Sramana Mitra: What happens after?
Ryan Caldwell: I went to do consulting. I wanted to be at the heart of San Francisco. I did consulting for companies like Microsoft and Visa in London and Singapore.
Sramana Mitra: What was the next major thing that you did after selling this company?
Ryan Caldwell: I gained some experience with large corporations and how they work. I owned about 90% of the company when I sold it, so it was a meaningful exit for me personally. I wanted to see how large companies work, how they made decisions, and what that side was like.
For about a year, I was living in San Francisco. I got to see how they made decisions. It was informative to see the massive scale of these larger organizations and how, as more agile startups, there could be great possibilities by partnering with them. That year of my life changed my paradigm about how I might do entrepreneurship in the future.
Sramana Mitra: What were the takeaways? What did you learn?
Ryan Caldwell: Larger organizations aren’t always doing things because they make sense. Often, they’re doing things because of inertia. It’s just what they already are doing. It’s easy for a startup to come in and innovate and find a solution that can meet a significant need for that larger organization, and be able to help the startup get scale. There’s a symbiotic relationship between startups and large corporations if you can just find a common area that the startup could deliver benefit for.
Sramana Mitra: After that experience, what was the next thing you did?
Ryan Caldwell: There was a lot of great things going on in Utah at that time. I had met a few people in Utah years before. I was born in Germany but moved around quite a bit. Some of my formative years were in Texas. I considered myself from Texas but had been in Utah a few times. I had met some really great entrepreneurs in the state. I watched Josh Ames in their very early days when they built Omniture and ended up going public.
I thought that Utah was a great place to build a company. I came to Utah and had a few friends that I had met before. I worked with a few of them on a handful of different startups. The first major commitment that I made was working with a company called Zinch. Sid Krommenhoek was there and was one of the founders. I got to know him and the other two founders pretty well.
I worked with them for about five months and got to see the good and the bad of the early days of a startup in a different form than I had seen before. It was really cool to see the challenges that they were taking on. I decided that startup wasn’t for me so I didn’t stay there, but I got to watch their journey as they built that company and sold it to Chegg. I stayed friends with Sid and saw him go through that whole process.
Sramana Mitra: What year does this bring us to?
Ryan Caldwell: That was in 2007.
Sramana Mitra: What’s next?
Ryan Caldwell: There was a time in the 2008 and 2009 timeframe where I was working with different companies. However, I focused only on MX. It was the first company where I was tackling something that I was passionate about. It was something that bothered me. That first Internet company that I described, that was one where there was great utility there and I definitely had a strong interest in that, but it wasn’t anything that I felt really passionate about.