Our guest this episode is Jamie Golombek—Managing Director of Tax & Estate Planning at CIBC and a widely respected voice in the Canadian financial industry. Jamie is a frequent guest on BNN, CTV and CBC’s The National, and in 2023 was awarded the prestigious CPA Fellow designation.

In this episode, Dave and Jamie dive deep into the world of tax and estate planning in Canada. They cover everything from RRSPs and FHSAs to the most tax-efficient ways to donate to charity. Jamie shares practical advice on how to think about your tax return (hint: a big refund isn’t a good thing), how to avoid common estate planning mistakes and why keeping a net worth statement with your will might be one of the smartest moves you can make.

Whether you’re saving for retirement, thinking about gifting an early inheritance or just want to better understand Canada’s tax system, this episode is filled with insights, tips and examples every Canadian can learn from.

Show Notes

(00:00:00) Intro & Disclaimer

(00:00:55) Intro to Jamie Golombek

(00:03:43) What is Tax Planning and Estate Planning?

(00:08:17) You Shouldn’t Want a Large Tax Refund

(00:13:53) Employer Matching is a Fantastic Deal

(00:17:49) Registered Accounts in Canada 

(00:22:32) FHSAs are Incredible

(00:24:26) RRSPs and the Advantages of Tax-Free Investing

(00:27:00) Tax on RRSPs and Investments

(00:31:02) Our Tax System is Unfair for Single People

(00:33:25) The Most Tax-Efficient Way to Donate to Charity

(00:39:25) Tax Deductions if You Work From Home

(00:41:37) Changing the Principal Residence Exemption in Canada

(00:45:21) Joint Powers of Attorney for Personal Care

(00:48:01) Cottages and Estate Planning

(00:49:32) The Importance of Keeping a Net Worth Statement with Your Will

(00:52:02) Would Dave or Jamie Ever Be an Executor?

(00:53:18) Corporate Executors 

(00:55:42) How to Avoid Family Fights with The Estate Items

(00:59:38) Early Inheritance Gifts

(01:02:58) Probate Fees

(01:06:01) Beware of Joint Ownership with Your Kids

(01:08:20) Conclusion

Our guest this episode is Aaron Hector—Founding Partner of TIER Wealth, President of the Institute of Advanced Financial Planners and a fellow personal-finance nerd like Dave.

In this episode, Dave and Aaron explore some of the most overlooked opportunities in Canadian financial and estate planning. From optimizing RESP withdrawals to gifting tax deductions to your kids, Aaron shares smart, actionable strategies that can help families build and preserve wealth more effectively. They also cover timely topics like when to defer RRSP or FHSA deductions, how to handle joint accounts, why every Canadian needs a will and the difference between a beneficiary and a successor holder.

Whether you’re just building your financial plan or revisiting it with an eye for tax efficiency, this episode is full of practical tips and clear explanations you can put to use.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Aaron Hector & TIER Wealth

(04:23) Detailed Optimizations in Financial Planning

(07:22) When Should You Defer FHSA or RRSP Tax Deductions?

(10:41) A FREE Strategy for Parents to Help Their Kids Buy a Home (Gifting a Tax Deduction)

(15:22) TFSA vs. RRSP

(17:13) RESP Lump-Sum vs. Gradual Contributions

(20:34) Optimal RESP Withdrawal Strategies

(26:45) A Simple—But Powerful—Estate Planning Exercise

(30:17) Joint Tenancy on Non-Registered Accounts

(32:01) Get a Will!

(34:44) What’s the Difference Between a Beneficiary and a Successor Holder?

(37:23) The Importance of Estate Planning

(39:10) Corporate Executors

(42:24) Tax Opportunities When the Stock Market Pulls Back

(44:49) Are More Grandparents Giving Money to Their Grandchildren?

(46:24) Conclusion

Our guest this episode is Brian Scudamore—founder and CEO of O2E Brands, the parent company of 1-800-GOT-JUNK, the world’s largest junk removal business. Brian started the company at just 18 years old after dropping out of high school, and has since built it into a $700 million empire.  Along the way, he’s expanded into other home service brands like WOW 1 DAY PAINTING and Shack Shine, and today is also a Dragon on CBC’s “Dragons’ Den.”

In this conversation, Brian joins Dave to share the story behind his entrepreneurial journey—from naming the company after a phone number to franchising it internationally to turning “ordinary” home services into premium, trusted brands. They dive into the lessons Brian learned while building the business, why he believes anyone can be an entrepreneur and how his grandfather’s advice on kindness continues to shape his leadership style. 

Whether you’re a budding entrepreneur or just curious how a scrappy Canadian startup turned into a household name, this episode is packed with insights and inspiration.

Show Notes

(00:00) Intro & Disclaimer

(00:57) Intro to Brian Scuadmore

(02:47) How Brian’s Grandparents Taught Him to Treat People Kindly

(04:23) 1-800-GOT-JUNK Today

(08:10) Brian’s New Brands

(09:26) Business Differences in Canada vs. the U.S.

(11:23) How Brian Started 1-800-GOT-JUNK

(13:54) Naming the Business a Phone Number

(15:32) Keys to Success in Home Services

(19:23) Successes and Failures of Growing Internationally 

(20:56) The Franchise Model

(23:54) Premium Pricing in the Service Industry

(26:55) Finding $400k in the Floorboards

(28:13) Business Formation in Canada

(30:31) Starting New Home Service Brands

(37:54) Dragons’ Den

(41:54) Anyone Can Be an Entrepreneur 

(42:45) The Future of Brian’s Businesses

(44:39) The Impact of Dragons’ Den

(47:52) Conclusion

Our guest this week is Ben Rabidoux—Founder of Edge Realty Analytics and North Cove Advisors and one of the most respected voices on Canadian housing and economics. In this episode, he joins Dave to tackle some of the biggest questions facing Canada’s real estate market today.

From the condo market crash to vacancy rates for rentals to the role of HELOCs and immigration policy, Ben explains how we got here, what’s coming next and what it all means for affordability in this country. He also shares the story of catching Fortress as a fraud and offers a candid take on whether Canada is too soft on white-collar crime.

If you care about housing, affordability or the future of Canada’s economy, this episode is a must-listen.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Ben Rabidoux

(02:19) Catching Fortress as a Fraud

(09:26) Is Canada Too Soft on White-Collar Crime?

(11:56) Are Rents Going to Come Down in Canada?

(15:12) How Much Do Home Prices Need to Drop to Become Affordable Again?

(16:33) The Condo Market is Hyper-Cyclical

(17:58) The Condo Market Crash

(24:34) Who Was Buying These Pre-Sale Condos?

(25:27) Where is This Condo Crisis Headed?

(28:18) The Impact HELOCs Have on Canada’s Economy

(32:51) Immigration and Its Impact on Canadian Real Estate

(38:47) A Challenge Our Government Faces Over Immigration

(41:01) The Impact of AI on Immigration Levels

(44:46) How Does Canada Fix Its Affordability Challenges?

(48:09) Conclusion

Our guest this episode is Adam Bornn—Founder and Managing Partner at Parallel Wealth, a Canadian financial planning firm that specializes in helping people retire with confidence. Adam also runs an educational YouTube channel (@ParallelWealth) with over 138,000 subscribers where he shares practical and approachable retirement advice for Canadians.

In this conversation, Dave and Adam dive deep into the world of retirement planning—from understanding the “Go-Go, Slow-Go, and No-Go” phases of retirement to managing taxes through RRSP meltdowns to whether you really need $1 million to retire. Adam shares why retirees need a financial plan, common mistakes people make and how strategies like delaying CPP, TFSAs and even reverse mortgages can play a role in a well-structured retirement.

If you’re planning for retirement—or even just starting to think about it—this episode is packed with insights, myths debunked and practical advice tailored to Canadian listeners.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Adam Bornn

(03:35) Why Did Adam Specialize in Retirement Planning?

(05:23) Why Retirees Need a Financial Plan

(10:45) The Go-Go, Slow-Go and No-Go Phases of Retirement

(11:57) What is an RRSP Meltdown?

(13:16)  Your Average Tax Rate Should Be Consistent Through Retirement

(14:38) OAS Clawback

(16:07) Do Reverse Mortgages Fit Into Retirement Plans?

(17:08) Annuities

(18:03) The “Die With Zero” Concept

(19:11) Building Generational Wealth

(20:44) People Underestimate How Long They’re Going to Live

(22:44) Single Retirees Are at a Massive Disadvantage

(23:57) When Does Whole Life Insurance Make Sense?

(25:57) Most Retirees Need Stocks in Their Portfolios

(27:33) Should You Plan for Large Late-Life Healthcare Costs?

(29:41) Pre-Retirees Should Do Their Research

(31:28) The Biggest Mistakes Adam Sees Retirees Make

(32:20) Myth: You Need $X Number to Retire

(33:01) TFSAs Add Flexibility for Retirees

(34:56) Conclusion

Our guest this week is Amanda Lang—longtime Canadian business journalist and host of Taking Stock, a weekly business news program on CTV, BNN Bloomberg and CP24.

In this episode, Dave and Amanda dive into the state of Canada’s economy from our productivity struggles and housing crisis to the US tariffs to whether the capital gains tax on real estate needs to change. They also unpack the profound impacts artificial intelligence is already having on the job market, the economy and business formation.

It’s a wide-ranging and thought-provoking episode you won’t want to miss!

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Amanda Lang

(02:48) Lang & O’Leary

(06:12) Canadian Productivity Growth & Losing Top Talent

(09:38) How Can We Solve Canada’s Housing Crisis?

(12:02) Should We Change the Capital Gains Tax on Real Estate?

(15:40) How AI is Going to Change Our Economy

(20:01) The Dangers of New Technology Being Used for Evil

(25:11) Professions at Risk From AI

(27:52) US Tariffs 

(30:32) Dave’s Biggest Worry: The US Debt

(36:39) Fewer Young People Are Starting Businesses

(42:16) The Changing Media Landscape

(44:30) Dave Has Only Been to ONE Concert in His Life

(46:24) Worried For Young People Today

(48:44) Can We Get Big Projects Done in Canada?

(51:36) Conclusion

Our guest this week is Bruce Sellery, CEO of Credit Canada—a non-profit credit counselling agency that’s helped millions of Canadians avoid bankruptcy, get out of debt and reclaim control of their financial lives.

In this episode, Bruce joins Dave to talk about the growing debt problem in Canada and the personal stories behind it. They dig into everything from credit scores to the rising cost of kids’ sports to the impact of divorce on your finances. Bruce also shares his own unique journey—leaving a corporate job to become a business journalist and help launch BNN, before becoming a financial educator with a bestselling book and podcast “Moolala.”

If you’ve ever felt overwhelmed by debt or just want to understand how credit counselling really works, this is a candid, insightful and engaging conversation you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Bruce Sellery

(03:37) Leaving a Corporate Career to Be a TV Reporter and Help Launch BNN

(07:06) Personal Finance vs. Business/Investing News

(09:05) How Bruce Developed His Communication Skills

(12:17) The Grace of a Well-Lived Life

(13:44) The Affordability Crisis in Canada

(16:04) What is Credit Canada?

(17:52) Credit Canada’s Non-Profit Structure

(22:12) What Happens if You Need to Claim Bankruptcy?

(23:30) How Do People Get Into Trouble with Debt?

(29:50) What Impacts Your Credit Score?

(32:28) The Housing-Affordability Crisis’s Impact on Debt Levels

(37:42) Divorce and Debt

(39:30) Kids’ Sports Have Become CRAZY Expensive

(43:56) Conclusion

Our guest this week is Jim Chuong—better known online as “The Lazy Canadian Investor.” With over 1 million followers across TikTok and Instagram, Jim has built a massive audience by breaking down investing concepts in a clear, no-BS way.

In this episode, Dave and Jim cover a wide range of investing topics—from how Jim first got into real estate investing to whether it still makes sense today. They dig into Jim’s philosophy on using leverage, his take on individual stocks vs. ETFs, and why he prefers US-only investing over global diversification. Jim also shares what motivates him to create content and how he approaches simplifying complex financial ideas for everyday Canadians.

If you’re curious about real estate, passive investing or just want to hear from someone who’s built a personal finance brand from scratch—this episode is packed with practical insights. 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jim Chuong

(01:44) How Jim Learned About Personal Finance

(06:52) Jim’s Early Investing Approach

(09:49) Getting Started with Real Estate Investing

(15:54) Is Real Estate Investing Still Attractive Today?

(20:34) The Toronto Real Estate Market

(22:12) Is Crypto An Investment?

(23:57) Jim’s Philosophy on Leverage and Investing

(25:49) Canada is a Wonderful Country 

(27:43) Parenting Teenagers

(29:12) Why Does Jim Make Content Online?

(33:15) US-Only Investing Versus Global Diversification

(36:43) Investing in Individual Stocks vs. Broad-Market ETFs

(39:56) Why Private-Market Investing Isn’t Well Suited for the Average Investor

(42:05) Conclusion

Our guest this week is Kelley Keehn—best-selling author, personal finance expert and media personality who is on a mission to help Canadians build healthier relationships with money.

In this episode, Dave sits down with Kelley to unpack some of the most pressing financial challenges people face today. From the emotional weight of debt to the psychological traps that make it so easy to overspend, Kelley brings both empathy and expertise to the table. They dive into why debt happens in the first place, practical strategies to get out of it and how to avoid the subtle (and not-so-subtle) pressures that push people to spend more than they should. Kelley also shares crucial tips on how to spot and prevent financial fraud in a world where scams are becoming increasingly sophisticated.

Whether you’re struggling with debt, trying to get a better handle on your spending or simply want to protect yourself from financial fraud, this episode is full of valuable insights.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Kelley Keehn

(03:57) The Crushing Weight of Debt 

(06:10) Strategies to Get Out of Debt

(08:31) Snowball vs. Avalanche Method

(10:41) Why Do People Get Into Debt?

(12:01) It’s So Easy to Spend Today

(14:23) Everybody Wants You to Spend

(17:24) Spending Summaries

(20:32) How Taking a Timeout Can Help You to Spend Purposely

(21:59) Credit Scores

(25:48) Pay Yourself First, But Revisit the Amount

(27:39) Are FHSAs Always Best?

(29:05) Don’t Chase Discounts on Things You Don’t Need

(32:39) Buying Used Can Come With Opportunity Costs

(34:17) How to Prevent Financial Fraud

(43:45) What’s The Worst Investment Kelley Has Ever Made?

(44:17) What’s The Smartest Investment Kelley Has Ever Made?

(45:39) Conclusion

Our guest this episode is the legendary Canadian comedian Gerry Dee! You know him as the creator and star of “Mr. D” and the host of “Family Feud Canada”—but did you know “The Wealthy Barber” is one of the five books he’s ever read?

In this 15ish minute episode, Gerry sits down with Dave to talk about the lessons he learned during his early career as a teacher, his leap into stand-up comedy, his big break with “Mr. D” and how all of those experiences shaped how he thinks about money.

Tune in for laughs, insights and a fun dose of nostalgia! 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Gerry Dee

(02:14) Gerry’s Early Life

(04:20) Gerry’s Career as a Comedian & Entrepreneur

(07:56) Lessons Learned From Gerry’s Athletic Background

(12:16) When Gerry’s Career Took Off

(13:43) The Story of Mr. D

(14:33) Gerry’s Investing Approach

(17:41) The Best Investment Gerry Ever Made

(18:17)  Does Gerry Follow The Wealthy Barber Principles?

(20:08) Conclusion