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 |
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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. — Yogi Berra
Most AI strategy isn’t strategy. It’s a reaction.
A vendor demo lands. A board member reads an AI article on a flight. A competitor announces a Chief AI Offi...
The Founders Bet Everything. What Are You Betting?
“We have it in our power to begin the world again” — Thomas Paine, Common Sense
This July 4th, we mark 250 years since our founding fathers made their biggest bet, and it paid off.
In January 1776, a small pamphlet hit the streets of Phi...
Good Strategy versus Bad Strategy?
Good strategy works by focusing energy and resources on one, or a very few, pivotal objectives whose accomplishment will lead to a cascade of favorable outcomes — Richard Rumelt
Have you ever pondered the "job to be done" by a truly effect...
Chasing the AI Illusion
There is surely nothing quite so useless as doing with great efficiency what should not be done at all. — Peter Drucker
We have a French Bulldog named Bossman Rossman. He is bold. He is confident. He is certain he is in charge. And on sunn...
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
Good ideas travel faster when you share them — forward this to someone who'd find it useful.
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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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