Obsidian Odyssey

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Leadership

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.

Obsidian Essay] Death of the Enemy: Notes on UK Citizenship and Sovereignty

Obsidian Essay] Death of the Enemy: Notes on UK Citizenship and Sovereignty

Personal Essay.

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,

Obsidian Essay] 🍁 Softening is a Form of Strength: A Thanksgiving from the ICU

Obsidian Essay] 🍁 Softening is a Form of Strength: A Thanksgiving from the ICU

Personal Essay: Thanksgiving reflection.