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

Our guest this episode is Shannon Lee Simmons — Certified Financial Planner®, Chartered Investment Manager®, bestselling author, media personality and founder of the New School of Finance™. Shannon is widely recognized as a trailblazer in Canada’s fee-only financial planning movement and her latest book is “Making Bank,” a financial guide for teens.

In this conversation, Dave and Shannon explore what real-world financial planning looks like for everyday Canadians. They dive into fee-only and modular financial planning, budgeting in real life, turning advice into action and how rising housing prices, down payments and “financial dysmorphia” are reshaping how Canadians think about money.

Whether you’re just getting started with your finances or feeling squeezed by today’s economic realities, this episode is full of perspective, practical advice and much-needed hope.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Shannon Lee Simmons

(02:22) Leaving Bay Street to Serve Everyday Canadians

(04:10) The Barter Babes Project

(08:01) Writing “Making Bank” for Teenagers

(11:59) What is Fee-Only Financial Planning?

(14:06) Modular Financial Planning for Real Life

(15:30) The Importance of Knowing How Much Money is Coming In and Going Out

(18:49) Who Typically Seeks Fee-Only Financial Planning?

(20:19) Turning Financial Advice Into Action

(22:26) Why Fee-Only Financial Planners Are Starting to Specialize

(25:58) Software vs. Spreadsheets

(26:55) Scaling a Fee-Only Practice

(28:43) Housing Prices are Squeezing Canada’s Middle Class

(32:15) More People Are Risking Their Own Retirement to Help Their Adult Children Financially

(34:33) Down Payments Squeeze All Other Savings

(36:20) Financial Dysmorphia and “Normal” Spending

(38:50) Hope is Your Biggest Asset

(41:23) Real Estate Prices and Divorce

(43:03) Some Young People Are Still Doing Well Financially

(44:19) Retirement Planning is a Different Beast

(49:43) Reasons for Optimism and Hope

Our guest this episode is Melissa Leong — national media personality, a sought-after speaker and award-winning author of the feel-good finance guide “Happy Go Money.” Melissa has been the resident money expert on Canada’s leading daytime talk show “The Social” for 14 years and is also a repeat guest on “The Drew Barrymore Show” on CBS.

This is an amazing episode for anyone looking to better manage their money in 2026. In their conversation, Dave and Melissa explore the idea that money should support happiness, not compete with it. They dig into behavioural finance and simple “brain hacks” that can lead to better decisions, from the 24-hour rule for spending to the power of spending summaries. Melissa also shares insights on social media comparison, why experiences tend to bring more lasting happiness than stuff, the joy of anticipation, and why big purchases like cars so often fail to deliver long-term satisfaction.

The discussion also touches on generosity and happiness, valuing time over money, financial challenges women face, managing money as a couple, and practical ways to get started building healthier financial habits — without guilt or perfectionism.

Whether you’re trying to spend more intentionally in the new year, stress less about money, or align your finances with what actually makes you happy, this is a thoughtful and refreshing conversation you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Melissa Leong

(02:09) Melissa’s Path from Journalism to Money

(05:42) Behavioural Finance & Brain Hacks

(09:32) The 24-Hour Rule for Spending

(14:16) Social Media & The Pressures of Comparison

(16:41) Money Should Support Happiness, Not Compete With It

(18:56) Spending Now vs. Spending Later

(22:39) Experiences Create More Lasting Happiness Than Stuff

(24:12) The Joy of Anticipation

(30:29) Dave Doesn’t Have FOMO, He Has FOBI

(32:07) The Power of Spending Summaries

(36:16) Charity, Generosity & Joy

(39:17) Valuing Time Over Money

(40:31) Why Cars Rarely Deliver Lasting Happiness

(43:32) How Melissa Became a Regular on The Drew Barrymore Show

(45:11) Financial Challenges Women Face

(51:22) Managing Money as a Couple

(56:43) How to Get Started Managing Your Money Well

(59:01) Conclusion

Our guest this episode is Shaun Maslyk — a practicing Certified Financial Planner® and Certified Financial Behavior Specialist® who blends financial planning with positive psychology to help people understand their money stories and flourish beyond their finances. Shaun holds a master’s degree in positive psychology from the University of East London, where his research focused on the relationship between money, behaviour change and human happiness.

In this conversation, Dave and Shaun explore what the research really says about money and happiness — from whether happier people make better financial decisions to why more money doesn’t always lead to more joy. They unpack concepts like hedonic adaptation, the “arrival fallacy” of wealth and the unconscious money scripts that quietly shape our spending, saving and relationships. Shaun also challenges the idea that financial success is purely about optimization, making the case for peace of mind, values-based decisions and “sailing to the right island” in life.

If you’ve ever wondered whether you’re chasing the wrong financial goals — or how to make money decisions that actually improve your well-being — this episode is full of thought-provoking insights and practical takeaways.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Shaun Maslyk

(03:39) Do Happier People Make Better Money Decisions?

(05:25) Research on Money, Happiness & Hedonic Adaptation

(11:45) The Arrival Fallacy of Wealth

(13:22) Money Stories & Unconscious Scripts

(16:17) How Money Scripts Affect Relationships

(20:51) Peace of Mind vs. Mathematical Optimization

(24:42) Do Walkers Have Better Financial Behaviour?

(26:57) Spending Summaries

(28:44) Make Sure You’re Sailing to the Right Island

(31:51) The Three Questions That Clarify Money Decisions

(35:43) Spending on Experiences vs. Possessions

(39:55) Too Much Luxury Can Reduce Joy

(41:02) What Would You Do If You Only Had 24 Hours to Live?

(43:10) Conclusion

Our guest this episode is Aravind Sithamparapillai, a financial planner at Ironwood Wealth Management Group. Earlier this year, Aravind earned his CFP® designation with the highest exam score in the country, placing him at the top of the CFP® Exam President’s List, and was also selected for FP Canada’s Emerging Leader’s Award.

In this conversation, Dave and Aravind walk through what great financial planning actually looks like in practice. They discuss the “financial quarterback” model, Aravind's four-step process for investing and why assessing true risk tolerance goes far beyond a simple questionnaire. Aravind explains how biology and financial stress affect investor behaviour, why unusually high returns are unlikely to last forever and how personal preferences should factor into a well-designed plan.

The episode also dives into estate and tax planning topics that are often overlooked—from common estate planning mistakes and the risks of joint accounts to when RRSPs should be left to an estate, how taxes work at death and traps grandparents can fall into with RESPs. The conversation wraps up with a practical comparison of TFSAs vs. RRSPs, a discussion on alternative investments and Aravind’s personal story about discovering The Wealthy Barber.

Whether you’re building your first financial plan or refining an existing one, this episode is packed with clear, thoughtful insights from one of Canada’s brightest young planners.

Show Notes

(00:00) Intro and Disclaimer

(00:55) Intro to Aravind Sithamparapillai

(04:47) ​​The Financial “Quarterback” Model

(10:32) The Four-Step Investing Process

(14:38) How Do You Assess True Risk Tolerance?

(16:47) A Financial Planner’s Role in Changing Risk Tolerance

(19:04) Biology and Financial Stress

(21:38) 20% Returns (Probably) Won’t Go On Forever

(23:30) Personal Preferences & Maximizing Return

(25:05) Common Estate Planning Mistakes

(26:50) Reasons Why RRSPs Should Be Left to the Estate

(31:47) The Risks of Using Joint Accounts to Avoid Probate

(34:44) The Benefits of Leaving a Letter of Direction with Your Will

(36:43) What Happens Tax-Wise When You Die?

(38:26) The RESP Trap for Grandparents

(45:00) TFSA vs. RRSP

(49:09) The Risks of Alternative Investments

(56:13) Aravind’s Personal Story About The Wealthy Barber

(58:45) Conclusion

Our guest this episode is Daniel Foch, a Canadian real estate broker, co-host of “The Canadian Real Estate Investor” podcast and Chief Real Estate Officer at Valery.ca. Daniel creates widely-followed content at the intersection of data, news and insights for the Canadian housing market.

In this conversation, Dave and Daniel tackle the big questions facing the real estate market today. They discuss the Ontario government’s move to take over RECO, whether realtors should be able to represent both sides of a deal, and the evolving role of municipalities, development charges and zoning in housing affordability. Daniel shares his perspective on where the market goes from here, why most Canadians still want a detached home and what it will take to make those homes more affordable.

The conversation ranges far beyond prices, touching on the challenges of an aging population, mortgage stress tests and why older generations are staying “overhoused.” There’s also a fascinating discussion about the impact of AI, First Nations’ land claims and the rise in Powers of Sale.

If you’re interested in the state of Canadian real estate — from policy to affordability to where things might be headed — this episode is full of insights you won’t want to miss.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Daniel Foch

(05:06) Ontario Government Taking Over RECO

(07:57) Should Realtors Be Able to Represent Both Sides of a Deal?

(10:36) Housing Affordability and the Role of Government

(16:30) Should Municipalities Lower Their Development Charges?

(18:00) Where Does the Real Estate Market Go From Here?

(20:56) Most Canadians Still Want a Detached Home

(23:15) Owning vs. Renting

(26:25) How Do We Make Detached Homes More Affordable?

(28:40) Older Generations Are Overhoused But Not Downsizing

(34:07) Mortgage Stress Tests

(38:42) Daniel Thinks Municipal Governments Could Go Away

(40:13) The Potential Impact of AI on Societies

(41:54) First Nations’ Land Claims in Canada

(44:31) Bill 60

(46:47) Valery AI

(50:15) Increasing Powers of Sale

(54:57) Conclusion