Who's that gal x 2: Katy & Kathleen of Trill

Time is ticking! Ladies Lounge: Tech is just one day away and today we have another preview of who's going to be talking shop on our panel. Meet two childhood friends Katy, a software engineer / graphic designer, and Kathleen, an opera singer / acoustical consultant / MIT Sloan graduate. Together they are the co-founders of Trill, Boston's newest app that let's you know all the happenings for music and performing arts in your area. So, how'd they combine all their talents and launch their own tech  company in Boston? Let's find out!

(And don't forget to save more questions for for tomorrow night's panel at WeWork)

Name: Katy Harris
Age: 36
Occupation: Co-Founder and Head of Design + Product at Trill 
Hometown: Dallas, TX
Current Hood: Davis Square, Somerville
Favorite Summer Activity: Sunny rooftop drinks after work, and picnics at Shakespeare on the Common

Name: Kathleen Stetson
Age: 34
Occupation: Co-Founder and CEO, Trill 
Hometown: Dallas, TX
Current Hood: Kendall Sq, Cambridge
Favorite Summer Activity: Runs along the Charles, sailing on the Charles, picnicking on the banks of the Charles

You guys have two very different backgrounds. Can you tell us more about previous career / life experiences that lead to starting a company together?

KBH: Kathleen and I go way back — we actually played sisters in a production of Fiddler on the Roof in high school! Despite studying business in college, I worked for many years at a large ecommerce company as frontend software engineer. I became really fascinated with the organized chaos that goes into producing interactive content, and realized I had a lot of opinions about the flow of products and interfaces that got tossed over the cubicle wall for my team to build. I got my MFA in graphic design to better understand the real dialogue that design and engineering teams could be having, and have been living and breathing web and mobile experiences ever since. When Kathleen came back to Boston for her MBA, I was at a boutique information design firm creating interactive data visualizations. We still shared this passion for the performing arts, and I began to get really curious about the data driving the live show industry.

KS: Looking back, it’s easy for me to tell the story of my past 10-15 years as a pretty linear path leading to Trill. I majored in music in college and then steadily went about gathering experience in each of the three main areas necessary to run Trill: arts, science and technology, and business. But in reality, I had no grand plan; I was just putting one foot in front of the other trying to find my passion and purpose. I first explored being an opera singer, but after too many voice teachers told me to “get out of my head and feeeel the music”, I realized that rather than fight my “thinker” nature, I should embrace it. I then got a quick one-year MS in architectural acoustics and worked in NYC as an acoustical consultant, advising architects on the design of opera houses and recital halls. As I applied to MIT Sloan for my MBA, I finally figured out how to combine my interests (which all have music at their core); I would use my experience in front of and behind the curtain to start a tech business to further the arts. The seeds of Trill began in my first semester at Sloan and then grew into something real when Katy and I joined forces!

Trill first launched as a database for all local entertainment and then added a mobile app for just day-off entertainment listings a few months later. Why did you decided to differentiate the two? 

KBH: Aside from strategic decisions, we were acutely aware of how differently we encounter Trill depending on context, and we wanted to think critically about those contexts instead of simply duplicating functionality across platforms. On the web, for example, we learned that the busiest day to look up a show was Wednesday, and overwhelmingly from a desktop computer. Intuitively this made sense: who hasn’t had that sleepy, post-lunch Wednesday lull where planning the weekend (or figuring out when the Lone Bellow is coming to town) seems way more appealing than real work? Toss time, space, and screen real estate into the mix and planning ahead makes sense. But our phones are much more intimate. We are often in transit, or doing several things at once, or with other people, and both acknowledging and facilitating that immediacy was a big goal as we planned a mobile app. Of course the lines between these contexts are getting blurrier by the day, but it was a useful thought process for us.

Building an engaged community of entertainers, vendors, and audience members for your brand is important. How have you gone about doing that?

KS: The wonderful thing about working at Trill is that not only do all of us have a deep love of the arts, but most of us are or have even been performers or artists. Because of that, building an engaged community on Trill has been relatively easy actually; we began with our personal networks and then it has grown naturally from there.

What does a typical day look like for you guys in the office? Who handles what?

KBH: I alternate a lot between my maker and manager hats. As head of product I’m looking several months out and mapping what we’re building (and when) to our larger strategic goals, as well as coordinating user testing and watching our usage data. We have weekly sprints to make sure development and design and marketing work is in sync, so each morning we’ll do a quick stand up to check in with the week’s goals. As head of design, I’m also maintaining big picture wireframes of our products so that we all have something to point at as we discuss nitty gritty details, and so the engineers know the end goal of what they’re building. As we build working prototypes of those wireframes for testing and iterating, I’ll take several passes through a more refined set of comps to resolve graphic systems and typography, as well as incorporate any usability feedback we get. Some days I also get to make fun swag like t-shirts, stickers, and temporary tattoos!

KS: As the “hustler” of the team, much of my time is spent outside the office, meeting with arts organizations, artists, members of the entrepreneurial community, advisors, and investors. Katy and I are lucky; because of our history, we have trust each other implicitly, and because of our different backgrounds, our skill sets compliment each other really well. It’s awesome for me to be able to be out and about, knowing that Katy is making it all happen back at the office.

What has been the biggest reward so far for starting your own company?

KS: Our goal with Trill is to make an impact in the arts and entertainment industry, upgrading the online/mobile presence of the arts and making culture a part of people’s everyday digital lives. It’s been so exciting to see the beginnings of that happening. 

KBH: Having grown up in a family of artists, pianists, and architects, starting this particular company was both a logical progression for me as well as deeply fulfilling.

Any advice for someone looking to launch their own online website and app?

KS: Sure! I have been given a lot of advice over the past two years, primarily because MIT Sloan’s entrepreneurship program brings in soooo many entrepreneurs to share their stories. I found that incredibly helpful; any challenge that we run into already feels familiar, as I’ve heard at least one entrepreneur tell his or her story about tackling that same challenge.

The key piece of advice I’ll share here comes from my mother: “When in doubt, do something.” When starting a business, it’s really tough to know where to start. But the key is to just start. Take one step, and that will invariably lead to another step, and so on. Get a designer friend to make basic mockups. Make a little prototype with prototyping software like Proto.io or Invision. Put up a landing page. Pitch at a pitch competition. Have lots of coffee chats.

What’s next for Trill?

KS: We actually have a new product in the works that includes not only performing arts but visual arts as well, and is at its core a much more social experience. Stay tuned!

Quick Questions

Show you are most looking forward to this summer:

KS: BSO at Tanglewood
KBH: Who doesn’t love free Shakespeare? This summer’s production is King Lear, and I’m excited to see the Commonwealth Shakespeare Company tackle this meaty tragedy.

Favorite Venue in Boston:

KS: Boston Symphony Hall (Such a storied history. Any evening feels special there.)
KBH: I have a very public love affair with the Somerville Theater, which happens to be around the corner from my apartment. It’s a century-old vaudeville stage turned movie theater that still hosts live acts, community theater, opera, and festivals all year round. 

On a Saturday in Boston you can be found here: 

KS: Oohwee, at one of the 300+ arts venues in the Boston area!
KBH: Outside! Now that we’ve survived this past winter, I have been taking advantage of the warmth and walking a lot downtown, along the Charles, or through the Common. The new Janet Echelman public art installation on the greenway outside of South Station is really incredible to walk under at night, and Boston has an embarrassment of riches in terms of free outdoor music, movies, and public spaces to take in.

Currently Reading: 

KS: I’m just starting Who Gets What — and Why: The New Economics of Matchmaking and Market Design, by Alvin E. Roth. Just finished B.J. Novak’s One More Thing: Stories and Other Stories - very funny stuff.
KBH: I am finishing up Professor Stewart’s Incredible Numbers by Ian Stewart, with On the Move: A Life by Oliver Sacks on deck.


Join the JUGs, General Assembly, and WeWork for a night of inspiration, tech and some lovely speakers including Katy and Kathleen, Rachel of She Geeks Out, and Laura Fitton of Hubspot.

Thursday, June 25, 2015 at 6:30pm - 8:30pm

WeWork Fort Point
51 Melcher St.
Boston, MA 02210