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.

Rational Reminder on YouTube — https://www.youtube.com/channel/

Benjamin Felix — https://pwlcapital.com/our-team/

Benjamin on X — https://x.com/benjaminfelix

Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/

About The Author

Benjamin Felix

Benjamin is a Portfolio Manager and PWL Capital’s Chief Investment Officer. He co-hosts the Rational Reminder podcast and also hosts a popular YouTube series

Dan Bortolotti

Dan works with clients to combine investment management with long-term financial planning. He also promotes investor education through his blog, articles and podcast.