Obsidian Odyssey

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Leadership

Obsidian Memo] Leadership Lessons for Founders: Building “You, Inc.” Without Burning It Down

Obsidian Memo] Leadership Lessons for Founders: Building “You, Inc.” Without Burning It Down

Most founders overestimate what they can do in 2 years and underestimate 10 years. Learn the leadership lessons from APR's $1B journey—and how to run your life like a sustainable company.

Leadership] Inside Europe’s Economic Crises — How Christine Lagarde Leads in a Fragmented, Volatile World (ft. Francine Lacqua)

Leadership] Inside Europe’s Economic Crises — How Christine Lagarde Leads in a Fragmented, Volatile World (ft. Francine Lacqua)

Inside Europe’s Economic Crises With Christine Lagarde —Lagarde's leadership style: mandate-led, calm under pressure, consensus-driven where possible (but also authoritative where needed), and direct about trade-offs.

Leadership] The Dimon Operating System — How to Run a Scaled Institution Without Losing Speed (ft. David Rubenstein)

Leadership] The Dimon Operating System — How to Run a Scaled Institution Without Losing Speed (ft. David Rubenstein)

Jamie Dimon's leadership style: direct, detail-first, allergic to bureaucracy, and anchored in “do the right thing, fast.”

Leadership] AI Is the Main Thing — What's in Jon Gray's Winning Leadership Recipe to CEOs & How Blackstone Stays Ahead at $1.2T+ Scale

Leadership] AI Is the Main Thing — What's in Jon Gray's Winning Leadership Recipe to CEOs & How Blackstone Stays Ahead at $1.2T+ Scale

AI is driving a once-in-a-generation infrastructure buildout. The edge isn’t predicting outcomes—it’s executing through disruption risk, staying paranoid in the right ways, and preventing scale from turning into bureaucracy.

Obsidian Memo] 1929 — Lessons from the 1929 Crash & A Reminder That Craft Still Wins (ft. Andrew Ross Sorkin's London Talk)

Obsidian Memo] 1929 — Lessons from the 1929 Crash & A Reminder That Craft Still Wins (ft. Andrew Ross Sorkin's London Talk)

Lessons from the 1929 crash + Andrew Ross Sorkin’s London talk: what today’s CIOs must learn about hidden leverage, AI-driven growth illusions, and trust decay—plus reflections on leadership, policy, and a signed-copy moment for a New Yorker in London.

Leadership] Sallie Krawcheck: Contrarian Turnarounds → Startup Volatility → A Wealth Platform Built for Women

Leadership] Sallie Krawcheck: Contrarian Turnarounds → Startup Volatility → A Wealth Platform Built for Women

Sallie Krawcheck’s edge isn’t “finance celebrity.” It’s repeatable: see the industry’s blind spot, call it early, and build (or fix) the machine around it—even when it’s uncomfortable.

Book] Leadership | Classics Circle: The Republic - Plato (12/12)

Book] Leadership | Classics Circle: The Republic - Plato (12/12)

A Conversation Across Centuries Reading Time: 16 minutes Classical Period: ~380 BCE (Ancient Greece, Socratic dialogue) Core Philosophy: Justice is harmony. The philosopher must return to the cave. The examined life is the only life worth living. Why I'm Reading This Final month. Twelve months of reading classics,