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 mistake of leaving registered accounts sitting in cash or GICs. Along the way, Brian shares how Calm Money Coach has evolved since his last visit, why basic cash flow management still matters most, how extreme spending on kids' sports can quietly derail savings goals and the peace of mind that comes from finally getting on top of your finances.
Whether you or someone in your family may qualify for an RDSP, or you simply want to understand a savings program that only a fraction of eligible Canadians are using, this episode is full of clear, practical guidance you can act on right away.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Brian Orlando
(02:33) The Making of Calm Money Coach
(06:52) Brian's Business Models
(09:06) Who Qualifies for an RDSP?
(12:57) Organizations That Offer RDSP Support
(13:53) RDSP Matching Rules
(16:10) The Canada Disability Savings Bond
(17:32) The 10-Year Look-Back Rule for Retroactive Grants
(20:07) Someone Should Become a Dedicated RDSP Specialist
(20:58) Prioritizing the RDSP Over an RRSP or TFSA
(24:15) How to Invest Inside the RDSP
(26:46) RDSPs Can Be Worth $90,000 in Government Grants and Bonds
(27:51) How the RDSP Affects Other Government Benefits
(28:54) How RDSPs Are Taxed
(29:48) The Costly Mistake of Leaving Registered Accounts Sitting in Cash or GICs
(32:13) Misunderstanding Around the 10-Year Clawback Rule on RDSP Withdrawals
(33:32) Why Basic Cash Flow Management Matters Most
(35:29) How Extreme Spending on Kids' Sports Derails Savings Goals
(36:39) Pay Yourself First
(38:11) How Getting on Top of Your Finances Brings Peace of Mind
(40:02) Conclusion

Our guest this episode is Julia Chung — CFP, FEA, TEP, Co-Founder and CEO of Spring Planning and Chair of the Financial Planning Association of Canada. Julia has worked in financial services since 1997 and has run an advice-only planning practice since 2011. She first joined Dave back on Episode #43 and returns for a second wide-ranging conversation.
In this episode, Dave and Julia dive into women and money: why young women are so hungry for financial education, what the research actually shows about female investors and why fewer women are entering the financial profession. They also cover how differences in life expectancy between men and women should shape a financial plan, and why cash flow management and simple spending summaries remain the foundation of good planning. Julia also challenges some of the conventional thinking around the great wealth transfer.
The conversation also explores what separates table-stakes service from what clients really need from an advisor, why Julia chose the advice-only model and how she is scaling that practice at Spring Planning. Along the way, Dave and Julia weigh in on whether affluent Canadians are leaving the country for tax reasons, why Dave adds 15% to insurance needs and whether a young planner can succeed without years of experience.
Whether you're a financial professional, a longtime listener or someone trying to get a better handle on your own money, this episode is full of candid, practical insights you won't want to miss.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Julia Chung
(02:49) Why Julia Gives Back to the Financial Planning Industry
(05:49) Why Young Women Are Hungry for Financial Education
(11:01) What the Research Shows About Female Investors
(14:23) Why Are Fewer Women Becoming Financial Professionals?
(17:33) Life Expectancy Differences Between Men and Women
(19:32) The Importance of Cash Flow Management & Spending Summaries
(27:15) Rethinking the Great Wealth Transfer
(32:49) Table Stakes vs. What Clients Really Need From Advisors
(35:25) Why Julia Chose the Advice-Only Model
(37:28) Scaling an Advice-Only Practice
(39:48) Are Affluent Canadians Moving Away for Tax Reasons?
(42:06) AI in Financial Planning & Confidentiality
(45:07) Insurance Needs: Why Dave Adds 15%
(50:55) Can a Young Planner Succeed Without Experience?
(53:02) Spring Planning
(54:09) Conclusion

Our guest this episode is Adam Chapman — Certified Financial Planner and founder of YESmoney, a London, Ontario practice built around helping Canadians spend with confidence in retirement. With nearly two decades in financial planning, Adam chairs the Estate Planners Council of London and is a founding member of the Financial Planning Association of Canada. He has spent his career helping retirees figure out what they actually want and start saying "yes" to their money.
In this episode, Dave and Adam dive into the practical side of retirement income planning, from paying yourself first in retirement to managing cash flow once the paycheques stop. Adam walks through his three retirement planning checkpoints, the real costs of long-term care versus in-home care and why guaranteed income floors matter more than ever. They also break down annuities in detail, including copycat annuities, piggyback annuities and how pairing them with delayed government benefits can take the sting out of inflation fears.
The conversation also explores the emotional side of money in later life, including the struggle many couples face when selling the family home and the psychology of spending in retirement, the subject of the book Adam is currently writing. 
Whether you're approaching retirement or already there and wondering how to spend without worry, this episode is full of practical, grounded advice from a planner who spends every day helping Canadians make the shift from saving to spending.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Adam Chapman
(02:08) What East Side Mario's Taught Adam About Business
(06:18) How to Pay Yourself First in Retirement
(08:22) Living in the Woods in Forest City
(09:37) Retirement Advice for Dave
(11:32) The Real Costs of Long-Term Care vs. In-Home Care
(13:06) Retirement Income Planning and Cash Flow Management
(16:40) Adam's Three Retirement Planning Checkpoints
(19:44) The Emotional Struggle of Selling the Family Home
(23:39) Writing a Book on the Psychology of Spending Money in Retirement
(27:28) Why Guaranteed Income Floors Matter More Than Ever
(29:50) Copycat Annuities
(32:31) Managing Inflation Fears with Annuities and Delayed Benefits
(37:18) Piggyback Annuities and Financial Peace of Mind
(39:55) Giving Living Legacies vs. Inheritances
(45:56) Die With Zero and Turning Money into Memories
(48:12) Conclusion

Our guest this episode is Daniel Foch — Chief Real Estate Officer at Valery, host of The Canadian Real Estate Investor Podcast and one of Canada's most-followed voices on housing data and market analysis. He first joined us back on Episode #35, and with so much having changed since then, we brought him back for a full update.
In this episode, Dave and Daniel dive into the current state of Canadian real estate, starting with where prices and sales actually sit in Ontario and BC today. They break down the Toronto condo crash and the supply crisis it has created, why unrealistic sellers are keeping the market stuck and whether rents are going to keep falling. They also cover how tariffs and AI could push unemployment higher and what that would mean for housing.
The conversation also explores the policy side of the picture, including CMHC's financing programs for rental developers, the government's housing incentives and why so many municipalities are now cutting development charges. Daniel explains why builders have stopped building small homes, lays out his concept of "houseflation" and shares his take on the biggest macroeconomic surprises of the year. Along the way, Dave and Daniel tackle whether downsizing baby boomers will flood the market, how immigration cuts are reshaping demand and how Daniel is using agentic AI to rebuild the way real estate businesses operate.
Whether you're a homeowner, a renter trying to decide when to buy or simply trying to make sense of where Canadian housing goes from here, this episode is full of data-driven insights and candid analysis you won't want to miss. 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Daniel Foch
(03:35) The Current State of Real Estate in Ontario and BC
(06:44) How Tariffs and AI Could Impact Unemployment
(11:22) Why Unrealistic Sellers Are Hurting the Market
(13:44) The Toronto Condo Market Crash and Supply Crisis
(16:20) CMHC's Financing for Rental Developers
(19:35) Are Rent Prices Going to Keep Falling?
(20:18) The Impact of the Government's Housing Policy Incentives
(22:53) Why Municipalities Are Cutting Development Charges
(26:51) Why Builders Don't Build Small Homes Anymore
(28:52) "Houseflation"
(35:10) The Biggest Macroeconomic Surprises of the Year
(38:53) Will Downsizing Baby Boomers Flood the Housing Market?
(41:33) How Immigration Cuts Impact Canadian Real Estate
(44:03) Using Agentic AI to Revolutionize Real Estate Businesses
(48:52) Conclusion

Our guest this episode is Ted Cadsby — former President and CEO of CIBC Securities, bestselling author and one of Canada's earliest champions of index investing. Ted brought index funds to CIBC in the late 1990s, wrote "The Power of Index Funds" to make the case to everyday Canadians and has since turned his attention to how people think, with books including "Closing the Mind Gap" and "Hard to Be Human."
In this episode, Dave and Ted dive into the case for index funds and the uphill battle Ted fought to bring them to the bank, including the clash with Wood Gundy brokers who saw indexing as a threat to their business. They break down why individual stocks are so hard to get right, how unknowable variables drive stock prices, whether "play money" accounts make sense and how Ted weights his own personal portfolio.
The conversation also explores how to evaluate active money managers, how to separate luck from skill in investment performance and what to make of private equity pitches (plus Dave's due diligence approach from his Dragon's Den days). Along the way, Ted shares insights from his work on the psychology of decision making: the dangers of oversimplification and overconfidence, why active managers stay so sure of themselves and how financial biases can quietly affect our happiness.
Whether you're a committed indexer or still wondering if you can beat the market, this episode offers a clear-eyed look at investing from someone who has seen both sides of the industry. 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Ted Cadsby
(02:16) A Disastrous Wealthy Barber Date
(03:22) Bringing Index Funds to CIBC
(05:52) The Clash With Wood Gundy Brokers
(09:15) Individual Stocks vs. Index Funds
(11:55) "Play Money" Accounts
(12:55) The Impact of Unknowable Variables on Individual Stocks
(15:34) Ted's Personal Portfolio Weights
(17:28) How to Evaluate Active Money Managers
(20:00) Luck vs. Skill in Investment Performance
(21:26) Private Equity Pitches
(24:36) Dave's Due Diligence Strategy on Dragon's Den
(27:23) The Psychology of Decision Making
(30:13) The Dangers of Oversimplification & Overconfidence
(35:03) Why Active Managers Stay Overconfident
(39:33) How Financial Biases Affect Happiness
(40:40) Money Should Be a Means to an End
(43:42) Conclusion

Our guest this episode is Jason Heath — Founder and Managing Director of Objective Financial Partners, one of Canada's largest advice-only financial planning firms. A Certified Financial Planner with more than 20 years in practice, Jason is a longtime personal finance columnist for the Financial Post and MoneySense and one of the country's most consistent voices for conflict-free financial advice. He last joined us on Episode #27 for Financial Planning 101, and this time the conversation looks ahead.
In this episode, Dave and Jason dive into where financial planning is headed. They explore the role of technology in democratizing planning, from financial planning software to the future of AI in financial advice, including a look at The Wealthy Barber's own AI planning tool. Along the way, Jason shares how often a plan should be updated, why implementation matters as much as the plan itself, how tax optimization gets trickier with corporate assets and why even financial professionals need advice. They close with the chronic gap in life and disability insurance and the secret behind Jason's famously calm demeanour.
Whether you're weighing the cost of an advice-only plan, curious how AI will change the way Canadians get financial guidance or simply want to make sure your retirement projections are realistic, this episode is full of clear, practical insights. 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Jason Heath
(02:49) Projected Rates of Return in Financial Planning
(05:06) Are Retirees Taking on More Investment Risk?
(06:10) The Danger of Forgetting Prolonged Market Downturns
(07:24) The Rarity of Average Stock Market Returns
(08:49) The Advice-Only Financial Industry
(11:07) Conflicts of Interest and Biases in Wealth Management
(13:50) The Evolution of Financial Planning
(15:30) Democratizing Financial Planning with Technology
(17:11) The True Cost and Value of an Advice-Only Financial Plan
(18:18) How Often Should You Update Your Financial Plan?
(21:00) Implementation and Financial Planning Through Conversation
(22:57) Why You Need a Solid Plan Before Retirement
(24:59) The Future of AI in Financial Advice
(29:17) Conquest Financial Planning Software
(32:06) Navigating Tax Optimization and Corporate Assets
(33:32) Even Financial Professionals Need Advice
(35:18) The Challenge of Asking AI the Right Financial Questions
(37:58) The Wealthy Barber's AI Tool for Financial Planning
(40:15) The Chronic Gap in Life and Disability Insurance
(43:18) Jason's Calm Demeanour
(45:45) Conclusion

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 I Die" binder. Along the way, Leanne shares her perspective on why you should talk to your beneficiaries while you still can, how to choose the right power of attorney for personal care and property, and the risks of naming co-powers of attorney.
Whether you're drafting your first will, updating an existing plan or have been named as someone's executor or power of attorney, this episode is full of clear, practical guidance to help you and your family avoid costly mistakes. 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Leanne Kaufman
(03:16) What Is Probate?
(06:06) Dave's Policy Idea for Probate Fees
(07:26) The Risks of Joint Accounts
(08:47) Supreme Court Rulings on Joint Accounts
(10:24) Gifting to Avoid Probate
(11:34) Why Do Inherited Cottages Cause So Much Family Friction?
(15:27) Capital Gains Tax on Family Cottages
(17:57) How Regular-Income Canadians Can Use Trusts
(22:36) Multi-Generational Planning with Trusts
(23:49) The Difference Between Formal and Informal Trusts
(25:10) The Tax Disadvantages of Trusts
(28:47) The Legal Obligations and Fiduciary Duties of a Trustee
(31:14) How Much Do Corporate Trustees Charge?
(32:41) The 21-Year Rule for Trusts
(34:21) What to Do Before Naming Someone as Your Executor
(36:23) Naming a Lawyer as Executor Is a Personal Appointment
(37:38) Think Through Your Beneficiary Designations
(39:27) The Importance of a "When I Die" Binder and What to Put In It
(43:50) Why You Should Talk to Your Beneficiaries Before You Die
(44:46) Hiring a Corporate Executor or Agency Service
(49:16) Choosing the Right Power of Attorney for Personal Care and Property
(53:18) The Risks of Naming Co-Powers of Attorney
(54:25) Conclusion 

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
(00:55) Intro to Jonathan Chevreau
(02:25) Jonathan Was Early to Criticize High-Cost Mutual Funds
(04:32) Jonathan's Semi-Retirement
(06:32) Handling the Pressure of Daily Writing Deadlines
(08:53) The 12 Best Years of Retirement & Travelling
(12:25) Exploring the Annuity Puzzle
(16:28) Home Affordability Challenges, FHSAs and the Bank of Mom and Dad
(20:39) Debating Downsizing Versus Aging in Place
(23:02) The Growing Strain on the Long-Term Care System
(24:55) Staying Active in Retirement
(27:04) Perspectives on Artificial Intelligence and the Job Market
(29:25) Sector ETFs vs. Index Funds
(30:48) Avoiding Crypto and NFT Investment Hype
(32:21) Long-Term Optimism for Canada's Economy
(33:28) Retaining Innovative Tech Talent and Funding in Canada
(35:03) Highlighting Outstanding Canadian Financial Educators
(37:47) Conclusion

Our guest this episode is Chad Wiebe — Certified Financial Planner and Founder of Pathway Wealth, a virtual, advice-only financial planning firm based in Winnipeg serving clients across Canada. 
In this episode, Dave and Chad take a deep dive into the fundamentals of retirement planning. They explore why so many retirees struggle to give themselves permission to spend, how to build a financial plan that accounts for spending shocks, and the massive potential costs of long-term care. Chad also breaks down the hidden benefits of downsizing your home, the factors to weigh when deciding how many more years to work, and the delicate task of telling a client they can't retire just yet.
The conversation also covers plenty of nuts-and-bolts strategy, including strategic RRIF withdrawals to smooth out your average tax rate, why the RRSP is still an outstanding vehicle for most people, whether everyone should delay CPP, and the tax disadvantages facing single seniors. Along the way, Chad shares his perspective on giving early inheritances to children, the assets you should consider selling before retiring, and the complexities of retiring with a corporate account.
Whether retirement is decades away or right around the corner, this episode is full of practical guidance to help you plan with confidence.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Chad Wiebe
(02:44) Why Chad Left K4 Financial to Start His Own Firm
(04:43) Scaling an Advice-Only Financial Planning Business
(06:06) The Value of Advice-Only Financial Planning
(07:16) Specializing in Deaccumulation and Retirement Planning
(10:00) Common Pre-Retirement Mistake: No TFSA
(12:05) The Permission Problem in Retirement
(14:15) Creating a Financial Plan with Spending Shocks
(19:22) Planning for the Massive Costs of Long-Term Care
(22:29) The Hidden Benefits of Downsizing Your Home in Retirement
(25:50) The Factors When Deciding How Many More Years to Work Before Retirement
(29:51) How to Tell a Client They Cannot Retire Yet
(31:49) The Risks and Rewards of Giving Early Inheritances to Children
(34:35) Strategic RRIF Withdrawals to Smooth Out Your Average Tax Rate
(39:09) Why the RRSP is Still an Outstanding Vehicle for Most People
(40:53) The Tax Disadvantages for Single Seniors
(43:24) Should Everyone Delay CPP?
(48:41) Assets You Should Sell Before Retiring
(50:32) The Complexities of Retiring with a Corporate Account
(53:10) Growing a YouTube Channel
(54:21) Conclusion

Our guest this episode is Mike Lipkin — motivational speaker, executive coach and founder of Environics/Lipkin, a Toronto-based research and motivation company. Mike has spoken to more than a million people across 43 countries, authored 18 books on leadership and high performance, and has built his career around helping people play at their best.
In this episode, Dave and Mike dive into what it takes to build a life of purpose in retirement, starting with the sobering statistics linking retirement and depression and why so many men in particular struggle once they stop working. They cover the habits that keep you energetic and fit as you age, including six daily practices that can extend your life span, the case for mini home workouts and the neuroscience behind why personal growth matters more than ever in your later years.
The conversation also gets personal. Mike opens up about his own battle with severe depression and how he rebuilt his life, shares inspiring stories of lifelong learning and choosing impact over comfort, and warns about the atrophy that can set in early in retirement if you don't stay involved. He also reflects on balancing travel and independence in marriage, his spectacular success investing in tech stocks, lessons from 44 years of marriage and a preview of his upcoming book.
Whether you're approaching retirement, already there or simply want to age with more energy and purpose, this episode is full of practical wisdom you can put to work right away. 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Mike Lipkin
(04:08) Retirement and Depression Statistics
(07:45) Staying High Energy and Fit as You Age
(09:39) Six Daily Habits to Extend Your Life Span
(12:08) The Benefits of Mini Home Workouts
(14:09) Mike's Story About Overcoming Depression and Rebuilding
(17:03) Why Men Struggle with Purpose in Retirement
(18:59) The Neuroscience of the Importance of Personal Growth in Retirement
(21:23) Staying in Shape as You Age
(23:29) Inspiring Stories of Lifelong Learning
(26:17) Impact Over Comfort
(28:06) The Danger of Atrophy in Early Retirement if You Don't Stay Involved
(31:44) Balancing Travel and Independence in Marriage
(33:53) Mike's Spectacular Success Investing in Tech Stocks
(39:51) Lessons From 44 Years of Marriage
(42:35) Mike's Upcoming Book
(45:21) Conclusion