#30 — Preet Banerjee Interviews Dave: The Incredible Story Behind "The Wealthy Barber" and Its Update
SPECIAL EPISODE: To commemorate the launch of the fully updated “The Wealthy Barber,” we’re doing a very special episode this week where Dave is the guest on his own podcast!
We brought back fan favourite and financial-educator extraordinaire, Preet Banerjee, to host the conversation and turn the tables on Dave. Together, they dive into the stories behind “The Wealthy Barber” — from why Dave first wrote the book and how it was tested, to his early days shipping copies with his mom and the moment he realized his life was about to change forever.
They also touch on his time on “Dragons’ Den,” the pressure (and fun) of updating the book for a new generation, the behind-the-scenes team that helped make it happen, and even a few lighter topics — like Dave’s love of A&W, black nibs and eating every meal out.
It’s a funny, nostalgic and inspiring look at one of Canada’s most beloved financial voices and the incredible journey behind one of the bestselling books in Canadian history.
Show Notes
(00:00) Intro & Disclaimer
(00:55) A Special Episode
(03:23) Why Dave Wrote the Original “The Wealthy Barber”
(06:11) How Important Testing is For Dave’s Books
(10:32) Dave’s Goal Was to Sell 10,000 Copies
(12:31) Dave’s Life in 1989
(14:15) Dave and His Mom Fulfilled Orders at First
(17:49) When Dave Realized His Life Was Going to Change Forever
(20:52) Becoming a Reluctant Publishing Consultant
(24:16) Dragons’ Den
(30:16) The Pressure of Updating “The Wealthy Barber”
(33:19) Preet’s Review of the New Book
(35:57) The Team Behind The Wealthy Barber Podcast and Socials
(39:30) Who is The Wealthy Barber’s Barber?
(40:25) Benefitting From Having Kids in the Book’s Target Market
(41:38) Dave Eats Every Meal Out
(45:36) Dave’s Love of A&W and Black Nibs
(47:11) A Day in the Life of The Wealthy Barber
(48:27) Who is the Updated “The Wealthy Barber” For?
(51:55) Conclusion
--------
54:55
--------
54:55
#29 — Jason Pereira: The Evolution of Financial Advice in Canada
Our guest this episode is Jason Pereira — Senior Partner & Financial Planner at Woodgate Financial and one of Canada’s most prolific voices in the financial planning industry.
Jason has spent over two decades immersed in the world of financial planning — earning nine professional designations, contributing to hundreds of articles and podcasts and becoming a trusted expert on everything from practice management to fintech to insurance strategy.
In this wide-ranging conversation, Dave and Jason explore the evolution of financial advice in Canada including how it compares globally, why many Canadians still have blind trust in big institutions and what younger advisors are doing differently. They also dig into some of the thorniest financial planning topics: over- and under-insurance, capital gains at death, intergenerational wealth transfers, life insurance for children, rental real estate in 2025 and much, much more.
Jason doesn’t hold back — sharing candid insights on the gaps in Canada’s advisory landscape and how consumers can better navigate the system. Whether you’re a new investor or just someone trying to make smart decisions with your money, this episode is packed with thought-provoking ideas and practical takeaways.
Show Notes
(00:00:00) Intro & Disclaimer
(00:00:55) Intro to Jason Pereira
(00:02:13) The Different Ways to Pay for Financial Advice
(00:05:26) How Does Canada’s Financial Advisory Industry Compare to Other Parts of the World?
(00:10:52) Young Advisors Want To Do More Financial Planning
(00:12:57) Canadians Have Misguided Trust in Large Financial Institutions
(00:16:17) Jason Thinks People Are Being Sold Too Much Insurance They Don’t Need
(00:19:06) Term vs. Cash Value Insurance
(00:21:27) Using Insurance to Cover Large Capital Gains Taxes
(00:25:25) Passing On Cottages Can Cause Much Family Friction
(00:26:45) Corporate Executors
(00:29:37) Many Young Canadians Don’t Have Enough Life Insurance
(00:34:50) How Much Life Insurance Do You Need?
(00:41:20) Buying Life Insurance on Young Children
(00:44:54) It’s So Hard to Max Out All of Your Registered Accounts
(00:46:23) AI and Financial Planning
(00:52:59) Rental Real Estate in 2025
(00:55:32) Any Risks with the Rise of Passive Investing?
(00:58:13) Parents Are Gifting More Money
(01:00:39) When Financial Advisor Fees Are Worth It
(01:04:10) Conclusion
--------
1:04:48
--------
1:04:48
#28 — Dave Chilton on The Rational Reminder Podcast
We’re doing something a little different this week! Instead of posting one of our usual episodes, we’re sharing a recent conversation Dave had on "The Rational Reminder Podcast" — one that resonated deeply with listeners.
The feedback on this episode was overwhelmingly positive, with many saying it offered timeless insights, humour and refreshingly practical advice. So, we wanted to make sure our audience didn’t miss it.
Enjoy this special replay of “The Rational Reminder Podcast” featuring Dave Chilton, and we’ll be back next week with a brand-new regular episode.
Show Notes
(00:00:00) Intro
(00:03:50) Introducing Dave Chilton
(00:06:16) What wisdom from the first print of Dave's book, The Wealthy Barber, still holds true today
(00:08:50) If someone read that first print today, the advice Dave would tell them to ignore
(00:12:10) How the success of that first book changed Dave's life
(00:17:55) The sections or topics in Dave's forthcoming book that he is most excited to share with the world
(00:21:29) How (and why) is Dave using other media like videos and podcasts to connect with his audience
(00:27:14) How often individual investors send Dave their portfolios looking for feedback
(00:34:48) How Dave thinks investors should decide between lump sum vs. dollar cost averaging when someone has a big pile of cash to invest
(00:39:50) How Dave tells people to think through whether it makes sense to invest or pay off debt
(00:41:53) The role Dave sees for financial advisors in people's lives
(00:45:28) The number of people who have shared the full details of their home purchases, ongoing costs, and eventual sales with Dave
(00:52:59) The biggest mistakes people make with respect to homeownership
(00:55:51) How Dave thinks people should approach repaying their Home Buyer’s Plan RRSP withdrawals
(01:02:18) What people can do to save more
(01:06:15) The spending categories Dave finds people are most surprised by when they tabulate their spending
(01:11:18) What “good savers” splurge on, based on Dave's experience reviewing people's budgets
(01:19:49) How people can avoid the effects of upward social comparison making them want perpetually more stuff
(01:24:31) Dave's biggest lessons learned from being a Dragon on Dragon's Den
(01:31:12) Dave defines success in his life
--------
1:35:48
--------
1:35:48
#27 — Jason Heath: Financial Planning 101
Our guest this episode is Jason Heath—Managing Director at Objective Financial Partners and one of Canada’s most respected fee-only/advice-only financial planners.
In this episode, Dave and Jason cover the foundations of financial planning in Canada, tackling hot-button topics like RRSPs vs. TFSAs, reverse mortgages, annuities, CPP/OAS timing, insurance planning, estate-planning pitfalls and more. They also discuss how to prioritize financial goals, avoid common mistakes and build a plan that actually works in the real world.
Whether you’re planning for retirement, building your financial future or just want a clearer understanding of how all the pieces fit together, this episode is a masterclass in financial planning.
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Jason Heath
(03:00) The Rising Cost of Living in Canada
(05:00) The Pros and Cons of Getting Financial Information from Finfluencers
(10:06) Investing vs. Financial Planning
(12:47) Objective Financial Partner’s Clients and Services
(15:10) Estate Planning
(18:41) Reverse Mortgages Get a Bad Rap
(21:04) Use Cases for Annuities
(24:24) People Don’t Want to Listen to the Experts and Defer CPP and OAS
(25:31) TFSAs vs. RRSPs
(27:54) Decumulation Planning for Retirees
(33:01) Disability Insurance
(35:29) Life Insurance
(40:04) Gifting Money to Kids
(41:52) Estate Planning Mistakes
(44:24) The Importance of Prioritization in Financial Planning
(49:34) Financial Education and Finding Balance
--------
51:43
--------
51:43
#26 — Steve Saretsky: Canadian Real Estate—CRAZY Times Have Led to CRAZY Times
Our guest this episode is Steve Saretsky—a top 1% realtor in Vancouver and the host of one of Canada’s most popular real estate YouTube channels and the podcast “The Loonie Hour.”
In this wide-ranging conversation, Dave and Steve explore the current state and uncertain future of Canada’s real estate market. They talk about the collapse of the condo market, cancelled development projects, rising risk for lenders and whether sellers are finally starting to accept reality. Steve also shares his insights on affordability challenges, the impact of immigration, which markets still offer value and why detached homes remain the dream for many Canadians.
If you’re trying to make sense of the Canadian housing market—whether you’re a buyer, seller, investor, or just a curious observer—this episode offers a candid, data-driven and often surprising look at where things stand.
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Steve Saretsky
(03:06) The Collapse of Canada’s Condo Market
(06:45) Where Are Real Estate Prices Headed?
(10:08) Are Real Estate Developers and Lenders in Trouble?
(14:38) Layoffs at Real Estate Development Companies
(17:01) Lend and Pretend
(19:00) Cancelled Development Project in Vancouver
(21:15) What Caused the Crazy Real Estate Market in 2021?
(24:46) Are Sellers Being Too Stubborn?
(26:50) First-Time Homebuyers Can’t Move Up
(30:49) The Impact of Immigration on the Real Estate Market
(32:40) Most People Still Want a Detached Home
(39:02) Which Markets Are Still Affordable in Canada?
(41:44) Landlord Challenges & Investing Across Provinces
(48:49) The Cottage Real Estate Market
(50:56) Policy Changes to Fix the Canadian Real Estate Market
(53:45) Land Costs Drive All Prices Up
(56:01) Conclusion
The Wealthy Barber Podcast is Canada’s go-to source for approachable, entertaining, and free financial education. Hosted by none other than David Chilton—former Dragon on CBC’s ”Dragons’ Den” and the best-selling author of ”The Wealthy Barber” and ”The Wealthy Barber Returns”—this podcast is here to help Canadians manage their money better. Much better.Dave Chilton has spent over 35 years demystifying personal finance, offering understandable, unbiased, and actionable advice that has empowered millions of Canadians to achieve their financial goals. Now, he’s bringing that same wisdom to your favourite podcasting platforms, with regular episodes designed to make personal finance simple, relatable, and yes, even entertaining.Episodes of The Wealthy Barber Podcast features Dave in conversation with expert guests from across the spectrum of Canadian personal finance. From investing and real estate to taxes, RESPs, and even money psychology, no topic is off-limits. Plus, don’t miss our special “Office Hours” episodes, where Dave answers real questions from audience members, delivering informed, balanced, and sometimes downright funny advice.Follow for Canadian personal finance made simple.
Canada - english