Regret (and How to Read More w/ Neil Pasricha) (EP.189)

Episode Summary

Executive Summary: Episode 189 centers on two themes: why low-ego, high-drive leadership matters (via the book Humbitious) and how people make sense of regret in financial and life decisions. The episode also covers the Rational Reminder reading challenge, a critique of Wealthfront’s shift away from value investing, and a wide-ranging interview with Neil Pasricha on building a reading habit and finding better books.

Main Topics: Humbitious and low-ego leadership (Priority: 5/5): The hosts praise Humbitious as a framework for ambitious but humble leadership, tying it to their firm’s values, psychological safety, vulnerability, and long-term team performance. Regret, counterfactual thinking, and decision quality (Priority: 5/5): A substantial segment explains how regret works, what people most often regret, and how to reduce future regret through better decisions, justifiability, reversibility, and reflection. Reading challenge growth and book recommendations (Priority: 4/5): The reading challenge is growing quickly, with hundreds of books completed and extensive participation; the hosts discuss tools, reviews, and upcoming author guests. Wealthfront drops value and shifts toward profitability (Priority: 4/5): The hosts critique Wealthfront’s decision to remove the value factor from model portfolios, arguing that the change misunderstands factor evidence and may be inferior to combining value and profitability. Neil Pasricha interview on reading habits (Priority: 4/5): Neil explains why reading matters, how he built a reading routine, how he discovers books, and why public commitments and physical books help sustain reading behavior. Tools and systems for learning and note capture (Priority: 3/5): The discussion highlights ReadWise, Kindle note capture, and Evernote integration as a modern workflow for retaining and organizing insights from reading.

Key Arguments: Humble leaders are better able to self-assess, learn, and support high-performing teams, while ambition should be directed toward the organization rather than personal ego. Psychological safety, vulnerability, and purpose are essential ingredients for sustained team greatness. Regret arises from decisions, not outcomes alone, and is driven by counterfactual thinking; understanding it can improve future decision-making. People regret inaction more than action, especially in family, romance, career, and finances; these regrets persist longer and are harder to undo. Reducing regret can involve better decision quality, greater justifiability, decision reversibility, and limiting exposure to unchosen alternatives. Wealthfront’s explanation for dropping value is viewed skeptically; the hosts argue that combining value and profitability is more defensible than abandoning value entirely. Neil Pasricha argues that reading is the most compressed form of knowledge and that public commitment, screen-free spaces, and book discovery systems can dramatically increase reading. Physical books and single-tasking devices are favored because they reduce distraction and help readers stay engaged deeply. A good reading habit can be built by cutting competing media, making reading public, and reading books as a buffet rather than forcing every book cover-to-cover.

Data Points: Reading challenge participants: 260 people - Number of participants in the Rational Reminder reading challenge Books completed in challenge: 292 books - Books completed so far that year Top book in challenge: Psychology of Money - Most-read book in the reading challenge Second-most-read book: Trillions - Ranking in the reading challenge Third-most-read book: Dopamine Nation - Ranking in the reading challenge Book reviews written: 30 reviews - Number of book reviews posted in the challenge Badges earned: 607 badges - All badges earned, including welcome badges Badges excluding welcome badge: 347 badges - Badge count after removing the automatic welcome badge Contest votes for next book: 173 people - Votes collected to choose the next book for review LinkedIn messages mentioned: 5 locations named - Sampling of listener messages from Stockholm, Doha, South Africa, Canada, and Philadelphia Instagram followers: over 1,000 - Rational Reminder Instagram following YouTube subscribers: over 12,000 - Rational Reminder YouTube subscriber count Peloton group members: 81 members - Hashtag Rational Reminder Peloton group HBR article ranking: #1 downloaded article in 2017 - Neil Pasricha’s article Eight Ways to Read a Lot More Books This Year Average words consumed daily: 200,000 words per day - Neil uses this figure to argue people do have time to read Average knowledge worker emails: 147 emails per day - Used to illustrate daily reading volume already consumed Americans reading zero books for pleasure: 65% - Neil cites this as a major reading gap Pasricha reading goal: 50 to 100 books per year - His increased annual reading rate after changing habits Past Wealthfront risk parity fund fee: 50 basis points - Initial fee when Wealthfront launched the product Later Wealthfront risk parity fund fee: 25 basis points - Reduced fee after customer backlash Olympic medal counterfactual example: silver medalists less satisfied than bronze medalists - Used to illustrate how counterfactuals affect regret and satisfaction Regret survey category share: 21.8% family - Dan Pink 2020 U.S. regret survey category distribution Regret survey category share: 19.2% partners - Dan Pink 2020 U.S. regret survey category distribution Regret survey category share: 15.6% education - Dan Pink 2020 U.S. regret survey category distribution Regret survey category share: 15.1% career - Dan Pink 2020 U.S. regret survey category distribution Regret survey category share: 13.5% finances - Dan Pink 2020 U.S. regret survey category distribution Regret survey category share: 6.6% health - Dan Pink 2020 U.S. regret survey category distribution

Pivotal Quotes: "There is no better form of compressed knowledge, period." — Neil Pasricha: Neil explains why reading is foundational and uniquely efficient as a learning tool "compete fiercely but remain humble." — Cameron Passmore: Used to connect the book Humbitious to the firm’s internal values and leadership culture "You are what you eat and you are what you read." — Neil Pasricha: Neil’s closing line summarizing his philosophy of reading and personal growth

Implications: Listeners are encouraged to rethink leadership, regret, and reading as trainable habits. For investors, the episode reinforces disciplined decision-making over reactive changes; for teams, it highlights humility and safety; for readers, it offers practical ways to build sustainable reading systems.