Our guest this episode is Amber Kanwar, host of the “In the Money” Podcast and former BNN Bloomberg anchor who has spent over a decade covering financial markets and interviewing hundreds of portfolio managers, CEOs, political leaders and major newsmakers across North America.

In this episode, Dave and Amber explore the world of investing and the ongoing debate between active and passive strategies. They discuss whether active managers can truly beat the market, whether retail investors should pay attention to the daily moves of the stock market and whether strategies like private equity are right for everyday Canadians.They also discuss why women remain underrepresented in finance, the differences in investing behaviour between men and women, and what lessons investors can learn from their mistakes.

It’s a wide-ranging conversation filled with thoughtful insights on investing, markets and the future of the economy.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Amber Kanwar

(04:08) How Amber’s First-Ever Article Become Front Page News at The Globe and Mail

(08:38) Leaving BNN Bloomberg to Start a Media Company

(13:45) The Debate: Active vs. Passive Investing

(19:38) Hard-Hitting Interviews and Past Performance Metrics

(21:05) Is Private Equity a Good Investment for Retail Investors?

(25:39) Learning From Investing Mistakes

(27:30) Why Are Women Underrepresented in Finance?

(28:30) Investing Differences Between Men and Women (on Average)

(32:38) The Difficulty of Investing Based on Macro Forecasts

(37:56) Outperformance in Small- and Mid-Cap Companies

(40:46) AI and the Impending Loss of Entry-Level Jobs

(43:04) Real Estate Trends

(45:14) Regulation and Business Formation in Canada

(48:14) Talent Retention Challenges for Canadian Businesses

(50:00) Could Passive Investing Break the Market?

(54:58) Conclusion

Our guest this episode is Gary Teelucksingh, author of “Roots of Prosperity” which is a guide to preserving wealth, values and family unity across generations. Gary is also a seasoned financial services expert and consultant with over two decades of experience spanning operations, technology and strategic transformation across North America and beyond.

In this conversation, Dave and Gary explore one of the most challenging topics families face: inheritances and how to talk about money with the people you love. They discuss why estate planning conversations are often avoided, how to add clarity and context to your will to prevent misunderstandings and strategies for navigating unequal inheritances, family cottages and potential hard feelings. Gary also shares insights from his new book, “Roots of Prosperity,” including how families can preserve not just wealth, but values and relationships across generations—and why open communication is the key to a lasting legacy.

If you’ve ever wondered how to start money conversations with your parents or children or want to avoid conflict around inheritances this episode is packed with thoughtful insights and practical advice.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Gary Teelucksingh

(02:09) Why Families Struggle to Talk About Money

(04:51) Why Estate Planning Conversations Are Considered Taboo

(06:22) Why You Need to Add Colour and Context to Your Will

(08:56) How to Avoid Hard Feelings with Inheritances

(12:30) Leaving Unequal Inheritances to Multiple Children

(14:26) The Challenges of Passing on a Cottage

(16:33) Why Gary Wrote “Roots of Prosperity”

(21:57) How to Talk with Aging Parents About Money

(23:37) The Inheritance Economy

(26:12) Creating the Impetus to Act

(28:07) Conclusion

Our guest this episode is Jon Flynn — Broker of Record at Flynn Real Estate Inc. and a well-respected Realtor with more than 15 years of experience. Jon is also the creator of the popular YouTube channel “Jon Flynn Real Estate Stats” where he analyzes Canadian housing trends and market data to help consumers better understand what’s happening in real estate.

In this conversation, Dave and Jon dive into Canada’s housing market, from how Jon correctly predicted the current downturn to where prices could be headed next. They explore the impact of interest rates, affordability challenges and even artificial intelligence on jobs and housing demand. The discussion also tackles controversial industry topics like realtor commissions, lead generation, double representation and the iPro scandal involving misappropriated trust funds. Jon shares insights on why many markets are stuck, the risks of overpricing in a declining market and why some speculative builds could be in serious trouble.

Whether you’re a homeowner, buyer, investor or just trying to make sense of Canada’s real estate headlines, this episode is packed with insights and practical perspective you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jon Flynn

(03:04) How Jon Predicted the Real Estate Crash

(05:26) Where is the Real Estate Market Headed?

(08:57) The Impact of AI on Jobs and Real Estate

(11:16) Do Realtors Make Too Much Money?

(14:58) The Debate Over Double Representation

(17:05)  The iPro Scandal and Misappropriation of Trust Funds

(21:32) The Impact of the Cost of Living on Home Buyers

(25:05) “Lowball” Offers

(26:04) Real Estate Markets Around the Country

(28:35) The Dangers of Overpricing Your Home in a Down Market

(32:08)  The Market is Stuck Because of Negative Equity and an Inability to Move Up

(36:08) Speculative Country Home Builds Are in Trouble

(38:46) Conclusion

Our guest this episode is Meagan Balaneski — Portfolio Manager and Certified Financial Planner® with Aligned Capital Partners in Vermilion, Alberta. Meagan earned a place on the CFP® President’s List for top exam performance in 2013 and recently won the FPAC 2025 Financial Planning Award.

In this conversation, Dave and Meagan explore both the opportunities and challenges shaping the financial planning industry today. They dig into what a great financial plan actually is, why meaningful planning starts with deep, thoughtful questions and the strengths and weaknesses of the traditional Assets Under Management model. Meagan shares her perspective on the growing advice-only movement, fiduciary standards under the new RFP rules and whether products like cash value life insurance are being overused. They also tackle practical topics like disability insurance, insuring children and why there is so much misinformation around RRSPs.

Whether you work in financial planning, are seeking advice, or are simply curious about how the industry is evolving, this episode offers a thoughtful, insider look at where financial planning is headed.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Introduction to Meagan Balanski

(04:54) Meagan’s Recent Financial Planning Award and Flow State

(08:46) What is a Financial Plan?

(10:09) Why Great Financial Planning Starts With Deep Questions

(12:29) The Assets Under Management Model

(15:30) Challenges of the Advice-Only Model and Implementation Gaps

(20:03) Reasons for Concern and Optimism About the Financial Planning Industry

(26:25) Fiduciary Responsibility and the New RFP Standard

(29:27) Is Cash Value Life Insurance Overused?

(34:15) Disability Insurance

(37:31) The Pros and Cons of Insurance on Children

(41:31) Is the Media Too Harsh on Financial Advisors?

(45:08) The Opportunity for Micro-Modular Financial Planning in Canada

(48:34) Debunking Misinformation About RRSPs

(50:42) Conclusion

Our guest this week is Julia Chung, CFP®, FEA, TEP — CEO of Spring Planning, President of FPAC and a Financial Planning & Family Enterprise Consultant with over 25 years of experience helping people navigate complex financial decisions.

In this episode, Dave and Julia explore what advice-only financial planning really means and why human-led planning matters more than ever. Their conversation ranges from the challenges of implementing financial plans to the rise of niche specialization in the industry and how retirees should think about the mosaic of retirement income. Julia also shares her insights on difficult but critical topics like planning for when one spouse passes away, choosing the right executor/POA and why adding kids as joint owners can be risky.

Whether you’re building a plan, managing a family business, or simply thinking more deeply about your financial future, this thoughtful and wide-ranging conversation is packed with insight.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Julia Chung

(03:38) What Advice-Only Financial Planning Really Means

(05:46) What Type of Clients Are Best Suited for Advice-Only Planning?

(09:30) Human-Led Financial Planning

(12:03) Cooperation in the Advice-Only Planning Community in Canada

(13:16) Challenges with Financial Plan Implementation

(17:25) The Growth of Niche Specialization in Financial Planning

(20:55) The Mosaic of Retirement Income

(24:09) Retirement Planning for When One Spouse Passes Away

(26:43) Julia’s Views on “Competitors” in the Financial Management Industry

(28:21) Choosing the Right Executor

(30:35) The Pros and Cons of Corporate Executors

(31:50) Beware of Adding Kids as Joint Owners

(34:57) The Critical Importance of Powers of Attorney

(37:17) Financial Institutions Are Resisting POA Documents More and More

(39:27) Qualities to Look for in Your POA for Personal Care

(41:46) Debunking RRSP Misinformation

(44:05) Why Disability Insurance is Underrated

(47: 31) Paying Off Your Mortgage or Investing

(49:34) The Evolution of Family Business Transitions

(53:42) Recommended Reading: “Designing Your Life”

(55:17) Financial Pet Peeves and Conclusion

Our guest this episode is Jason Watt — a Canadian financial education leader and long-time contributor to the professional training and development of financial planners, advisors, and insurance professionals across the country. Jason has spent years helping shape how financial advice is taught in Canada, including previously serving as the lead instructor at Business Career College, where he developed curriculum and continuing education for industry professionals.

In this conversation, Dave and Jason explore the financial advice landscape in Canada — from the differences between financial planners and advisors to which credentials actually matter and what it truly means to act as a fiduciary. They dig into how the CFP program has evolved, the pros and cons of advice-only planning, why the middle market is so underserved, and how revenue models shape client outcomes. Jason also shares his thoughts on broken insurance licensing, commission conflicts, specialization in planning and why communication and psychology are becoming just as important as technical expertise.

If you’ve ever wondered how financial advice really works in Canada (or where it needs to go next!) this episode is packed with thoughtful insights, practical perspectives and reasons for optimism about the future of the profession.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Jason Watt

(03:14) Pro Bono Financial Planning

(04:27) Jason’s Background with Business Career College

(05:53) What is a Financial Planner vs. a Financial Advisor?

(08:47) What Credentials Actually Matter for Financial Advisors?

(10:52) What Does it Mean to Be a Fiduciary?

(12:46) How the CFP Program Has Evolved

(16:36) Different Revenue Models for Financial Advice

(18:49) Why the Middle Market is Underserved in Canada

(21:00) Advice-Only Planning: Strengths and Weaknesses

(23:29) Specialization and Niches in Financial Planning

(24:22) Financial Advisors are Focusing More on Communication and Psychology

(26:06) Why Insurance Licensing is Broken in Canada

(31:28) The Commission Conflict in Insurance Sales

(32:53) An Idea to Redesign Licensing: Certify by Complexity (Not Products)

(34:56) Cross-Border Financial Planning Gets Complicated Fast

(37:39) The Updated “The Wealthy Barber”

(39:33) Canada Has Some Great Financial Educators

(42:17) Should You Commute a Pension or Leave It?

(44:01) Reasons for Optimism in the Financial Advice Industry in Canada

(48:31) Gambling Worries

(49:57) Housing Affordability and Expectations

(51:43) Conclusion

Episode #41 is out now! Our guest this episode is Chris Guillebeau — author, entrepreneur, blogger and speaker best known for “The $100 Startup,” “Side Hustle,” and his latest book, “Time Anxiety.” Chris first rose to prominence through his blog “The Art of Non-Conformity,” where he shared stories of unconventional work, travel and building income on your own terms.

In this conversation, Dave and Chris dive into the world of side hustles and small entrepreneurship — how to turn skills and hobbies into income, why reselling is one of the easiest ways to start and why action always beats overplanning. Chris shares what successful side-hustlers have in common, how to find your first customers, why farmers’ markets are an underrated testing ground for business ideas, and how knowing when to quit can be just as important as knowing when to push forward.

Whether you’re thinking about starting a side hustle, testing a business idea, or just want a fresh perspective on work and time, this episode is full of practical insights and encouragement. Listen now on our website, YouTube, Apple Podcasts, Spotify and all major podcast platforms.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Chris Guillebeau

(02:05) Chris’s Unconventional Early Career

(05:03) The Why Behind Writing “The $100 Startup”

(08:06) Turning Skills and Hobbies Into Income

(11:04) Reselling is a Great Place to Start for Entrepreneurship

(11:56) Action Beats Overplanning

(13:06) How to Find Your First Customers

(14:45) What Do Successful Side-Hustlers Have in Common?

(21:12) The Impact of “The $100 Startup”

(22:09) Knowing When to Quit is Vital

(23:40) Farmers’ Markets Are Great for Testing Business Ideas

(25:44) Why Enjoyment Matters More Than Scale for Side Hustles

(27:16) What is Time Anxiety?

(29:02) ADHD & Neurodiversity

(33:16) Conclusion

Our guests this episode are Heather and Doug Boneparth — co-authors of the book Money Together: How to find fairness in your relationship and become an unstoppable financial team. Doug is the founder of Bone Fide Wealth in New York City and serves on the advisory councils for CNBC and Investopedia. Heather is a lawyer-turned-financial-writer, Bone Fide Wealth’s Director of Business and Legal Affairs and a rising voice at the intersection of love, money and family.

In this conversation, Dave sits down with Heather and Doug to explore how couples can navigate money as a team — from shifting income dynamics and caregiving to power, communication, and the invisible labour that often goes unrecognized. They share why they wrote Money Together and why strong financial partnerships aren’t built with spreadsheets, but with trust, curiosity, and shared values.

Whether you’re in a long-term relationship, newly partnered, or just want to understand how money and relationships intersect, this episode is packed with thoughtful insights and practical takeaways.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Heather & Doug Boneparth

(03:15) Why They Wrote “Money Together”

(07:22) How Power and Income Shift Relationship Dynamics

(09:13) Caregiving is a Real Economic Contribution

(14:26) The Breaking Point That Forced Change

(17:08) Division of Labour and How to Truly Create Space for Your Partner

(21:57) How to Talk About Money as a Team

(24:27) Start with Money Wins, Not with Spreadsheets

(27:42) Both Members of a Couple Need to Understand Their Finances

(29:04) Managing Your Finances Together is an Ongoing Activity

(30:12) Teaching Kids Values, Not Financial Math

(32:58) Money is Finite

(35:36) Money, Divorce and Difficult Conversations

(37:43) Growth Requires Discomfort & Curiosity

(39:02) Strong Couples Are Resilient to Whatever Life Throws at Them

(40:38) Conclusion