Veering Off Topic With Rapid7 CEO Corey Thomas

Xconomy Boston — 

It’s time to revive my ongoing series of executive interviews that take a bit of a left turn. Next up is Corey Thomas, president and CEO of Rapid7.

Thomas has worked at the Boston-based cybersecurity firm (NASDAQ: RPD) for almost a decade, and has served as its chief executive since late 2012. The 17-year-old company has been mostly known for selling software that helps organizations find and fix security flaws in their IT infrastructure. In recent years, Rapid7 has added more capabilities in attack detection and response, data analytics, and services to help large enterprises manage their security programs.

So far, one of the highlights of Thomas’s tenure was taking the company public in 2015—one of the few Boston tech companies to IPO in the past couple of years. He says a focus of the company right now is on simplifying security for its customers, which, if done right, could lighten the burden on security teams dealing with the industry’s shortage of skilled workers.

A native of the Atlanta area, Thomas majored in computer science and electrical engineering at Vanderbilt University, but the history buff says he also took a lot of courses on that subject. In addition to Rapid7, his career has included stints with Deloitte Consulting and Microsoft.

I recently sat down with Thomas and Rapid7 senior PR manager Rachel Adam at their firm’s downtown Boston office. Our conversation covered President Donald Trump’s impact on cybersecurity, tech’s diversity problem, career advice from one of Thomas’s former bosses, what he does for fun with his 3-year-old son and 14-year-old daughter, and much more.

Here are some of the highlights of our chat:

Xconomy: How will the Trump administration affect the cybersecurity industry? Or is it too early to tell?

Corey Thomas: I think that I am a student of history. I’ve always said I might not be the smartest, but I learn fast. The only losers so far are those that try to predict anything around Donald Trump.

I cannot predict, in any way, what a Trump administration will do for cybersecurity. All I can do is reflect on the comments that have been made, in that it’s a focus area. And we think that it’s a wise focus area. But I can’t predict what that means … from a policy standpoint.

X: What do you think should be done to make the tech industry more diverse?

CT: I’m a big believer that you have to address root causes. … A big part of it is we have to address education, which I do think that we are, as a country, woefully inefficient. Educating really is the greatest barometer of the capacity of a future society. How well any country educates its citizens is the biggest barometer about what’s the likely opportunity for the people, but also the growth and the role that the country plays. I think that there’s massive work to do there.

Specifically, in the tech sector, I think [it] has to get out of its bubble. I am a big proponent, even with our team, about spending time not just with customers, but in communities. This is part of the reason that we have offices all over the world. This is part of the reason that when we travel and we engage, we try to be engaged with a broad cross-section of people.

I would say part of the issue is tech operates in a bubble. It operates in a small number of cities, by and large. It pulls its staff from a small number of universities, which I would say don’t necessarily have representative student bodies of society.

Until you address that bubble phenomenon, then it’s going to be hard—things that live in a bubble are inherently non-diverse. That’s just the fact of the matter. And I think the bubble hurts tech.

X: What’s something that a former boss said to you that has stuck with you?

CT: I was very aggressive and aspirational. I really wanted my career to move fast. And the thing that [the boss] hit me with was like, “OK, you’re going to get where you’re going. The question is, do you want to be good when you get there? Or do you just want to get there?”

He made me answer the question. “So, do you want to be good?” I’m like, “Of course I want to get there fast, and I want to be good.” He was just like, “All right, in what ways can getting there fast make you not good when you get there?” And that was one of the big reflection points where I had to think about how do you develop yourself, how do you actually prepare yourself?

X: If you could go back in time and get five minutes with any major historical figure, who would it be, and what would you want to say to them?

CT: My daughter would beat me raw if I didn’t say Alexander Hamilton. She’s so obsessed with [“Hamilton,” the musical].

My personal one—I would say it’s personal. It would be the Reverend Dr. Martin Luther King Jr. But the question would be this: If you get the stuff that you want, what next? If the people get voting rights and they get some stuff, what next? What would you focus on? He tells some of it about the poverty and the focus of that, but my question would be about … Give me the full roadmap. You’re a genius. Where would you go after this step right here?

X: How do you relax outside of work when you want to tune out the noise?

CT: It’s a good question. I don’t.

Rachel Adam: You play the ukulele!

CT: I do that with my son. I’ve learned to play the guitar. He plays the ukulele. I’m not very good at it.

No matter what’s happening, every two or three minutes he’s like, let’s go back to tuning it. That tuning thing is fun. He doesn’t know lots of songs. Let’s just say the only song I can play well is “Twinkle, Twinkle, Little Star.” It’s the hit single.

My daughter and I, we read. I read a lot. It is the task-switching that actually is relaxing. And so, I’m always reading three or four books.

… I jog for relaxation. And I used to do martial arts.

X: What’s your favorite book? Or maybe one you’ve read recently?

CT: I loved Gore Vidal’s “Lincoln.” I also like “Team of Rivals” better, by Doris Goodwin. The story all around the Civil War is just fascinating. It’s human drama on steroids.

The play, “Hamilton,” I told my daughter [the Civil War] was my equivalent. I consumed every story in and around the Civil War because there were so many perspectives, from the slaves to the—it was just so many different perspectives. It was a wide tapestry. Much like the Revolutionary War.

In the comic area, “Lamb: The Gospel According to Biff.” I call it “The Book of Biff.” … It’s the reimagining of the missing 30 years of Jesus’s life. The fascinating part—I actually asked some historians about this—is the history is actually quite good in the book. … It was a book that was clearly heavily researched.

… I’m midway through Deval Patrick’s book, which is turning out to be a really good book. I’m immensely enjoying that. He has a fascinating life.

X: What’s your most impressive or most quirky skill that has nothing to do with your day job? You talked about playing guitar.

CT: That’s not a skill though.

X: All right, so what would be a skill?

CT: People always say if you had a superpower, what would it be. I can sleep really easily. It sounds horrible, but it’s actually been so impactful. It allows me to keep a fairly intense [schedule]. I can sleep on airplanes; I can sleep in cars; I can sleep in trains. I get my six hours almost no matter what. And I can have a fairly intense schedule and be rested.

That helps me hugely. I don’t know if it’s a skill, but it’s a huge benefit.

RA: Corey is a Cards Against Humanity shark. He crushed everyone in his latest bout with team members.

CT: That’s just being an observer.

X: Or having a dark sense of humor.

CT: Both of which I have. The dark sense of humor definitely is in ready supply.