20 years ago this month, I launched a website out of my Middlebury College dorm room that led to what is now Union Street Media. Of course, I had no idea at the time that when we pushed www.middkid.com onto the Internet, it would lead to a company, hundreds of client relationships many of which have surpassed 10 years of collaboration and a life in Vermont.

As soon as I understood what it meant to be an entrepreneur, I knew that’s who I was. From setting up a corner lemonade stand to fund my baseball card collection to selling Christmas wreaths for my Boy Scout troop, I always had a fascination in creating things. My senior year of college, while everyone else was going through the more traditional interview process, I was trying to figure out if there’s a way that I could drop-ship college town microbrews to alumni who lived far away from their alma maters or import 1970’s Toyota Land Cruisers from Europe, restore and sell them in the United States. Those ideas were probably more indicative of what I was interested in at the time than a real business idea. However, it was the entrepreneurial idea generation process that I was really pursuing.

It certainly helped that many of the role models in my life were entrepreneurs themselves. I didn’t know it at the time and yet there was a clear correlation between what my father and grandfather had done and what I was going to do. I also was blessed to witness their strong work ethic. My grandfather, quite happily, went to work on Tuesday and died on Wednesday in his late 80s. My father, in his 70s, is still going to the office. The way I look at it, 20 years into this, I am about one-third of the way through my career.

Some of my classmates would ask why I wasn’t taking a more predictable path to a well-paying job. After all, I was graduating in the midst of one of the best business cycles in history and could have gotten a very good offer right out of school. Much of it had to do with what came with the job, not the roles themselves. I realized that I had a strong aversion to the paradigm that you either lived within a metro area spending hours of your week commuting or took a vow of professional irrelevance to live somewhere else. I didn’t want that dichotomy and I wanted to provide others the opportunity to have the same choice. It certainly helped that I came of age at the dawn of the Internet which provided an opportunity to figure out where you want to live and then figure out what you want do in a way that was never available to previous generations.

I once heard a Vermont philanthropist say that life was built in three stages: learn, earn and return. Upon reflection, I felt that they are not distinct. We all want to be lifelong learners, we all need to be lifelong earners, and we should all be lifelong returners.

After 20 years, I feel that I have learned a few nuggets that may be of interest to you. Over the next couple of months, I will be sharing those thoughts through video… As I believe the future of the Internet is to be watched and not read. Stay tuned for my 20 for 2020.

And in the meantime, I would like to say a big thanks to all of you who have been part of Union Street Media over the past 20 years. You know who you are. Thank you!