585 – Small Business: Mixing Personal and Business Debt Pros & Cons
Release Date: 11/15/2025
592 – The Wealthy Barber on Debt Free in 30: Financial Issues Canadians are Struggling with Most
Debt Free in 30
David Chilton, author of The Wealthy Barber and one of Canada’s most influential voices on personal finance, joins Doug Hoyes on Debt Free in 30 for an extra special double–long episode. Doug and David dig into the issues Canadians are struggling with most: the true cost of inflation, a “K-shaped” economy, housing affordability, rising student debt, the growing gap between financial knowledge and financial discipline, and more. 00:00 – David Chilton on the updated Wealthy Barber book 02:27 – Why storytelling works for personal finance (and how he tested it) 06:52 –...
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591 – Why Debt Is Rising, but Bankruptcies Aren’t (Yet) — and 2026 Insolvency Predictions for Canadians
Debt Free in 30
Debt is at record highs, yet insolvencies are flat. Why? In this episode of Debt Free in 30, Licensed Insolvency Trustees Doug Hoyes and Ted Michalos explain a financial paradox that’s leaving millions of Canadians stressed, exhausted, and confused. The answer isn’t that people are okay. It’s that people are enduring. If you’re paying your bills but still feel like you’re drowning, this episode is for you. Coming Up Next Next episode: a special double episode with David Chilton (The Wealthy Barber) — a practical conversation about money, debt, and what Canadians are really facing...
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590 – Will Your Investments Survive Serious Debt?
Debt Free in 30
If you’re carrying serious debt but also have money in an RRSP, TFSA, or other investments, one of the biggest fears is this: Will I lose everything if I get help? Doug Hoyes and Ted Michalos, Licensed Insolvency Trustees, break down what actually happens to your investments when debt becomes unmanageable. They explain which assets are protected under Canadian insolvency law, which are at risk, and when cashing out savings can do more long-term harm than good. (00:00) Debt and investments: will savings survive serious debt? (02:10) The fear of “losing everything” when seeking...
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589 – Debt Collectors Busier Than Ever? - What They Are Really Looking For from You
Debt Free in 30
Debt collectors are contacting Canadians more than ever. In this episode, Doug Hoyes and Ted Michalos explain why activity is increasing, what collectors are actually looking for, and how to respond without accidentally restarting the clock on old debts. They also cover how to spot scams, understand your rights, and know when it’s time to get professional help. Search the Ontario government’s website to verify that a collection agency is licensed (00:00) Why debt collectors are busier than ever (02:00) What’s driving higher delinquencies in Canada (04:10) When creditors...
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588 – Are You Financially Fit Enough to Invest?
Debt Free in 30
Start investing because your numbers say “go,” not because the internet says “now.” This episode will remove the guesswork from entering the world of investing and provide a straightforward way for you to judge your readiness. Using simple math in layman’s terms (think “why paying 20% interest beats chasing a maybe 10% return”), we discuss what to do first, how to keep bills safe from market swings, and when it makes sense to get professional help. (00:00) Welcome Charlie Kovacs from Hoyes Michalos (02:00) Do Canadians need to take big risks to get ahead? Myth vs. Reality...
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587 – Should Parents Help Adult Children with Debt?
Debt Free in 30
With housing costs, student loans, and everyday expenses skyrocketing, more young adults are turning to their parents for financial support. Doug Hoyes and Ted Michalos unpack the emotional, financial, and practical realities behind “helping” adult children, including why many parents feel compelled to assist, and break down the real risks of co-signing, lending money, or tapping home equity to solve a child’s debt issues. (00:00) How costs, debt, and housing pressures shape young adults’ expectations (03:10) Why parents feel compelled to help financially (06:20) When helping becomes...
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586 - Should You Use Your Home Equity to Pay Off Debt in This Market?
Debt Free in 30
Turn your home equity into a plan, not a panic button! This episode gives a clear, practical checklist for using a HELOC or second mortgage wisely: how they work, what they cost, when they help, and when alternatives (like a consumer proposal) will protect your cash flow and your home better. Listen first, then decide with the numbers. (00:00) Toronto condo stress and Welcome to Scott Terrio (05:00) What a HELOC is and how it works (07:30) Second mortgages: key risks (09:00) Home “value” is changing in this market (11:00) HELOC pitfalls and personal risk (15:30) Why many homeowners resist...
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585 – Small Business: Mixing Personal and Business Debt Pros & Cons
Debt Free in 30
Many Ontario small business owners use personal credit to get a venture off the ground, because banks rarely lend to brand-new businesses. That convenience can help with early cash-flow gaps and sometimes costs less than a high-risk business loan, but it also creates serious personal exposure: guarantees, blurred books, CRA headaches, and credit-score damage. Doug and Ted walk through when using personal debt might make sense, the major risks to watch for, and practical ways to structure your finances. (00:00) Self-employment: Opportunity vs. Necessity (02:00) Capital-Intensive vs. Lean...
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584 – Top Mistakes Debtors Make and How to Avoid Them
Debt Free in 30
Drawing on experience from 25+ years and 73,000+ filings, Doug and Ted break down the top debt mistakes Canadians make, and how to avoid them. They explain how problems creep up, why waiting narrows your options, high-cost credit and payday-loan cycles, CRA’s real collection powers, and so much more. Canada-specific guidance for debtors with tips on protecting your long-term financial health. (00:00) How debt mistakes happen (02:00) Spotting debt problems early (04:30) Waiting too long is costly: interest, stress, fewer options (06:30) Choosing the right help: Licensed Insolvency Trustees...
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583 – Job Loss: What to Do Financially in Your First 30 Days
Debt Free in 30
Laid off or let go? Your first 30 days matter. This is a practical, Canada-specific guide to unemployment, covering everything from applying for EI to discussing when upskilling or a pivot makes sense, as well as the risks of jumping into self-employment and how to handle debt while unemployed. If you’re currently employed, treat this episode as a readiness checklist to ensure you feel prepared and confident about whatever comes next. (00:00) Why the first 30 days of unemployment matter (02:00) Day-one checklist: severance, benefits, documents (05:30) EI basics: ROE, timing with severance,...
info_outlineMany Ontario small business owners use personal credit to get a venture off the ground, because banks rarely lend to brand-new businesses. That convenience can help with early cash-flow gaps and sometimes costs less than a high-risk business loan, but it also creates serious personal exposure: guarantees, blurred books, CRA headaches, and credit-score damage. Doug and Ted walk through when using personal debt might make sense, the major risks to watch for, and practical ways to structure your finances.
(00:00) Self-employment: Opportunity vs. Necessity
(02:00) Capital-Intensive vs. Lean Start-Ups (with examples)
(04:00) Why banks don’t fund brand-new businesses and what “collateral” means
(06:30) Pro #1- Easier access to credit for start-ups
(08:00) Pro #2 - Cash flow and other short-term advantages
(09:30) Con #1- Personal liability: when business failure becomes personal insolvency
(12:00) Con #2 - Blurred finances: bookkeeping pitfalls, CRA risk, and collection stress
(14:00) Con #3 - Credit-score impact: utilization and missed-payment damage
(16:00) Best practices and tips
(19:00) The three roles every small business owner needs
Debt Traps of Buying a Business with David Barnett – Debt Free in 30
Bad Funding Choices for Small Businesses with David Barnett – Debt Free in 30
Want to Buy a Business? Here’s What to Know First – Debt Free in 30
Starting or Buying A Business Out of Necessity – Debt Free in 30
DIY Free Credit Repair Course
Sign Up for the Monthly Debt Free Digest
Hoyes Michalos YouTube Channel
Learn About Debt Relief Options in Ontario
Disclaimer:
The information provided in the Debt Free in 30 Podcast is for entertainment and informational purposes only and is not intended as personal financial advice. Individual financial situations vary and may require personal guidance from a financial professional. The views expressed in this episode do not necessarily reflect the opinions of Hoyes, Michalos & Associates, or any other affiliated organizations. We do not endorse or guarantee the effectiveness of any specific financial institutions, strategies, or digital tools/apps discussed.