Technology Strategy February 11, 2026 3 min read

Full Circle: Why I’m Going Back to What Got Me Started

In 1998, I started my first company, helping healthcare organizations figure out how to use technology. Initially, I wasn’t managing servers or doing support tickets. I was helping people learn how to take advantage of the rapidly growing internet. I liked the work, but I saw a bigger need. Small businesses needed web hosting support. So I put consulting aside and launched rackAID in 2001.

My first office was above the Gotham Nightclub.
My first office in New Haven, CT

In the trenches

Then I spent the next 25 years in the trenches. rackAID started as just me — working out of a 120-square-foot room above a nightclub. Over time, it grew to a team on two continents. We managed systems for startups, biotech companies, vacation rentals, and e-commerce – just about every kind of business. We kept things running, solved problems, and fixed servers in the middle of the night. It was good work. I’m proud of what we built. I moved from New Haven, CT, to Jacksonville, Florida, and built out a real office for my growing team. I spoke at conferences throughout the US and even managed a few trips abroad. Some of my first clients are still with me over 20 years later.

The work changed

But the work changed. Hosting turned into a commodity. Margins got tight. I always wanted rackAID to deliver real value. Not some vague idea, but actual help. Making your business easier to run. Helping you sleep at night. Getting that project off the ground when you thought it couldn’t happen. Now, the value I bring isn’t about managing operations. It’s about asking one question: Is your technology actually helping your business do what it needs to do? Not “is the server up.” Not “did the backup run.” Not “can we get a faster server”. It’s easy to get distracted by the latest tech: new hosting trends, shiny marketing tools, and the latest programming language. Remember ColdFusion? Or CoffeeScript? As business relies more on tech, it’s easy to get lost in the hype. Sometimes, a basic HTML site with a contact form is all you need—if it gets the job done.

WHT — Where every outage was someone else’s fault.
What’s a conference without swap?

A different path

So I needed a change. Not because I no longer enjoy what I do — I love it. Like Web 2.0 and the cloud, AI promises an exciting path ahead. But after 25 years, I wanted to get back to the part that got me into this in the first place. I now focus on helping businesses get more from their IT. It’s what pulled me away from a career in biology in the first place—helping people do what they care about. I still have long-term clients who count on me for technical work. That won’t change. But my focus is different now. I’m back to helping people figure out how to use technology, not just keep things running.

Full circle

It took 25 years to come full circle. Now I’m ready to get back to where I started.