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

Our guest this episode is Morgan Housel, international bestselling author of “The Psychology of Money,” “Same as Ever” and his newest book, “The Art of Spending Money.”

In this conversation, Dave and Morgan explore the timeless principles that shape how we think about money, happiness and decision-making. Morgan shares the story behind writing “The Psychology of Money,” why earning more didn’t change his life as much as he expected and why he believes money is “the greatest show on Earth.” They dig into core ideas like why firsthand experiences are more persuasive than data, why “no one’s crazy” and how comfort (not speed) is often the real goal in personal finance.

The discussion also covers the emotional side of money — from spending mistakes and regrets to what Morgan actually enjoys spending on — along with big-picture themes like luck, independence, volatility and how to think in terms of what’s reasonable rather than purely rational.

If you’re fascinated by human behaviour, personal finance or simply want to make better decisions with your money, this episode is packed with thoughtful insights and memorable lessons from one of today’s most influential financial thinkers. 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Morgan Housel

(03:01) The Story of Writing “The Psychology of Money”

(07:37) How Making More Money Changed Morgan’s Life (Spoiler: Not Much)

(09:56) Why Morgan Calls Money "The Greatest Show on Earth"

(11:25) Nothing is More Persuasive Than What You’ve Experienced Firsthand

(13:42) “No One’s Crazy”

(17:16) You Can Either Make the Train Twice as Fast or Twice as Comfortable

(19:33) Was There Pressure Writing a Follow-Up Book?

(21:26) Nobody is Paying as Much Attention to You as You Are

(23:32) Volatility is the Price of Admission in Investing

(26:05) Buying Independence vs. Buying Expensive Things

(29:12) Spending Mistakes vs. Regrets

(32:17) What Does Morgan Like to Spend Money On? 

(35:08) The Role of Luck in Our Lives

(40:33) Reasonable vs. Rational in Personal Finance

(43:21) The Most Overrated Financial Advice 

(44:48) Conclusion

Our guest this week is John Y. Campbell — a globally respected Harvard economist and one of the most influential voices in academic financial economics. Over his career, John has published more than 100 academic papers spanning fixed-income markets, equity valuation, portfolio theory and household finance.

John’s newest book, “Fixed: Why Personal Finance Is Broken and How to Make It Work for Everyone,” makes a compelling case that the financial system — while vital — is failing ordinary people. Between unnecessary complexity, steep fees, confusing products and poor incentives, most households are left navigating a system that isn’t built with their best interests in mind. John draws on decades of research to explain what’s gone wrong and how better product design, smarter regulation and clearer advice could dramatically improve financial outcomes.

In this episode, Dave and John explore how the system can be fixed — from mandatory universal retirement accounts to simpler, standardized financial products, to improving disclosures on credit cards. They also discuss the pitfalls of active mutual funds, the challenges of financial advice models, the role of technology in impulse spending and the rise of gambling and meme-stock behaviour. It’s a wide-ranging and accessible conversation with one of the world’s top financial thinkers.

If you care about personal finance, financial policy or simply understanding why the system feels so confusing this episode is a must-listen.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to John Campbell and His Book “Fixed”

(05:14) How Should the Financial Industry be Fixed?

(09:30) Mandatory Universal Retirement Accounts

(12:52) Active Mutual Funds Have Costly Fees 

(15:48) The Different Models for Financial Advice

(18:37) How Standardized Financial Products Could Help

(21:07) Life Insurance and Complexity

(24:57) Two Thoughts on Debt

(26:21) Technology and Impulse Spending

(29:24) Gambling & Meme Stocks

(31:19) Policy Ideas to Fix the Financial System

(36:21) How Disclosures on Credit Cards Could Be Improved

(38:33) Conclusion

Episode #32 is out now! Our guest this episode is Leanne Kaufman — President and CEO of RBC Royal Trust, the division of RBC that helps Canadians with estate, trust and incapacity planning/professional administration. Leanne is a lawyer by training and is extremely knowledgeable about all things estate planning in Canada.

In this conversation, Dave and Leanne dive deep into the fundamentals of estate planning — why every Canadian needs a will, the real cost of getting one and what qualities make for an ideal executor. They explore tricky questions like whether you should choose a family member as your executor, if co-executors are ever a good idea and why keeping a “When I Die” binder can spare your loved ones a world of stress.

From corporate executors to cottages (and the conflict they often create) to the risks of joint ownership and the scenarios where trusts actually make sense, this episode covers the most common estate-planning pitfalls Canadians face—and how to avoid them.

Whether you’re creating your first will or updating your entire estate plan, this episode is packed with practical advice, clear explanations and guidance every Canadian should hear.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Leanne Kaufman

(02:34) Why Everyone Needs a Will

(05:01) How Much Does it Cost to Get a Will?

(07:29) What Qualities Does an Ideal Executor Have?

(13:28) Should You Choose a Family Member as Your Executor?

(15:46) Co-Executors: Yay or Nay?

(18:06) The Importance of a “When I Die” Binder

(20:33) Should You Keep Old Wills?

(22:05) What is a Power of Attorney?

(26:52) Why Dave Doesn’t Like Co-Powers of Attorney for Personal Care

(28:39) When Do POAs Take Effect?

(30:56) Name Alternate Executors & POAs

(32:41) How to Make Sure Your POA Will Be Accepted

(34:46) Corporate Executors

(40:50) Cottages and Family Conflict

(44:26) Use Cases for Trusts

(47:28) The Dangers of Joint Ownership in Estate Planning

(50:39) Estate Planning is a Holistic Exercise

(54:00) Conclusion