All
In
Are you all in — or standing on the sideline? How I went from racking my own servers to steering global AI strategy, and what every technologist can learn from the journey.
The Pitch in One Paragraph
Every enterprise says it wants to "transform." Almost none understand that transformation is not a technology decision — it is a leadership one. All In is the memoir of a technologist who spent ten years as a developer, database administrator, and small-business owner — building one of the first CMS-with-eCommerce platforms — establishing himself as a builder from nothing, decades before the boardroom. From those roots he climbed to owning the P&L for a global consulting practice steering AI strategy for the world's largest enterprises, and today has come full circle as a founder again with Herd AI Inc. It is the rare book written by someone who has been in both chairs: the engineer who ships the work, and the executive who bets the budget. But it is also, unmistakably, a human story — of loss, resilience, an improbable love, and a family that includes a daughter with Down syndrome who is its beating heart. Part origin story, part field manual, part love letter to the people who make the climb worth it, it shows readers how deep technical mastery becomes durable influence — and why the people who understand both the code and the boardroom, without losing sight of what matters, will define the next decade of business.
Overview
We are living through the most significant technology inflection since the internet itself, and yet the shelves are crowded with two kinds of books: abstract futurism written by people who have never shipped a feature, and dry implementation manuals written by people who have never sat in a boardroom. There is almost nothing written by a practitioner who has genuinely traveled the full arc — from hands-on-keyboard technical contributor to the executive who decides where an enterprise places its AI bets.
That arc is my story, and it is the spine of this book.
I did not begin in a Fortune 500 boardroom. I began as a developer and database administrator, and for ten years I ran my own small business — during which I built one of the first Content Management Platforms with integrated eCommerce, at a time when the web was still deciding what it wanted to be. That decade taught me to build things from nothing, to own the outcome when there was no one else to blame, and to understand systems from the metal up. Only later did I go deep on a single enterprise platform: Salesforce — not as a strategist talking about it, but as the person building it. I rose to become Salesforce Americas Practice Leader at IBM, carrying P&L ownership across the largest enterprises in the world. Today I am a startup founder, building Herd AI Inc — a company of AI-native products born from watching, up close, exactly where enterprise software fails the humans who use it.
This book is not a victory lap. It is an argument, told through story: technical depth is not something you graduate from on the way to leadership — it is the source of your leadership. The most dangerous executive in the AI era is the one who has forgotten how the machine works. The most valuable is the one who never let themselves forget.
Table of Contents
All In? · A Memoir of the Climb, the Code, and the Age of AI
Are You All In?
The Plan That Fell Through
Born three pounds, twelve ounces — and the plan that didn't survive contact with life
The Ground Floor
Starting at the bottom and learning the building from the foundation up
From the Database Up
Why the data layer taught me how everything above it really works
Own the Outcome
Taking responsibility for the result, not just the task
Building Ahead of the Curve
Betting on where technology is going, not where it is
Build Once, Serve Everyone
The discipline of reusable, multi-tenant thinking
The Everest of Certifications
The long climb to technical credibility
The Credibility Divide
Earning the right to be believed
Speaking Two Languages
Fluency in both business and technology
The Sherpa Doesn't Carry You
Guiding clients without doing the climb for them
Owning the Number
Taking the revenue line as your own
The Blue Badge
Distinguished Engineer, and what a title really means
Building the Practice
Standing up a team, a P&L, and a way of working
P&L Is a Point of View
Reading the business through its numbers
The Herd Moves Together
Governance, data quality, and trust at scale
Steering the Bet
Treating AI adoption as a portfolio of bets
The Human Layer
Why 80% of AI is people and only 20% is technology
Signal Through the Noise
Cutting through the infinite workday to what matters
Seeing the Gap
The chasm between strategy and execution
The Unfair Advantage
Using AI to build capabilities that don't have to call AI
Machines of Loving Grace
A hopeful close — technology, medicine, family, and the journey
Acknowledgments
About the Author
Who This Book Is For
Written for the ambitious technologist who has hit — or can see — the ceiling of pure individual contribution, and wants a credible map to the next level. The audience clusters into four concentric rings.
The Rising Technical Professional
Admins, developers, consultants, architects and data engineers 3–12 years in — excellent at their craft, frustrated it isn't translating into scope. They ask: "How do I turn what I know into influence?" This book answers directly.
The Aspiring Technology Leader
Newly promoted managers and directors who won their roles on technical merit and now face P&L ownership, cross-market teams, and defending an AI strategy to a board. They want the parts of the story that live above the code.
The Founder & Intrapreneur
Technologists building — or wanting to build — a company, and operators launching new practices inside giants. The Herd AI founding story speaks to the tension of building new when you know exactly how the incumbents operate.
The Non-Technical Executive
CxOs and board members who must make AI and platform decisions they don't fully understand. This gives them a technologist's mental model without a line of code — and helps them recognize the hybrid leaders they should be hiring.
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Every career decision is made by a whole person.
The professional climb happened against a backdrop of real loss and real love — uprooted mid-8th-grade, losing my mother in high school, earning West Point admission I couldn't take. It was carried, through all of it, by Dr. Lindsay, my wife of 24 years, and centered on family: three children, including a 10-year-old daughter with Down syndrome who is the heart and soul of our entire family.
This thread gives the book its humanity and stakes — the reminder that resilience, not just skill, is what actually carries you up the ladder.