Catching Up with Our 2017 Winners – Y2Y

Meet Y2Y, a 2017 alum and $50K winner that is building a network of student-run homeless shelters for young adults.

Using a trauma-informed approach, Y2Y provides guests ages 18-24 with a safe, welcoming, and gender-inclusive overnight environment. The startup also serves as a critical entry point to advocacy, programming, and resources like case management, job training, mentorship, mental health, creative expression, and more.

We had a chance to catch up with Sam Greenberg, Co-Founder, about his experience going through the MC accelerator:


Take us back to MassChallenge Awards... what was going through your mind when you heard your startup name called to the stage?
​We were the last $50K winner, so we were pretty sure we hadn't won. Our team was reminding each other how valuable the experience had been overall and remembering just how honored we had been to be a top 26 finalist at all. We were so surprised to hear our name that it took us a few seconds longer to get up on stage, so the MC staff and other top 26 winners backstage basically propelled us up. As soon as we saw Scott Bailey walking towards us and smiling with the trophy, we came back to life, and from there we were able to just enjoy the moment.

As a winner, how do you plan to use the cash prize to further accelerate growth?
Y2Y is at a very exciting moment, and this cash prize will enable us to significantly accelerate our work. With the momentum we've built at MassChallenge, we are working toward opening a second shelter and beginning to explore growth. At the same time, we are honing in on our program quality and building the organizational capacity for long-term sustainability. The $50,000 we've received will enable major investments in each of these.

What would you say has been the key driver of your success throughout the program?
​We have been lucky to benefit again and again from a key cohort of staff and mentors, who have demonstrated a totally remarkable belief in our work.​ They have supported us in every way – from coaching us through our pitch to coming up and giving us hugs when we were having a rough day. We're so grateful for all of the support, large and small!

What has been the hardest lesson to learn?
Balancing everything. Between supporting the day-to-day shelter operations, managing our staff, supporting our students, fundraising, and taking advantage of all the programming at MassChallenge, we often find ourselves pretty overwhelmed. We would recommend treating balance just like any other critical component of your work. When we did that, we were able to force ourselves to prioritize achieving the right balance. ​

What advice do you have for startups thinking about applying to MC?
​One of our good friends who had gone through MC before us told us that we should know exactly what we are hoping to get from the experience. We would totally co-sign that and add that you should make sure that you have the time to genuinely engage. There are so many remarkable resources and so much going on at MC, that it's worth making sure you can really take advantage of it.