Lessons on Kindness and Business from Dragon's Den

What if the most impactful financial advice isn’t about picking the right investment—but about understanding human behaviour, simplifying your life, and laughing along the way? In this episode of the Rational Reminder podcast, we’re joined by none other than David Chilton, author of the legendary personal finance book The Wealthy Barber. David shares insights from decades of experience helping Canadians improve their financial well-being through simplicity, frugality, and clarity. We dig into the enduring lessons of his 1989 classic, why the new edition took even longer to write, and what’s changed (and what hasn’t) in the personal finance landscape. From his views on insurance and home ownership to the psychology of spending, his entertaining yet practical approach makes complex ideas feel surprisingly accessible. We also explore the challenges of dollar-cost averaging, the role of financial advisors, and what it really costs to own a home. And yes, you’ll also hear how his mom helped launch Canada’s most successful cookbook series.

Key Points From This Episode:

(0:20) Introducing David Chilton and his impact on the PWL team

(3:22) Why Dave believes the original Wealthy Barber still holds up

(6:44) His enduring belief in term life insurance and investing the difference

(8:08) What he got wrong: mutual funds, high fees, and underestimating behavioural traps

(11:16) How the book’s success changed his life—and what stayed the same

(13:32) The unexpected tipping point that drove its breakout popularity

(15:13) Why he wrote The Wealthy Barber Returns after a long break

(16:41) What excites him most about the new revision and who it’s for

(18:29) His kids, Rob Carrick, and the housing crisis: why now was the time

(20:13) Transitioning to videos and podcasts to reach modern audiences

(22:41) The best part of being “The Wealthy Barber”—and what he’s learned from readers

(25:34) The surprising volume of portfolios people send him—and why he still reviews them

(27:12) What decades of portfolio analysis taught him about investor underperformance

(32:50) On lump sum vs. dollar-cost averaging—and the role of psychology

(37:52) Should you pay down debt or invest? Dave’s practical framework

(39:49) What a good financial advisor should (and shouldn’t) do

(43:08) The hidden costs of homeownership—and why people underestimate them

(48:29) Misleading conclusions about wealth, university, and home ownership

(50:40) The biggest home ownership mistakes people make

(52:24) Writing the new Wealthy Barber at the same card table

(53:25) Should you pay back the Home Buyer’s Plan early? Dave says no—and here’s why

(55:52) Why small optimizations—like minimizing RRSP fees—can really add up

(56:55) Spending rises with home size—and the real trap of lifestyle creep

(57:05) The most important financial variable of all: saving (and not borrowing too much)

Links From Today’s Episode: Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p

Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.

Rational Reminder Website — https://rationalreminder.ca/ 

Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/

Rational Reminder on X — https://x.com/RationalRemind

Rational Reminder on TikTok — www.tiktok.com/@rationalreminder

Rational Reminder on YouTube — https://www.youtube.com/channel/

Rational Reminder Email — info@rationalreminder.ca Benjamin Felix — https://pwlcapital.com/our-team/

Benjamin on X — https://x.com/benjaminwfelix

Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/

Dan Bortolotti — https://pwlcapital.com/our-team/

Dan Bortolotti on LinkedIn — https://ca.linkedin.com/in/dan-bortolotti-8a482310

Cameron Passmore — https://pwlcapital.com/our-team/

Cameron on X — https://x.com/CameronPassmore

Cameron on LinkedIn — https://www.linkedin.com/in/cameronpassmore/

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)