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

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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More Gas Requires Much Better Brakes

Rethinking Governance in the Age of Reinvention and AI. If everything seems under control, you’re just not going fast enough. — Mario Andretti

The Only Constraint on Your Ambition

Travis Kalanick just raised $1.7 billion to automate three industries at once. The lesson is not about mining, food, or robots. It is about the one constraint you are probably ignoring.

AI Models have hit the commodity curve.

Kimi K3 just hit near-frontier intelligence at the lowest price on the board. The lesson isn't the model. First say to yourself what you would be; and then do what you have to do — Epictetus

Before You Develop Your AI Strategy, Write Down What You Believe. Here Are Mine.

If you don’t know where you’re going, you’ll end up someplace else.

The Founders Bet Everything. What Are You Betting?

The Pig, The Lipstick & The Playbook of Champions

Good Strategy versus Bad Strategy?

A book review of the iconic Good Strategy/Bad Strategy by Richard Rumelt

Chasing the AI Illusion

Most AI investments produce nothing. The companies that win are asking a completely different question.

I Was Wrong About AWS in 2008. Here’s What That Tells You About The Future.

“The future is already here — it’s just not evenly distributed.” — William Gibson. Todd Bishop recently published a 20-year history of AWS in GeekWire — required reading if you want to understand how “rent a computer on the internet” became a $129 billion business.

Why a16z Wanted to Interview Goldman's CEO

Avoiding Risk Is Not Risk Management. His core lesson: risk-taking and risk management are not opposing forces but two halves of one discipline, and most leaders run one half and call it the job.

Ten Wildly Successful Innovations — Except They Didn't Actually Work

Phantom Innovation, and Why AI Is About to Make It Worse