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