Examining the Validity of Trend Following Strategies

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 — info@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/

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