Practicing Wisdom — Issue #8
This week I kept circling one theme: power hides in architecture. Hackers expose assumptions, founders learn too late that equity isn’t ownership, and investors crowd into “quality” stocks without seeing the math stacked against them. From FanDuel’s founders losing everything to Robinhood replacing Caesars in the S&P, the lesson is clear: if you don’t study the system, you’re not playing the game—you’re being played.
Practicing Wisdom — Issue #7
This week I unpacked the operating system of Elon Musk. Love him or hate him, his habits reveal what extreme ambition demands: urgency as oxygen, belief as fuel, and vertical integration as a weapon. Musk deletes layers, compresses timelines, and forces urgency into every system. His method is brutal, brilliant, and a reminder to ask: what would it look like if I built my own system with this kind of clarity?
Practicing Wisdom — Issue #6
This week I explored how scale reshapes meaning — and often corrodes it. Google grew from a search engine into a civilization-scale operating system, but lost narrative coherence along the way. Open source ideals eroded under commercial pressure. Even intimacy is now monetized through platforms like OnlyFans. Yet in education, Alpha School shows scale can be rebuilt human-first. The age of “platform decay” demands we return systems to a scale where integrity thrives.
Practicing Wisdom — Issue #5
This week I kept circling one theme: context is everything. From Mark Bertolini’s father’s rules for survival, to Benn Stancil’s “context layer” for data and AI, to Rolex as a brand that manufactures scarcity through narrative — the common thread is clear. Content is cheap. Integrity, frameworks, and meaning are what actually endure.
Practicing Wisdom — Issue #4
“High-flying growth with shaky roots” defines today’s economy: soaring Mag7 valuations mask the decay on Main Street, while private equity avoids facing losses in a new rate regime. Value is eclipsed by price, optionality always carries cost, and defaults—set quietly by tech and politics—shape the rules of engagement. True capitalism thrives when it disrupts, not when it entrenches.
Practicing Wisdom - Issue #3
In a world where facts are cheap and narratives compound, the ultimate currency is belief—story sells, and those who master narrative hold the real power.
Practicing Wisdom Issue #2
This week’s edition explores risk calibration in investing, the fragility of AI analysis, and why quitting can be a powerful strategy. From Alan Waxman’s unitized risk model to Cate Hall’s case for walking away, discover how capital, cashflow, and culture demand recalibration—not just ambition.
Practicing Wisdom Issue #1
Explore Practicing Wisdom, a weekly newsletter blending deep learning, reflective synthesis, and timeless insight. Each issue distills powerful ideas from books, essays, and conversations—offering mental models, contrarian takes, and thought-provoking reflections for lifelong thinkers and curious minds.
The Outsiders - William Thorndike
Discover how eight unconventional CEOs outperformed Wall Street by mastering capital allocation, rejecting corporate trends, and focusing relentlessly on per-share value. Based on The Outsiders by William Thorndike, this article reveals the contrarian blueprint behind decades of market-beating returns.
Awakening the Soul - Michael Meade
Explore Michael Meade’s Awakening the Soul, a profound guide to finding purpose in chaos through myth, imagination, and deep soul work. Discover how personal and cultural crises can spark inner transformation, awaken calling, and reconnect us to the forgotten wisdom that sustains humanity in turbulent times. A timely antidote to a world in disarray.
Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life - Rory Sutherland
Why do ideas that seem illogical often succeed? Alchemy by Rory Sutherland unpacks the power of irrational thinking, behavioral psychology, and counterintuitive strategies that shape business and marketing. From Red Bull’s bizarre success to the hidden forces behind decision-making, this book reveals why logic isn't always the answer. Discover the magic behind human behavior!
Working Backwards: Insights, Stories, and Secrets from Inside Amazon - Bill Carr & Colin Bryar
Unlock the secrets of Amazon’s unmatched success with insights from Working Backwards. This blog explores how customer obsession, long-term thinking, and innovation fuel their growth. Learn about the Bar Raiser hiring process, narrative-driven decision-making, and the 'Working Backwards' methodology—a roadmap for building high-performing, scalable organizations.
The Effective Executive - Peter Drucker
Key concepts and distillations from The Effective Executive by Peter Drucker
The Eternal Pursuit of Unhappiness - Ogilvy & Mather
Key concepts and distillations from The Eternal Pursuit of Unhappiness - Ogilvy & Mather