When people hear that I didn't study software development in college, and that I owned and operated a restaurant for seven years before I got into the software business, the first question is usually:
So how did you end up in software development?
Let me explain. My family owns a chain of restaurants in the Rockford, Illinois, area, so running a restaurant was a natural step for me. My grandfather started the chain in 1928 and sold it to my father in 1953. The family owns the chain but operates only one unit itself. That unit is where it all started, and it's where I worked from the time I was old enough to handle a broom and mop, at about 14. I worked there until my father was ready to retire in 1990. He wanted to pass the legacy on to his son, so in 1991 he sold me the unit he operated and kept the rights to the other units, which paid him a fee.
As a boy I loved playing with computers, and I used to tell my father he needed to computerize the business. He always turned me down with the old line: "This is how I've been doing it all my life, and it works fine for me." I couldn't really argue. It did work for him, and he'd done very well with his style of management. But once he retired, nothing could stop me from carrying out my master plan.
From my first day in charge I wanted to modernize the restaurant's operations. I started shopping for a computer right away, and it became the centerpiece of the effort. I spent the next few years learning everything I could about computers, and software in particular. By the time I sold the business, I had moved all of its financial management to QuickBooks from the basic ledgers my father and grandfather had used for more than 60 years. I used WordPerfect for the menus and Publisher for posters, table tents and advertisements. But computerizing the inventory was the most fun. I built databases and data-entry forms, and I got my first chance to write meaningful code. I'd stay up until all hours on these projects, and I enjoyed every minute. I found I had a natural aptitude for it.
When the internet was just beginning to take shape, I started designing websites. I remember telling everyone, with great enthusiasm, how the internet was going to change the way we did everything, at a time when many people still didn't believe it. More important, I was sure it was where I wanted to be. I no longer enjoyed the day-to-day work of running a restaurant. So I hatched a plan: I'd hire a manager to run the restaurant and start an internet development company.
That was 1996. Besides my restaurant's website, I designed a site for a local rock band called The Good Year Pimps, and I did computer installation and maintenance. It was slow going, and I quickly realized I wanted to go deeper into the technical side of the business. Development itself was where my passion was.
Around then I started building an online personal information management application called cyberPIM. I really enjoyed the work, and it was my single greatest learning tool. My philosophy was, and still is, that the best way to learn something is to do it. Reading is great, but you learn the most by putting what you've read into practice. That's when it starts to make sense, and when it starts to stick.
By 1997 I'd decided to leave the restaurant business altogether and focus on software. Having a manager run the restaurant wasn't working out as well as I'd hoped, and it was a major distraction from the future I had in mind. I also decided to look for a job in the software industry, to speed up my learning and get real experience under my belt. I'd always intended to start my own software company, but for the time being I put that goal on hold. In early 1998 I sold the restaurant and took a programming job in Oregon, Illinois. I'll be forever grateful to my manager there, who took a leap of faith on me.
That's how I went from restaurant owner to software engineer. I kept working on cyberPIM as a side project.
First published on termondt.com around 2019. Revised October 2026.