The Rational Reminder Podcast

• Episode 363 - The (Underappreciated) Risk of Individual Stocks

  What if holding just a few “winning” stocks is riskier than it seems? In this episode, Ben and Cameron explore the hidden dangers of concentrated portfolios and unpack the data that makes a strong case for diversification. Drawing from research by Hendrik Bessembinder, J.P. Morgan, and others, Ben lays out the harsh reality behind individual stock returns: the odds are stacked against long-term success. From skewed return distributions and catastrophic losses to behavioral traps like the endowment effect and familiarity bias, this conversation breaks down why most stock pickers lose—and why diversification remains the only “free lunch” in investing. Whether you're holding onto a single stock for tax reasons, overconfidence, or just inertia, this episode is a must-listen reality check on portfolio risk. They also share thoughts on advisor adoption of indexing, the slow shift in Canada, and how a Rational Reminder YouTube video sparked debate between stock pickers and indexers in the comments section. For anyone navigating concentrated positions—voluntarily or otherwise—this episode is packed with data-driven insight and real-world takeaways. Key Points From This Episode:   (0:00) Welcome to Episode 363: catching up in person and the value of working together in-office. (1:07) Why advisors are slow to adopt indexing—and how culture, compensation, and inertia play a role. (2:58) Demand is rising: indexing awareness among young advisors and investors continues to grow. (4:08) Main topic: The hidden risks of individual stock concentration. (5:40) The Nortel example: taxes, timing, and the illusion of "free" stock. (6:51) Individual stocks are far riskier than most people realize—especially recent winners. (9:09) Most investors hold between 3–7 stocks. Why that’s a problem. (11:29) Portfolio concentration = fugu prepared by an amateur chef. (12:45) Diversification reduces risk without reducing expected return. (14:04) JP Morgan’s “Agony & Ecstasy” report: 44% of stocks suffer catastrophic losses. (16:26) Why investors overweight the chance of a big win and underweight the risk of losses. (17:07) The reality of skewed returns: a few big winners, many losers. (24:35) The 2023 study on concentrated stock positions: recent top performers underperform the most. (28:40) How many stocks do you need for real diversification? Way more than 20–30. (32:00) Wealth dispersion and the long-term consequences of concentration. (35:24) Why even 100-stock portfolios only beat the market 47.5% of the time. (36:55) Taxes, control, and psychological hurdles make diversifying even harder. (38:14) Diversification depends on your preference for risk and skewness—but beware the odds. (39:08) Behind the scenes: Ben’s research process and content development workflow. (43:14) Ben’s guest appearance on Morningstar’s The Long View. (44:00) Meetups, t-shirt scarcity, and what’s next for PWL outreach.   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 Website — https://rationalreminder.ca/  Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/ Rational Reminder on X — https://x.com/RationalRemindRational Reminder on TikTok — www.tiktok.com/@rationalreminder Rational Reminder on YouTube — https://www.youtube.com/channel/ Rational Reminder Email — [email protected] Felix — https://pwlcapital.com/our-team/ Benjamin on X — https://x.com/benjaminwfelix Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/ Cameron Passmore — https://pwlcapital.com/our-team/ Cameron on X — https://x.com/CameronPassmore Cameron on LinkedIn — https://www.linkedin.com/in/cameronpassmore/` Episode 346: Hendrik Bessembinder - https://rationalreminder.ca/podcast/346 Papers From Today’s Episode:    ‘The Agony & The Ecstasy’ - https://privatebank.jpmorgan.com/nam/en/insights/latest-and-featured/eotm/the-agony-the-ecstasy ‘Why Index Works’ - https://www.top1000funds.com/wp-content/uploads/2017/07/Why-indexing-works.pdf ‘Underperformance of Concentrated Stock Positions’ - https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4541122 ‘How Many Stocks Should You Own?’ - https://ndvr.com/journal/how-many-stocks-should-you-own ‘Fund Concentration: A Magnifier of Manager Skill’ - https://discovery.researcher.life/article/fund-concentration-a-magnifier-of-manager-skill/67964b7ccc9d3cae87761f6ef19241a0

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• Episode 362 – AMA #7

  What if the hardest part of investing isn’t building a portfolio—but sticking to it? In this AMA edition of the Rational Reminder podcast, Ben Felix and Dan Bortolotti tackle listener questions ranging from sustainable retirement withdrawals to the dangers of structured products, with plenty of philosophical insights on risk, behavior, and financial planning. The episode opens with a deep dive into the 4% rule, exploring how time horizon, asset allocation, and global data can shift the definition of “safe.” They also explore the behavioral challenges of the “boring middle” of investing and why consistency may be the greatest alpha. Other standout segments include a sharp critique of bank-sold structured notes, an evidence-based takedown of trend following, and a fascinating discussion on the long-term impact of demographic shifts and index investing. Throughout, Ben and Dan blend technical insight with practical wisdom and academic research, delivering a thoughtful and entertaining conversation for both DIY investors and those working with advisors.   Key Points From This Episode: (0:01:07) What the latest data says about safe withdrawal rates, especially for early retirees with 100% equity exposure. (0:08:45) How variable vs. fixed withdrawals affect outcomes—and the trade-offs retirees must consider. (0:17:01) The behavioral risks of the “boring middle” and how automation or advice helps investors stay disciplined. (0:26:13) Reflections on market crashes—why hindsight downplays the emotional reality of volatility. (0:33:27) Commission conflicts: Why bank advisors push structured notes and the incentives behind them. (0:44:22) Education vs. malice: Are bad financial advisors untrained, conflicted, or both? (0:49:08) Are structured notes ever justified? (Spoiler: very rarely.) (0:56:44) Trend following: Legitimate strategy or fancy market timing? Examining the live track records. (1:02:52) Diversifying your life like a portfolio: Applying the PERMA model to personal growth. (1:10:18) The one use of leverage that actually makes sense—and why most others don’t. (1:14:20) Will aging demographics crash ETF markets? What the data and theory suggest. (1:19:02) Why even complex macro trends don’t justify deviating from a simple, low-cost investment plan.   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 Website — https://rationalreminder.ca/  Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/ Rational Reminder on X — https://x.com/RationalRemind Rational Reminder on TikTok — www.tiktok.com/@rationalreminder Rational Reminder on YouTube — https://www.youtube.com/channel/ Rational Reminder Email — [email protected] Benjamin Felix — https://pwlcapital.com/our-team/ Benjamin on X — https://x.com/benjaminwfelix Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/ Dan Bortolotti — https://pwlcapital.com/our-team/ Dan Bortolotti on LinkedIn — https://ca.linkedin.com/in/dan-bortolotti-8a482310 Episode 261: Felix Fattinger - https://rationalreminder.ca/podcast/261 Episode 314: Valentin Haddad - https://rationalreminder.ca/podcast/314 Episode 302: Michael Green - https://rationalreminder.ca/podcast/302 Episode 222: Cassie Holmes - https://rationalreminder.ca/podcast/222 Episode 278: Juhani Linnainmaa - https://rationalreminder.ca/podcast/278 Episode 212: Ralph S.J. Koijen - https://rationalreminder.ca/podcast/212 Episode 322: Marco Sammon — https://rationalreminder.ca/podcast/322Marco Sammon  

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• Episode 361: Alex Edmans - Finding "The Truth" in Economics, Finance, and Life

  Today, Ben plays lone host for the first time as we welcome Alex Edmans to the show. Alex is a Professor of Finance at London Business School as well as an accomplished speaker, author, investment banker, and financial advisor. To start, Alex describes his involvement in the formation of a new law in the UK before defining ‘misinformation’ and where confirmation bias fits in. Then, we assess the impact severity of confirmation bias, biased search versus biased interpretation, the role of generative AI in confirmation bias, and the levels of susceptibility within confirmation bias. We also explore the role of black-and-white thinking in concealing the truth, Alex’s Ladder of Misinference as seen in May Contain Lies, the 10,000-hour rule and other famous statements of misinformation, and how the idea of a narrative may influence how people interpret and misinterpret facts. We end with how to guard against the plague of data mining in research, data as evidence and what this implies for evidence in financial economics, and Alex shares helpful advice for determining truth in any circumstance.   Key Points From This Episode:   (0:03:27) Alex Edmans walks us through the erroneous evidence that influenced a new UK law. (0:07:13) Misinformation; living in a post-truth world; and where confirmation bias fits in. (0:12:06) The severity of confirmation bias, and biased search versus biased interpretation. (0:18:19) Unpacking generative AI and the susceptibility thresholds of confirmation bias.   (0:21:25) How black-and-white thinking makes the truth more elusive. (0:25:40) Understanding Alex’s Ladder of Misinference as seen in May Contain Lies. (0:28:17) Debunking the 10,000-hour rule and other enduring statements of misinformation. (0:38:10) The second step on the Ladder of Misinference: Why facts are not data. (0:42:42) How the idea of a narrative influences how people interpret or misinterpret facts. (0:44:25) Why data is not evidence, and examining the plague of data mining in research. (0:48:36) Guarding against data mining and the consequences of investing with misinformation.   (0:53:01) When data is evidence, and what this says about evidence in financial economics. (0:55:49) Why evidence may not be proof. (0:59:14) Practical advice for seeking the truth for important decisions and in everyday life.   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 Website — https://rationalreminder.ca/  Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/ Rational Reminder on X — https://x.com/RationalRemind Rational Reminder on TikTok — www.tiktok.com/@rationalreminder Rational Reminder on YouTube — https://www.youtube.com/channel/ Rational Reminder Email — [email protected] Benjamin Felix — https://pwlcapital.com/our-team/ Benjamin on X — https://x.com/benjaminwfelix Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/ Alex Edmans — https://alexedmans.com/  Alex Edmans on LinkedIn — https://www.linkedin.com/in/aedmans  Alex Edmans on X — https://x.com/aedmans  London Business School — https://www.london.edu/  Fulbright Fellows | MIT — https://ir.mit.edu/projects/fulbright-fellows/  Atkins — https://www.atkins.com/  ‘Matthew Walker's “Why We Sleep” Is Riddled with Scientific and Factual Errors’ — https://guzey.com/books/why-we-sleep/  ‘Grit: The Power of Passion and Perseverance | Angela Lee Duckworth | TED’ — https://www.youtube.com/watch?v=H14bBuluwB8    Books From Today’s Episode:   May Contain Lies — https://maycontainlies.com/  Grow the Pie — https://mybook.to/Grow-the-Pie Outliers — https://www.amazon.com/Outliers-Story-Success-Malcolm-Gladwell/dp/0316017930  Why We Sleep — https://www.goodreads.com/book/show/34466963-why-we-sleep  Start with Why — https://www.amazon.com/Start-Why-Leaders-Inspire-Everyone/dp/1591846447  Grit — https://www.amazon.com/Grit-Passion-Perseverance-Angela-Duckworth/dp/1501111108    Papers From Today’s Episode:   ‘CEO-Employees Pay Ratio, Employees’ Productivity and Firm Performance: Evidence from UK’ — https://www.researchgate.net/publication/391787593_CEO-Employees_pay_ratio_employees'_productivity_and_firm_performance_evidence_from_UK  ‘A Theory of Fair CEO Pay’ — https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4294589 

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• Episode 360 – Gerard O'Reilly: The Components of Net Returns

  What if “just buying the market” isn’t the end of the story? In this episode, we are joined by Gerard O’Reilly, Co-CEO and Co-CIO of Dimensional Fund Advisors, for a deep dive into what really drives net investment returns. Gerard returns to the Rational Reminder podcast to explain the key principles that differentiate Dimensional’s approach from traditional indexing—and why implementation, flexibility, and detail matter so much more than investors might think. We explore the concept of hidden costs in index investing, how index reconstitution and trading frictions erode returns, and the nuanced decisions that shape a market portfolio: defining the market, excluding low-returning stocks, optimizing tax efficiency, and more. Gerard breaks down how Dimensional’s rules-based, evidence-backed process improves outcomes through smart exclusions (like IPOs and high asset-growth firms), precise trading, securities lending, and better handling of corporate actions. From the dangers of chasing low fees to the surprising benefits of thoughtful execution, this conversation is a masterclass in next-level investing.   Key Points From This Episode:   (0:01:07) Why Gerard was invited back: Dimensional’s approach to hidden costs and net returns. (0:02:38) Looking beyond “index good, fees bad”—why investors should dig deeper. (0:04:21) Gerard’s background: From Caltech rocket scientist to Dimensional co-CEO. (0:06:22) How Dimensional differs from market-cap weighted index funds. (0:08:42) Four components of net returns: Two increase returns, two decrease them. (0:12:45) Defining the market: Free float, liquidity thresholds, and dynamic inclusion. (0:17:52) How small-cap index definitions can create return differentials as high as 10%. (0:22:03) What securities Dimensional excludes—and why: low-profitability growth, high asset growth, IPOs, and REITs. (0:29:26) Why IPOs are excluded for 6–12 months and the mechanics behind inclusion. (0:33:16) Why Dimensional’s exclusions aren’t like traditional active management. (0:35:09) The “Great British Bake-Off” analogy: baking better portfolios with the same ingredients. (0:38:13) How securities lending boosts returns—and how Dimensional does it better. (0:42:09) Managing corporate actions (like M&A) to reduce cash drag. (0:45:18) How Dimensional deals with buybacks and new share issuance.  (0:47:29) Momentum, short-term reversals, and securities lending fees as trading signals. (0:50:36) Why Dimensional may lend out stocks that have negative momentum. (0:52:42) How trading costs affect net returns and Dimensional’s execution edge. (0:56:06) Hidden costs of indexing: Index fund rebalancing and price impact. (1:03:19) Why focusing solely on fees is misleading—and what “value for service” really means. (1:06:18) DFUS: A case study of Dimensional’s market series outperforming index funds. (1:08:44) How Dimensional builds portfolios with intentional tilts toward higher expected returns. (1:12:35) What excites Gerard: Expanding access, ETF innovations, and global growth.   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 Website — https://rationalreminder.ca/  Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/ Rational Reminder on X — https://x.com/RationalRemindRational Reminder on TikTok — www.tiktok.com/@rationalreminder Rational Reminder on YouTube — https://www.youtube.com/channel/ Rational Reminder Email — [email protected] Felix — https://pwlcapital.com/our-team/ Benjamin on X — https://x.com/benjaminwfelix Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/ Cameron Passmore — https://pwlcapital.com/our-team/ Cameron on X — https://x.com/CameronPassmore Cameron on LinkedIn — https://www.linkedin.com/in/cameronpassmore/ Gerard O’Reilly — https://www.dimensional.com/us-en/bios/gerard-k-oreilly Dimensional Fund Advisors: https://www.dimensional.com/ Episode 322: Marco Sammon — https://rationalreminder.ca/podcast/322Marco Sammon  Episode 198: Gerard O’Reilly — https://rationalreminder.ca/podcast/198

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• Episode 359 - The Most Controversial Topics in Personal Finance

  For the first time as a host combination, Ben, Dan, and Cameron sit down to discuss the most controversial topics in personal finance. We begin with identity and how it informs decision-making. Then, we revisit the renting versus buying debate, why this remains a highly controversial topic, the ins and outs of income investing, and understating the fervor of dividend investing. We also unpack FIRE as a branch of self-help; how it informs happiness; and how personality influences one’s approach to the FIRE principle. To end, we closely examine Bill Bengen’s 4% rule, and the Aftershow encourages us to maintain high podcasting standards while revealing what you can look forward to in our latest Rational Reminder t-shirt release.    Key Points From This Episode:   (0:01:25) Cameron’s positive LinkedIn experience regarding insurance.  (0:08:10) How identity informs decision-making.  (0:15:24) Why renting versus buying a home remains a controversial topic.  (0:27:50) Income investing, covered calls, and the fervor of dividend investing. (0:46:34) FIRE: Financial independence, retire early. (0:54:36) Unpacking FIRE as a branch of self-help, and the role of FIRE in happiness.  (1:07:07) How personality and identity inform one’s approach to FIRE. (1:10:34) Addressing the 4% rule.  (1:14:16) The Aftershow: Setting and keeping high standards, and Rational Reminder t-shirts.    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 Website — https://rationalreminder.ca/  Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/ Rational Reminder on X — https://x.com/RationalRemindRational Reminder on TikTok — https://www.tiktok.com/@rationalreminder Rational Reminder on YouTube — https://www.youtube.com/channel/ Rational Reminder Email — [email protected]  Rational Reminder Merchandise — https://shop.rationalreminder.ca/ Benjamin Felix — https://pwlcapital.com/our-team/ Benjamin on X — https://x.com/benjaminwfelix Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/ Cameron Passmore — https://pwlcapital.com/our-team/ Cameron on X — https://x.com/CameronPassmore Cameron on LinkedIn — https://www.linkedin.com/in/cameronpassmore/  Dan Bortolotti on LinkedIn — https://www.linkedin.com/in/dan-bortolotti-8a482310/  Episode 358: Eli Beracha: An Academic Perspective on Renting vs. Owning a Home — https://rationalreminder.ca/podcast/358  Episode 214: Jay Van Bavel: Shared Identities and Decision Making — https://rationalreminder.ca/podcast/214   Episode 260: Prof. James Choi: Practical Finance — https://rationalreminder.ca/podcast/260  Episode 273: Professor Samuel Hartzmark: Asset Pricing, Behavioural Finance, and Sustainability Rankings — https://rationalreminder.ca/podcast/273   Episode 95: Scott Rieckens (Playing with FIRE): Finding Financial Education, Perspective, and Freedom — https://rationalreminder.ca/podcast/95  Episode 258: Prof. Meir Statman: Financial Decisions for Normal People — https://rationalreminder.ca/podcast/258   Bonus Episode - Prof. Meir Statman: A Wealth of Well-Being — https://rationalreminder.ca/podcast/2024/4/18/bonus-episode-prof-meir-statman-a-wealth-of-well-being   Episode 230: Prof. Robert Frank: Success, Luck, and Luxury — https://rationalreminder.ca/podcast/230   Episode 135: William Bengen: The 5% Rule for Retirement Spending — https://rationalreminder.ca/podcast/135  Episode 164: Comprehensive Overview: The 4% Rule — https://rationalreminder.ca/podcast/164   Episode 357: AMA #6 — https://rationalreminder.ca/podcast/357  Morgan Housel — https://www.morganhousel.com/   ‘Renting vs. Buying a Home: What People Get Wrong’ — https://www.youtube.com/watch?v=j4H9LL7A-nQ   MobLand — https://www.imdb.com/title/tt31510819/  Ray Donovan — https://www.imdb.com/title/tt2249007/  Animal Kingdom — https://www.imdb.com/title/tt5574490/    Books From Today’s Episode:    Rich Dad Poor Dad — https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612680194    Self Help, Inc.: Makeover Culture in American Life — https://www.amazon.com/Self-Help-Inc-Makeover-American/dp/0195337263    Papers From Today’s Episode:    'Motivated Numeracy and Enlightened Self-Government' - https://www.cambridge.org/core/journals/behavioural-public-policy/article/abs/motivated-numeracy-and-enlightened-selfgovernment/EC9F2410D5562EF10B7A5E2539063806    ‘Nevertheless, They Persist: Cross-country differences in homeownership behavior’ — https://www.sciencedirect.com/science/article/abs/pii/S1051137721000590    ‘Rent or Buy? Inflation Experiences and Homeownership within and across Countries’ — https://www.researchgate.net/publication/379974645_Rent_or_Buy_Inflation_Experiences_and_Homeownership_within_and_across_Countries     ‘Dividend Policy, Growth, and the Valuation of Shares’ — https://www.researchgate.net/publication/24102112_Dividend_Policy_Growth_and_the_Valuation_Of_Shares    ‘Chapter 3 - Behavioral Household Finance*’ — https://www.sciencedirect.com/science/article/abs/pii/S2352239918300046    ‘Common Risk Factors in the Returns on Stocks and Bonds’ — https://www.sciencedirect.com/science/article/abs/pii/0304405X93900235     ‘The Dividend Disconnect’ — https://papers.ssrn.com/sol3/papers.cfm?abstract_id=2876373    ‘A Devil's Bargain: When Generating Income Undermines Investment Returns’ — https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4580048    ‘The Financialization of Anti-Capitalism? The Case of the “Financial Independence Retire Early” Community’ — https://www.tandfonline.com/doi/full/10.1080/17530350.2021.1891951    ‘High Income Improves Evaluation of Life But Not Emotional Well-Being’ — https://www.pnas.org/doi/10.1073/pnas.1011492107     ‘Income And Emotional Well-Being: A Conflict Resolved’ — https://www.pnas.org/doi/10.1073/pnas.2208661120   

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