This Transportation Company Makes the Complex Simple

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In 1997, four years before the London Underground transit system launched an online trip planner, Matt Caywood built one for a college computer science class project.

He spent the following decade in San Francisco earning a Ph.D. in neuroscience. There, he never knew which bus or streetcar to take. He had three equally convenient options from the UCSF campus, but each stopped at a different location, so he would have to guess which would most likely arrive first.

This frustration stayed with him in his next career moves, until in 2011, he had the opportunity to help Arlington, Va., build a public display, so people would easily understand the transportation options around them in real time. This became the basis for TransitScreen, the company he co-founded in 2013.

Related: Why One Founder Says It’s Crucial to Question Assumptions and Constantly Improve

Today, TransitScreen shows people in 30 cities across five countries which form of transportation, from Uber to bikeshare to bus, will be most convenient or efficient at any given time. It puts all available options on equal footing by calculating the number of minutes each will take.

Here’s what Caywood has learned about how open-mindedness can create opportunity.

This conversation has been edited.

What have you learned about growth while doing good?
What was once a fairly slow-moving industry, transportation, is now hyper competitive and exciting. 

There’s also enormous potential for people to improve their choices and to create economic value that benefits all kinds of other businesses and people within the city. For example, we installed a TransitScreen in a Seattle hospital. Two months later, the manager of the lobby coffee shop told our sales person, ‘My afternoon sales are up 33 percent because of the screen.’ People are no longer waiting on the bench in the Seattle fog for their bus; they’re now waiting in the warm coffee shop and buying coffee and muffins. He had had to hire another barista during that shift.

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What have you learned about culture while doing good?
We like people who are open to new ideas and trying out things, especially when it comes to cities and transportation. One interesting fact about us is that no one in our company drives to work. Everyone commutes some other way. We think that’s, in some ways, the future of work.

Beyond that, we like people who have an understanding of the kind of problem we’re trying to solve. I’ll often ask hires, ‘When was the last time you rode transit? What was the experience like?’

Related: 11 Crucial Interview Questions to Ensure a Culture Fit

What advice do you have for other businesses looking to do good?
Often, if you’re a growing startup, you need to find customers who can buy your product fast. So think about who else might be a stakeholder in whatever problem it is you’re trying to solve.

A lot of people think that the logical customer for us is going to be a city itself or a transit agency. We’ve done a little bit of business with those sectors, but I think the thing that really surprised us was how many private sector customers there are out there. We had a meeting early on with a real estate developer in DC. Now our largest customer group is apartment complexes in cities.

Lydia Belanger

Lydia Belanger

Lydia Belanger is an associate editor at Her work has appeared in Inc. and Wired.

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