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)

In this episode, we are joined by Dr. Paul Kaplan, economist, CFA charterholder, former Director of Research at Morningstar Canada, and co-author of Lifetime Financial Advice, for a fascinating exploration of life cycle finance. Drawing on decades of research in economics, portfolio construction, and asset allocation, Paul explains how financial planning should be grounded in optimizing lifetime consumption rather than relying on disconnected rules of thumb.

We explore how life cycle finance integrates consumption, saving, investing, and retirement spending into a single framework, why risk tolerance and risk capacity are fundamentally different concepts, and how human capital should be treated as part of an investor's balance sheet. Paul also walks through the life cycle model he and Tom Idzorek developed, explains why traditional retirement rules like the 4% rule lack theoretical foundations, and demonstrates an open-source spreadsheet that allows anyone to experiment with the model for themselves. This conversation brings together economics, portfolio theory, and financial planning into a practical framework for making better lifetime financial decisions.

Key Points From This Episode:

(0:04) Introduction to Dr. Paul Kaplan and the topic of life cycle finance.

(4:38) What life cycle finance is and why consumption smoothing is its central objective.

(5:20) How life cycle models optimize saving, investing, retirement spending, insurance, and annuities.

(6:36) Linking life cycle finance with Harry Markowitz's mean-variance optimization.

(8:38) Why consumption—not wealth accumulation—is the true focus of financial planning.

(9:56) The concept of an economic balance sheet: financial assets, human capital, liabilities, and net worth.

(10:59) Holistic investor profiling beyond traditional risk tolerance questionnaires.

(13:23) Why risk tolerance and risk capacity should never be combined into a single score.

(16:48) Assessing the risk characteristics of human capital.

(17:36) Applying utility theory behind the scenes in financial planning software.

(19:15) Sample profiling questions that measure lifetime consumption preferences.

(20:54) Why maximizing lifetime utility ultimately means optimizing consumption.

(22:55) How preferences, needs, and circumstances shape lifetime financial plans.

(24:13) The primary outputs of a life cycle model: consumption and asset allocation.

(25:01) The roles of life insurance and annuities in lifetime financial planning.

(27:44) How uncertain investment returns influence both spending and asset allocation.

(28:19) Why longevity assumptions are critical in retirement planning.

(29:37) Simplifying complex life cycle optimization into practical formulas.

(30:27) Why life cycle finance challenges rules of thumb like the 4% withdrawal rule.

(31:12) Flexible retirement spending versus fixed withdrawal strategies.

(34:01) Why consumption should be treated as an output rather than an input.

(36:05) The importance of asset location and after-tax portfolio construction.

(37:04) Why asset allocation and asset location should be solved simultaneously.

(38:19) Harry Markowitz on why asset allocation became the foundation of modern investing.

(40:06) The need for financial planning software built on life cycle theory.

(41:55) A walkthrough of Paul's open-source life cycle finance spreadsheet.

(46:58) Understanding economic balance sheets and asset mix visualizations.

(49:17) Which investor characteristics have the greatest influence on optimal asset allocation.

(50:52) Why Nobel Prize-winning life cycle finance research has yet to become mainstream practice.

(51:37) The evolving role of financial advisors in helping clients make rational financial decisions.

(52:50) How Paul's own investment philosophy emphasizes indexing and asset allocation.

(54:13) Factor investing, popularity theory, and connecting behavioral finance with asset pricing.

(56:42) Paul's definition of success: applying first principles with rigor and integrity throughout his career.

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/

Dr. Paul Kaplan: https://www.paulkaplan.com/

Lifetime Financial Advice (CFA Institute Research Foundation): Lifetime Financial Advice| Research Foundation

Life Cycle Finance Spreadsheet (Paul Kaplan's website): https://www.paulkaplan.com/lifetime-financial-advice *Disclosure: Links to third-party materials are provided for your convenience and do not constitute an endorsement or recommendation of the products or services offered therein.

Frontiers of Modern Asset Allocation (Wiley): https://www.wiley.com/en-us/Frontiers+of+Modern+Asset+Allocation-p-9781118029689

Popularity: A Bridge Between Classical and Behavioral Finance (CFA Institute Research Foundation): https://rpc.cfainstitute.org/research/foundation/2021/popularity-a-bridge-between-classical-and-behavioral-finance

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

In this AMA episode, Benjamin Felix, Dan Bortolotti, and Ben Wilson tackle a wide range of listener questions covering portfolio construction, diversification, active management, pensions, fiduciary duty, and short-term investing decisions. They examine whether breaking apart all-in-one ETFs is worth the complexity, why global diversification remains the default despite long stretches of underperformance, and how investors should think about risk when they have defined benefit pensions or short-term financial goals. Along the way, they discuss the limits of active management, why simplicity often beats optimization, and even reveal their favorite board games.

Key Points From This Episode:

(0:01:12) Whether investors should replace asset allocation ETFs with individual component ETFs to save on management fees.

(0:01:40) Why simplicity has real economic value—and how small fee savings compare to behavioral costs.

(0:05:38) Portfolio drift, rebalancing discipline, and the hidden costs of managing multiple ETFs.

(0:06:08) How recent fee reductions narrowed the cost gap between VEQT and its component funds.

(0:06:51) When using individual ETF components may make sense for larger portfolios or asset location strategies.

(0:11:16) The hosts share their favorite board games—and why poker has surprising parallels to investing.

(0:15:01) What true diversification actually means beyond simply owning the S&P 500.

(0:16:07) Why the global market portfolio remains the logical starting point for most investors.

(0:19:46) Addressing claims that modern index funds have become "too concentrated."

(0:21:52) Why active managers tend to lose their edge as assets under management grow.

(0:22:15) Diminishing returns to scale and the efficient market for manager skill.

(0:27:03) How defined benefit pensions should factor into portfolio construction and risk capacity.

(0:33:53) Understanding fiduciary duty for Canadian portfolio managers and financial advisors.

(0:37:17) Why publicly holding yourself out as a fiduciary carries legal and ethical implications.

(0:39:22) Can individual investors outperform active funds by picking stocks themselves?

(0:42:32) Why time, effort, and research alone rarely translate into market-beating performance.

(0:45:04) Why international stocks have lagged U.S. equities—and why diversification still matters.

(0:47:10) The role of valuation expansion in explaining decades of U.S. outperformance.

(0:50:05) How to invest money earmarked for a home down payment over a three-to-five-year horizon.

(0:53:31) Applying the same time-horizon framework to RESP investing and education savings.

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 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.

• (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)