The Wealthy Barber Podcast

#36 — Aravind Sithamparapillai: Financial Planning Tips from a CFP® Gold Medalist

Our guest this episode is Aravind Sithamparapillai, a financial planner at Ironwood Wealth Management Group. Earlier this year, Aravind earned his CFP® designation with the highest exam score in the country, placing him at the top of the CFP® Exam President’s List, and was also selected for FP Canada’s Emerging Leader’s Award.
In this conversation, Dave and Aravind walk through what great financial planning actually looks like in practice. They discuss the “financial quarterback” model, Aravind's four-step process for investing and why assessing true risk tolerance goes far beyond a simple questionnaire. Aravind explains how biology and financial stress affect investor behaviour, why unusually high returns are unlikely to last forever and how personal preferences should factor into a well-designed plan.
The episode also dives into estate and tax planning topics that are often overlooked—from common estate planning mistakes and the risks of joint accounts to when RRSPs should be left to an estate, how taxes work at death and traps grandparents can fall into with RESPs. The conversation wraps up with a practical comparison of TFSAs vs. RRSPs, a discussion on alternative investments and Aravind’s personal story about discovering The Wealthy Barber.
Whether you’re building your first financial plan or refining an existing one, this episode is packed with clear, thoughtful insights from one of Canada’s brightest young planners. 
 
Show Notes
(00:00) Intro and Disclaimer
(00:55) Intro to Aravind Sithamparapillai
(04:47) ​​The Financial “Quarterback” Model
(10:32) The Four-Step Investing Process
(14:38) How Do You Assess True Risk Tolerance?
(16:47) A Financial Planner’s Role in Changing Risk Tolerance
(19:04) Biology and Financial Stress
(21:38) 20% Returns (Probably) Won’t Go On Forever
(23:30) Personal Preferences & Maximizing Return
(25:05) Common Estate Planning Mistakes
(26:50) Reasons Why RRSPs Should Be Left to the Estate
(31:47) The Risks of Using Joint Accounts to Avoid Probate
(34:44) The Benefits of Leaving a Letter of Direction with Your Will
(36:43) What Happens Tax-Wise When You Die?
(38:26) The RESP Trap for Grandparents
(45:00) TFSA vs. RRSP
(49:09) The Risks of Alternative Investments
(56:13) Aravind’s Personal Story About The Wealthy Barber
(58:45) Conclusion

#35 — Daniel Foch: The State of the Canadian Real Estate Market

Our guest this episode is Daniel Foch, a Canadian real estate broker, co-host of “The Canadian Real Estate Investor” podcast and Chief Real Estate Officer at Valery.ca. Daniel creates widely-followed content at the intersection of data, news and insights for the Canadian housing market.
In this conversation, Dave and Daniel tackle the big questions facing the real estate market today. They discuss the Ontario government’s move to take over RECO, whether realtors should be able to represent both sides of a deal, and the evolving role of municipalities, development charges and zoning in housing affordability. Daniel shares his perspective on where the market goes from here, why most Canadians still want a detached home and what it will take to make those homes more affordable.
The conversation ranges far beyond prices, touching on the challenges of an aging population, mortgage stress tests and why older generations are staying “overhoused.” There’s also a fascinating discussion about the impact of AI, First Nations’ land claims and the rise in Powers of Sale.
If you’re interested in the state of Canadian real estate — from policy to affordability to where things might be headed — this episode is full of insights you won’t want to miss.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Daniel Foch
(05:06) Ontario Government Taking Over RECO
(07:57) Should Realtors Be Able to Represent Both Sides of a Deal?
(10:36) Housing Affordability and the Role of Government
(16:30) Should Municipalities Lower Their Development Charges?
(18:00) Where Does the Real Estate Market Go From Here?
(20:56) Most Canadians Still Want a Detached Home
(23:15) Owning vs. Renting
(26:25) How Do We Make Detached Homes More Affordable?
(28:40) Older Generations Are Overhoused But Not Downsizing
(34:07) Mortgage Stress Tests
(38:42) Daniel Thinks Municipal Governments Could Go Away
(40:13) The Potential Impact of AI on Societies
(41:54) First Nations’ Land Claims in Canada  
(44:31) Bill 60
(46:47) Valery AI
(50:15) Increasing Powers of Sale
(54:57) Conclusion

#34 — Morgan Housel: Timeless Lessons From “The Psychology of Money” & “The Art of Spending”

Our guest this episode is Morgan Housel, international bestselling author of “The Psychology of Money,” “Same as Ever” and his newest book, “The Art of Spending Money.”
In this conversation, Dave and Morgan explore the timeless principles that shape how we think about money, happiness and decision-making. Morgan shares the story behind writing “The Psychology of Money,” why earning more didn’t change his life as much as he expected and why he believes money is “the greatest show on Earth.” They dig into core ideas like why firsthand experiences are more persuasive than data, why “no one’s crazy” and how comfort (not speed) is often the real goal in personal finance.
The discussion also covers the emotional side of money — from spending mistakes and regrets to what Morgan actually enjoys spending on — along with big-picture themes like luck, independence, volatility and how to think in terms of what’s reasonable rather than purely rational.
If you’re fascinated by human behaviour, personal finance or simply want to make better decisions with your money, this episode is packed with thoughtful insights and memorable lessons from one of today’s most influential financial thinkers. 
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Morgan Housel
(03:01) The Story of Writing “The Psychology of Money”
(07:37) How Making More Money Changed Morgan’s Life (Spoiler: Not Much)
(09:56) Why Morgan Calls Money "The Greatest Show on Earth"
(11:25) Nothing is More Persuasive Than What You’ve Experienced Firsthand
(13:42) “No One’s Crazy”
(17:16) You Can Either Make the Train Twice as Fast or Twice as Comfortable
(19:33) Was There Pressure Writing a Follow-Up Book?
(21:26) Nobody is Paying as Much Attention to You as You Are
(23:32) Volatility is the Price of Admission in Investing
(26:05) Buying Independence vs. Buying Expensive Things
(29:12) Spending Mistakes vs. Regrets
(32:17) What Does Morgan Like to Spend Money On? 
(35:08) The Role of Luck in Our Lives
(40:33) Reasonable vs. Rational in Personal Finance
(43:21) The Most Overrated Financial Advice 
(44:48) Conclusion

#33 — John Y. Campbell: Why the Financial System is Broken and How to Fix It

Our guest this week is John Y. Campbell — a globally respected Harvard economist and one of the most influential voices in academic financial economics. Over his career, John has published more than 100 academic papers spanning fixed-income markets, equity valuation, portfolio theory and household finance.
 
John’s newest book, “Fixed: Why Personal Finance Is Broken and How to Make It Work for Everyone,” makes a compelling case that the financial system — while vital — is failing ordinary people. Between unnecessary complexity, steep fees, confusing products and poor incentives, most households are left navigating a system that isn’t built with their best interests in mind. John draws on decades of research to explain what’s gone wrong and how better product design, smarter regulation and clearer advice could dramatically improve financial outcomes.
In this episode, Dave and John explore how the system can be fixed — from mandatory universal retirement accounts to simpler, standardized financial products, to improving disclosures on credit cards. They also discuss the pitfalls of active mutual funds, the challenges of financial advice models, the role of technology in impulse spending and the rise of gambling and meme-stock behaviour. It’s a wide-ranging and accessible conversation with one of the world’s top financial thinkers.
If you care about personal finance, financial policy or simply understanding why the system feels so confusing this episode is a must-listen.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to John Campbell and His Book “Fixed”
(05:14) How Should the Financial Industry be Fixed?
(09:30) Mandatory Universal Retirement Accounts
(12:52) Active Mutual Funds Have Costly Fees 
(15:48) The Different Models for Financial Advice
(18:37) How Standardized Financial Products Could Help
(21:07) Life Insurance and Complexity
(24:57) Two Thoughts on Debt
(26:21) Technology and Impulse Spending
(29:24) Gambling & Meme Stocks
(31:19) Policy Ideas to Fix the Financial System
(36:21) How Disclosures on Credit Cards Could Be Improved
(38:33) Conclusion

#32 — Leanne Kaufman: The Do’s and Don’ts of Estate Planning

Episode #32 is out now! Our guest this episode is Leanne Kaufman — President and CEO of RBC Royal Trust, the division of RBC that helps Canadians with estate, trust and incapacity planning/professional administration. Leanne is a lawyer by training and is extremely knowledgeable about all things estate planning in Canada.
In this conversation, Dave and Leanne dive deep into the fundamentals of estate planning — why every Canadian needs a will, the real cost of getting one and what qualities make for an ideal executor. They explore tricky questions like whether you should choose a family member as your executor, if co-executors are ever a good idea and why keeping a “When I Die” binder can spare your loved ones a world of stress.
From corporate executors to cottages (and the conflict they often create) to the risks of joint ownership and the scenarios where trusts actually make sense, this episode covers the most common estate-planning pitfalls Canadians face—and how to avoid them.
Whether you’re creating your first will or updating your entire estate plan, this episode is packed with practical advice, clear explanations and guidance every Canadian should hear.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Leanne Kaufman
(02:34) Why Everyone Needs a Will
(05:01) How Much Does it Cost to Get a Will?
(07:29) What Qualities Does an Ideal Executor Have?
(13:28) Should You Choose a Family Member as Your Executor?
(15:46) Co-Executors: Yay or Nay?
(18:06) The Importance of a “When I Die” Binder
(20:33) Should You Keep Old Wills?
(22:05) What is a Power of Attorney?
(26:52) Why Dave Doesn’t Like Co-Powers of Attorney for Personal Care
(28:39) When Do POAs Take Effect?
(30:56) Name Alternate Executors & POAs
(32:41) How to Make Sure Your POA Will Be Accepted
(34:46) Corporate Executors
(40:50) Cottages and Family Conflict
(44:26) Use Cases for Trusts
(47:28) The Dangers of Joint Ownership in Estate Planning
(50:39) Estate Planning is a Holistic Exercise
(54:00) Conclusion

#31 — Andrew Hallam: “Millionaire Teacher” and Finding Balance

Our guest this episode is Andrew Hallam—bestselling author of “Millionaire Teacher,” “Millionaire Expat” and “Balance.”
Andrew’s journey into personal finance started in an unlikely place: at 19 years old, he met a millionaire mechanic who taught him that building wealth isn’t about earning a high salary — it’s about making your money work harder than you do. Since then, Andrew has become one of the most respected voices in financial literacy, known for his practical and globally minded approach to investing and life.
In this conversation, Dave and Andrew discuss everything from the timeless principles of index investing and global diversification to the rise of robo-advisors and the pros and cons of real estate investing. Andrew also opens up about his nomadic lifestyle and shares lessons from his book Balance — on finding happiness, health, and purpose beyond the pursuit of money.
It’s an inspiring and insightful episode for anyone looking to build wealth and a better life.
 
Show Notes
(00:00) Intro & Disclaimer
(00:55) Intro to Andrew Hallam
(01:30) How Andrew First Learned About Finance
(03:13) How a Teacher Became a Bestselling Personal-Finance Author
(11:59) How one Key Review Led to Massive Sales
(15:16) Does the Millionaire Teacher Still Believe in Index Investing?
(17:57) All-in-One Asset-Allocation ETFs
(19:27) Chasing Active Outperformance
(23:27) Robo-Advisors vs. Asset-Allocation ETFs
(25:48) The Importance of Global Diversification
(29:29) Real Estate Investing
(32:23) Andrew’s Nomadic Lifestyle
(36:26) Finding Balance in Life
(42:17) What Changes Are Needed to The Financial Industry?
(47:28) Conclusion

#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

#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

#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

#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