The Decision-Making Playbook for the AI Era

Focusing The Digital Leader on High-Stakes Decision Making

Sep 04, 2025

For the past four and a half years, "The Digital Leader" has been dedicated to a single mission: providing practical coaching to help you and your company win in the digital era. I'm incredibly grateful for the community of nearly 7,000 leaders we've built together.

Today, winning in the digital era has converged on one dominant reality: we are entering the age of AI. It is the ultimate "Big Bet"—a landscape of unprecedented opportunity and significant risk.

Almost every conversation I have with company leaders confirms a critical insight: The challenge isn't understanding or believing that AI is important or that they need to engage with it. The real struggle is knowing how to make great high-stakes decisions about it.

Leaders don't need more hype or example prompts on AI. They need a playbook and a partner for making high-stakes decisions on how to transform their business and create business value and advantage.

To meet this moment, The Digital Leader is evolving.

Going forward, we are sharpening our focus to become your essential briefing on the most critical leadership competency for the next decade. Our new subtitle reflects this mission:

The Digital Leader: A Big Bet Briefing on Strategy & AI

Our commitment to providing practical, actionable frameworks remains the same. Our thinking will now be relentlessly focused on equipping you to make winning decisions about AI, innovation, and the disruptive forces shaping your market. We'll be diving deeper into the principles from Big Bet Leadership and sharing proprietary insights from my advisory work with companies on the front lines of this transformation.

This isn't a change in direction, but a sharpening of our own Big Bet Vector. The goal is to deliver even more targeted, indispensable value to you each week.

Thank you for being part of this journey. The stakes have never been higher, and I'm excited to navigate them with you.

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What You’ll Be Getting — Strategic Insights

After leading and advising dozens of enterprises through high-stakes transformations, one pattern is unmistakable: the winners aren’t lucky or bold. They deliberately take calculated risks by creating clarity around desired outcomes, moving with disciplined velocity, and they validate risk and value early.

These organizations don’t just place strategic bets—they shape them, test them, scale them, or kill them long before competitors even realize the game has changed.

This isn’t about technology adoption or flawless execution—it’s about decision-making superiority when the stakes are highest and ambiguity is thick. Big Bet legends win not by avoiding uncertainty, but by confronting it head-on with clarity, velocity, and a ruthless focus on risk and value. They choose to be the shark at the poker table of Big Bets—aggressive, deliberate, and unwilling to let ambiguity slow them down.

They are better high-stakes decision makers.

Because of this, they have higher ambition, higher standards, and take more calculated risks. And the virtuous cycle of competitive advantage builds.

Two Tiers of Strategic Insight

Essential Big Bets™ Briefings (Free): Weekly insights decode major shifts in the competitive and technological landscape, paired with high-level applications of Big Bets System™ frameworks to help you see around corners and act with conviction.

Big Bets™ Briefing — Premium: Twice-monthly proprietary strategies, research and reports. These are typically done through an industry or functional filter, so they fit you. These are meant to propel you from the sidelines and into the game.

Proprietary Strategy Applications – Actionable tools and methods built on the Big Bets System™ frameworks, designed to challenge status quo thinking and drive decisive outcomes.
Industry-Specific AI Playbooks – Strategic AI plans that break free from incrementalism and de minimis ROI, unlocking transformative opportunities in real business contexts.
Real-World Case Studies – Unfiltered insights from active Big Bet transformations, complete with measurable results and lessons from the field.
Exclusive System Tools & Templates – Access the full Big Bets System™ playbook: tested frameworks, memo templates, experiment planners, and environment checklists used by top operators.
Private Quarterly Briefings – Direct access to Big Bet advisors through invitation-only sessions, including candid Q&A, emerging insights, and strategy calibration.

Your Strategic Advantage Starts Now

The companies that will dominate the next decade are being built today by operators and investors who understand this: