Jason has built a disciplined, profitable business and scaled it to $40 million in 2017 revenue. The company was first bootstrapped using services, and later raised ~$20 million in funding.
Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?
Jason VandeBoom: I was born and raised in a small town in Wisconsin about an hour out of Milwaukee, and started in technology from a consulting side of things at a very early age. Around 13 or so, I started taking on small projects. I was always interested in engineering and design. That ultimately led me to go to art school. I chose a school in Chicago for art school. That’s what brought me to Chicago.
Sramana Mitra: Your background is more of a designer background.
Jason VandeBoom: Yes. I’ve been into engineering as well. The initial products we developed were all programmed by myself but the design interest went along with that.
Sramana Mitra: When you came out of school, what kind of jobs did you do? Put a timeline on it. What’s happening in the world at that time?
Jason VandeBoom: I started going to art school in 2003 and started the business immediately at that time. I didn’t have a bunch of things going on in school outside of the business I still run today. It wasn’t started with some grand idea. I was just looking to simplify the consulting work I was doing and provide a solution within a box essentially, but in a digital form.
I was providing software that people would download and install on their web server. At that time, SMBs were looking for solutions on who to communicate with their customers. That was just lacking in the market. I ended up customizing this over and over again. By packaging up and selling the license, it was just saving myself time.
Sramana Mitra: Where are we now in the chronology?
Jason VandeBoom: That was 2003 when I started the company. We started with one product and then I created up to eight different products at one point, all having to do with helping the customer experience. The interesting there is I was actually just solving my own problems along the way.
I needed to communicate with my customers so I needed to market to them. I needed to help them with support. I needed to get more information out of them so we had a survey product. This brings us all the way up to 2012 to 2013 when I had eight products and a small team of eight or so people spread way too thin in terms of focus. Our customer experience wasn’t exactly ideal.