Alumni Weekend: A Lesson In Building Strong Communities

by Kailey Raymond, Program Manager & Rachel Feely-Kohl, Sales & Biz Dev Track

Picture this: Saturday afternoon, Central Park, wide-open fields, freshly mowed grass, 50 strapping young athletes, and the smell of victory, sweat and tears. Well, that might be a bit glorified, but that’s what we imagined as SI took over the fields of Central Park for its very first NYC Alumni Weekend, featuring a crowd-favorite activity: kickball. While a kickball game might not sound so significant, let us explain the context, and why this simple game became a symbol for the strength of this community.

Earlier this Summer, Startup Institute expanded to New York City with it’s inaugural class kicking off downtown in the Financial District. Having graduated three classes previously in Boston, we were excited to begin building another strong community, similar to the one we’ve grown and fostered over the past year, alongside the growing NYC tech and startup community.

Over the past six weeks, we’ve certainly felt NY tech come together to help support this program, and we couldn’t be more thankful to be here. But something unexpected happened as well. The city where we started our journey, Boston, forgot about all the sports rivalries and rallied around this new class, our alumni leading the charge.

Last weekend was dubbed, “SI Takes over NYC.” The energy was electrifying as we saw thirty-plus alumni bus, drive, train, and/or walk into the city to support their cousins in this experience, and more importantly, to welcome them into the family.

We (Kailey and Rachel) are excited to share with you all/y’all what we did, how we felt about it, and the massive lovefest/knowledge-dropping weekend we had.

As former SI student, turned Program Manager, in both Boston and New York, Kailey was anxious to see how Boston or New York would interact. She was delighted and filled with joy all weekend long; every which way she looked, alumni and students were connecting and bonding. Kailey quickly realized it isn’t SIB vs. SINY, but rather, we are all just one unified SI. From happy hours to kickball to skill building sessions, alumni and students engaged as new friends, fellow peers, and future teammates. One major highlight of the weekend was our internal skillshare sessions, led by former roommates and fellow alumni.

Sunday afternoon, SI alumni dropped knowledge left and right at the SI campus in a mini-marathon of skillshare sessions. Students were able to receive expert help in troubleshooting dev issues, building their design skills, and sharpening their Startup tool-kit. Sending lots of love and gratitude to our skill-sharing alums: Dean Dieker, Nicki Haylon, Roberto Fuentes, Ajay Dhesikan, Katherine Yasi, Liz Cormack, David Ohayon and Raheem Ghouse for driving forward peer-peer learning.


As a student in NY’s inaugural class, this was Rachel’s first experience interacting with anyone from SI outside of her own tight-knit class. She was surprised at all the things she had in common with the alumni and how helpful and genuine each alum was in the ways they made a genuine effort, having traveled great distances, to interact and engage with their new peers. After seeing the alumni personally invest their time and energy in welcoming this new class into the family, she is definitely looking forward to the day of being able to pay-it forward to the next class of SI students.

This was definitely the common theme felt throughout all activities during the weekend: paying it forward. If this weekend could have a catchphrase (which it most certainly can) it was “what I can I do to help?” Whether that was facilitating dev office hours, providing emotional support, or offering insights on their experience with SI and graduating into the startup community, all of the alumni were ready to do whatever they could for the SINY-ers to help them succeed.

We are lucky to have incredibly engaged alumni that provide stellar examples of this common theme. While what we described has been specific to Startup Institute, the pay-it-forward attitude and eagerness to support those around you are truly indicative of the entire startup universe as a whole. What drives the global startup community forward is the peer-to-peer learning, mentorship-driven culture, and willingness to help. While SI Alumni Weekend was really fun and a great way to reminisce with old friends, it also provided a great lesson; reminding us of this network of support and ultimately, of the true importance of community.

Alumni, we <3 you.