The Rational Reminder Podcast

In this episode, we welcome back William Bernstein to discuss the final book of his longtime friend Jonathan Clements, Money and Me. Bill reflects on Jonathan's ideas about spending, happiness, retirement, investing, inheritance, and the psychology of financial decision-making, while sharing personal stories that bring those ideas to life.
 
We explore why material purchases often lose their appeal quickly, why autonomy can be one of the best things money can buy, and how worrying about money can be a greater problem than spending it. Bill also discusses the four horsemen of financial disaster—inflation, deflation, confiscation, and destruction—why diversification matters, and why investors should be skeptical of assumptions about future returns and market forecasts.
 
The conversation also examines what it means to "win the game" financially, why retirement should be thought of as a verb rather than a destination, and the three foundations of well-being: connection, competence, and autonomy. Bill shares Jonathan's approach to teaching children about money, the concept of "Omega" as a way to think about spending versus saving, and why the people around us can have an enormous influence on our expectations and consumption.
 
Key Points From This Episode:
(4:56) Why success can contain the seeds of its own destruction—and the role of competition, organizational hubris, and luck.
(6:15) Why dynastic wealth is so difficult to preserve across generations.
(8:28) A hierarchy of spending: material purchases, experiences, autonomy, and the relief from worrying about money.
(10:54) Why some people continue worrying about money no matter how much they have.
(11:44) Why we are poor at predicting what purchases and lifestyle changes will actually make us happy.
(13:36) How to pressure-test large purchases by considering their downsides and their effect on your time.
(14:20) Why the happiness generated by spending does not necessarily scale with the price of a purchase.
(15:21) The importance of gratitude and savoring small pleasures.
(16:39) The four horsemen of financial apocalypse: inflation, deflation, confiscation, and destruction.
(18:15) Why inflation is the financial risk Bill focuses on—and how investors can blunt its effects.
(19:26) Why relatively inexpensive international markets can still offer optimism for long-term investors.
(21:02) Jonathan Clements' "investment sin": slightly overbalancing when rebalancing.
(22:04) What it means to have "won the game" financially.
(24:36) Why a TIPS ladder or annuity can help defuse retirement spending needs.
(25:19) Why the math of financial planning often fails to account for human psychology.
(27:21) Why diversification matters when bad returns arrive at the same time as bad circumstances.
(28:20) The challenge of variable spending in retirement.
(29:10) Why retirement should be a verb—and why simply stopping work can leave people searching for meaning.
(30:00) The three foundations of happiness: connection, competence, and autonomy.
(32:03) Investment assumptions people should avoid, including confusing great companies with great stocks.
(33:10) Why eloquence can be an alarm bell when evaluating financial forecasts.
(34:18) Jonathan's three-pronged strategy for getting more out of your money: pause before making important decisions.
(35:01) How to audit your past spending to identify what actually made you happy.
(37:11) Hedonic versus eudaimonic happiness—and why life satisfaction can outlast momentary pleasure.
(39:05) Why enjoying your work can be more valuable than maximizing your salary.
(40:56) A different perspective on FIRE: working less and doing work you enjoy rather than simply retiring early.
(41:37) Why giving money to children while you're alive can be more useful than leaving it as an inheritance.
(42:29) How parents teach children about money by modeling their own spending behavior.
(44:13) Jonathan's practical approach to teaching children about spending and saving.
(44:49) The "Omega" concept: avoiding both YOLO spending and dying as the richest person in the graveyard.
(46:26) How social comparisons influence spending and expectations.
(48:54) Why rising markets can encourage investors to take on more risk.
(49:06) How recency and the availability heuristic shape investment beliefs.
(49:46) Bill's favorite memories of Jonathan and his remarkable outlook while facing a terminal diagnosis.
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)

Barry Ritholtz returns to the Rational Reminder podcast to discuss the biggest mistakes investors make—and why avoiding them may matter more than finding the next great investment. Drawing on decades of experience in markets, wealth management, and financial media, Barry explains why forecasting consistently fails, how investors can distinguish good advice from noise, and why humility, probabilistic thinking, and disciplined behavior are among the most valuable investing skills.
 
Throughout the conversation, Barry shares lessons from his new book, How Not to Invest, covering everything from media consumption and behavioral biases to index investing, portfolio concentration, market cycles, and choosing a financial advisor. He explains why experts are often better at providing context than making predictions, why social media amplifies poor financial advice, and how investors can build processes that help them stay disciplined through uncertainty. The discussion blends academic research, practical experience, and memorable stories into a comprehensive guide for becoming a better long-term investor.
 
Key Points From This Episode:
(0:04) Cameron and Ben welcome Barry Ritholtz back to the podcast and discuss his new book, How Not to Invest.
(4:12) Why successful billionaires often make poor economic forecasters and how the halo effect leads people to overestimate expertise.
(6:39) Why Wall Street professionals are generally poor at forecasting future market returns despite their domain expertise.
(7:42) What experts are actually good at: providing context, historical perspective, and nuanced analysis rather than predicting the future.
(8:47) Barry's checklist for identifying bad financial advice, including emotional appeals, false certainty, and conflicts of interest.
(10:35) How social media algorithms reward outrage and overconfidence instead of thoughtful investing.
(11:21) Why 24/7 financial news encourages unnecessary action that often hurts long-term investment returns.
(12:17) Why long-term investors are often better off ignoring financial news altogether.
(13:52) How short-form financial content on platforms like TikTok encourages misinformation and poor investing decisions.
(15:22) Gell-Mann Amnesia and why investors should remain skeptical even of trusted news sources.
(18:00) How reading books, consuming long-form content, and building a trusted information network improves decision making.
(20:21) Barry's definition of investing as making probabilistic decisions with imperfect information in an unknowable world.
(22:55) How successful investors focus on controlling savings, asset allocation, discipline, and behavior instead of unpredictable events.
(24:52) Why recognizing the limits of your own knowledge is one of investing's greatest advantages.
(26:30) How experience, losses, and continuous learning help investors become more self-aware.
(27:16) Three ideas that heavily influence Barry's investment philosophy: Sturgeon's Law, George Box's models, and William Goldman's "Nobody knows anything."
(30:18) Whether artificial intelligence changes Sturgeon's Law that "90% of everything is crap."
(31:46) Three forms of economic innumeracy that lead investors astray: denominator blindness, survivorship bias, and misunderstanding compounding.
(36:04) Why understanding secular bull and bear markets is useful psychologically—but not as a timing strategy.
(39:12) Why investors should understand market cycles without attempting to trade around them.
(40:44) What stock valuations can—and cannot—tell investors about future returns.
(42:18) How investors should respond to wars, pandemics, and other major external events.
(45:53) The biggest investing lessons from the COVID-19 market crash and why personal experience often differs from market performance.
(49:04) Why index investing remains one of the most reliable approaches to long-term wealth creation.
(50:44) Why every market forecast should be expressed probabilistically rather than with certainty.
(52:06) The lies traders tell themselves and why disciplined risk management separates successful professionals.
(56:11) What active investors need if they hope to consistently outperform.
(57:24) The biggest behavioral mistakes investors make, including lack of planning, excessive concentration, and ignoring taxes.
(59:43) Why concentrated stock positions become dangerous—even after creating substantial wealth.
(1:02:33) How sudden wealth and large financial windfalls frequently lead to costly mistakes.
(1:05:14) How to identify trustworthy financial advisors by evaluating their process, temperament, and communication.
(1:07:27) Why advisors who consistently communicate their thinking help investors avoid emotional mistakes.
(1:09:26) Barry's practical blueprint for becoming a better long-term investor: create a plan, invest consistently, define the purpose of money, and build around a diversified index portfolio.
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 Ask Me Anything episode, Ben Felix, Ben Wilson, and Louai Bibi tackle a wide-ranging collection of listener questions spanning investing, retirement, family finance, and financial planning. Along the way, they combine academic research, practical experience, and thoughtful discussion to separate evidence-based decisions from intuition.
 
The conversation explores everything from teaching children healthy money habits and the long-term behavioral challenges of value investing to sequence of returns risk, retirement spending strategies, and global portfolio construction. The episode concludes with an in-depth discussion of Louai Bibi's National Financial Planning Award-winning financial plan, highlighting the importance of holistic advice, evidence-based planning, and continuous improvement through client feedback.
 
Key Points From This Episode:
(00:00:00) Introduction
(0:05:30) Advice for aspiring financial planners: Building skills, credentials, networks, and mentorship early in your career.
(0:07:35) Why young advisors should be "a sponge" and learn from both good and bad professional experiences.
(0:09:41) Ben Felix on completing the CFA, CIM, and CFP early—and why creating content accelerated his learning.
(0:11:51) Why getting large numbers of client-facing "reps" can dramatically improve an advisor's ability to communicate advice.
(0:15:44) Choosing the right firm, team, and mentors—and how networking helped Ben Felix ultimately join PWL.
(0:18:53) Should a young physician borrow from a professional line of credit to invest?
(0:24:55) Robert Merton's perspective on leverage for young investors and the risks of implementing leverage through margin borrowing.
(0:28:21) Why the psychological experience of investing borrowed money can be very different from owning an unleveraged portfolio.
(0:30:35) How much leverage is needed before it meaningfully changes a long-term financial plan.
(0:31:36) Should investors increase their equity allocation before considering leverage?
(0:33:39) Louai's experience working with physicians and why becoming debt-free can change how people feel about borrowing to invest.
(0:36:00) Louai and Ben Felix share their own experiences with leverage.
(0:36:59) How to teach children about money, scarcity, saving, generosity, and spending.
(0:38:26) Ben Wilson's approach: Save 50%, give 10%, and let his kids decide what to do with the remaining 40%.
(0:40:02) Using wealth for memorable family experiences rather than simply giving children more money.
(0:42:51) Why anticipating an experience can be an important part of the enjoyment it creates.
(0:43:42) Is the value premium worth the behavioral challenge of potentially enduring years of underperformance?
(0:44:11) Ben Felix explains why the difficulty of sticking with value may itself contribute to the premium.
(0:45:47) Can having a sufficiently large portfolio eliminate sequence-of-returns concerns?
(0:49:41) Reframing "sequence of returns" as "sequence of withdrawals"—and why flexible spending matters.
(0:51:21) Separating retirement expenses into fixed needs and flexible spending.
(0:52:47) The purchases that have delivered the best personal ROI for Ben, Ben, and Louai.
(0:53:08) Ben Felix on his indoor basketball hoop, family travel, sauna, and prepared meal delivery.
(0:56:56) Ben Wilson on family vacations, skiing, cycling, and why his family chose a pool over a cottage or boat.
(0:58:27) Louai on his 49-inch monitor, his dog, and investing in health and fitness.
(1:00:42) How should investors geographically weight a global small-cap value portfolio?
(1:05:13) Why a globally diversified portfolio that an investor can actually stick with matters more than finding a theoretically perfect country allocation.
(1:07:19) What should investors approaching retirement or FIRE do about sequence-of-returns risk?
(1:09:00) Research comparing declining, rising, and static equity allocations during retirement.
(1:13:38) Why risk tolerance, time horizon, spending needs, and financial-plan resilience should drive retirement asset allocation.
(1:15:07) The National Financial Planning Awards, the judging process, and the sponsorship conflict disclosure surrounding Louai's award.
(1:18:37) Inside Louai's 47-page award-winning financial plan and the range of planning issues it addressed.
(1:20:06) What Louai believes actually distinguished the submission: Not one clever strategy, but a holistic decision-making process.
(1:21:39) Why Louai sought feedback from planners outside PWL and how the award process can improve the broader team.
(1:23:26) Why Louai believes financial-planning knowledge and feedback should be shared rather than "gatekept."
(1:23:56) How feedback from the Rational Reminder community changed Louai's thinking about investment risk.
(1:24:40) Why defining risk purely as short-term volatility can overlook the bigger risk of failing to achieve financial goals.
(1:27:59) How public feedback through the podcast creates a powerful learning loop for the PWL team.
(1:28:29) A PWL client review on the value of planning, professional experience, and advice that puts the client's interests first.



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 Jean-Pierre Aubry, Associate Director of Retirement Plans and Finance at the Center for Retirement Research at Boston College, for a research-driven conversation about retirement investing, financial advice, pension fund management, and inflation. Drawing from years of empirical research, Jean-Pierre shares insights into how households actually invest, how financial advisors shape portfolio decisions, and why investors often hold asset allocations that differ from their own stated preferences.
 
We also examine the investment strategies of public pension plans, why their increasing reliance on alternative assets has largely failed to deliver superior performance, and the institutional forces driving those decisions. Finally, Jean-Pierre explains how inflation disproportionately affects retirees, why many households overreact during inflationary periods, and why understanding retirement risks—from market volatility to sequence of returns—is critical for long-term financial security.
 
Key Points From This Episode:
(0:06) Introduction to Jean-Pierre Aubry and the Center for Retirement Research at Boston College.
(6:29) The Center's mission: producing objective, accessible retirement policy research.
(7:03) Why investors' actual stock allocations are higher than their stated ideal allocations.
(9:31) Defaults and target-date funds may explain the gap between desired and actual portfolios.
(10:46) Investors tend to underestimate long-term stock returns and overestimate market risk.
(11:22) Financial advisors generally encourage higher equity allocations by reducing investor pessimism.
(12:06) How advisor compensation can create incentives to recommend higher stock exposure.
(13:42) Research showing advisor recommendations vary more across advisors than across client profiles.
(16:56) The "advisor fixed effect": advisors largely recommend portfolios consistent with their own philosophy.
(18:57) Why working with an advisor often leads investors to hold more equities.
(20:26) How target-date funds work and why auto-enrollment is reshaping retirement investing.
(22:57) Why advisors and target-date funds are generally improving retirement security.
(23:57) The evolution of public pension investing from bonds to equities and then alternative assets.
(30:12) The growing influence of consultants and peer effects on public pension investment decisions.
(31:14) Why pension plans with greater allocations to alternatives have generally underperformed peers.
(32:23) Comparing public pension performance against a simple 60/40 index benchmark.
(36:43) Whether indexing may be a better long-term solution for public pension investing.
(39:35) Concerns about adding private assets to default retirement plan options.
(40:15) Maintaining objectivity while researching politically sensitive retirement issues.
(42:58) Why investment policy remains the "final frontier" for improving public pension systems.
(46:45) Why retirees are especially vulnerable to inflation.
(50:06) How inflation affects retirees differently across age and wealth levels.
(51:52) Why households tend to overspend during inflationary periods.
(53:38) How financial advisors adjust recommendations when inflation and interest rates rise.
(54:11) Why inflation ultimately reduces retirement security for many households.
(54:42) Which retirees face the greatest market risk.
(55:35) Why most retirees have little understanding of sequence of returns risk.
(55:56) Advisors understand sequence risk, but that knowledge doesn't appear to transfer to clients.
(57:23) Why declining equity exposure over time remains the canonical life-cycle investing approach.
(58:25) Jean-Pierre's definition of success: purpose, meaningful relationships, and financial security.
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 AMA episode, Ben Felix, Dan Bortolotti, and Ben Wilson tackle a wide range of practical investing questions submitted by listeners. They begin by discussing one of the most common investing mistakes—market timing—and explain why getting back into the market is often harder than getting out. From there, they explore the evidence behind lump sum investing versus dollar-cost averaging, why high valuations rarely justify sitting in cash, and how your discomfort with investing may reveal a mismatch between your portfolio and your true risk tolerance.
 
The conversation also pulls back the curtain on PWL Capital's investment committee, detailing how new investment products are evaluated, how due diligence is conducted, and why even seemingly simple index funds require ongoing scrutiny. They then examine whether any recent Canadian ETF innovations are genuinely useful, discuss retirement-focused T-Series asset allocation ETFs, debate whether gamified trading creates opportunities for active management, and respond to questions about inflation, currency debasement, and the real drivers of long-term stock returns. As always, the episode closes with a lighter listener question before reading a review from the audience.



Key Points From This Episode:
(0:04) Introduction and why AMA episodes continue to resonate with listeners.
(0:55) A listener asks how to reinvest after selling half their portfolio over bubble concerns.
(2:00) Why successful market timing requires being right twice.
(3:04) Why all-time market highs are normal and poor signals for investment decisions.
(4:00) What market valuations can—and cannot—tell us about future returns.
(5:00) The evidence comparing lump sum investing with dollar-cost averaging.
(6:34) Why even the worst historical entry points rarely favor dollar-cost averaging.
(9:07) How investment anxiety often points to an overly aggressive asset allocation.
(11:37) The psychology of buying after market crashes and why investors rarely do.
(13:20) Why the best strategy is often whichever gets you invested and keeps you there.
(16:14) A behind-the-scenes look at PWL Capital's investment committee.
(17:23) How new securities are researched, reviewed, and approved.
(19:10) How acquisitions have changed the firm's investment oversight process.
(20:15) Annual due diligence on ETF providers and fund managers.
(21:55) Why even plain-vanilla index funds require performance monitoring.
(25:17) Are there any genuinely innovative new Canadian ETFs?
(26:27) Why most ETF innovation is driven by investor demand rather than better investing.
(28:19) Avantis ETFs and discount bond ETFs as notable recent developments.
(33:52) Why ETF issuers tend to launch products after investment themes become popular.
(33:52) Where investors should spend their planning time when wealth is still relatively small.
(35:00) Why growing human capital often has a greater impact than optimizing investments.
(37:59) Budgeting, saving, and account selection early in an investing journey.
(39:14) BMO's new T-Series asset allocation ETFs and how they generate retirement income.
(41:56) Understanding managed distributions and return of capital.
(44:08) Why these retirement ETFs may suit DIY investors but not every retiree.
(48:31) Whether gamified trading and meme stocks create opportunities for active managers.
(50:08) What the evidence says about active management in small-cap growth stocks.
(53:39) Why market competition limits persistent opportunities from retail speculation.
(53:39) Do stocks only rise because governments debase currencies?
(55:59) Inflation measurement, currency debasement, and common misconceptions.
(58:10) Why productive businesses—not money printing alone—drive long-term stock returns.
(59:53) Ben answers a listener's basketball shoe question.
(1:02:02) A listener review from Switzerland and closing remarks.
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/
Dollar Cost Averaging vs Lump Sum Investing - https://pwlcapital.com/wp-content/uploads/2024/08/Dollar-Cost-Averaging-vs-Lump-Sum-Investing.pdf

Buy The Dip - https://pwlcapital.com/wp-content/uploads/2024/08/PWL-Felix-Warwick-Buy-The-Dip_A.pdf
 
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)