The Digital Leader: A Big Bets Briefing on Strategy and AI
John Rossman, Kevin McCaffreyThe 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"
| Platform |  | Pricing | Freemium | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 167 | Founded | 5 years ago | Last Issue | 6 days ago |
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The 2025 Amazon Shareholder Letter Has a Key Signal. Most Leaders Will Miss It.
When spring comes, snow melts first at the periphery, because that is where it is most exposed. — Andy Grove, Only the Paranoid Survive
Andy Jassy’s 2025 Amazon Shareholder Letter1 was published just over a month ago. I’ve been studying it...
As Much As Needed, As Little As Possible: Jensen Huang on the Operating Principle Behind Nvidia’s Run
Perfection is achieved, not when there is nothing more to add, but when there is nothing left to take away. — Antoine de Saint-Exupéry
I invested the 1:43 required to listen to Dwarkesh Patel’s recent interview with Jensen Huang, co-founde...
Commitment Without Direction: The Hidden Flaw in Every Failed AI Transformation
The hype on LinkedIn says everything has changed, but in our operations, nothing fundamental has shifted. We’re processing some contracts faster, but that’s all that has changed.(1)
I normally start my newsletter with a related famous qu...
The Equation Just Broke: What Block’s AI Restructuring Means for Every Company & Industry. Highlights from A16Z Podcast.
You never change things by fighting the existing reality. To change something, build a new model that makes the existing model obsolete. — Buckminster Fuller
For decades, the most reliable equation in business was so consistent it became a...
One Simple Thought: Feature the Bad News
The status report that makes everything look fine is the most expensive document.
The status report that features the bad news is the most valuable.
After leading and doing QA reviews of hundreds of complex initiatives, I’ve noticed the...
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The writers behind this newsletter.
John Rossman is the leading authority on high-stakes decision-making in the AI-driven era. An early Amazon exec who launched the Marketplace, author of Big Bet Leadership & The Amazon Way. He delivers his frameworks as a keynote speaker and advisor.
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