Resources & Solutions

Big Bet™ Briefing Report on Disruptive Technologies

This Big Bets™ Briefing Report provides an executive leadership playbook for navigating the Hyper-Digital Era through strategic technology investments. Written by former Amazon executive John Rossman, it presents the “Big Bet Vector” framework—a proven methodology for identifying asymmetric opportunities where limited downside meets unlimited upside. The report analyzes ten breakthrough technology domains including AI, blockchain, quantum computing, synthetic biology, and fusion energy, translating each into actionable strategies with “What Sucks” problem diagnoses, outcome definitions, and experimentation plans designed to validate critical assumptions before committing major resources.

Project Nucleus: An AI-Led Turnaround to Fulfill the Target Promise

Project Nucleus is a comprehensive AI transformation strategy for Target Corporation, developed by former Amazon executive John Rossman. The report outlines a three-layered approach to revitalize Target’s operations: deploying AI copilots to boost associate productivity by 30%, reengineering core workflows to achieve 25% cost reduction, and building a proprietary Hyperlocal Demand & Fulfillment Engine to create a defensible competitive moat. Based on the Big Bet Leadership framework, the strategy addresses Target’s declining sales, margin erosion, and operational friction through systematic AI implementation over 18-24 months.

High-Stakes Decision Making Framework

A fast, disciplined way to turn big, risky choices into advantaged bets. It starts by nailing the wicked problem and a vibrant future state, then isolates the few must-be-true hypotheses that drive value and risk. We classify the choice with the Door Test (reversible vs. irreversible), design cheap experiments to learn quickly, and mine hidden jewels—assets that create option value even if we pivot. Canaries and tripwires make risk visible early; meeting mastery keeps decisions crisp; and we hedge the downside, bank the upside with staged commitments and exit ramps. Use regret minimization only as a rare tie-breaker when data and tests can’t decide. The result: faster clarity, bounded downside, and a higher chance of asymmetric wins.

State of AI Report by MIT

Here’s the full MIT Report on AI and the Enterprise

The Amazon Annual Planning Process — OP1. From the best seller Think Like Amazon, by John Rossman

This is chapter 37 from Think Like Amazon: 50 1/2 Ideas to Become a Digital Leader.

The Big Bets™ Meeting Design GPT

Big Bet Systems – Rethink Meetings. Design for Impact.

Here’s the harsh truth: we’re addicted to meetings that don’t matter.When you’re in a meeting, you’re not designing. You’re not solving. You’re not thinking. You’re certainly not moving fast. You’re just… talking. Most meetings are the lazy way to get things done.

Rossman’s Business Manifesto for Competitive Advantage — The Pig, the Lipstick & the Playbook of Champions

Cut through the noise and confront the enemy of every great company—mediocrity. The Pig, the Lipstick, and the Playbook of Champions is a no-nonsense guide to building a high-performance culture, reclaiming your competitive edge, and achieving sustained success in today’s unforgiving business landscape.

In The Pig, the Lipstick, and the Playbook of Champions, John Rossman delivers an unflinching manifesto for leaders who refuse to settle for “good enough.” This essential business guide dismantles the myths that keep organizations stuck, revealing the bold truths of modern leadership and transformation.

The Chief Repeating Officer PDF

“The single biggest problem in communication is the illusion that it has taken place.”
— George Bernard Shaw

Big Bets fail when leaders don’t repeat the right messages. The Chief Repeating Officer ensures clarity through repetition until it’s second nature to the team.

#Leadership #BigBetSuccess

Free “Why Memos?” Appendix for Big Bet Leadership

The research and benefits for using memos to think through hard problems and to work as a team is extensive. Here’s the appendix to Big Bet Leadership titled “Why Memos?”.

Click the “download” button at the bottom of this page.

Three Chapters from Think Like Amazon: 50 1/2 Ideas to Become a Digital Leader

Amazon’s famous “working backwards” approach to writing narratives, a future-press release and a set of FAQs is outlined in this set of chapters.

Big Bet Leadership GenAI Prompt Worksheet

Supercharge your thinking and writing using these GenAI prompts. Engineered to deliver the Big Bet Leadership memos. Get ready to 10x your ideas and writing with these prompts!

Big Bet Playbook Advisory Session

Embark on a transformative journey with Big Bet Leadership One-on-One Coaching a premium, personalized coaching session designed to supercharge your strategic initiatives. Directly engage with the authors of Big Bet Leadership for an hour of in-depth advice and tailored guidance. This exclusive session offers you a unique opportunity to explore the nuances of your specific challenges, gain insights into applying the Big Bet Leadership framework effectively, and develop actionable strategies for your ambitious projects. Whether you’re navigating complex transformations, spearheading innovative ventures, or seeking to drive significant growth, this coaching experience equips you with the wisdom and clarity needed to lead with confidence and achieve groundbreaking success.

Big Bet Leadership Journal

Big Bet Leadership is a playbook, meant to be put to work in developing your Big Bet Thinking, Environment and Management. This journal bridges the book into action and serves as an essential guide to become a Big Bet Legend.

The Digital Leader Newsletter

Strategy and Techniques for Change Agents, Strategists and Innovators. A newsletter from the author of “Big Bet Leadership”, “The Amazon Way” and “Think Like Amazon” John Rossman. A substack newsletter with thousands of subscribers.