Authentic &


Matt Douglas, Founder and CEO of Sincere Corporation

Build Culture with Team Offsites

From the early days of Punchbowl, we’ve had outings as a team. We didn’t have an office, so once a month we would get together at my house to discuss the product and brainstorm about the future. After we spent the morning together, we would head out to have lunch. Once in a while, we would go out and do something after lunch. We called these days “Punchbowl Pow-wows” and they were an important part of establishing the culture at the company.

Even as the team has grown (and after we opened an office), we’ve maintained this culture. A few years ago, I walked into the office on a random day in June, and declared it to be “Summer Day.” (hat tip to Mountain Day at Mount Holyoke College for the inspiration). We shut down the office in the afternoon and had lunch as a team. Afterwards, I took everyone to the local brew-your-own beer place, and we brewed many gallons of beer. In other years, we’ve played mini-golf. This most recent year, I took the entire Punchbowl team to Fenway Park for a special on-the-field day (more on that below).

These office outings play an important role in establishing the culture of the company. It’s not just about doing something fun, it’s about creating shared memories together. Like most start-ups, the people at Punchbowl work exceptionally hard, and they are asked to work long hours at certain times of year. Team outings, lunches, and “Summer Days” all play an important role in helping bond the team together and reminding our employees that rewards come with hard work.

Are you looking for inspiration of outings you can do with your start-up team? Here is a sampling of some of the Punchbowl Pow-wows, random outings, and Summer Days that we’ve had over the years:

•  IMAX movie day: I took the team to have lunch, and afterwards we saw an IMAX movie about Dinosaurs (if memory serves me, I believe the movie was in 3D!)

•  Beer brewing: We went to lunch, and then brewed our own beer together at Barleycorns in Natick. I split the group into 3 teams and we created a competition for best beer. The Punchbowl Board of Directors were our judges (at our next Board meeting) and teams were judged on taste, pitch, and brand image.

•  Pumpkin Carving: I brought the team back to my house where we enjoyed take-out food and then carved pumpkins together. We handed out a prize for the best pumpkin carving.

•  Miniature Golf: One of the key members of our team (Devin) was celebrating his 30th birthday, so I took everyone out to play miniature golf. Afterwards, we went to Dairy Queen for ice cream.

•  Fenway Day: We participated in a special charity day with the Genesis Fund. The entire team was able to go on the field at Fenway, take batting practice, and field balls in the outfield. Punchbowl was listed as one of the sponsors on the big screen at the park (see image above). We also met a handful of Red Sox legends. Here’s a link to pictures from that day.

Do you want to build culture and team camaraderie at your start-up? Set aside a few times a year where you take your team out of the office to do something fun. To keep it fresh, don’t announce the day ahead of time — just surprise everyone. It will make the day more memorable and build that close team dynamic that is worth so much to your business.

©2024 Matt Douglas