (not speed) is often the real goal in personal finance. The discussion also covers the emotional side of money — from spending mistakes and regrets to what Morgan actually enjoys spending on — along with big-picture themes like luck, independence, volatility and how to think in terms of what’s reasonable rather than purely rational. If you’re fascinated by human behaviour, personal finance or simply…

Our guest this week is John Y. Campbell — a globally respected Harvard economist and one of the most influential voices in academic financial economics. Over his career, John has published more than 100 academic papers spanning fixed-income markets, equity valuation, portfolio theory and household finance. John’s newest book, “Fixed: Why Personal Finance Is Broken and How to Make It Work for Everyone,” makes a compelling case that the financial system — while vital — is failing ordinary people. Between unnecessary complexity, steep fees, confusing products and poor incentives, most households are left navigating a system that isn’t built with their best interests in mind. John draws on decades of research to explain what’s gone wrong and how better product design, smarter regulation and clearer advice could dramatically improve financial outcomes. In this episode, Dave and John explore how the system can be fixed — from mandatory universal retirement accounts to simpler, standardized financial products, to…

Episode #32 is out now! Our guest this episode is Leanne Kaufman — President and CEO of RBC Royal Trust, the division of RBC that helps Canadians with estate, trust and incapacity planning/professional administration. Leanne is a lawyer by training and is extremely knowledgeable about all things estate planning in Canada. In this conversation, Dave and Leanne dive deep into the fundamentals of estate planning — why every Canadian needs a will, the real cost of getting one and what qualities make for an ideal executor. They explore tricky questions like whether you should choose a family member as your executor, if co-executors are ever a good idea and why keeping a “When I Die” binder can spare your loved ones a world of stress. From corporate executors to cottages (and the conflict they often create) to the risks of joint ownership and the scenarios where trusts actually make sense, this episode covers the most common estate-planning pitfalls Canadians face—and how to avoid them. Whether you’re creating…

Our guest this episode is Andrew Hallam—bestselling author of “Millionaire Teacher,” “Millionaire Expat” and “Balance.” Andrew’s journey into personal finance started in an unlikely place: at 19 years old, he met a millionaire mechanic who taught him that building wealth isn’t about earning a high salary — it’s about making your money work harder than you do. Since then, Andrew has become one of the most respected voices in financial literacy, known for his practical and globally minded approach to investing and life. In this conversation, Dave and Andrew discuss everything from the timeless principles of index investing and global diversification to the rise of robo-advisors and the pros and cons of real estate investing. Andrew also opens up about his nomadic lifestyle and shares lessons from his book Balance — on finding happiness, health, and purpose beyond the pursuit of money. It’s an inspiring and insightful episode for anyone looking to build wealth and a better life. Show Notes (00:00) Intro &…

SPECIAL EPISODE: To commemorate the launch of the fully updated “The Wealthy Barber,” we’re doing a very special episode this week where Dave is the guest on his own podcast! We brought back fan favourite and financial-educator extraordinaire, Preet Banerjee, to host the conversation and turn the tables on Dave. Together, they dive into the stories behind “The Wealthy Barber” — from why Dave first wrote the book and how it was tested, to his early days shipping copies with his mom and the moment he realized his life was about to change forever. They also touch on his time on “Dragons’ Den,” the pressure (and fun) of updating the book for a new generation, the behind-the-scenes team that helped make it happen, and even a few lighter topics — like Dave’s love of A&W, black nibs and eating every meal out. It’s a funny, nostalgic and inspiring look at one of Canada’s most beloved financial voices and the incredible journey behind one of the bestselling books in Canadian history. Show Notes (00:00) Intro &…

Our guest this episode is Jason Pereira — Senior Partner & Financial Planner at Woodgate Financial and one of Canada’s most prolific voices in the financial planning industry. Jason has spent over two decades immersed in the world of financial planning — earning nine professional designations, contributing to hundreds of articles and podcasts and becoming a trusted expert on everything from practice management to fintech to insurance strategy. In this wide-ranging conversation, Dave and Jason explore the evolution of financial advice in Canada including how it compares globally, why many Canadians still have blind trust in big institutions and what younger advisors are doing differently. They also dig into some of the thorniest financial planning topics: over- and under-insurance, capital gains at death, intergenerational wealth transfers, life insurance for children, rental real estate in 2025 and much, much more. Jason doesn’t hold back — sharing candid insights on the gaps in Canada’s advisory landscape…