We Made Space for Hard Conversations in Chicago. Here's What Happened.
On a grey March morning in Chicago, something rare happened: funders and nonprofits sat in the same room, dropped the performance, and actually talked to each other.
UpMetrics gathered nonprofit leaders, funders, and civic innovators at Impact House around one simple premise: the most important conversations in the social impact sector often don't happen. But for at least one morning, this event was going to change that.
UpMetrics' VP of Community Stephen Minix and Managing Director Vinay Mullick opened the morning with exactly that provocation, and built the day around it.
The People in the Room
The guest list reflected the breadth and depth of Chicago's social impact community, with leaders from the Foglia Family Foundation, IMC Chicago Charitable Foundation, The Bloc, Mikva Challenge, Gray Matter Experience, Chicago Lights, Women Employed, and more.
Two voices opened the conversation in what we called Lightning Moments:
Verneé Green, CEO of Mikva Challenge, a national civic education nonprofit that has engaged more than 300,000 young people in building real civic power.
Jamyle Cannon, Founder of The Bloc and a CNN hero who built a youth development organization rooted in boxing and education on Chicago's West Side.
Both brought the kind of grounded, hard-won perspective that set the tone for everything that followed.
The Questions No One Usually Asks Out Loud
The facilitated conversation went to the places most convenings don't. The room leaned in around questions like:
- What changes when funders listen instead of just collecting data?
- When do you feel like you're performing for a funder vs. genuinely partnering?
- Where does data build trust, and where does it create distance?
These aren't rhetorical questions in Chicago's funding ecosystem. They're live ones, and people in the room had real answers.
What the Room Said
After small-group table conversations, attendees responded live via Mentimeter about what they think a good partnership requires. The results were candid. Here's what surfaced:
Trust led by a wide margin (17 responses), followed by honesty, understanding, transparency, and humility.
When asked what one shift the ecosystem needs to make, responses clustered around themes that have been named before but rarely acted on:
- Trust-based philanthropy — "for real, not just in name"
- Multi-year and general operating support — named repeatedly across the room
- Funder flexibility — "Be as flexible as you expect your grantees to be"
- More listening — "Learn to listen in order to lead"
- Collaboration over competition
And when asked what one action they'd take in the next 30 days, attendees committed to concrete next steps. The most common: reaching out. To funders, to new connections made in the room, and to The Bloc specifically, with multiple attendees committing to visiting.
Other Comments from Attendees:
Our Work in Chicago - By the Numbers
8
Years UpMetrics has partnered in Chicago
75+
Chicago nonprofits supported since 2018
$1.4M
Capital support across anchor funders
4.5/5
Average Event Satisfaction
4.2/5
Value of this event for building connections
~90%
Attendees would recommend this event to others
This Is What Eight Years Looks Like + What's Next
This breakfast wasn't a one-off. UpMetrics has been rooted in Chicago for eight years, through cohorts, partnerships, and now convenings like this one.
Our Chicago Cohort brings funders and nonprofits together around shared measurement frameworks, common language, and the kind of sustained relationships that make mornings like this one possible.
The next chapter for UpMetrics in Chicago includes expanding common measures across funders, deepening cohort engagement, and growing the ecosystem that makes this work real.
If you weren't in the room this time, you can still check out the slide deck from the event (including the Mentimeter responses).
Interested in joining the next conversation? Connect with the UpMetrics team.
