The Wealthy Barber Podcast

#15 — Gerry Dee: Lessons Learned From Comedy, Athletics and “Mr. D” (15ish Minute Money)

Our guest this episode is the legendary Canadian comedian Gerry Dee! You know him as the creator and star of “Mr. D” and the host of “Family Feud Canada”—but did you know “The Wealthy Barber” is one of the five books he’s ever read?
In this 15ish minute episode, Gerry sits down with Dave to talk about the lessons he learned during his early career as a teacher, his leap into stand-up comedy, his big break with “Mr. D” and how all of those experiences shaped how he thinks about money.
Tune in for laughs, insights and a fun dose of nostalgia! 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Gerry Dee
(02:14) Gerry’s Early Life
(04:20) Gerry’s Career as a Comedian & Entrepreneur
(07:56) Lessons Learned From Gerry’s Athletic Background
(12:16) When Gerry’s Career Took Off
(13:43) The Story of Mr. D
(14:33) Gerry’s Investing Approach
(17:41) The Best Investment Gerry Ever Made
(18:17)  Does Gerry Follow The Wealthy Barber Principles?
(20:08) Conclusion

#14 — Office Hours #1 (Live Call-In Q&A)

Welcome to the very first “Office Hours” episode of The Wealthy Barber Podcast where Canadians call in with real financial questions and Dave Chilton offers guidance through his signature mix of wisdom, wit and practical advice.
From coast to coast, listeners asked about everything from budgeting for big home repairs to whether “Pay Yourself First” applies to before- or after-tax income to investing tips for those who got a later start and much, much more. No jargon, no fluff—just honest, helpful education from one of Canada’s most trusted voices in personal finance.
Don’t miss this candid, fast-paced and surprisingly fun Q&A session. Got a question of your own? Submit it through our website’s contact form or DM us on social media and you might be featured in the next “Office Hours” episode!
FILMED: April 1, 2025
Show Notes
(00:00) Intro & Disclaimer
(00:48) Best Investments for the Short-Term?
(03:18) Which Index Funds to Pick as a Passive Investor?
(06:47) Advice if You Started Investing Later in Life?
(11:13) Is “Pay Yourself First” Before or After Tax?
(14:26) How to Budget for Major Home Expenses?
(16:56) What Should You Look For in a Financial Advisor?
(19:58) Lump Sum vs. Dollar-Cost Averaging
(23:51) Is the 4% Rule Still Valid Today?
(28:51) Send Us Your Questions!

#13 — Mark Scheifele: The Wealthy Barber’s Impact on an NHL Star (15ish Minute Money)

Our guest this episode is Winnipeg Jets star Mark Scheifele! Mark was given a copy of “The Wealthy Barber” early in his career and it still influences the way he manages his finances today.
In this 15ish minute episode, Dave and Mark chat about Mark’s experience playing the NHL, what he likes to spend his money on, his approach to investing and, most importantly, Mark’s role on Dave’s fantasy hockey team.
Enjoy this quick episode with NHL star Mark Scheifele!
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Mark Scheifele
(01:26)  Mark and the Winnipeg Jets' Great Year
(04:01)  Dave's Fantasy Hockey Team
(04:41)  When Mark First Read "The Wealthy Barber”
(06:00)  What Does Mark Like to Spend Money On?
(07:10)  The Parallels Between Hockey and Golf
(09:45)  How Exciting Would it Be to Win the Stanley Cup in Winnipeg?
(10:25)  Mark's Investing Approach
(11:59)  Playing and Living in Winnipeg
(13:04) Conclusion

#12 — Mark McGrath: TFSAs vs. RRSPs (15ish Minute Money)

In our very first 15ish-minute episode, we cover a big question: TFSAs or RRSPs? To help answer it, we’ve got Mark McGrath—Associate Portfolio Manager at PWL Capital and co-host of the “Rational Reminder” podcast—who’s spent plenty of time looking at all of the pros and cons.
In this podcast, Mark and Dave break down key points including why RRSPs get a bad rap (but shouldn’t), how RRSP withdrawals can actually be tax-efficient and why a TFSA’s flexibility isn’t always an advantage. All that, and more, in a fast-paced, insight-packed episode.
Don’t miss this one—20 minutes could save you thousands in retirement savings! 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Mark McGrath
(02:27) TFSAs vs. RRSPs
(05:19) Comparing Tax on TFSAs vs. RRSPs
(09:09)  Why RRSP Withdrawals Can Often Be At a Lower Tax Rate
(14:53)  What if The Government Raises Taxes in the Future?
(17:31)  How the Canada Child Benefit (CCB) Changes the Math
(18:40)  TFSAs Are More Flexible—A Double-Edged Sword
(20:47) Conclusion

#11 — Robb Engen: Navigating Retirement and Advice-Only Financial Planning

Our guest this episode is Robb Engen—creator of the Canadian personal finance blog “Boomer & Echo” and advice-only financial planner based in Lethbridge, AB.
In this podcast, Dave and Robb discuss navigating retirement and the world of advice-only financial planning—what it is, why it’s not as common in Canada and Robb’s unconventional career path in finance. Much of the conversation has Robb sharing his expertise on retirement planning, covering everything from when to take your CPP to safe withdrawal rates to planning for big expenses and much more.
Whether you’re nearing retirement or just curious about fee-only financial planning, this episode is packed with insights you won’t want to miss!
Show Notes 
(00:00:00) Intro & Disclaimer
(00:00:55) Intro to Robb Engen
(00:06:39) What is Advice-Only Financial Planning
(00:12:26)  What Type of Clients Are Best for Advice-Only Planning
(00:17:09)  Why Isn't Advice-Only Planning More Popular in Canada
(00:19:17) Upsizing in Retirement
(00:21:04)  When Should You Take Your CPP?
(00:25:11) Spending in Retirement
(00:29:29) ​​ All-in-One ETFs
(00:30:56) Robo-Advisors Turning Into Speculative Investment Platforms
(00:35:01)  Safe Withdrawal Rates in Retirement
(00:37:47)  Planning for Large One-Time Expenses in Retirement
(00:42:57)  Giving Kids Money for a Down Payment
(00:44:02)  Housing Prices Are Unfair For The Younger Generation
(00:45:49) Postnups
(00:46:55)  Options for Accessing Your Home Equity in Retirement
(00:50:43)  Giving Money Away if You Have Enough for Retirement
(00:53:58) Life Insurance
(00:55:43) Grandparents Helping to Fund RESPs
(00:57:28) Robb’s Big Three Takeaways
(00:59:51)  You Just Retired… Now What?
(01:02:40)  Dave's Dad's "Solution" to Financial Planning
(01:03:46) Die With Zero
(01:04:48) Conclusion

#10 — Arlene Dickinson: Dragons’ Den, Her Early Career Struggles & The Current Economic Climate

Our guest this episode is none other than Arlene Dickinson—famed businesswoman, investor, author and the longest-serving Dragon on CBC’s "Dragons’ Den." 
In this episode, Dave and Arlene reminisce about their time on "Dragons’ Den" together and chat about everything from Arlene’s early career struggles to the potential US tariffs to the current economic climate for Canadian entrepreneurs and much, much more.
Don’t miss this fantastic episode! 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Arlene Dickenson
(02:46) Dragons’ Den
(04:26)  Handling Online Criticism
(08:21) Arlene’s Early Career Struggles
(16:13) How Did Arlene Become a Dragon?
(19:46) Reflecting on the Impact of Dragons’ Den 
(22:14)  Two Lessons Arlene Taught Dave
(24:24)  The Time Arlene Accidentally Got Drunk on Dragons' Den
(25:53) The Current Economic Climate for Canadian Entrepreneurs
(30:03) Potential US Tariffs
(33:48) Younger Canadians Are Frustrated
(36:08) Taxes & Government Spending in Canada
(37:56)  How Do We Build Up the Canadian Entrepreneur Ecosystem?
(42:46) The Impact of AI
(47:12)  Arlene's Closing Message for the Audience

#9 — Dan Bortolotti: Index Investing, ETFs and Financial Planning

We’re joined this episode by Dan Bortolotti—Portfolio Manager at PWL Capital, creator of the hugely popular “Canadian Couch Potato” blog, author of “Reboot Your Portfolio: 9 Steps to Successful Investing with ETFs” and co-host of the “Rational Reminder” podcast.
In this episode, Dan and Dave dive deep into index investing, covering everything from active vs. passive investing styles to tips for DIY investors, asset allocation strategies, the pros and cons of all-in-one ETFs in Canada and much more. There’s a lot to unpack, but Dan and Dave make it all easy to understand.
This episode is a must-listen for anyone serious about DIY investing—tune in now!
 
Show Notes
(00:00:00) Intro & Disclaimer
(00:00:55) Intro to Dan Bortolotti
(00:02:04) The Origins of the “Canadian Couch Potato”
(00:06:56) What is an Index Fund
(00:08:52) Why Don't Most Active Managers Outperform the Market?
(00:15:12) How Dave's Dad Can Beat Professional Money Managers
(00:16:57) Group Retirement Plans
(00:19:25) Mutual Fund Underperformance
(00:22:42) Should People Speculate with 5-10% of Their Portfolio?
(00:26:31) The Financial-Planning-First Model
(00:33:42) How to Construct An Index-Fund Portfolio
(00:35:52) Risk Tolerance and Asset Allocation
(00:42:50) When Stocks & Bonds Both Went Down
(00:44:56) What Goes Into a Financial Plan?
(00:46:34) Get Life Insurance!
(00:47:59) There is No "Optimal" Financial Plan
(00:49:52) When to Take CPP
(00:51:21) The Risks of Helping Kids/Grandkids with Down Payments
(00:53:52) All-in-One ETFs
(00:58:16) Withholding Taxes on US Stocks
(01:02:27) Online Investment Platform Recommendations
(01:04:26) Conclusion

#8 — Ron Butler: Real Estate, Mortgages and The Housing-Affordability Crisis

Our guest this episode is Ron Butler—a 30-year veteran of the mortgage industry and owner of Butler Mortgage. Some of you may recognize Ron from his social media rants or his “Angry Mortgage Podcast” where he uses colourful language and profanity to express his opinions (and share his wisdom!) on the world of real estate and mortgages. 
In this episode, Dave and Ron discuss all things real estate including the pros/cons of using a mortgage broker, where they think interest rates are headed, whether people should use fixed- or variable-rate mortgages and much, much more. 
Enjoy this entertaining and insightful episode.
Show Notes
00:00 – Intro & Disclaimer
00:57 – Intro to Ron Butler
03:20 – Pros/Cons of Using a Mortgage Broker
05:29 – Canada vs. USA Use of Mortgage Brokers
08:19 –  Where Ron Thinks Interest Rates Are Headed
09:47 –  Divergence Between Haves vs. Have-Not
11:48 – Fixed vs. Variable Mortgage Rates
13:54 – Parents Helping with Down Payments
18:02 –  The Financialization of Housing
20:07 – Where Are Housing Prices Headed?
25:51 – The Small-Condo Market
30:09 – 30-Year Amortizations
32:10 – High Transaction Costs in Real Estate
34:46 – Renovations
39:37 – Big vs. Small Homes
43:23 – High Housing Costs Causing People to Leave Canada
46:10 –  The Housing-Affordability Crisis
51:42 – Rapid-Fire Questions
57:16 – An F-Bomb-Filled Ron Rant
59:03 – Conclusion

#7 — Richard Coffin (The Plain Bagel): "Finfluencers" and Behavioural Finance

Our guest this episode is Richard Coffin—better known to many as "The Plain Bagel." Richard is a CFA and CFP professional working as a Portfolio Manager in Ottawa. He has nearly 1 million subscribers on his YouTube channel where he creates entertaining and educational videos on finance, investing and economics.
In this episode, Dave and Richard discuss the rise of "Finfluencers" in today’s social-media-driven world and explore the fascinating landscape of behavioural finance. They cover everything from the origins of “The Plain Bagel,” to the pros and cons of getting financial advice online, to the biases that affect us all and much, much more. 
Enjoy this fantastic episode featuring two of Canada’s top financial educators.
Show Notes
00:00:00 – Intro & Disclaimer
00:00:55 – Intro to Richard Coffin
00:03:28 – Origin of “The Plain Bagel”
00:08:13 – Richard’s Work & Educational Background
00:12:13 – The Rise of Finfluencers
00:16:34 –   The Laws Around Giving Financial Advice Online
00:20:14 –  How to Evaluate Online Financial Advice
00:21:24 – Trusting Finfluencers More than Wall Street
00:25:20 – The “Beginner” Finfluencer
00:28:58 – Investing Courses
00:38:42 – Trustworthy Canadian Finfluencers
00:44:41 – It’s Easy to Fake Wealth Online
00:47:57 –  YouTubers Being Paid to Promote Stocks
00:55:27 – Behavioural Finance & Loss Aversion
01:02:56 – Confirmation Bias
01:06:35 –  The Skills Behind Creating Content People Enjoy Watching
01:08:46 – Recency Bias
01:13:41 – Framing Bias
01:19:02 – Conclusion

#6 — Barry Choi: Credit Cards and Loyalty Points—How to Get the Most Value

Our guest this episode is Barry Choi, the ultimate expert on all things credit card points and loyalty programs in Canada. You may also know him from his frequent TV appearances or his personal finance website www.moneywehave.com.
In this episode Dave asks Barry everything Canadians need to know about credit card points and loyalty programs including which programs offer the most lucrative sign-up bonuses, tips for how to maximize the value of your points, which card is best for travel and much, much more. 
This is a highly informative episode and you’ll be sure to take away a few valuable tips by listening.
 
Show Notes
00:00 – Intro & Disclaimer
00:56 – Intro to Barry Choi
03:02 – Loyalty Programs and Data
06:35 – Learn a Few Programs Inside Out
08:51 – Transferring Points to Increase Value
10:47 – Credit Card Points as an Employee Benefit
12:04 – Tips to Maximize Points
14:39 – How to Optimize Points for Travel
17:12 – Which Credit Card is Right for You
18:56 – Sign-Up Bonuses
22:16 – Dave’s Reservations About Credit Cards
25:32 – High-Income Canadians with Credit-Card Balances
28:01 – Barry’s Spending
30:02 – When Barry Took His Family to Hong Kong
34:09 – American Express
37:37 – Dave Doesn't Use Airport Lounges
38:26 – Non-Point Benefits
41:20 – The Lifecycle of a Fintech Company
42:25 – Consumerism & Stuff
45:49 – Donating Loyalty Points
46:58 – Fraud with Loyalty Points
48:37 – Conclusion