Interview with Hilary Mason

Series: Entrepreneurial Heroes

Release Date: February 1, 2013

Hilary Mason, Chief Scientist at bitly, describes problem solving and the development of technology as a super power - "the ability to do something we really couldn't do before." She goes on to say "we're extremely lucky to live at a moment in time, when if you're willing to put in the time and energy, it is actually possible to build things that have not existed before, that actually do make people's lives a bit more interesting.

Hilary Mason

Hilary Mason is the Chief Scientist at bitly, a company that provides link-shortening services for sharing on social media platforms. Hilary is also the co-founder of HackNY, a non-proft that helps talented engineering students find their way into the startup community of creative technologists in New York City. She created dataists, is a member of NYCResistor and the Technology and Innovation Advisory Council, advises organizations like, collective[i], and DataKind, and is a mentor to BetaSpring and TechStars New York. Hilary’s recent honors include the TechFellow Engineering Leadership award, Forbes 40 under 40 Ones to Watch list, and Crain’s New York 40 under Forty list. Hilary speaks on topics like how to replace yourself with a very small shell script, email hacking, and machine learning.

Hilary Mason


Interview with Hilary Mason

Lucy Sanders:  Hi, this is Lucy Sanders. I'm the CEO for the National Center for Women in Information Technology, or NCWIT. Today, we're continuing with our series of wonderful interviews with women who have founded technology companies. We really love this interview series and are very excited about the person we're talking to today. With me is Larry Nelson from Hi, Larry.

Larry Nelson:  Hi. Boy, I'm really happy to be here. This is a wonderful series. It's extremely popular on our website. In fact, we archive all the interviews so you can go back and listen to them also.

Lucy:  Also, listeners you can find this interview on the NCWIT website as well. Today, we're interviewing a very special person, Hilary Mason, who is the chief scientist at Bitly. We'll have to have Hilary explain it more precisely than I will, of course. But Bitly is primarily a URL shortening service, a bookmarking service. It really provides a fun and easy way to save and share and discover links from the web, by using links that they call bit marks. Reducing that URLs pretty important. Those things can get pretty beefy. You can't really share them very easily when you have only so many bytes that you can send along. This is pretty important to services like Twitter, for example, and others. Hilary's got a great job at Bitly. She's the chief scientist and her work crosses peer research, math and the development of product focused systems.

Another thing we know about Hilary. She loves New York. Absolutely loves New York. Loves everything about New York, entrepreneurship, I'm sure she's going to tell us about that. She also gave one of my very favorite TED talks of all time, Replacing Yourself with a Very Small Shell Script, which I listened to several times. Hillary, welcome.

Hilary Mason:  Thank you so much.

Lucy:  Tell us a little bit about what's going on at Bitly.

Hilary:  You gave a great overview of what Bitly is. But it's a fantastic example of something that is extremely simple that becomes quite interesting at a large scale. At Bitly, we see the links that people are sharing across all their different social networks. These are things like Twitter, Facebook, Tumblr, WordPress, Live Journal. Even strange places like YouTube or inside a virtual world like Habbo Hotel. Then we analyze the data in aggregate that comes from that social behavior. The kind of work that my team does is looking at human behavior through our social data. We work on things like building a search engine to try and find the most popular links about any topic you might be interested in. We also work on content recommendations.

Some other really fun applications that are only possible because of the data set that comes from that very simple mechanism of shortening and sharing a link.

Larry:  Wow.

Lucy:  That's pretty interesting. All the social networking and sharing that's going on, we just redeveloped our website so we could more easily share our resources and also shorten our URLs. Very timely for us. Hilary, tell us a little bit about how you first got into technology and as you look out across the landscape today, which technologies do you find particularly interesting?

Hilary:  The question about how I first got interested in technology was actually when I was a little girl. I was fascinated by computers. I taught myself to write code from reading the back of magazines when I was still in elementary school. I remember my first program. It was the Absolutely Wonderful 10 Print Hilary is Great 20 Go to 10 Run. [laughter]

Hilary:  I thought it was amazing because it was an infinite loop and my teacher had no idea how to turn it off, who was even funnier.

Lucy:  I know, infinite loops are pretty funny anyway.

Larry:  Yes. [laughter]

Hilary:  Yes, so I've always been fascinated by it and I always knew that it was what I wanted to study. Then I went off and majored in computer science. As to what technologies I think are exciting right now, they're so many different ways to think about that. On the human side, I think the way that I can carry a computer in my pocket that's more powerful than that computer I had when I was in elementary school is amazing. I'm excited to see how our devices interact with the real world in the next few years through projects like Google Glass and other sorts of augmented reality things, things people have been trying to build for decades. Only now has the tide caught up to the idea that people have.

I'm also really excited about data technologies and the way that we can use data. We have data available, we have compute capacity available. We can use it to make our lives better and more interesting.

As a throwaway side project, I went and got all the menu data for all of the restaurants that are not fast‑food restaurants in Manhattan and was able to find...If you want Thai food, you should go to the area around Hell's Kitchen because it has the highest density of high‑quality Thai restaurants in the city. That's something I could do in a day that never would've been possible even a couple years ago.

Larry:  Wow.

Lucy:  Things are changing really quickly.

Larry:  Very quickly. I must say, just a couple days ago, a colleague of mine sent me an email. The link was so long, it was incredible and I get these long links from him frequently. I'm going to make sure I send him your website. [laughs]

Hilary:  Definitely should. I think email is still the biggest social network.

Larry:  Yes. Now, let me ask this, Hilary. It's two parts, all related. Why are you an entrepreneur and what is it about entrepreneurism that makes you tick?

Hilary:  I've always had mixed feelings about the word "entrepreneur" because it's so overloaded in our culture and it's become really trendy in a way that I'm not sure is healthy. The way that I like to describe the work that I do is that I tend to find problems and then try to make things that solve those problems. Sometime those things might be hacks, like the one I just described to you.

At one point, we also built a door knob that you could text to unlock a door. That was very clearly a hack to solve a problem. It was not a company, it was not a product. Sometimes they're products, sometimes they're companies, sometimes they're non‑profits, like HackNY, which is an organization I co‑founded a couple years ago.

The way I like to think about it is more engineering the right thing to solve the problem. Not so much about starting a business just for the sake of being an entrepreneur.

Lucy:  That's pretty interesting.

Larry:  It is.

Lucy:  What is it about that problem solving that you really like? Can you expand a bit more on that?

Hilary:  Sure. It's very much my philosophy about how we should build and develop technology. I really think it should give us super powers. The ability to do something we really couldn't do before. We're extremely lucky to live at a moment in time, when if you're willing to put in the time and energy, it is actually possible to build things that have not existed before, that actually do make people's lives a bit more interesting.

Lucy:  That's a great answer. I have to think a lot about your answer around entrepreneur being too overloaded.

Larry:  Yes, me, too.

Lucy:  That's a fascinating point of view. So far along your career path, who would you say influenced you? Who would your role models be, or your mentors?

Hilary:  That's a really wonderful question. I've had a few. One of them is definitely my mother, who, in her retirement years, went and became a ski instructor. Because it was something she really wanted to do. Now she's kicking ass with people much younger than her and having a great time. But really, I realized a couple years ago that the idea of entrepreneurship has always been in my family. I think it's also tied to the traits of stubbornness and impatience that tend to run in our family as well. But several people in my family who I admire, including my dad, have started their own businesses. Generally doing something that was not entirely normal. So, creating a solution to something that had never quite existed before.

I've also really been inspired by certain authors. People who write things that just change the way you think about the world. In computer science, I've been reading the work of Richard Hamming, who was a mathematician who worked on the Manhattan Project and taught at West Point for many years. He has a wonderful book called On Science and Engineering that has quotes like, "In science, if you know what you're doing, you should stop. In engineering, if you don't know what you're doing, you should stop."

Most of us live in the middle of that. I'd highly recommend it to any scientist and engineer.

Lucy:  I need to get out and read it because I love quotes like that.

Larry:  Boy, yeah, me, too.

Lucy:  I think that's really interesting.

Larry:  You've done so many different things. I want to congratulate you for that. But let me just ask you this... What is the toughest thing that you've ever had to do in your career?

Hilary:  Wow. Thank you. I really feel like I'm just getting started so it's really a pleasure to hear something like that. I think the toughest thing I ever had to do, and this may be an artifact of my own failings and weaknesses, is that it took me a long time to realize that, to succeed at anything, you really need other people to want you to succeed. And you need their help. The hardest thing, for me, was to learn how to get other people excited about the things I'm excited about and to work with them, hopefully helping them at the same time, to build things together in a community.

Lucy:  That's a hard lesson for, I think, a lot of people. That kind of a lesson, they don't teach that in school.

Larry:  Nope.

Hilary:  Not at all. Especially for somebody who grew up very nerdy and very independent, it's a hard thing to realize that you really do need other people to accomplish what you want to accomplish.

Lucy:  That leads directly to being able to communicate about, to be able to enlist people to be passionate about it in some external way, right?

Hilary:  Absolutely.

Lucy:  So that people can really sign on. When I worked at Bell Labs we had, obviously, hundreds and hundreds of engineers who had to excite other engineers about their approaches. Many of us had to learn that the hard way. That's a great lesson to learn for anybody, entrepreneur or not, I think. I you were sitting here, though, with a young person and giving them advice about entrepreneurship, given our prior conversation about the word itself... But given that we'll call it that for now. If you were giving a young person advice, what would you tell them?

Hilary:  Funny. I was invited to speak to a bunch of college students from NYU on Saturday. I spent quite a long time thinking about the answer to this question. I actually do have one for you. My answer to that is just to have adventures and to say yes when you're not sure about something. You're going to learn something fascinating along the way.

Larry:  That's really good. I like that.

Hilary:  Also, if you keep that spirit of adventure with you, even if the thing you're doing is a total failure, you'll have had a great time. It doesn't matter.

Lucy:  This is important for technologists, especially, because technology's on the edge. Like Hilary and others, who are inventing new things. That whole invention process is really an adventure. You can't invent something you already know what the end is.

Larry:  [laughs] Yes.

Lucy:  That's a pretty important observation.

Larry:  There's a real good question here that's good for any entrepreneur. They ought to take a look at it. That is, how do you, Hilary, bring balance into your personal and your professional lives?

Hilary:  Another good question. It's one that, I think, we tend to set up personal life and work life as if they're diametrically opposed and they're two things that should have a wall between them. I don't really look at it that way. I try and make sure I enjoy what I'm doing in my professional life. I try to make sure that it doesn't overwhelm what I'm doing in my personal life. But, in general, a lot of the things that I do are on that line of both. Where, for example, I'm taking a trip to San Francisco this week. I'm giving three talks. That's definitely professional. I'm also meeting up with friends. It's going to be a great time. I think it is a challenge. But it's one that, as long as you're happy, it's OK.

Lucy:  That blended answer, we get that a lot. One of our most popular answers and also an answer that says, "What balance?"

Larry:  [laughs] Yeah.

Lucy:  Totally imbalanced. You've already achieved a lot. You mentioned you were just starting out. You mentioned your love of adventure and always keeping that adventuresome attitude. What can you say about your next big adventure?

Hilary:  That's really a good question and one that I try to think about quite a lot. There are a couple of things I'm pretty excited about that I don't think have really caught on in the community, which means it might be an opportunity. Or it might be a terrible idea. I'd like to pursue those things. In general, themes around how technology can help us be better people.

Lucy:  That's interesting. That's one of the themes today, in fact, as the beginning of computer science education week. Some of the themes around technology to serve the world, technology to make people better, those are great things.

Larry:  Yes, absolutely. I love it.

Lucy:  Well, thank you so much, Hilary. It's been a pleasure talking to you. Have fun on your trip to San Francisco.

Hilary:  It's been great speaking with both of you, too.

Lucy:  I just want to remind listeners that they can find this interview at and

Larry:  All right.

Lucy:  All right, thank you.

Larry:  Thanks Hilary.

Hilary:  Thank you.

Lucy:  Have a safe trip and have fun. [music]