HeyJaredThe 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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- Sep 15, 2026
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- Jul 9, 2026
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Anduril Shows What Mach 1 Speed Is (opens the original)
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The real barrier wasn’t in the sky but in our knowledge and experience of supersonic flight. — Chuck YeagerOn January 16, 2025, Anduril announced it would build a five-million-square-foot factory on farmland in Pickaway County, Ohio, near Rickenbacker International Airport. No existing building. No existing workforce. A production date most of the industry filed under “great marketing”.On July 27, 2026, the first Ohio-built Fury rolled off the Arsenal-1 line.<a class="footnote-anchor" href="#foo
The Tyranny of Today (opens the original)
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Someone's sitting in the shade today because someone planted a tree long ago — Warren BuffettI’ve heard it so often, it’s cliche. I know it’s coming. “Our big bet is a top priority.” “Reinvention is critical.” “We have to build the future while we run the present.”They mean it and believe it when they say it.The Digital Leader: A Big Bets Briefing on Strategy and AI is a reader-supported publica
The Self-Improving Company (opens the original)
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The process of Creative Destruction is the essential fact about capitalism -Joseph Schumpeter, Capitalism, Socialism and Democracy (1942)“More Gas Requires Better Brakes.” That was one of the key insights from a fantastic conversation with Alejandro Maza, Chief Product & AI Officer at Kavak, on the A16Z podcast. That one required its own newsletter. The combination of, relationship between, and opportunity for innovating “governance” and “risk management” to enable more calculated risk taking is
More Gas Requires Much Better Brakes (opens the original)
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If everything seems under control, you’re just not going fast enough — Mario AndrettiYou’ve been given the mandate. You are now the Chief Transformation Officer, the EVP of AI, the futurist for your organization. You’ve been asked to reinvent a critical value stream or capability. To put AI at the center of the operating model. To reinvent either the core value propopostion, the operating model and culture, or both. What a great opportunity.Maybe.Now the harder question, the one nobody put in th
The Only Constraint on Your Ambition (opens the original)
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Ideas are common. The entrepreneur who can execute them is rare. — Ben Horowitz Travis Kalanick, founder of Uber, is back. His new company, Atoms is attacking automation of mining, food production, and transport. Three physical industries. Each a multi-trillion-dollar market. Simultaneously.How can one startup company work to reinvent three industries at once?The Digital Leader: A Big Bets Briefing on Strategy and AI is a
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