Jame Mackson’s personal website: useful technology, small-business ownership, work and community, his story, Field Notes and ways to connect.

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A small business invested in me

I didn’t start out as a programmer. I started in drafting, and one thing kept leading to another. Drafting became CAD. CAD became application customization. GIS brought databases into the picture, and eventually I found myself trying to connect systems that weren’t built to work together.

A small business invested in me along the way. There were programming lessons over lunch, a company-funded course, and people willing to give me a nudge when I got stuck. I did a lot of figuring things out with the internet and a little help. I’m grateful for that investment. It changed the direction of my career.

A fairly ambitious first project

The course was a weeklong introduction to ArcObjects: programming within Esri’s ArcGIS system. The problem waiting for me afterward was considerably bigger than a classroom exercise.

Our GIS department spent a lot of time posting work orders for changes to electric utility distribution networks. We had an in-house staking system and a GIS system, both highly customizable, with data that could look different from one implementation to another. We thought there had to be a better way to move work between them.

There wasn’t a development team available to take it on, so I started building the integration. It needed to map data between the systems, let people select work orders, move them into GIS, and validate the result. That was my introduction to programming: a real problem, plenty to learn, and people who gave me a chance to work through it.

Learning by building

At Origin GeoSystems, I was hired as a database administrator and became involved in a broad mix of database and infrastructure work. When the company was sold, I stayed with a small group that went on to Agile Innovations. That became my first startup experience as the lead technologist.

We consulted for transmission utilities and built prototypes, including a way to bring transmission designs into GIS in three dimensions. I was learning how to take an idea, figure out what was possible, and make something people could use.

Marketing agency work followed, including web-to-print and custom software development at Brand Spring. Then I had the opportunity to become the sole developer at EstateMap, a bootstrapped estate-planning startup.

EstateMap put me deep into custom web development and lean startup practice. Build something, get it in front of customers, listen, and keep learning. Moving quickly mattered, but so did learning whether we were building something people wanted.

Knowing what to build

At the Wedding Shoppe, I worked on tools for a busy retail operation and the path toward a modern e-commerce platform. I managed contractors, served on the leadership team, and worked across the product cycle.

As we worked through the business’s priorities, we realized that continued custom development wasn’t central to what the company needed. I helped put it on a path toward Shopify and more standard tools. In a way, I consulted myself out of the role. Helping the business choose the right tools was part of the job, too.

Next came Upsie. I started as head of engineering and became VP of Engineering, leading a team that ranged from about eight to ten people. Later, I took on responsibility for product alongside engineering, working under the guidance of our CEO. It gave me a broader view of the work: the people building it, the decisions behind it, and the business it needed to support.

Small business is personal

Alongside my technology career, I’ve spent fifteen years co-owning petite salon with my wife, Brandi. Our business partners are Tom and Haley Fruen. We have two locations, and I serve as CEO with a focus on the business side.

My drafting background came back into use when we designed and built out our spaces. There’s a connection between laying out a room, working with a contractor, and building software: you have to understand how people will actually use what you’re making. We’re currently implementing Conversated at the salon, so that learning continues in my own business.

What I’m building now

After Upsie, I knew I wanted to build something of my own. AI opened up possibilities I wanted to explore. I incorporated Space Three LLC and later registered Humble Good as its DBA.

Humble Good is the company around my software and creative partnership efforts, including Conversated. It brings together what I’ve learned in technology and what I keep learning as a small-business owner. I want to build tools that fit the work, respect people’s time, and help them make decisions. A small company once gave me room to grow. I carry that gratitude into what I build next.

Away from the screen

Away from the computer, I like woodworking, snowboarding and RV road trips. I still enjoy making something with my hands, and travel gives me room to look at the work from somewhere different.