As 2025 draws to a close, Motley Fool co-founder David Gardner presents a distinctive reflection on the Rule Breaker Investing podcast by highlighting ten episodes that made a lasting impact over the past year. This curated selection, termed the "Besties of 2025," features not only outstanding conversations but also includes brief return appearances by many of the voices that shaped the podcast’s meaningful moments. It offers listeners the chance to revisit insightful stories and to glean perspectives both retrospective and forward-looking.
Gardner draws a parallel between the annual celebratory events in entertainment—like the Oscars, Emmys, Grammys, and Tonys—and the podcast’s own tradition of spotlighting its most engaging content from the year. Though there’s no formal ranking, the ten episodes chosen stand out for their educational value, entertainment, and lasting influence.
Honoring a Decade of Contribution: "A Fool for Life" with Rick Engdahl
First among the highlights is the June 11 episode titled "A Fool for Life," featuring Rick Engdahl, the original producer of the Rule Breaker Investing podcast. Engdahl’s role spanned a decade from the podcast’s inception in 2015 through his retirement in mid-2025. This episode provided a rare opportunity for Engdahl to step from behind the scenes and reflect on his journey of self-education in investing, the philosophy of patient holding, and the value of compounding, not only financially but also in relationships and experience. His candid insights underscored sustained quality work and partnership as essential to the podcast's character.
In a subsequent cameo interview, Engdahl discussed his ongoing endeavors in music composition and his evolving life following his retirement from producing the podcast. He conveyed optimism for emerging technologies such as drone-style vertical takeoff air taxis, citing companies like Joby and Archer as pioneers bringing this innovation into public awareness. Additionally, he expressed a hopeful prediction that Team USA would reach the World Cup semifinals in 2026.
Intersecting Stories: Morgan Housel and Randi Zuckerberg on Narrative and Life Changes
Among the year's standout episodes was the January 22 discussion "Three Fools," which united Morgan Housel and Randi Zuckerberg in a conversation about the power of storytelling within investing and life decisions. The dialogue explored how narratives often guide market and personal choices more compellingly than mere numbers. Zuckerberg shared her transformative experience completing a 250-mile ultramarathon across Arizona and breaking a course record in a 100-mile race, emphasizing resilience gained through physical challenges.
Housel reflected on the modern preoccupation with investing bubbles and the value of cultivating saving and investing habits at a young age. He emphasized that the behavioral discipline acquired early on outweighs the immediate financial return of smaller investments. Both guests considered hopeful perspectives for 2026, including a cyclical return to civility in public discourse and the advancing opportunities in women’s longevity and endurance sports research.
Ten-Year Perspective and Practical Wisdom: Long-Term Investing and Communication Skills
September 3 marked the debut of the "Ten Years Later" series, beginning with a review of the first five-stock sampler from 2015. Gardner revisited how time allows investors to witness the true performance of stocks over a decade, offering nuanced lessons in compounding, the impact of buyouts, and the inevitability of winners alongside inevitable losses. This approach promotes a patient, reflective investment philosophy rather than short-term speculation.
In August, Sam Horn appeared on the podcast to share her expertise in improving difficult conversations. Her book "Talking With Egg Shells" and practical advice, such as swapping "but" for "and" to maintain communication goodwill, resonated as tools for personal and professional betterment. In a subsequent conversation, Horn illustrated how humor serves as an effective means to diffuse tension and enrich interactions.
Mindfulness and Mental Fitness: Insights from Shirzad Chamine
Returning on June 4, Shirzad Chamine provided a fresh take on positive intelligence, highlighting the importance of shifting mental focus from fear-driven responses to cultivating love and positive intentions. His examples spanned from reducing anxiety in childbirth to enhancing public speaking. Chamine encouraged listeners to develop greater self-command over their minds and to focus on maximizing love-based outcomes individually and relationally going into 2026.
Character and Persistence: Reflecting on Core Values and Athletic Preparedness
October 10’s “Blast from the Past” revisited timeless principles of character, responsibility, and embracing diverse friendships as underpinnings for success. Meanwhile, on July 23, Wimbledon champion and Fool Sam Verbeek recounted his journey highlighting perseverance, preparation, and neurological training that bolstered his athletic career and investing approach, demonstrating how mental and physical discipline translate across pursuits.
Community Stories and Market Cap Gamification
July 2's episode "What You’ve Done to Create Financial Freedom, Volume Three," spotlighted contributions from listeners sharing real-life steps toward financial independence, reinforcing Motley Fool’s mission of making individuals smarter, happier, and richer. The March 19 Market Cap Game Show World Championships showcased analysts Emily Flippen and Andy Cross competing in a lively display that educated listeners on market capitalization’s role in investing, while featuring humor, friendly rivalry, and notable stock discussions.
Passing the Torch: Authors in August Featuring Chris Hill
On August 20, longtime Fool colleague Chris Hill assumed hosting duties for the first time, interviewing David Gardner about the book "Rule Breaker Investing." This episode was noted for its candid and unscripted nature, underscoring the strength of shared experience between the two. Hill’s reflections on managing comparison and cultivating personal peace closed the year’s Besties on a thoughtful note.
Closing Reflections and Appreciation
Gardner concluded by expressing gratitude to the podcast’s guests, the new producer Bart Shannon, and the listeners who engaged with the content over the year. Emphasizing both the fun and educational value of the Besties episodes, he iterated the timeless goal of continuous learning and positive community impact through investing dialogue.