The Rational Reminder Podcast

In this episode, we are joined by Shannon Lee Simmons—Certified Financial Planner, Chartered Investment Manager, bestselling author, and founder of the New School of Finance—for a wide-ranging conversation about the emotional side of money. Drawing on more than two decades of working directly with Canadians, Shannon explains why financial stress has become so pervasive, how social comparison shapes spending habits, and why a well-built financial plan can be one of the most powerful antidotes to money anxiety.
We also explore decision-making during financial crises, the psychology of regret, why traditional budgeting often fails, and how couples navigate money differently—particularly in retirement. Shannon shares practical frameworks for aligning spending with personal values, avoiding emotional financial mistakes, and helping households make confident decisions through life's biggest transitions.
Key Points From This Episode:
(0:03:56) Why people worry about money—and why financial uncertainty often feels like uncertainty about life itself.

(0:04:24) Why so many middle- and upper-income Canadians still feel broke despite earning good incomes.

(0:05:18) The importance of having a financial plan and reducing harmful social comparison.

(0:06:55) How social media fuels overspending, comparison, and "financial dysmorphia."

(0:08:35) Why cashless spending has fundamentally changed our relationship with money.

(0:11:52) How perceived life milestones—especially home ownership—shape financial decisions and expectations.

(0:13:36) Practical ways to manage financial stress, restore confidence, and build resilience.

(0:15:55) The growing "spending arms race" and how rising expectations have redefined what's considered normal.

(0:18:09) Why Shannon dislikes traditional budgeting—and what to do instead.

(0:20:32) Her four-bucket framework for worry-free spending and maintaining financial flexibility.

(0:22:35) A practical test for deciding whether a large purchase is truly affordable.

(0:25:01) Aligning spending decisions with personal values using an "emotional return on investment."

(0:28:12) Helping couples navigate different financial priorities without turning disagreements into conflict.

(0:30:28) Separating good decisions from bad outcomes to overcome financial regret.

(0:33:48) The major financial decision crises people commonly face—from divorce to illness to retirement.

(0:35:16) Using "micro financial plans," guardrails, and scenario planning during periods of uncertainty.

(0:37:45) The three phases of a financial decision crisis and how planners can help through each stage.

(0:41:41) Why retirement often reveals differences in couples' relationships with money that never surfaced while saving.

(0:45:19) The psychological challenge of withdrawing from investment portfolios after decades of accumulation.

(0:46:41) Using cash wedges and realistic retirement projections to reduce anxiety around spending in retirement.

(0:49:42) How saver-versus-spender dynamics can evolve into power struggles during retirement.

(0:53:12) The question almost every client is really asking: "Am I going to be okay?"

(0:54:41) Why planners should ask about clients' hidden DIY investment accounts.

(0:56:21) The risks of becoming emotionally attached to concentrated investment gains.

(0:57:16) The most impactful parts of a financial plan: realistic spending projections and actionable next steps.

(0:58:25) How often financial plans should be updated—and when life events require immediate revisions.

(1:01:08) Who benefits most from fee-only planning and who may be better served with ongoing advice.

(1:07:00) Why implementation—not recommendations—is often the hardest part of financial planning.

(1:10:00) The strengths and trade-offs of fee-only planning versus assets-under-management advice models.

(1:15:05) Shannon's advice for improving financial well-being: build a plan, focus on your own values, and stop comparing yourself to everyone else.

 
Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p
Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/
Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/
Benjamin on X — https://x.com/benjaminwfelix
Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/
Shannon Lee Simmons – https://shannonleesimmons.com/ 
New School of Finance – https://www.newschooloffinance.com/ 
Worry-Free Money – https://www.amazon.ca/Worry-Free-Money-guilt-free-approach-managing/dp/1443454451 
Making Bank: Money Skills for Real Life – https://www.amazon.ca/Making-Bank-Money-Skills-Real/dp/1443469815 
 
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

In this episode, Ben Felix and Ben Wilson tackle a wide range of listener questions covering portfolio construction, home-country bias, currency exposure, ETF selection, retirement decumulation, leasing versus buying a car, discounted cash flow valuations, and the real work of portfolio management. Along the way, they revisit the Rational Reminder model portfolios, discuss how new products like CAGE have changed the DIY investing landscape, and explore whether Warren Buffett's long-term record still provides evidence that active management can outperform.
The conversation also offers a behind-the-scenes look at PWL Capital's planning-centric approach to wealth management and why helping clients make better financial decisions often matters more than portfolio construction itself.
Key Points From This Episode:
(0:28) Why AMA episodes have become less frequent despite hundreds of listener questions waiting to be answered. 
(2:07) Ben shares observations from PWL's growing institutional investment business and why low-cost, planning-focused institutional advice remains surprisingly rare. 
(6:37) Revisiting the original Rational Reminder model portfolios and how newer products have simplified implementation. 
(10:09) Should U.S. investors underweight the U.S. market relative to global market-cap weights? 
(11:07) Research, home-country bias, and Ken French's arguments for overweighting domestic stocks. 
(18:11) Asset-allocation ETFs in retirement: Is there any benefit to separating stocks and bonds during withdrawals? 
(21:03) Leasing versus buying a vehicle, opportunity costs, depreciation, and convenience. 
(26:13) Currency exposure, RRSPs, withholding taxes, and common misconceptions about USD-denominated ETFs. 
(30:30) If Dimensional funds were unavailable, what would Ben choose instead? 
(31:26) Are there any popular ETFs investors should avoid? A look at Canada's largest ETF holdings. 
(38:28) Why discounted cash flow models often produce wildly different valuation estimates. 
(41:47) What portfolio managers at PWL actually do when they are not trying to beat the market. 
(45:57) Concentrated stock positions, client coaching, and helping investors make better long-term decisions. 
(50:02) Why financial planning questions are often portfolio management questions—and vice versa. 
(52:53) Helping clients navigate the transition from wealth accumulation to wealth preservation and spending. 
(58:06) Revisiting Berkshire Hathaway's long-term performance versus broad-market index funds. 
(1:02:35) The challenges of active management as assets under management grow larger. 
(1:04:22) Aftershow: Ben reflects on his experience appearing on Diary of a CEO with Steven Bartlett.
Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p
Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/
Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/
Benjamin on X — https://x.com/benjaminwfelix
Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/



Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

In this episode, we are joined by Morley Conn, Director of Sales and Strategy, ETF Services at Scotia Global Banking and Markets, for a deep dive into the mechanics of the ETF ecosystem. With more than 30 years of experience across equities, foreign exchange, and money markets, Morley pulls back the curtain on the creation and redemption process, ETF liquidity, block trading, market making, and the often-overlooked infrastructure that allows ETFs to trade efficiently every day.
We explore how authorized participants and market makers facilitate liquidity, why ETF liquidity is driven by the underlying holdings rather than trading volume, and how large institutional ETF trades are executed. Morley also explains the differences between Canadian and U.S. ETF markets, discusses common misconceptions investors have about ETF trading, and shares practical advice for retail investors seeking better execution. This conversation offers a rare look at the operational machinery behind one of the most important innovations in modern investing.



Key Points From This Episode:
 
(0:04) Introduction to Morley Conn and his role in ETF market making.
(4:29) The key participants in the ETF ecosystem: issuers, custodians, market makers, advisors, and dealers.
(5:53) What market makers and authorized participants actually do.
(7:03) How ETF creation and redemption works and why it matters for liquidity.
(10:58) How ETF portfolio management differs from traditional mutual fund management.
(12:44) Why ETF trading volume often greatly exceeds primary-market creations and redemptions.
(13:35) The capital gains refund mechanism and its relationship to ETF trading activity.
(16:04) What happens when ETF market prices diverge from net asset value (NAV).
(18:24) Lessons from the March 2020 bond ETF dislocations and what they revealed about market pricing.
(19:16) How market makers price ETFs when underlying securities are illiquid or difficult to value.
(20:38) Managing ETF market-making risk when underlying markets are closed.
(21:35) The major factors that influence ETF bid-ask spreads.
(23:26) Why market makers prioritize trading volume and investor experience over wide spreads.
(26:45) How large ETF block trades are executed and hedged behind the scenes.
(29:26) Why ETF liquidity is determined by the underlying holdings rather than visible trading volume.
(30:43) The difference between NAV trades and at-risk trades.
(32:46) How market makers contribute to the development of new ETF products.
(34:20) Best practices for retail investors when trading ETFs.
(37:34) Factors that determine when block trades make sense.
(38:46) Why pricing ETF blocks is both an art and a science.
(43:14) What happens when an ETF is shut down and how investors are affected.
(46:22) The balance between retail and institutional participation in the Canadian ETF market.
(48:27) How institutions and retail investors use ETFs differently.
(51:23) Key differences between Canadian and U.S. ETF markets.
(54:56) ETF tax efficiency in Canada versus the United States.
(56:23) Common misconceptions investors have about ETF liquidity and assets under management.
(1:00:13) How CRM3 total cost reporting could influence ETF adoption in Canada.





Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p
Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/
Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/
Benjamin on X — https://x.com/benjaminwfelix
Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/



Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

In this episode, we are joined by Ben Carlson, Director of Institutional Asset Management at Ritholtz Wealth Management and author of Risk & Reward, for a wide-ranging conversation about market history, investor psychology, and the realities of long-term investing. Ben brings his trademark blend of data-driven thinking and plainspoken storytelling to topics like market crashes, inflation, diversification, and why investors are so tempted to time the market.
We explore the lessons from Japan's historic asset bubble, the lingering impact of the Great Depression, and why diversification remains one of the few true free lunches in investing. Ben also explains the difference between volatility and risk, why the stock market is not the economy, and how investor behavior—not market performance—is often the biggest determinant of success. Along the way, we discuss inflation hedges, lost decades, speculative behavior, and the psychological challenge of staying invested through inevitable downturns.
 
Key Points From This Episode:
(0:00:20) Introducing Ben Carlson, his new book Risk & Reward, and his long-running blog A Wealth of Common Sense.
(0:03:16) Why investors shouldn't panic about investing at all-time highs.
(0:03:58) The Japanese bubble and crash as one of history's biggest market anomalies.
(0:05:39) Why Japan's long-term returns look very different when viewed over 50 years.
(0:06:27) Lessons from the Great Depression and the worst stock market crash in U.S. history.
(0:07:43) Why the best long-term returns often follow the worst crashes.
(0:08:53) The role of diversification and self-awareness in managing portfolio risk.
(0:09:55) Defining investment success by achieving personal goals—not beating benchmarks.
(0:10:42) Why inflation feels so painful psychologically for investors and households.
(0:11:42) Ben's three favorite long-term inflation hedges: human capital, housing, and stocks.
(0:13:47) Why market timing is psychologically seductive—and so difficult to execute successfully.
(0:15:00) Why handling losses is the single most important skill in investing.
(0:16:13) How devastating the economic side of the Great Depression really was.
(0:18:49) What policymakers learned from the Great Depression and 2008.
(0:20:39) The difference between recessionary and non-recessionary bear markets.
(0:21:52) Why the biggest up days and down days tend to cluster together in bear markets.
(0:23:18) Preparing for inevitable bear markets with a durable long-term plan.
(0:25:07) Why the stock market and the economy can diverge dramatically.
(0:28:10) The difference between volatility and risk—and why risk is often personal.
(0:29:37) Why comparing the stock market to a casino is fundamentally wrong.
(0:31:55) How modern investing platforms encourage speculative behavior.
(0:33:18) How extreme Japan's 1980s asset bubble became before collapsing.
(0:35:43) The most important diversification lessons from Japan's lost decades.
(0:37:39) How common "lost decades" actually are in stock market history.
(0:40:58) Three dimensions of diversification: geography, asset class, and strategy.
(0:41:53) Why there is no perfect portfolio—only the right portfolio for you.
(0:42:52) Common ways investors lose money in markets.
(0:44:03) Why investors should be skeptical of billionaire market predictions.
(0:45:57) Ben's evolving definition of success and raising good, kind children.
 
Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p
Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/
Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/
Benjamin on X — https://x.com/benjaminwfelix
Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/



Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

In this episode, Ben Felix and Braden Warwick unpack the surprisingly complex world of expected return modeling and why it matters so much for retirement projections, portfolio construction, and financial advice. They explain how PWL Capital currently estimates expected returns across asset classes, why traditional Monte Carlo methods relying on Gaussian distributions may miss important market behaviors, and how new research could improve the realism of long-term financial planning simulations.
The conversation also explores a fascinating collaboration between PWL and Columbia Engineering student John Yang, who worked with Professor Michael Robbins on a project to build more realistic synthetic return data for financial planning. John explains how his team used empirical distributions, t-copulas, and Extreme Value Theory to better capture market crashes, fat tails, and asset co-movements during periods of stress. Ben and Braden then analyze how these improved simulation methods affect financial planning outcomes, sustainable spending estimates, and projections for long-term wealth accumulation.
 
Key Points From This Episode:
(0:00:00) Introduction to expected return modeling and why it matters for financial planning. 
(0:00:25) The importance of volatility, correlations, distribution shape, and time-series behavior in portfolio projections. 
(0:01:26) How Scott Cederburg's research on block bootstrapping influenced PWL's thinking on simulations. 
(0:02:03) Introduction to Columbia Engineering student John Yang and the industry research collaboration. 
(0:03:30) How Conquest Planning allows PWL to upload custom return simulations. 
(0:04:05) A new PWL client's detailed reasoning for moving from DIY investing to working with an advisor. 
(0:06:22) Why financial planning and Monte Carlo simulations were central to the client's decision. 
(0:07:22) Cross-border financial complexity and the value of professional advice. 
(0:08:03) Estate planning, cognitive decline, and the role of trusted financial relationships. 
(0:10:02) Research on cognitive decline and its impact on financial decision-making. 
(0:12:00) Delegation, accountability, and reducing mental overhead through advisory relationships. 
(0:13:47) Why the client chose PWL specifically and the appeal of evidence-based investing. 
(0:15:25) Ben and Braden discuss the perceived disconnect between online discourse and demand for AUM advisors. 
(0:16:12) Overview of PWL's methodology for estimating expected returns across asset classes. 
(0:17:05) How PWL combines historical returns with market-implied expected returns. 
(0:18:07) The use of factor premiums and expected return composition in taxable projections. 
(0:18:48) Why PWL previously relied on Gaussian multivariate normal distributions for simulations. 
(0:19:41) Arithmetic vs. geometric mean returns and why the distinction matters. 
(0:21:01) A simple example illustrating volatility drag. 
(0:23:29) Why diversification benefits must be incorporated into expected portfolio returns. 
(0:25:15) How correcting portfolio math improved expected return estimates by 20–30 basis points. 
(0:27:12) Transition to John Yang's interview and introduction to synthetic data generation. 
(0:30:07) John explains the limitations of Gaussian return assumptions. 
(0:31:04) Why realistic sequences of returns matter for retirement planning. 
(0:32:16) Empirical evidence that returns are not truly random. 
(0:33:25) The three modeling challenges: unique asset behavior, realistic co-movement, and tail risk. 
(0:37:49) Separating marginal distributions from dependency structures in the modeling process. 
(0:38:48) Using a t-copula to better model asset co-movement during market stress. 
(0:39:39) Why historical data alone struggles to capture rare crisis events. 
(0:40:06) Applying Extreme Value Theory and Generalized Pareto Distributions to model tail risk. 
(0:42:15) How Monte Carlo simulations generate many realistic future return paths. 
(0:43:00) Imposing forward-looking expected returns and volatility assumptions onto the simulations. 
(0:44:56) How the new framework better preserves skewness and kurtosis. 
(0:46:38) Evaluating the new model using marginal shape, tail behavior, and co-movement scores. 
(0:48:10) Why the new model significantly improved tail realism without sacrificing correlations. 
(0:49:05) Future extensions including dynamic correlations and volatility clustering. 
(0:50:28) Potential future use of GANs and machine learning for synthetic financial data. 
(0:52:02) Key takeaway: financial planning requires realistic return paths, not just summary statistics. 
(0:53:41) Braden analyzes how the new simulation framework affects financial advice. 
(0:55:04) Why monthly index data produced fatter tails than long-term annual DMS data. 
(0:58:47) The new model improved Monte Carlo success rates by roughly 2–3%. 
(1:00:25) Sustainable spending estimates changed only modestly under the new simulations. 
(1:02:27) Why the improved methodology matters more for alternative asset classes. 
(1:04:25) The surprising finding that median wealth outcomes increased while mean outcomes decreased. 
(1:05:47) Why Gaussian simulations can create unrealistic runaway wealth scenarios. 
(1:07:20) The practical implications for estate planning and multi-generational wealth projections. 
(1:08:30) Why better simulation methods are especially important for concentrated and alternative investments.
 
Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p
Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/
Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/
Benjamin on X — https://x.com/benjaminwfelix
Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/
 
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)