The Wealthy Barber Podcast

Our guest this episode is Jamie Golombek — Managing Director of Tax & Estate Planning at CIBC Private Wealth and one of Canada's most trusted voices on personal tax. A CPA, CFP and CLU, Jamie has written a weekly tax column for the Financial Post for close to 25 years and is a regular on BNN, CTV and CBC. He's back for his second appearance on the show as a fan favourite his first time around.

In this episode, Dave and Jamie dive into the tax mistakes that trip up Canadians and how to steer clear of them. They break down the harsh CRA penalties for accidental TFSA over-contributions, the foreign property reporting rules behind Form T1135, why you should always file your return on time and how the Alternative Minimum Tax actually works. Jamie also explains where the line falls between accountant negligence and taxpayer responsibility when an error ends up on your return.

The conversation also covers year-end tax-loss selling strategies, the difference between naming a successor holder and a beneficiary on your TFSA, why donating appreciated securities in-kind can eliminate capital gains tax and where corporately owned permanent life insurance fits into an estate plan. 

Whether you're trying to avoid a costly slip-up with the CRA or looking to tighten up your tax and estate planning before year-end, this episode is full of practical, expert-backed advice.

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jamie Golombek

(04:01) Automatic Tax Filing for Lower-Income Canadians

(07:05) Will the Government Change the TFSA and RRSP Rules?

(10:39) Why the OAS Clawback Is Justified

(12:36) Harsh CRA Penalties for Accidental Over-Contributions to Your TFSA

(16:44) Foreign Property Reporting Rules and Form T1135 Penalties

(21:06) Why You Should Always File Your Tax Return on Time

(22:59) How the Alternative Minimum Tax (AMT) Works

(28:26) Accountant Negligence vs. Taxpayer Responsibility for Errors

(30:25) Year-End Tax-Loss Selling Strategies

(35:10) TFSA Successor Holder vs. Beneficiary Explained

(37:40) Using a Net Worth Statement to Map Out Your Estate Plan

(39:56) Donating Appreciated Securities In-Kind to Eliminate Capital Gains Tax

(43:14) More People Are Simplifying Their Estate While Alive

(46:28) Corporately Owned Permanent Life Insurance for Estate Planning

(49:43) Conclusion

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