#24 — Jamie Golombek: Tax and Estate Planning in Canada
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
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1:11:59
#23 — Aaron Hector: Optimizing Your Finances and Estate Planning
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
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48:28
#22 — Brian Scudamore: Building a $700M Business
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
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#21 — Ben Rabidoux: The State of Canada’s Real Estate Market
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
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#20 — Adam Bornn: Retirement Planning For Canadians
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
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.
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