Entrepreneurs Interviews, October 2017

For the October Boston EdTech Meetup, the organizing group decided to try something new! The Boston EdTech Foundation specifically invited a few entrepreneurs to participate in the October’s event. The goal of the Meetup was to allow entrepreneurs to engage with the EdTech community in order to  get feedback and suggestions on their ideas or products or any other business/technical challenges.

Nearly 50 people showed up at the Education First office in Boston - each one of them was eager to help out the 7 entrepreneurs with their EdTech ideas. What ensued was an eclectic discussion, each of the startup company teams took back with them some actionable ideas.

Over the course of the next 3 months, we will showcase these startup companies on our blog and newsletter by conducting interviews that will provide a glimpse of their individual journeys.

School Square

“What they say is true - it really takes a village to raise a child!” - Simon Williams


Simon Williams is a highly passionate entrepreneur who has started School Square – a platform designed to connect teachers and administrators with people from communities. Simon strongly believes that by involving the larger community, schools and teachers can often help students connect with the right resources. This not only provides students with skills to tackle real life challenges, but also opportunities to shadow and learn from experts.

Simon - who comes from Portland, Maine - was always a good student and an exceptional athlete. Simon played professional baseball for six years, and moved on to coaching and teaching baseball, before he landed in Ukraine as a youth development volunteer for the Peace Corps. Simon says that his two years in Ukraine helped him view life differently. During his teaching stint at a K-11 village school, he witnessed the positive effect a community can have on the success of a school. He saw how the time adults spent with kids translated into better learning outcomes. He pondered about the school systems back home – which mostly were islands in their communities. Having identified an opportunity to make a real impact, a highly inspired Simon returned to Maine in 2015 to pilot a program with the Portland school system by involving 10 teachers and 30 volunteers. From then till now, while the passion and drive has remained intact, few things have changed. 

School Square has pivoted to becoming a for-profit organization, and Simon is now actively involved with raising money (through his upcoming Kickstarter campaign - http://kck.st/2ADrUbK) to build a new platform for several school districts in Maine. “I want to improve student engagement using technology, by connecting actual classroom lessons with the real world”, says an emphatic Simon.



School Square from Simon Williams on Vimeo.

Simon decided to join the Boston EdTech Foundation’s October meetup, and came prepared to pitch his idea to the group. He articulated clearly the challenges he is facing, and hoped to take the help of the group to arrive at a solution! He wasn’t disappointed! “Power of networks is fascinating – I have started to view the problem differently now”, speaks Simon of the Meetup group which worked with him during the meetup. Much like his own idea, the Boston EdTech community gave Simon a few tips to boost his startup’s growth! Few of the opinions included ways to utilize Facebook as a tool to search and find people with common values and beliefs, besides some insights on funding early stage companies. Simon has now approached the University of Maine to work on a few prototypes and to conduct some impact studies.

“I came to Boston all the way from Maine for this Meetup. I had multiple takeaways. It was really nice to speak with people who are so passionate about the EdTech space. It was amazing to share triumphs and tribulations – of starting and building a startup like what I am trying to do. It’s a wide world of opportunities” says the highly energetic and motivated Simon.

Further details are available on: http://www.schoolsquare.org/.


Pooja Prasanna

Written by Pooja Prasanna