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 | 170 | Founded | 5 years ago | Last Issue | 6 days ago |
| Active | |||||
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Why a16z Wanted to Interview Goldman's CEO
The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function. — F. Scott Fitzgerald
Andreessen Horowitz (a16z) recently sat down with the retired CEO of Go...
Ten Wildly Successful Innovations — Except They Didn't Actually Work
There is nothing so useless as doing efficiently that which should not be done at all. — Peter Drucker
You are already familiar with item #10 on this list.
You press the button every time you drive. Somewhere near the gear shift, dependin...
SpaceX Didn't Win on Technology. They Won on Unit Cost Reinvention.
The most important thing is trying to find a business with a wide and long-lasting moat around it — protecting a terrific economic castle with an honest lord in charge of the castle. — Warren Buffett
For more than thirty years, the aerospa...
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...
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Authors
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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