My summer at Runscope has been the best internship experience that I’ve had in my three years of college. Runscope provides a suite of API monitoring and testing tools that help developers build better apps and better businesses. When Christiaan from True sent me an email that I would be interviewed by Runscope, I was a bit puzzled—how could I contribute to a dev tools company as a designer? However, once I spoke with John Sheehan, Runscope Co-founder and CEO, and Matthew Ginnard, Principal Designer, I was really moved by their sincerity in not only helping developers grow, but also in helping me grow as a front-end developer. It was the people at Runscope who made me want to work there. Throughout the internship, they have also made me realize how important product design is in creating development tools, which is often distilled from fancy visual elements to pure functional design. Apart from design, I learned a lot from simply experiencing the company culture of Runscope under the great management of John and Co-founder and CTO Frank Stratton.

I recently had the opportunity to ask John more about his life as an entrepreneur, which taught me a lot about being resourceful and the factors that have influenced his practices that make Runscope a great place to work.

About John Sheehan

John is the co-founder and CEO of Runscope with more than 15 years of experience working in various IT infrastructure and tech roles. As an early employee at Twilio, John led the developer evangelism program and managed the Developer Experience. After Twilio, John became Platform Lead at IFTTT (If This Then That), a service that allows users to make conditional actions across different apps like Gmail and Pinterest, and worked closely with API providers to create new channels.

Q: How did you get into technology and entrepreneurship in the first place?

Interest in Software from as Early as Eighth Grade

I started to learn programming in eighth grade after joining a computer club after school. We learned BASIC on old Apple II computers that had a black background with green text. I started by writing a little bit of BASIC, but I didn’t understand any problems that could be solved with programming, except silly games like random number guessers and tic-tac-toe.

Shortly after that, on my birthday, my family and I went to a computer software store where I discovered Visual Basic 3.0. I convinced my parents to buy it for me. When I got home, I couldn’t figure out what to do with it—but what I did figure out was how to make fake error messages pop up in a dialogue box telling you that your computer had crashed. I started uploading this as shareware on CompuServe, the first major commercial online service in the United States that was later acquired by AOL,and would mail people a disk with the shareware on it. The shareware was completely harmless and the free version was called Joke and Prank, but I also made one that I charged people for called Error with 10 or more error messages. I was 14 years old at that time, and although I didn’t get a lot of money, I did get featured in PC Computing Magazine’s 1001 Best Downloads.

Transitioning into Self-Taught Entrepreneurship

After that, I went back to fixing computers because that was what people were mostly willing to pay for. I started attending college, but hated it, so I decided to quit after a semester and start my own company making websites. That was during the dot-com boom, so I figured I could make a bunch of small websites doing various things, but it didn’t go well. I went broke, moved back home, and then tried different jobs like pizza delivery and working for a health club.

When I was 19, I got a job doing website development and computer repair for a company in the Twin Cities (Minnesota). For a few years, I worked at various similar jobs, mostly doing web development. I was working with a lot of sports organizations (Minnesota Vikings, Minnesota Twins, Minnesota State High School League), and that’s when I decided to start another business in 2005 (yes, the third one!) to make software for recreational sports groups to manage their leagues.

When that didn’t take off, I joined another creative agency called Treefort. While I was there, we started a side product called Screenfeed that produced content for digital signage. You can actually see Screenfeed content in the Montgomery Street BART Station in San Francisco today! It was essentially content being delivered via an API. I liked working there, but right around this time I got particularly interested in working with APIs, especially in what Twilio was doing.

From Employee of Twilio and IFTTT to Co-Founder of Runscope

I was getting pretty involved using Twilio’s platform, so when I ran into a few early Twilio employees at a conference, I introduced myself and quickly got a job offer to be its first Developer Evangelist. When I started, there were only about 10 people in the company. For the first year, I worked remotely, based in Minnesota and then Colorado, but I was flying all around the country promoting Twilio to developers at conferences and hackathons. I later became a Product Manager for Developer Experience, making sure the day-to-day tools developers used with the Twilio APIs worked well. After two years with Twilio, I headed to IFTTT where I worked on helping partners integrate their APIs to the IFTTT platform. I found that a lot of these APIs had performance issues that other tools weren’t helping us solve. I got together with Frank Stratton, with whom I worked at Twilio, to build tools to solve those problems, which became Runscope.

It’s been a long road to get to the point where I felt ready to start a company like Runscope. I’ve had a lot of companies in the past, but this is by far the most successful. All of my previous experiences really built up to this, and it’s nice to have found my calling. It’s the one thing that I want to focus on for as long as possible—I want this to be my last job. I want the company to be so successful that none of us have to work anywhere else ever again. That’s my goal.

Q: How was your experience at Twilio and IFTTT?

They were both really great experiences, both really small when I started. At Twilio, there were about 10 people when I started back in 2010. Twilio now has more than 500 employees and has raised over $230 million in funding—it’s worth over a billion dollars. But back when I started, I would have been excited if we were acquired for $10 million. Over the two years I worked there, it grew so quickly that you had no choice but to learn as fast as you could to keep up. There was no opportunity to be lazy or complacent because if you did, the machine would grow past you. Even now, I get impatient when I feel like we’re not moving as fast at Runscope.

It was also interesting to see the progression within Twilio and IFTTT. Twilio was very different when it started at 10, versus 20, versus 50, versus 100+ when I left. There were different challenges at each stage, and being able to watch that progression has helped us prepare for similar changes at Runscope and avoid some of the common pitfalls associated with growth.

Q: How has your experience at Twilio and IFTTT impacted your present work?

There’s probably not a day that goes by that these two companies haven’t influenced how Runscope works. Runscope shares a lot of philosophy with Twilio, which is prioritizing features and products to be focused on developers above all. Our goal as a dev tools company is to help developers become more productive and successful at work.

From the IFTTT side, I took a lot of inspiration from the IFTTT product design. For example, we use a lot of whitespace, and IFTTT uses whitespace probably more than anybody else on the Internet. Trying to keep things simple and distilling everything down to its essence is core to Runscope’s design and is definitely a carry-over from IFTTT.

Q: How is it like to manage Runscope?

When the team was small I didn’t have much of a management strategy. We hired smart, self-directed people and let them do their thing. We still do that, and I mostly just coordinate among all the moving parts. My goal is to distribute as much responsibility as possible so that people can have enough autonomy and authority to be responsible for the outcome of their decisions. I do not want people to fear making mistakes. As a startup we have to try new things and many of them are not going to work.

Everyday I am trying to push decision making and responsibility to other people. I want other people to be as responsible for as much as they are willing to be responsible for. My goal is to get people who can recognize a problem, determine a course of action and implement the solution—even when things might not be very well defined.

Q: What do you see in the future of Runscope and the API economy?

There are a lot of problems left to solve in software development. There will never be perfect software, so as long as we keep coming up with tools that can bring value to developers and the companies they work for, we have a bright future ahead of us.

As for the API economy, the industry is standing on the ground floor. The world is becoming more and more connected via APIs, and there is going to be no shortage of devices or pieces of software talking to each other. It is really just the beginning of anything related to APIs. It’s a big opportunity now, and it’s going to become gigantic.