A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another with a more ambitious agenda. Jeremy’s journey is a great case study in this method.
Sramana Mitra: Let’s go to the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?
Jeremy Swift: I was born in Beaverton, Oregon. Most people know about Beaverton because of Nike. It’s a small suburb outside of Portland. I grew up in what I would consider a small middle class family. Both my parents were a rare breed and especially different from the path that I’ve taken in my life. The first job they got out of college is the same job that they retired with 40 plus years later.
My dad was an inside salesman for an electrical supply company and my mom was an operating room nurse. They sacrificed a lot for me and my sister in terms of trying to provide a good education for us. In the middle of that, you don’t appreciate that or respect that mom and dad are rubbing two nickels together to make things work. As an adult, I have a whole level of appreciation being a father of four now.
Sramana Mitra: What happens after high school? What kind of education did you pursue?
Jeremy Swift: I saw a picture on a brochure in my senior English class of a school down here in San Diego, California which is where I live right now. The rite of passage that my family told me was you go to Oregon State University. That was just where you went. I saw this picture and I thought, “My parents have been fooling me my whole life. I didn’t know you could go to such places that existed.”
The school in San Diego sat on a sunset cliff overlooking the Pacific Ocean. I thought I could care less about the education; I was more interested in experiencing something that looked so beautiful to look that. I didn’t consider myself an academic either. I was very interested and driven in student government and athletics.
The school in San Diego had 2,500 students. It’s called Point Loma Nazarene University. I was interested in involving myself in all the things I did in high school. I was active in student government and athletics in college. Ultimately, it’s where my entrepreneur journey started.
Sramana Mitra: What were you studying?
Jeremy Swift: I was a Management Organizational Communications major. It’s a mouthful. It was an interdepartmental major. It was out of the Communications department. You took 60% communications and 40% business courses. I chose the path of communications because I love people and I love relationships. I love understanding the dynamics of people. Ultimately, I always knew that I wanted to pursue the idea of entrepreneurship.
Sramana Mitra: What did you do after college?
Jeremy Swift: My professional journey started before I got out of college. In my junior year, a couple of buddies at school had an idea for a software company. It was an e-communications platform. We were ultimately building an email service provider. This was an idea that they had.
Originally, it was for contractors or people on the job site and how they communicate with architects or people from the home office. I jumped at the opportunity. This was in 2000. The first internet bubble was still full of life. I just wanted to be a part of that. That was significantly important and valuable to me than finishing school.