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Boston Startup Weekend EDU

November 21st, 2014

In November 2013, I facilitated my first Startup Weekend EDU during Global Startup Battle (GSB) with an organizing team led by Jess Falkenthal.  It was Jess’ 15th or 16th Startup Weekend (I’m not sure how she keeps count!) and I was impressed by how many weekends she’d spent pitching, building, and presenting new startups.  A year later, after six SWEDUs in six different cities, I get it…these are addicting!

On November 21, ahead of the official beginning of the holiday season and as a part of GSB 2014, I organized and facilitated Boston Startup Weekend EDU.  This was our first event in over 2 years and only second education vertical in Boston – surprising for a city renowned for its academic prowess.  While the four months of planning and weekend packed full of logistics was certainly exhausting, I rolled back into work Monday morning feeling both grateful for and inspired by the people and teams that gave us a small glimpse into their interests, passions, and talents.

We kicked off the weekend on Friday night with 36 pitches, mostly targeted toward the K12 markets with some lifelong learners and higher ed enthusiasts mixed in.  I announced 11 ideas that had made it through the voting round and came out on top, but even as early as Friday close, these didn’t end up as the teams moving forward the next morning.  You see, the team formation process very much resembles real life – you’ve got a great idea and other people agree it’s great, but now you have to hustle and convince them that they should spend their next 48 hours helping bring your idea to life. This is usually our participants’ first lesson that execution is everything!

Saturday morning is always a bustling time.  People are still pumped from the night before and looking for their first cup of coffee to get things rolling.  To incentivize people to get started bright and early, we scheduled two workshops first thing.  I’ve done this a few times at SWEDUs and have always been fortunate that talented and generous people in the local startup community want to donate their time by giving free classes.  This time around, we chose a 90 minute session on Lean Startup Methodologies by Brendan Kohler and a crash course in coding from Firehose Project.  I liked that both taught participants something they could immediately put into practice, and acted as a teaser for topics they may want to explore in more depth later on.  Another thing I learned from #SWEDUBay with Jess and have successfully implemented a few times now is that ice cream breaks make people really happy and can pull you up out of your Saturday night slump.

By Sunday morning, I notice that people are rolling in later – a sign that it was a late night of working.  At this point, teams were still in flux and as we go into pitch practice with our group of coaches, the roster only partially resembles what we ended with on Friday night.  But this is what Startup Weekend is all about…the constant return back to the drawing board, some shuffling of team members, new people dropping in halfway through – organized chaos.  One team announced that they decided not to pitch the morning of, and by 5pm that day had come up with and presented a completely new idea entirely.  Another team decided to pursue a different idea on Friday night only to have all but one team member bail by Saturday morning, but made a compelling pitch all the same. If you only attend Friday and Sunday evenings, you’d probably only be able to connect half the dots.

After hearing 11 impressive presentations, our winning teams from Startup Weekend EDU were:

  1. Newhall: A dynamic community geared towards high school students that allows users to securely showcase personalized portfolios of their interests, hobbies, and talents both inside and outside the classroom and which can later be accessed by teachers, recruiters, colleges, and employers. Our judges endearingly called it a “social network for nerds” with many possibilities. Vote for them in Global Startup Battle here.
  2. Parent Primer: A site to help parents better engage with their students by providing them with videos about what their children are learning in school and how these lessons are commonly taught – a Khan Academy for parents. Our judges loved that the team identified a real barrier to better parent engagement.
  3. Lean Gap: A gap year / summer program for high schoolers to engage in real entrepreneurship by building a viable business during the course of the program. Team leader Eddy Zhong is a 17-year old three-time entrepreneur himself and made a compelling case for why high schoolers are both well-prepared for and need this kind of education.  I think we only need to look as far as the competitiveness of the Thiel Fellowship to get validation for Lean Gap.

We had great prizes for our winners with the goal of providing them with the resources and support they need to keep pursuing their ventures.  However, despite significant incentives to win, I would say that the level of competition is rather low with a strong emphasis on collaborative learning.  I tell participants upfront that perhaps the most valuable takeaway is the connections they form with each other, and at least one agreed, noting, “It was a valuable experience just being in a room full of passionate and talented people wanting to make an impact”.

And you inevitably end up learning a lot about yourself, which either points you in a new direction Monday morning or at least gives you the small push you needed.  Another participant contacted me after to say, “I came into this weekend not really knowing what to expect, but I had a sneaking suspicion I would be the only one who didn’t know what she was talking about and who would be able to contribute the least. I have no tech background, no business background, and I’m not even really an “educator” in the traditional sense of the word. But all of that hesitation fell away as I found myself in a room of people congregated around one inkling of an idea that we thought just might be worth something. Working tirelessly all weekend, I learned so much from the people on my team, and know I was able to teach them, too. So ultimately, what I walked away with as an incredibly transformative and validating experience. I am certain now that the education startup community is where I am going to thrive best, and I’m really eager to find companies that will help me grow into this space.”


I love to hear that our events help people realize their passions and interests or gives them the confirmation they needed that they can pursue them – it’s what sets SWEDU apart from a typical hackathon or business competition.  It’s the reason organizers and facilitators volunteer their time…they want to spread the magic!

I want to end with a big thank you to my organizing team, coaches, judges, and all of our participants who spent their weekend with us…and a call to action.  I was ecstatic to hear that people want to organize the next Startup Weekend in Boston and their hometowns.  I can’t wait to help you get started.  But there are still other ways to get involved, keep this community engaged, and open it up to new folks. Plan a bootcamp on topics you want to learn more about, launch a edtech meetup group (there are great examples from other cities), help me organize a SWEDUBos reunion! If any of this sounds interesting or you have your own brilliant idea, let me know at vicky.guo@startupweekend.org. Remember – No talk. All action.

For more coverage of Boston Startup Weekend EDU, check out these posts by Julie Zhou and Fernando Albertorio.  If you want to share your experience on the Startup Weekend EDU and UP Global blog, e-mail it to bostonedu@startupweekend.org.


Vicky Guo