Our guest this episode is Shannon Lee Simmons — Certified Financial Planner®, Chartered Investment Manager®, bestselling author, media personality and founder of the New School of Finance™. Shannon is widely recognized as a trailblazer in Canada’s fee-only financial planning movement and her latest book is “Making Bank,” a financial guide for teens. 

In this conversation, Dave and Shannon explore what real-world financial planning looks like for everyday Canadians. They dive into fee-only and modular financial planning, budgeting in real life, turning advice into action and how rising housing prices, down payments and “financial dysmorphia” are reshaping how Canadians think about money.

Whether you’re just getting started with your finances or feeling squeezed by today’s economic realities, this episode is full of perspective, practical advice and much-needed hope.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Shannon Lee Simmons

(02:22) Leaving Bay Street to Serve Everyday Canadians

(04:10) The Barter Babes Project

(08:01) Writing “Making Bank” for Teenagers

(11:59) What is Fee-Only Financial Planning?

(14:06) Modular Financial Planning for Real Life

(15:30) The Importance of Knowing How Much Money is Coming In and Going Out

(18:49) Who Typically Seeks Fee-Only Financial Planning?

(20:19) Turning Financial Advice Into Action

(22:26) Why Fee-Only Financial Planners Are Starting to Specialize

(25:58) Software vs. Spreadsheets

(26:55) Scaling a Fee-Only Practice

(28:43) Housing Prices are Squeezing Canada’s Middle Class

(32:15) More People Are Risking Their Own Retirement to Help Their Adult Children Financially

(34:33) Down Payments Squeeze All Other Savings

(36:20) Financial Dysmorphia and “Normal” Spending

(38:50) Hope is Your Biggest Asset 

(41:23) Real Estate Prices and Divorce

(43:03) Some Young People Are Still Doing Well Financially

(44:19) Retirement Planning is a Different Beast

(49:43) Reasons for Optimism and Hope

Our guest this episode is Melissa Leong — national media personality, a sought-after speaker and award-winning author of the feel-good finance guide “Happy Go Money.” Melissa has been the resident money expert on Canada’s leading daytime talk show “The Social” for 14 years and is also a repeat guest on “The Drew Barrymore Show” on CBS.

This is an amazing episode for anyone looking to better manage their money in 2026. In their conversation, Dave and Melissa explore the idea that money should support happiness, not compete with it. They dig into behavioural finance and simple “brain hacks” that can lead to better decisions, from the 24-hour rule for spending to the power of spending summaries. Melissa also shares insights on social media comparison, why experiences tend to bring more lasting happiness than stuff, the joy of anticipation, and why big purchases like cars so often fail to deliver long-term satisfaction.

The discussion also touches on generosity and happiness, valuing time over money, financial challenges women face, managing money as a couple, and practical ways to get started building healthier financial habits — without guilt or perfectionism.

Whether you’re trying to spend more intentionally in the new year, stress less about money, or align your finances with what actually makes you happy, this is a thoughtful and refreshing conversation you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Melissa Leong

(02:09) Melissa’s Path from Journalism to Money

(05:42) Behavioural Finance & Brain Hacks

(09:32) The 24-Hour Rule for Spending

(14:16) Social Media & The Pressures of Comparison

(16:41) Money Should Support Happiness, Not Compete With It

(18:56) Spending Now vs. Spending Later

(22:39) Experiences Create More Lasting Happiness Than Stuff

(24:12) The Joy of Anticipation

(30:29) Dave Doesn’t Have FOMO, He Has FOBI

(32:07) The Power of Spending Summaries

(36:16) Charity, Generosity & Joy

(39:17) Valuing Time Over Money

(40:31) Why Cars Rarely Deliver Lasting Happiness

(43:32) How Melissa Became a Regular on The Drew Barrymore Show

(45:11) Financial Challenges Women Face

(51:22) Managing Money as a Couple

(56:43) How to Get Started Managing Your Money Well

(59:01) Conclusion

Our guest this episode is Shaun Maslyk — a practicing Certified Financial Planner® and Certified Financial Behavior Specialist® who blends financial planning with positive psychology to help people understand their money stories and flourish beyond their finances. Shaun holds a master’s degree in positive psychology from the University of East London, where his research focused on the relationship between money, behaviour change and human happiness.

In this conversation, Dave and Shaun explore what the research really says about money and happiness — from whether happier people make better financial decisions to why more money doesn’t always lead to more joy. They unpack concepts like hedonic adaptation, the “arrival fallacy” of wealth and the unconscious money scripts that quietly shape our spending, saving and relationships. Shaun also challenges the idea that financial success is purely about optimization, making the case for peace of mind, values-based decisions and “sailing to the right island” in life.

If you’ve ever wondered whether you’re chasing the wrong financial goals — or how to make money decisions that actually improve your well-being — this episode is full of thought-provoking insights and practical takeaways.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Shaun Maslyk

(03:39) Do Happier People Make Better Money Decisions?

(05:25) Research on Money, Happiness & Hedonic Adaptation

(11:45) The Arrival Fallacy of Wealth

(13:22) Money Stories & Unconscious Scripts

(16:17) How Money Scripts Affect Relationships

(20:51) Peace of Mind vs. Mathematical Optimization

(24:42) Do Walkers Have Better Financial Behaviour?

(26:57) Spending Summaries

(28:44) Make Sure You’re Sailing to the Right Island

(31:51) The Three Questions That Clarify Money Decisions

(35:43) Spending on Experiences vs. Possessions

(39:55) Too Much Luxury Can Reduce Joy

(41:02) What Would You Do If You Only Had 24 Hours to Live?

(43:10) Conclusion

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

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

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

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

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

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

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