The Wealthy Barber Podcast

Our guest this episode is Brian Orlando — CPA and creator of the fast-growing Canadian personal finance account @CalmMoneyCoach. Brian has over 15 years of experience across accounting, finance and tech, before recently leaving the corporate world to pursue financial coaching full time. His mission is simple: reduce money stress and help people build plans they can actually stick to.

In this conversation, Dave and Brian explore why simplicity is often the most powerful strategy in personal finance — from automating savings and avoiding high-fee products to cutting through common misconceptions around RRSPs and investing. They also dive into real-world challenges Canadians are facing today, including the rising cost of living, lifestyle inflation and the pressure to “keep up.” Along the way, Brian shares practical insights on everything from the Smith Maneuver to employer RRSP matching, renting vs. buying, insurance decisions and how to make smarter financial choices in your 30s and beyond.

If you’re looking for straightforward, no-nonsense financial advice that actually works in the real world, this episode is packed with practical takeaways you can implement right away.

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Brian Orlando (The Calm Money Coach)

(02:26) Brian’s Background & Career Path

(05:37) How Brian Grew His Audience for Calm Money Coach

(07:55) Why Simplicity Beats Complexity in Investing

(11:03) Automating Savings & Paying Yourself First

(11:54) The Downside of Fintech Platforms & Expensive Investment Products

(13:52) The Rising Cost of Living & Financial Desperation

(16:10) The Smith Maneuver Explained

(23:08) Financial Advice for Canadians in Their 30s

(27:55) Canada is Lucky to Have Great Financial Educators

(29:59) RRSP Misconceptions & Tax Efficiency

(32:59) Getting Good Advice for Retirement is Financially and Emotionally Beneficial

(36:30) Will People Get Married in Retirement for the Tax Advantages?

(37:50) Rent vs. Buying a Home

(43:45) The FHSA & Its Triple Tax Advantage

(44:21) Term vs. Whole Life Insurance

(47:10) Employer Matching on Group RRSP & Fees

(49:46) Overspending on Cars & Lifestyle Inflation

(52:32) Conclusion

Our guest this episode is Moira Rose Váně — a full-time lawyer and Qualified Associate Financial Planner® who specializes in helping Canadian families save for their kids’ education through RESPs. 

In this conversation, Dave and Moira take a deep dive into everything you need to know about RESPs — from how they work to how to invest inside them to the often-overlooked pitfalls like high fees and estate planning risks when grandparents are involved. They also break down strategies for maximizing government grants, optimizing withdrawals and why family RESPs can be such a powerful tool. Along the way, Moira shares her perspective on passive investing, her unique career path as both a lawyer and financial planner and the financial planning challenges that disproportionately impact women.

Whether you’re a parent, grandparent or planning to have kids in the future, this episode is packed with clear, practical advice to help you make the most of RESPs and avoid costly mistakes.

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro Moira Rose Váně

(02:10) Being a Lawyer and a Financial Planner

(04:28) Why Moira is Focusing on RESPs

(07:27) RESP Basics: What Is It & How It Works

(10:33) How to Invest Inside Your RESP

(14:06) Index Funds & The Evidence for Passive Investing

(15:38) The Problem With Group RESPs

(16:43) Best Platforms for Self-Directed RESPs

(19:37) Getting Grandparents Involved in RESPs

(21:14) The Impact of Fees on RESPs

(22:19) Estate Planning Risks When Grandparents Are Subscribers

(24:19) How Taxes Work With RESPs

(27:35) Why Dave and Moira Like Family RESPs

(30:04) Withdrawing from Your RESP: Strategies & Common Mistakes

(32:21) Financial Planning Challenges Unique to Women

(38:26) Moira’s 12-Month Implementation Advice Model

(43:29) Conclusion

Our guest this episode is Doug Hoyes — Co-Founder of Hoyes Michalos, Licensed Insolvency Trustee and one of Canada’s leading experts on debt and personal insolvency. Doug has spent decades helping Canadians navigate financial hardship and is a passionate advocate for ensuring people understand their options and find the right path forward.

In this episode, Dave and Doug dive into the world of debt, bankruptcy and consumer proposals — what they are, how they work and when each option might make sense. They break down how Licensed Insolvency Trustees operate, how consumer proposals are negotiated and what actually happens if you file for bankruptcy (what you keep, what you lose and who typically ends up choosing each path). Doug also shares insights into why so many Canadians are struggling with debt today, from inflation and the “K-shaped” economy to mortgage renewals, rising vehicle costs and the financial impact of divorce.

The conversation also explores some of the lesser-discussed drivers of debt including gambling, travel spending and lifestyle creep, along with practical advice on when to seek help and why early action can make a significant difference. Doug brings decades of real-world experience to highlight common mistakes and what people can do to avoid them.

If you want a clear, practical understanding of debt and insight into the Canadian economy from someone with boots on the ground, this episode is packed with insights you won’t want to miss.

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Doug Hoyes

(01:51) Why Debt Education is So Important

(03:11) Inflation and the K-Shaped Economy

(07:29) Consumer Proposal vs. Bankruptcy Explained

(09:18) How the Trustee Negotiates Consumer Proposals

(10:37) Who Ends Up Filing Bankruptcy vs. Consumer Proposal?

(12:34) Who Should Talk to a Licensed Insolvency Trustee and When?

(17:03) If You Claim Bankruptcy, What Do You Lose vs. Keep?

(19:48) How Do People Get Into Trouble with Debt?

(24:02) Gambling's Role in Insolvency

(25:38) Historical Homeownership Rates Among Insolvency Clients

(27:02) Mortgage Resets and the Condo Crash

(29:56) Vehicles Can Be a Major Financial Trap

(32:54) Divorce and the Financial Cost of Separation

(34:53) Travel and Debt

(36:38) No One Cares About Your Money More Than You Do

(38:20) Rapid Fire Questions

(40:43) Conclusion

Our guest this episode is Ben Felix — Chief Investment Officer at PWL Capital, co-host of the Rational Reminder podcast and creator of one of the most respected investing YouTube channels, @BenFelixCSI. Ben is a returning guest from Episode #5, one of our most popular episodes to date.

In this episode, Dave and Ben go through a rapid-fire Q&A on some of the most important (and misunderstood) topics in investing. They cover everything from the biggest mistakes investors make to the difference between investing and gambling to why professional investors struggle to beat the market and common misconceptions about dividends. Ben and Dave also break down the flaws with covered call funds, market timing, and touch on other topics like annuities, crypto, homeownership, life insurance and all-in-one ETFs.

If you want clear, evidence-based answers to your biggest investing questions this is an episode you won’t want to miss. Tune in now on our website, YouTube, Apple Podcasts, Spotify and all other podcasting platforms!

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Ben Felix

(04:22) A Huge Investor Mistake: Not Owning Enough Equities 

(06:04) The Difference Between Investing and Gambling

(07:33) Increasing Your Income is One of the Best Things You Can Do for Your Personal Finances

(08:55) Dave and Ben’s Advice: Don’t Trade Options

(09:40) Why Professional Investors Struggle to Beat the Market

(13:40) Misunderstandings About Dividends

(16:11) Why Covered Call Funds Underperform Over the Long Run

(20:17) Even Experts Can’t Effectively Time the Market

(23:18) High Valuations and Expected Returns

(25:12) Behavioural Traps: Overconfidence and Pessimism

(27:31) The Role of Annuities in Retirement Planning

(32:03) Crypto and Prediction Markets

(35:21) Renting vs. Owning a Home

(38:56) The True Maintenance Costs of Home Ownership and “While We’re At It”

(40:46) Is Life Insurance a Good Investment Product?

(45:03) How Often Should You Check Your Portfolio?

(46:30) The Benefits of All-in-One Asset Allocation ETFs

(48:12) The Behaviour Gap in Investing

(48:53) The Positive Evolution of the Financial Advice Industry

(54:15) Conclusion

Our guest this episode is Ron Butler — owner of Butler Mortgage and a 30-year veteran of the Canadian mortgage brokerage industry. Ron returns as a repeat guest after being a fan favourite when he first joined us back in episode #8. He’s widely known for his blunt takes on the housing market through social media and the Angry Mortgage Podcast.

In this conversation, Dave and Ron tackle the current state of Canada’s housing and mortgage markets — from what Ron calls “the Ontario real estate disaster” to his outlook for real estate in 2026. They discuss the looming shortage of new single-family construction, whether municipalities will have to cut development fees and why housing prices remain so high relative to incomes. Ron also explains mortgage basics, why using a mortgage broker can matter, the hidden risks of co-signing a mortgage and the growing issue of homeowners sitting on mortgages with little or no equity.

They also explore several major trends shaping the market right now, including the huge wave of mortgage renewals coming in 2026, the rise of extended amortizations, questionable behaviour in the private mortgage market and why moving homes is often far more expensive than people realize. Along the way, Ron and Dave discuss their thoughts on inflation, job security, the future of real estate investors and even how AI could begin affecting white-collar employment.

If you want a candid, big-picture look at where Canada’s housing market might be headed, this episode is packed with insight, strong opinions and practical perspective.

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Ron Butler

(02:32) Real Estate Market Update: The Ontario Disaster

(03:36) Is a Real Estate Crash Good for Young Canadians?

(04:42) 2026 Real Estate Forecast

(05:36) The Looming Crisis of No New Single-Family Construction

(09:03) Do Municipalities Have to Cut Their Development Fees?

(11:45) Mortgage Basics

(13:17) The Impact of the War in the Middle East on Mortgage Rates

(15:51) Housing is Still Expensive Relative to Incomes

(18:25) Inflation and Its Impact on the Bottom 50% of Income Earners

(23:55) The Hidden Dangers of Co-Signing a Mortgage

(25:23) Underwater Mortgages With No Equity

(26:22) Why Should Someone Use a Mortgage Broker?

(28:40) 2026 Will Be the Biggest Year for Mortgage Renewals in Canadian History

(30:04) Are Many Canadians Extending Their Amortization

(31:24) The Vanishing Starter Home: Why We Only Build Big

(33:47) Private Mortgage Misbehaviour

(35:20) Moving is Way More Expensive Than People Realize

(37:03)  The Collapse of Rural Real Estate as Offices Call People Back

(38:47) Are Lenders Concerned About Job Security?

(39:52) Are Real Estate Investors Going to Come Back to the Market?

(42:37) How AI Is Already Cutting White Collar Hiring

(44:03) Conclusion