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“5 Things I Wish Someone Told Me Before I Became the CEO of TransitScreen”, with Matt Caywood

You should still spend time on the small stuff. Even though you’ve built a great team who certainly can get everything done, it can be validating to take a minute and solve some small engineering issue. It’s a great reminder of why you do what you do. I had the pleasure to interview Matt Caywood, […]

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You should still spend time on the small stuff. Even though you’ve built a great team who certainly can get everything done, it can be validating to take a minute and solve some small engineering issue. It’s a great reminder of why you do what you do.


I had the pleasure to interview Matt Caywood, CEO and cofounder of Washington, DC-based TransitScreen. Matt has a PhD in neuroscience from the University of California San Francisco, and degrees in neuroscience and computer science from Cambridge and Harvard. Matt is a frequent speaker on open data, sustainability, transportation and neuroscience, including at Harvard, MIT, Northwestern University, the World Bank, Dubai RTA, Consumer Electronics Show (CES), and Transportation Research Board (TRB).


Thank you so much for joining us Matt! Can you tell us the story about what brought you to this specific career path?

Mybackground is in neuroscience, more specifically in understanding how the brain processes visual information. When I was in San Francisco getting my PhD, I first realized the problem — there were so many transportation options, but no way to easily compare them to figure out which would make the most sense at any given time. It wasn’t until a few years later, when I was working out of a research center for transportation behavior and policy (MobilityLab) that I was able to turn this into what would eventually become TransitScreen.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

When I was first leading the company, I had a serious aversion to business jargon. I assumed it meant that people were just generally talking nonsense at me, but I came to realize the value in having a common language and using standard metrics across companies — I needed to get over myself a little. Now I can circle back and double-click into synergies with the best of them.

What are some of the factors that you believe led to your eventual success?

There were a few that really built off each other. One was having a clear version of the integrity of our product. This allowed us to stay focused on creating the best possible version of what we do; there were several potential investors along the way who wanted us to put advertisements on the screen. That would have required not only adjusting our entire business model to solicit advertising clients, but it would have degraded the actual product we were selling — real-time information about transportation options curated in a way people could read easily. At the same time, it was important to not invest too much of my ego in having the exact right idea early on when it came to who we sold do and what the company would look like. We’ve shifted from selling to governments and transit agencies, to real estate customers, to corporate workplaces. If I had been too insistent on sticking to the original plan, we would never be where we are today.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

  1. There will be a lot of people who don’t get it, and will never get it. And that’s okay! Early on, we were trying to get involved with a New York-based business incubator, but they didn’t understand our vision. One prominent architect in particular insisted it would never work, no matter how much we explained it. Eventually we realized we didn’t need to win everyone over, and we found an incubator in DC that really got what we were about.
  2. There are a lot of people who are too polite to tell you what you’re doing wrong, so you’ll need to read between the lines. In the beginning, people would be very impressed with our customer retention numbers, which were nearly 100%. But at the same time, very few were asking how many customers we were gaining in a certain time period — which was just as important. We needed to be moving faster, but nobody was saying anything.
  3. You’ll know when to go all-in if you surround yourself with the right people. In the beginning of TransitScreen, I still considered it a bit of a side project. One day, Evan Burfield, cofounder of the 1776 incubator, sat me down. He told me that I needed to make a decision: Was I going to go all-in on this? TransitScreen could really be something, but I was going to have to put all my cards on the table. I listened, and he was right.
  4. You’ll be the person who has to do things nobody wants to do. That includes reading pages and pages of legal documents, filing for patents, things like that. Every single decision, ultimately, comes down to you.
  5. You should still spend time on the small stuff. Even though you’ve built a great team who certainly can get everything done, it can be validating to take a minute and solve some small engineering issue. It’s a great reminder of why you do what you do.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

It’s important to make time for your personal life, both because of your own sanity and because it sets a good example for your employees. You’re going to get the most out of your employees, productivity-wise, if they are able to enjoy a flexible workplace. The same is true for leaders — if you don’t take vacations, you won’t be able to give your all to your job or your employees.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My wife, Melissa, certainly. When I first started TransitScreen, the company was based out of the spare room in our home. Once the business was up and running, we went to the West Coast on vacation with our daughter. Melissa was always very understanding about when I needed to be on calls extremely early in the morning, and needing to maintain that leve of structure. From the very beginning, she’s always given me her full support, 100%.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

In terms of personal goals, I’d like to find the time to get back into mountain climbing. Obviously it’s been difficult both because I now run a business and also because I live on the East Coast! Professionally speaking, I’d like to be able to sit down and take a step back to focus on self-reflection and leadership training. I know it would improve my ability to focus and to work with my employees, but it can be difficult to find the time when you’re caught up in the day-to-day hustle.

What do you hope to leave as your lasting legacy?

My goal would be to create something that’s so obviously the right solution for a problem that people can’t remember what it was like before it existed. Like Google Maps did for navigation — so many people today can’t imagine life without it.

If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

Probably something related to transit infrastructure, like making sure every American city adds 10 miles of bike lanes every year until we get to an Amsterdam-like status.

How can our readers follow you on social media?

You can find me on Twitter at @MattCaywood and connect with me on LinkedIn there as well.

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