John Rossman - Keynote Speaking
Free Big Bet Resources
The Big Bets System™
Creating Competitive Advantage is Hard.
But It Doesn't Need to be Complex
The Big Bets System™ equips executive teams to focus on what matters most—
solving the right problem, faster, to grow & win.
  • What is our strategy to grow and build defensible advantage?
  • Where will AI create measurable enterprise value—now and next?
  • How do we develop leadership capacity to match our ambition?
  • How do we scale our operations and create a cost model advantage?
Replace vague goals with critical thinking, hard choices & clarity to match your ambition.
Persecute the Problem
Obsess over truth seeking. If you're wrong here, you're wrong everywhere. Define the “what sucks” for your customers and business. Create clarity by staying in the problem space longer.
Envision the Edge
Define the outcomes and high-risk assumptions. Design the future and the advantaged economics. Work backwards from the defined advantaged future.
Engineer the Advantage
Design your unfair advantages and hard to catch moves. Craft the sequence of moves and experiments. Establish velocity, high-impact proof-points and a high-performance big bet culture.
Lead to Become Legendary
Legends are designed and built. Prepare and lead like a Big Bet Legend. Align teams, funding and communications. Accelerate risk & value.
John Rossman & Kevin McCaffrey, authors of Big Bet Leadership, on the Geekwire podcast
The Big Bets System™
Thinking, Methods & Frameworks
From the best minds in strategy — Rumelt, Martin, Porter, McKinsey, Chen & Rossman
PLUS +
Integrated AI Advantage
Leading AI Models, World Class Prompts, Agentic AI Solutions and Proprietary Data and Research..
PLUS +
Expert Advisors & Aligned Partners
We complement your experience & perspective with integrated world-class advisors & partners
— all using the Big Bets™ System.
AI is poised to disrupt the traditional strategy consulting industry. That obvious.
What’s less obvious? What replaces the traditional consulting firm?
Top-tier firms are slow, expensive, and optimized for staffing—not outcomes. Most companies can't afford them. And even those who can are questioning the return.
Here’s our answer:
We combine three powerful ingredients to create a 10x value compared to traditional management consulting:
  1. Proven thinking, methods + frameworks that drive structured thinking, not noise.
  1. AI and proprietary capabilities & prompts that compress time and cost, while improving analysis & insights.
  1. Independent seasoned advisors who guide, challenge, and help you act. No junior team driving billing hours.
Together, this model produces sharper strategy, far better insights & outcomes, and faster execution—at a fraction (1/10th) of the cost of McKinsey, Bain, or BCG.
The Big Bets System™
The clarity, speed, and AI edge to outthink your competition.
John Rossman — Author, Operator, Advisor, Keynote Speaker
Led by the early Amazon executive who played a key role in launching and scaling the Amazon Marketplace;
Author of "The Amazon Way", "Think Like Amazon" & "Big Bet Leadership"
Senior Technology Advisor to the Gates Foundation; Senior Innovation Advisor to T-Mobile; and leading keynote speaker.
Are you ready to compete and win in the hyper-digital era?
Here's some of our latest thinking
— Read Rossman's Substack for Free

thedigitalleader.substack.com

Times of Turbulence: Why this isn't the Age of AI

The greatest danger in times of turbulence is not the turbulence—it is to act with yesterday’s logic.— Peter Drucker But the real threat? It’s not the turbulence itself. It’s clinging to the logic and operating models of a bygone era. It’s acting with yesterday’s playbook in the face of today’s circumstances and tomorrow’s potential.This is why Big Bets™ matter now more than ever.

thedigitalleader.substack.com

You Don’t Have a Growth Problem. You Have a Growth System Problem.

You miss 100% of the shots you don’t take — Wayne Gretzky. In today’s volatile and hyper-digital environment, sustained growth isn’t just a strategy—it’s a survival imperative. Yet, most companies fail to grow consistently. That’s not due to a lack of effort, ambition, or intelligence, but because of an outdated playbook. The reality is clear: consistent and transformative growth requires Big Bets.

thedigitalleader.substack.com

Scaling vs. Growth: The Hazard Most Leaders Don’t See Coming

“More companies die from indigestion than starvation.” — David Packard, Co-founder of HP