Once a year, we plan a team retreat in a Midwest city to help strategize for the coming year and get to know everyone on the team better. After a successful 2022 team retreat in Cincinnati, OH, this year’s retreat brought us to the Dairy state where we enjoyed cheese curds with nearly every meal!
We headed out first thing on Wednesday morning from the Chicago office. Our first activity had us sailing across Lake Mendota with a plethora of sunscreen. There’s almost nothing better than spending a hot, Midwestern day on the lake. We treated ourselves to Culver’s for lunch and spent a few hours cruising past Madison.
After spending the afternoon on the lake, we docked the boat and headed to Eno Vino in downtown Madison for a Forward Fest happy hour that we co-hosted alongside Matchstick Ventures. It was great to see so many founders and investors in town, including a few of our Club M25 members! After three hours of networking and catching up with a few familiar faces, we walked around the corner to Old Fashioned for a team dinner before heading up to our Airbnb in Merrimac, WI for the next couple days.
With a fresh pot of coffee on standby, we started day two of our team retreat with a team strategy session for a few hours before heading to a local distillery for lunch: Driftless Glen. Afterwards, we grabbed some ice cream on the downtown square and headed back to home base. It may have been a hot one (aka record 🔥 heat in Wisconsin), but a few team members opted for a tedious hike at Devil’s Lake State Park. The rest of the team stayed in for some A/C and board games.
After a few rounds of badminton and disc golf back at the Airbnb, we headed to dinner at Tumbled Rock Brewery where we, of course, enjoyed some more cheese curds! We spent the rest of the evening chatting around the campfire in the backyard with some local brews and ginger beer.
For day three of the team retreat, we started off the morning with another team strategy session before heading out for some ice cream and lunch. We checked out of our Airbnb (which had an awesome tiki bar and slide by the way!) and drove an hour down to Madison. One car opted to take the ferry on the way there while the other car remained on land. From there the team split up and headed on their separate ways to get back to Chicago and Indianapolis.
Another successful team retreat in the books! It was great spending some time getting to know the team better and strategizing for the upcoming year. Which Midwest city should we travel to next year?
