The Wealthy Barber Podcast

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