Revolution, Resilience, and a Little Hockey: My Startup Journey

In the early 2000s, I took a leap into the startup world, joining a company that had patented fast GPS acquisition and was pioneering a SaaS vehicle telematics solution. We weren’t just software; we designed, manufactured, and sold hardware installed in vehicles, enabling near-real-time tracking and communication between dispatchers and drivers. I was roughly employee 162, and we would become one of the last three startups to IPO before the dot-com bust. My time there was transformational—both for me and for the company.

Bringing Big-System Thinking to a Startup

Coming from enterprise environments, I had certain expectations for platform design, availability, and resilience. I pushed for major redesign of our flagship solution, improving availability from below 90% to a consistent 99%, even as we scaled past a million subscribers. A big part of this was implementing dual-data centers with near-real-time replication—ensuring we could shift load seamlessly and deploy changes with zero downtime.

One particularly tricky issue I solved involved TTL (time-to-live) settings. We discovered that over half our devices weren’t sending data due to an unexpected routing issue. By redirecting devices to a backup receiver with fewer hops, we restored data flow while working with our network providers to fix the underlying problem. It was a small, crucial adjustment that reinforced my belief in deep system understanding and operational problem-solving.

A Patent, a Platform, and Practical Innovation

One of the most forward-thinking ideas I contributed was my patent (US 7,006,820)—a method for optimizing over-the-air programming of our in-vehicle devices. The idea? Instead of blindly pushing updates, we could leverage weather, historical signal strength, and other factors to determine the best time for successful delivery. It would improve update reliability and ensured our devices continued to perform well in the field. It was ahead of its time.

The Business Side: Compliance and M&A

As we prepared for our IPO, we had to implement key controls—a necessity for any public company. But the “Big 3” audit firms pushed expensive, boilerplate frameworks that were completely overkill for a company our size. I strove to right-size our controls, ensuring compliance without unnecessary complexity. The result? Clean audits, without the bloat.

I also had a front-row seat to mergers & acquisitions, both in integrating smaller companies we acquired and eventually being acquired ourselves. My role focused on absorbing technology, evaluating processes, and integrating teams. When our parent company took over, I was the last officer released—a testament to my deep operational knowledge and ability to bring others up to speed.

My First Brush with Agile (XP)

Before Agile was of working was a buzzword in my career, I saw it in action. Our developers and testers worked in tight, iterative loops, pairing up, and deploying changes rapidly; a stark contrast to the big upfront design models I was used to. Over eight years, we made more than 10,000 production changes (excluding web content updates), moving from months-long release cycles to an on-demand, high-speed deployment model... and this was before cloud!

At the time, I didn’t really grasp XP as a methodology, but I knew this was a better way to work and we were getting the right things done, and done well. It reinforced my later passion for Agile transformation and the efficacy of self-organizing, cross-functional teams.

A Little Hockey, a Lot of Business

Company culture was just as important as technology, and sometimes a little fun goes a long way. Our CEO—a great guy who half-jokingly thought I had magical powers—loved my daily flash reports on platform availability, upcoming changes, and open issues. I started adding highlights from our company ice hockey team (four employees played), and he was hooked.

When it came time to cover league fees, I made the case: we should sponsor the team. Not only did he agree, but he also paid for jerseys (with a custom logo designed by our webmaster) and even set up an open snack tab for employees and their families who attended the weekly games.

It turned out to be more than just team-building—it led to relationships with Sun and Oracle, which scored us great deals on hardware that directly contributed to our platform improvements. Win-win. And yes, I still have my signed Wrecking Crew jersey framed and hanging in my family room.

Beyond Business: Expert Witness and Real-World Impact

One of the most unexpected ways my work made a difference? Helping solve major crimes. Our technology was used as key evidence in multiple trials, including a murder case and an attempted murder retrial.

In one case, our data placed the assailant’s vehicle at the victim’s home—critical evidence that helped secure a conviction. In another, our system not only proved the assailant but also helped locate the victim. Because I deeply understood both our technology and its data, I served as an expert witness, translating complex technical findings into clear, undeniable facts for attorneys, judges, and juries. That experience reinforced my commitment to curiosity, integrity, and real-world impact.

Lessons from the Startup World

This chapter of my journey taught me a few things:

I thrive in environments where I can solve problems, not navigate bureaucracy.
Self-organizing, cross-functional teams are the backbone of great outcomes.
Collaboration—whether on a dev team or a hockey rink—leads to unexpected and valuable opportunities and more great outcomes.
Curiosity and deep system knowledge can take you places you never expected.

I came in as an operational architect of resilience and security and left with a deeper appreciation for agility, business strategy, and the power of a strong team. And while I love continuous improvement, sometimes the biggest wins come from just rolling up your sleeves and getting stuff done (#GSD).

What’s Next?

This was just one stop on my Journey Talent journey - a thread that connects my experiences, lessons, and growth over time. Each chapter builds on the last, and I look forward to sharing the next one soon... remember me mentioning a camping trip? ⛺