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