The Digital Leader: A Big Bets Briefing on Strategy and AI

The Equation Just Broke: What Block’s AI Restructuring Means for Every Company & Industry. Highlights from A16Z Podcast.

A real-world stress test of what high-performance teams look like in the age of AI agents. You never change things by fighting the existing reality. To…

Apr 9 • John Rossman

One Simple Thought: Feature the Bad News

The status report that makes everything look fine is the most expensive document. The status report that makes everything look fine is the most…

Apr 2 • John Rossman

Emergency Newsletter: How UConn Beat Duke — and Why Your Board Should Care

What Dan Hurley Taught Every CEO Last Night

Mar 30 • John Rossman

Zone to Win Meets Big Bet Leadership: An Independent Analysis of the Management Operating System for Navigating Transformation

"The electric light did not come from the continuous improvement of candles." — Oren Harari Here’s a question worth sitting with: Why do great operating…

Mar 5 • John Rossman

Presentation Theater, Consulting Decks, and Operating Model Transformation

The elaborate performance hiding what you're really afraid to fix. This is the presentation theater that kills organizational change—and it’s completely…

Nov 6, 2025 • John Rossman

Stop navigating your biggest challenges without a playbook. This is your weekly briefing on making high-stakes decisions in the AI era. Get the actionable frameworks Fortune 1000 leaders use to turn volatility into a competitive advantage and close the "execution gap"

The playbook for leaders making big bets in the AI era. Get actionable frameworks from former Amazon exec John Rossman to pursue market-shaping ambitions and make high-stakes decisions with confidence. Author of "Big Bet Leadership" & "The Amazon Way"

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The Digital Leader: A Big Bets Briefing on Strategy and AI