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

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

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OpenAI -- Could Leadership Principles Have Helped?
Considering the dynamic and explosive news out of OpenAI this week, I wonder…how could a business going so well, have such a massive and avoidable set…
 • John Rossman
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…
 • John Rossman
Do You Have Principles???
Operate by principles that are so clearly laid out that their logic can easily be assessed, and you and others can see if you walk the talk. — Ray…
 • John Rossman
Delete, Delete, Delete -- The Critical Technique from "Elon Musk" by Walter Isaacson
Perfection is achieved, not when there is nothing more to add, but when there is nothing left to take away." - Antoine de Saint-Exupery
 • John Rossman
The Critical Decision To Make on Innovation
Do We Develop a System for Innovation or Just Have Hope?
Kelly’s 14 Skunk Works Rules: Leadership Principles that Matter
Kelly Johnson, the pioneering aeronautical engineer who led Lockheed’s Skunk Works, articulated a set of guidelines—often referred to as “Kelly’s 14…
 • John Rossman
Is it "Day 2" at Amazon??? Rossman's Turnaround Plan for Amazon.
I believe Jeff Bezos's greatest fear for Amazon was that it becomes a bureaucracy. A place where people become more concerned about optics than building…
 • John Rossman
Experiment, Learn, Repeat, Scale
Plan and Operate Your Experiments for Growth & Innovation Success --THINKING BIG, NOT BETTING BIGI led the launch of the third-party business at Amazon…
 • John Rossman
Carta Destroys Trust and Enterprise Value
“Trust is like the air we breathe – when it’s present, nobody really notices; when it’s absent, everybody notices.” Warren Buffett
 • John Rossman
Pancakes: The AI Strategy Framework I’ve Been Holding Back
“It’s about damn time” — Lebron James. It's about damn time I outlined a Big Bet Leadership™ framework tailored specifically to create and execute a…
 • John Rossman
Insights from Peter Drucker's Iconic Book "The Effective Executive"
The Definitive Guide to Getting the Right Things Done
Is Your AI Plan Just Paving the Cow Paths?
Obliterate —>Integrate—>Automate: Always in that order.
 • John Rossman
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