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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"

  10 posts · theirs

Lately

• More Gas Requires Much Better Brakes

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-08-13

• The Only Constraint on Your Ambition

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-07-30

• AI Models have hit the commodity curve.

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-07-23

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

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-07-09

• The Founders Bet Everything. What Are You Betting?

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-07-02

• Good Strategy versus Bad Strategy?

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-06-25

• Chasing the AI Illusion

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-06-18

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

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-06-11

• Why a16z Wanted to Interview Goldman's CEO

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-06-04

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

  The Digital Leader: A Big Bets Briefing on Strategy and AI · 2026-05-28

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