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

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!

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

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

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

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

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

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