Ryan self-financed, with some seed money, a FinTech company selling to small financial institutions. Today, the company has delivered 185% y-o-y growth for five consecutive years.
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?
Ryan Caldwell: I was born in Berlin, Germany. My father was a lawyer in the military. He was stationed in Germany at that time. My older brother and I were both born in Germany.
Sramana Mitra: What did you do for college?
Ryan Caldwell: When I was 17, I was accepted to the United States Air Force Academy, and my older brother had already gone there before me a year earlier. I went to the Air Force Academy for two years. They have summer programs in between each year. At the end of my sophomore year, I went on my summer programs and was debating if I wanted to stay and fly jets or take part in entrepreneurial type ventures.
I had spent a lot of time coding and was rather fascinated with the very beginnings of the Internet, rather the rapid growth of the Internet. This was around 1995. I was debating if I would have more of an impact by staying in the military or staying on entrepreneurial type ventures. I decided to take the path of technology and entrepreneurship. I left the Air Force after my sophomore year and shortly thereafter, started my first venture.
Sramana Mitra: What year was this?
Ryan Caldwell: That would have been 1996.
Sramana Mitra: What did you start?
Ryan Caldwell: The first meaningful venture was one where we were an Internet service provider for multi-dwelling units. We would bring in the Internet to that group of 200 to 300 condos. We would deliver high-speed Internet where we would handle all the traffic-shaping to make sure that no one could abuse the network. We would allow them to have inexpensive blocks of static IP’s. I built that for a few years and sold it a few years later.
Sramana Mitra: How big did it become?
Ryan Caldwell: At the end, we were adding almost a complex per month. They’d sign a bulk contract. They’d be worth about $500,000 each for each deal. I don’t recall what the revenue was when we sold it but it was growing rapidly enough. We sold it for just shy of $3 million and negotiated a purchase buy-out payment plan for the acquiring company.
Sramana Mitra: What kind of company acquired that business?
Ryan Caldwell: It was another company that was trying to do something similar but they hadn’t had the same success that we had with multi-dwelling units. They had been delivering Internet to individual homes but they hadn’t focused on building out denser networks for things like a business park or an entire multi-dwelling unit location.
Sramana Mitra: What year did you sell this company?
Ryan Caldwell: That was in 2005.
Sramana Mitra: It was 1996 to 2005 that you did this company?
Ryan Caldwell: No. I was doing some side projects of building computers and custom network servers from 1999 to 2001. It was more of 2002 to 2004. 2005 was when I sold the company.