#57 — Daniel Crosby: How to Overcome Your Financial Biases

Our guest this episode is Adam Chapman — Certified Financial Planner and founder of YESmoney, a London, Ontario practice built around helping Canadians spend with confidence in retirement. With nearly two decades in financial planning, Adam chairs the Estate Planners Council of London and is a founding member of the Financial Planning Association of Canada. He has spent his career helping retirees figure out what they actually want and start saying "yes" to their money. In this episode, Dave and Adam dive into the practical side of retirement income planning, from paying yourself first in retirement to managing cash flow once the paycheques stop. Adam walks through his three retirement planning checkpoints, the real costs of long-term care versus in-home care and why guaranteed income floors matter more than ever. They also break down annuities in detail, including copycat annuities, piggyback annuities and how pairing them with delayed government benefits can take the sting out of inflation fears. The conversation also explores the emotional side of money in later life, including the struggle many couples face when selling the family home and the psychology of spending in retirement, the subject of the book Adam is currently writing. Whether you're approaching retirement or already there and wondering how to spend without worry, this episode is full of practical, grounded advice from a planner who spends every day helping Canadians make the shift from saving to spending.

Our guest this episode is Daniel Foch — Chief Real Estate Officer at Valery, host of The Canadian Real Estate Investor Podcast and one of Canada's most-followed voices on housing data and market analysis. He first joined us back on Episode #35, and with so much having changed since then, we brought him back for a full update. In this episode, Dave and Daniel dive into the current state of Canadian real estate, starting with where prices and sales actually sit in Ontario and BC today. They break down the Toronto condo crash and the supply crisis it has created, why unrealistic sellers are keeping the market stuck and whether rents are going to keep falling. They also cover how tariffs and AI could push unemployment higher and what that would mean for housing. The conversation also explores the policy side of the picture, including CMHC's financing programs for rental developers, the government's housing incentives and why so many municipalities are now cutting development charges. Daniel explains why builders have stopped building small homes, lays out his concept of "houseflation" and shares his take on the biggest macroeconomic surprises of the year. Along the way, Dave and Daniel tackle whether downsizing baby boomers will flood the market, how immigration cuts are reshaping demand and how Daniel is using agentic AI to rebuild the way real estate businesses operate. Whether you're a homeowner, a renter trying to decide when to buy or simply trying to make sense of where Canadian housing goes from here, this episode is full of data-driven insights and candid analysis you won't want to miss.

Our guest this episode is Ted Cadsby — former President and CEO of CIBC Securities, bestselling author and one of Canada's earliest champions of index investing. Ted brought index funds to CIBC in the late 1990s, wrote "The Power of Index Funds" to make the case to everyday Canadians and has since turned his attention to how people think, with books including "Closing the Mind Gap" and "Hard to Be Human." In this episode, Dave and Ted dive into the case for index funds and the uphill battle Ted fought to bring them to the bank, including the clash with Wood Gundy brokers who saw indexing as a threat to their business. They break down why individual stocks are so hard to get right, how unknowable variables drive stock prices, whether "play money" accounts make sense and how Ted weights his own personal portfolio. The conversation also explores how to evaluate active money managers, how to separate luck from skill in investment performance and what to make of private equity pitches (plus Dave's due diligence approach from his Dragon's Den days). Along the way, Ted shares insights from his work on the psychology of decision making: the dangers of oversimplification and overconfidence, why active managers stay so sure of themselves and how financial biases can quietly affect our happiness. Whether you're a committed indexer or still wondering if you can beat the market, this episode offers a clear-eyed look at investing from someone who has seen both sides of the industry.

Our guest this episode is Jason Heath — Founder and Managing Director of Objective Financial Partners, one of Canada's largest advice-only financial planning firms. A Certified Financial Planner with more than 20 years in practice, Jason is a longtime personal finance columnist for the Financial Post and MoneySense and one of the country's most consistent voices for conflict-free financial advice. He last joined us on Episode #27 for Financial Planning 101, and this time the conversation looks ahead. In this episode, Dave and Jason dive into where financial planning is headed. They explore the role of technology in democratizing planning, from financial planning software to the future of AI in financial advice, including a look at The Wealthy Barber's own AI planning tool. Along the way, Jason shares how often a plan should be updated, why implementation matters as much as the plan itself, how tax optimization gets trickier with corporate assets and why even financial professionals need advice. They close with the chronic gap in life and disability insurance and the secret behind Jason's famously calm demeanour. Whether you're weighing the cost of an advice-only plan, curious how AI will change the way Canadians get financial guidance or simply want to make sure your retirement projections are realistic, this episode is full of clear, practical insights.

Our guest this episode is Leanne Kaufman — President and CEO of RBC Royal Trust and one of Canada's leading voices on trust and estate planning. A lawyer by training, Leanne joined RBC Royal Trust in 1999 and has spent more than two decades helping Canadian families protect and transfer their wealth. She returns to the show after first joining us back in episode #32. In this episode, Dave and Leanne dive into the estate planning issues that trip up Canadian families most often. They break down what probate actually is, and the risks of using joint accounts and gifting to avoid it. Leanne also explains how regular-income Canadians can use trusts, covering formal vs. informal trusts, multi-generational planning, the tax disadvantages, the 21-year rule and the legal duties that come with being a trustee. The conversation also explores the practical side of getting your affairs in order, from what to do before naming someone as your executor to thinking through your beneficiary designations and building a "When I Die" binder. Along the way, Leanne shares her perspective on why you should talk to your beneficiaries while you still can, how to choose the right power of attorney for personal care and property, and the risks of naming co-powers of attorney. Whether you're drafting your first will, updating an existing plan or have been named as someone's executor or power of attorney, this episode is full of clear, practical guidance to help you and your family avoid costly mistakes.