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Startup Institute Boston’s Spring 2015 cohort is underway, and this new bunch of startup all-stars-in-training are true hustlers: eagerly ideating, innovating, networking, and skill-building so that– at the end of eight weeks– they’ll be high-impact at the high-growth companies they join.

At the end of week one we hosted our signature IdeaHack, a 24-hour brain-bending hackathon meant to solve real problems for an early-stage startup in Boston, helping that company to scale. With little time, little sleep, and stomachs full of pizza (in true startup-style), nine cross-functional teams went head-to-head to hack for Jess, Meet Ken— a platform that provides a unique approach to online dating. We followed-up with Ken (yes, the very one! He and wife Jess based the idea for this platform on their own love story!) to hear his thoughts on the hack and how the students’ work might help many more Jesses find love with many more Kens. Here’s what he had to say:

What problem were SI students hacking for you?

Ken: We are spending a lot of time at Jess, Meet Ken focused on user engagement; how we can drive it, increase it, and maintain it.  It’s one of the things that we live and breathe each day when we come in. Well, that and lunch. We love lunch, so all we really think about is user engagement and lunch. 😉 

So, we posed user engagement as one of a few challenges to the SI students. It made total sense for us because the students are a sample of our target demographic (i.e., they “get it”). Ultimately, user engagement is something that every new tech startup needs to focus on, so we felt it would be a good exercise for the students.

Why has this been a challenge for Jess Meet Ken?

K: In many ways we’re recreating the online dating conversation – Women talking to women about their guys is something that people aren’t really used to doing online. It may sound like a trivial user experience at face value, and it is trivial offline because it’s natural, but online it’s a behavior that users need to learn and get comfortable with.  

What were your expectations going into the event?

K: To be honest, I had no expectations. I had never done anything like this. I love the Startup Institute team and have met several impressive students from past classes so I figured it would be a fun thing to do. Zero expectations.

What was most exciting about the IdeaHack? What was most surprising?

K: The energy that these students have is contagious. It’s like they’re drinking some sort of startup juice every morning when they walk in. I was really impressed and excited by how engaged they were with our presentation and conversation – they took it seriously and took ownership of our challenge as if it were their own. It was like receiving free consulting from 42 incredibly smart and motivated individuals at once. Not to sound corny (which I am, I know), but I was moved by how committed they were to our mission.  

How were the winners chosen?

K: Two teams won, both with very different approaches. One team (consisting of Mike MaleszykMichelle RooyMolly Schuh, and Daniel Wheeler) presented relatively incremental changes to our existing user experience and flows. The other team (Kelsey BellMicah Martin, Lucas Mosele, Shannon Needleman, and Daniel Rotman) built a functioning test version of the app, making recommendations that required us to shift our current thinking completely. The one thing that both of the winning teams had in common though was that the solutions not only addressed the challenges we were presenting but the solutions were also feasible from user experience and implementation perspectives.

Did the IdeaHack give you any important takeaways? 

K: We took away a ton of new, interesting ideas to consider as we build our business.  Most helpful though… I walked away with some unsolicited validation of ideas that we’ve been considering – Multiple teams suggested variations of solutions that users had also requested and we were therefore considering.

Anything else that stands out?

K: I just loved it! Seriously… can I do it again?  Startup Institute NYC? No, really. I mean that.