News & Events

Ashley Kirsner, Skip the Small Talk, Somerville, MA

Volunteering at a suicide hotline, Ashley Kirsner noticed a pattern. Callers were reaching out because they felt uncomfortable opening up to or burdening those they felt closest to. However, if the roles were reversed, all callers yearned for their loved ones to seek them out in a crisis, so that they could provide support. Exploring further, Ashley discovered that it wasn’t just callers at a suicide hotline who felt that way. Almost everyone she spoke to had at least one thing they felt uncomfortable sharing with a loved one and, without exception, everyone wanted others to feel comfortable coming to them for help.  Ashley saw a perception gap that kept emotionally vulnerable individuals from getting the support they wanted and needed. It was an area of personal interest and she wanted to help. So began her journey to founding Skip the Small Talk.

That journey started in college where Ashley majored in psychology and was fascinated by the ways people connect or fail to connect. After graduating she worked as a researcher on social and clinical psychology topics at prestigious institutions like Harvard University's Safra Center for Ethics, McLean Hospital, and Boston Universities Psychotherapy and Emotional Research Lab. While at her researcher day job, Ashley met Devin Karbowitz, who shared her interests and passion.

Together Ashley and Devin founded communiT Boston. Taking the name from the nickname for the local public transportation system ("the T"), communiT was a series of free monthly events held at T stations, designed to provide fun and unique ways for strangers to interact with each other. From her start-up experience at communiT Boston, Ashley knew that for Skip the Small Talk to be successful, she needed to experiment and start small.

In the summer of 2016, she set up a Facebook page advertising the first Skip the Small Talk event at JFK Park. The event aimed to bring together strangers to talk to each other about more meaningful topics than they would usually discuss at a bar or other public setting. Ashley hoped to attract ten people, but before she knew it, over five hundred people had said they were "interested" on Facebook with almost a hundred marking themselves as "going".  Ashley quickly scaled up to host the first event. She sold out at fifty tickets weeks in advance for the first dinner and was soon swarmed with requests asking for the next event. With that, Skip the Small Talk was born!

Skip the Small Talk creates events based on psychology research to help people feel closer to each other, faster than socially norms usually allow. At Skip the Small Talk events, cards with questions prompt meaningful conversations amongst strangers to help build communication skills, teamwork, mindfulness, and improved cooperation. From its early success, the company has grown in popularity and currently hosts a twice-a-month public event at Aeronaut Brewing Company and private, customized events for clients like MIT, the Boston Public Market, IDEO, The Boston Trustees of the Reservation, WeWork, Tufts, and Emerson. Skip the Small Talk has also recently expanded to New York City, and they are slated to start hosting regular events at Threes Brewing Company in Brooklyn this October.

As attendance and interest continued, Ashley realized she needed to put some formal infrastructure in place so that she could scale up and accommodate the interest. She felt comfortable with the psychology research, but the business side felt harder and she did not know where to begin. A friend recommended CWE.

We Help People Get Closer, Faster

Ashley chose CWE because she needed advice to make her venture financially sustainable without feeling like she was selling out. At CWE Ashley was "blown away by how supportive, patient, and helpful everyone was." She was able to meet with different people for help with basic business planning, copyright and trademark questions, marketing advice, and many other unanticipated issues. CWE enabled Ashley to be able to be so much more ambitious with her goals than she might have been otherwise, knowing that she had the support she needed at CWE.

When asked about what she has learned, Ashley admits: "I used to be a perfectionist, so I’ve learned how to do things before I know every detail of how it will work out. I learned to take failure as indication of what I can do differently instead of a verdict about my competence. I learned that the more ambitious the goal, the more help I’ll need to ask for. I learned that the leaders I admired weren’t somehow immune to personal struggles-- the leaders who accomplished the most had just learned how to cope skillfully with hardships. And maybe most importantly, I learned to genuinely believe that Audre Lorde quote:

“When I dare to be powerful, to use my strength in the service of my vision, then it becomes less and less important whether I am afraid.”

Ashley strongly advises every aspiring woman entrepreneur in the Greater Boston area to go to CWE because "it’s the single most valuable resource I’ve come across so far in building my business, and it’s free". After stating that, she quickly laughs and follows-up with: "No, they didn’t tell me to say that -- it really is my first bit of advice I always give to women entrepreneurs."

Another important piece of advice: "I’d like to tell someone looking to start or grow their business that their values matter. Don’t forget to prioritize the things that matter most to you even when people around you are trying to convince you otherwise. I’ve found it much easier to commit to my values by surrounding myself with people who share them-- for me, that means people who are committed to vulnerability, authenticity, compassion, and relationship-building. Spending time with people who have similar values to mine makes it easier for me to say “yes” to opportunities that are aligned with those values and “no” to opportunities that aren’t. Because if I’m not prioritizing the things I care about, I might as well drop all of this and go make more money doing something else."

Skip the Small Talk 
Somerville, MA

Special thanks to CWE volunteer writer, Laila Partridge.