My Story
About Sheldon
Behind the books, the frameworks, and the engineering leadership is a kid from Jamaica who learned to type on a toy computer.
Born in Jamaica
I was born in Jamaica to parents who were public servants. My mother was a teacher. My father was a policeman. They taught me the value of discipline, service, and showing up every day whether you felt like it or not.
Growing up on the island shaped how I see the world. Resourceful, direct, and never taking opportunity for granted. The beaches of Ocho Rios, Kingston, and Negril are still where I go to recharge.
Where It All Started
My first computer was a VTech PreComputer 1000, a toy with a single-line LCD screen and a full QWERTY keyboard. I learned to type on that machine. I played every educational game it had until the batteries died, replaced them, and kept going.
That little blue computer started something. I went to the High School of Science and Technology, where my computer science teacher taught us Pascal, C++, Visual Basic, C#, and databases. By the time I graduated, I knew I wanted to build things with code for the rest of my life.
The Dumpster Computer
My first real computer wasn't bought. My brother and I found an x86 machine in the dumpster outside a bank near our local bookstore. We carried it home, plugged it in, and it worked. That dumpster find changed everything.
We taught ourselves to build computers, tear them apart, and put them back together. I discovered Linux, mastered the DOS prompt, and became fluent in UNIX systems. Bash, the terminal, the command line became my natural habitat. We connected to bulletin board systems like Renegade and read 2600. It was the hacker ethos before I knew what to call it: curiosity, resourcefulness, and the belief that if you could understand a system, you could make it do anything.
In high school, I joined the computer club, which became my second home. While other kids were on the basketball court, I was in the lab, writing code, building networks, and learning from a community of people who were just as obsessed as I was.
Serving My Country
I served in the National Guard, where I deployed during Operation Enduring Freedom. It was the hardest thing I've ever done and the experience that shaped me the most.
The military taught me how to lead under pressure, how to make decisions with incomplete information, and how to take care of the people around you before you take care of yourself. Every leadership principle I practice today, in engineering, in writing, in life, traces back to what I learned in uniform.
Coming home was its own battle. The transition back to civilian life forced me to confront my mental health in ways I wasn't prepared for. I learned that the discipline the military gave me could be redirected, into taking care of my mind the way I'd been trained to take care of a mission. Exercise became non-negotiable. Cycling became my therapy. Vacations to Jamaica became how I recharge. And voices like David Goggins on YouTube became the accountability partners who reminded me that the fight doesn't end when the deployment does, it just changes terrain.
Life on Two Wheels
Cycling isn't a hobby for me. It's how I take care of my mental health. After coming home from deployment, I needed something that was physically hard enough to quiet the noise and structured enough to give the day a purpose. Cycling became that thing. Last year I rode over 1,000 miles.
There's something about the rhythm of the pedals and the open road that clears my head and lets the ideas come through. You don't ride a thousand miles in a year by being motivated. You do it by showing up on the days you don't feel like it, which is the same discipline that applies to leadership, to writing, and to life.
Follow Me on StravaLearning to Fly
If I didn't have a career in technology, I would have been a pilot. A few years ago I started flight training and earned my student pilot license. Sitting in the cockpit of a single-engine aircraft and knowing that your decisions are the only thing between you and the ground is a feeling that never gets old.
The hardest parts? Learning to use the rudder, on the ground and in the air. Landing. Understanding flight patterns and traffic. But the real lesson flying teaches you is focus and trust. Focus on the procedure. Trust your instruments, even when your instincts are screaming something different.
That's a lesson that translates directly to leadership. Build the instruments, the metrics, the evals, the dashboards, and then trust them, even when the noise around you is loud.
Island Soul
No matter how far the career takes me, Jamaica stays in my bones. I go back whenever I can, to snorkel the reefs, to eat jerk chicken on the beach, and to remember where I came from.
The beaches of Ocho Rios, Kingston, and Negril aren't just vacation spots. They're home. And they're a reminder that the best ideas come when you slow down long enough to let the water clear.
That's the Short Version
From a VTech computer in Jamaica, through the deserts of the Middle East, to leading AI-first engineering teams at Fortune 100 enterprises, and writing the books I wished someone had handed me along the way.