Once a year, we plan a team retreat in a Midwest city to help strategize for the coming year and to get to know one another better. From Cincinnati and Madison, and now, back to Chicago, another successful M25 team retreat is in the books! Our three-day retreat was spent in the Windy City this year as we planned a “staycation” to gear up for the months ahead.
Team Bonding
There’s nothing more important than team bonding to help boost creativity, collaboration and culture. Most of our team retreat is spent getting to know each other better through a fun activity or maybe a couple of board games. This year, we rented our a loft-style Airbnb with some great views of Chicago and traversed the city from there.
We started the retreat with classic Chicago cuisine (aka Portillo’s) before heading to our first activity: the Prison Break Escape Game. The team was split up, and from there, worked together to break out. From searching for keys to solving puzzles, our team was able to work under pressure to escape with about three minutes to spare!
From there we headed back to our Airbnb after a quick river walk to get ready for our 1930s Mystery Dinner. While we weren’t able to solve the mystery, we shared a few laughs and were equally surprised to discover who the culprit was in the end. We can all agree that Mike took the award for best dressed of the evening.
On day two, we headed to lunch at Bar Siena for sangria and multiple shared lobster rolls and chicken sandwiches. We walked around the Fulton Market area, narrowly avoiding a heavy downpour, with some sweet treats in tow before heading to Game Night Out. We split into two teams of four and competed against each other in games that made you feel like you were facing off in Family Feud. While Sam’s team was in the lead with the most points, in the end, Victor’s team had a narrow victory by winning the final challenge. We wrapped up the day with some Pequod’s Pizza before heading back to our Airbnb for a few rounds of Spoons and a cutthroat game of Catan.
As we wrapped up the retreat, we concluded with one final strategy session in the morning and one final meal at City Social. There, we shared some lingering thoughts to wrap up a successful team retreat. The Indy team headed back to Indiana while the Chicago team stuck around for some gelato at Amorino.
Team Strategy Sessions
We kicked off our strategy sessions by highlighting team wins from the past few months to plan for the year ahead. A few highlights: not one, but two North Dakota investments (adding to our state count!), another successful Midwest City Rankings + Midwest Madness tournament and continued portfolio company satisfaction as a valued investor. While we didn’t take many photos, our strategy sessions are the most critical component of our annual retreat and allow us to chat about the year ahead while deep diving into some data. It’s always great to be able to collaborate and riff off each other in dedicated strategy sessions and to set the vision for the next 12 months.
Here’s to the year ahead, filled with teamwork, innovation and some Midwest spirit! Which Midwest city will we travel to next year?
