Coffee & Conversation: Stumbling On A Simple Recipe For A Strong Community Of Entrepreneurs

December 6, 2015
It started with brunch. Like many of his friends, Logan Square's Levi Baer spent Saturday mornings eating at a nearby restaurant. But instead of bringing a hangover, he'd bring an iPad and a to-do list.
 
One Saturday, thinking he might not be the only person in his circle with work to do on the weekend, Baer posted an open invite on Facebook for friends to join him at Reno. Encouraged by the restaurant's coworking-friendly picnic-table seating, he was soon surrounded by six laptop-wielding peers, all inspired to follow his productive lead. 
 
While some would see a group of friends intruding on their designated work time as a distraction, Baer saw it as an opportunity: he now had a sounding board, comprised of people with disparate skill sets and knowledge areas. These were friends from the neighborhood, not coworkers, so their collective expertise spanned industries and fields of study. He was surprised by just how many questions he could get answered, and resources he could discover, from asking this group instead of Google.
 
His friends were surprised, too, at just how inspiring this Saturday morning work group turned out to be. They insisted on doing it more, and more friends started coming—so much so that Baer had to choose a new restaurant to accommodate them. Letizia's on California fit the bill for a little while, until they ended coffee service.
 
Next was Parson's on Armitage. By this point, Baer had dubbed the loosely-structured meetups Coffee & Conversation (C&C). He'd also stopped taking his iPad, choosing instead to focus on the conversations happening around him so he could help foster connections among attendees. 
 
With his own expertise being in organizational communication and game design, Baer is a natural leader skilled at bringing people together to share ideas and solve challenges. The people that came together at Parson's were still mostly ones he'd personally met, but their areas of expertise spanned fashion, art, sustainability, media, tech, law, and education. The C&C concept was attracting diverse people with diverse interests, united by a desire to connect with other entrepreneurial-minded people in a casual venue. 
 
Baer knew he was onto something when they once again outgrew this venue. It was hard for him to lead any group introductions or give announcements over the din of brunch service at Parson's so he put the call out for a new, more private space. The community answered with C&C regular Harishi Patel referring Baer to his acquaintance Peter Grande, who offered up his open-layout State Farm office in West Town. This gave Baer a dedicated spot to host, subtracting brunch from the equation for the sake of being able to add more people.
 

Levi Baer (left, in purple) chats with a group of C&C regulars.

 
The biweekly meetups were then drawing 20-30 people at a time, with many being complete strangers to Baer. This was one of the most exciting points in the process for him: the community he'd serendipitously created didn't just outgrow the restaurant, but had expanded beyond his own social network. 
 
With people now coming from outside his circle, Baer considered tinkering with the event's format. He asked himself how best to keep the growing group engaged during meetups; He wanted to preserve the open exchange of ideas that made C&C what it was, but also thought it'd be harder to manage the bigger the group became. 
 
What he quickly realized is that the meetups were acting as a catalyst for collaboration, with many fruitful connections being made in the private Facebook group C&C newcomers are invited to join after their first attendance. By encouraging entrepreneurial people to first meet face-to-face, over coffee, he was making it easier for them to later reach out to one another for help online. This meant he could back off from thinking about how the group meets, and just focus on getting them to meet. 
 
He also realized that having a dedicated venue was less important than having a dedicated group of entrepreneurs. The people that would get the most out of the community—and give the most to it—would come out no matter where the meetups were held. 
 
Partly inspired by Built In Chicago's monthly Built In Brews events, C&C switched from meeting every other weekend at one place to meeting once a month at varying locations. But instead of touring different startup offices like Brews, C&C leads its curious crew to different coworking/community spaces, often in neighborhoods outside of the Loop. The I Paint My Mind gallery in Bucktown, The Logan Share in Logan Square, and Coalition: Impact in River North have already hosted, with Uptown's The Shift next on the list. 
 
By focusing on this type of space, Baer hopes to attract more entrepreneurs to the C&C community while introducing the existing community to places they might want to personally work from. It's a perfect match since most C&C attendees are either in the process of launching a business or working to turn a side project into a sustainable career. (Members affectionately describe C&C as a "side-hustle support group.")
 
For all its growth and evolution over the past two years, C&C still feels more like a group of friends talking over coffee than a rigid "networking" event—and that just might be the secret to its snowballing success.
 
 
Doing more together: The Facebook group is currently 100+ members strong, serving as a virtual sounding board where C&C attendees continue conversations started in person, share resources, and garner support/feedback for their projects. Join the conversation by attending the next C&C meetup on Saturday, December 12th
 
Follow C&C on Twitter @coffeeconvochi and send Baer a message if you'd like to host the group in 2016.