September 3, 2025

Recapping the 2025 Club M25 Summit

Every year, we bring together investors and founders from across the country in the heart of Chicago for our flagship event: the Club M25 Summit. On August 20–21, 2025, we hosted hundreds of attendees at Northern Trust’s stunning space on Wabash Avenue, where two full days of connection, learning and celebration unfolded. Started in 2017, the Club M25 Summit remains among the largest gatherings of VCs that happens in the Midwest each year, and this year’s Summit did not disappoint. 

Investor + Founder Connections

At the center of the Summit are our double opt-in 1:1 meetings—designed to connect M25 portfolio founders with investors. This year, we facilitated 1,100 total meetings, with investors from 136 firms averaging five hours of meeting across a two-day period. As one of the most active early stage funds in the Midwest, we know one of our biggest strengths is our network of likely next investors for our portfolio companies, and we’re able to make so many of those connections over the course of the Summit every year.

Happy Hour + Dinners

Of course, the Summit is about more than just meetings and content: it’s about creating space for connections to deepen. On day one, we gathered at Millennium Hall for a happy hour directly under Chicago’s iconic Cloud Gate—more famously known as the Bean. From there, we split into our Founder Dinner at The Marq and Investor Dinner at The Gage. Both dinners brought together incredible conversations over great food, just steps away from Chicago’s iconic Millennium Park in perfect late Summer weather.

The Founder Summit

While investors dove into meetings on day two, our founders gathered for a full agenda of programming, beginning with a warm welcome and M25 updates. Throughout the day, they heard from a powerhouse lineup of speakers, all current and former portfolio company founders:

  • Jonathan Poma, Loop — How Not to be a Soft-Ass Company
  • Jeff Courter, Waldo — 7 Sins of a First Time Founder
  • Arik Gensler, Benji — Building a Non-Human Engineering Team (plus an AI brainstorming session)
  • Rick Knudtson, Workshop — The Sprint to $10M ARR
  • Founder Vignettes — Ben Margolit (Rentgrata), Alex French & Andrew Healy (Bizzy), and Kyle Swinsky (AMOpportunities)

The afternoon wrapped with a Founder Roundtable, giving attendees the chance to share candid insights, swap lessons and build relationships with peers walking a similar journey. It’s an annual tradition that our founders look forward to every year.

This year’s Summit saw the most founders in attendance in the history of the event, and the M25 team relished the opportunity to catch up with longtime portfolio companies and new additions, including 6 companies we’ve welcomed to the Club in the past 11 months. One of our favorite parts of the Summit is seeing founders become mentors, collaborators and friends. 

Celebrating at the After Party

We closed out the Summit on August 21 with an after party at The Game Room. Between skeeball, shuffleboard and plenty of conversation, it was the perfect way to cap two jam packed days in Chicago. In classic M25 fashion, it wouldn’t be a successful Club M25 Summit with an obligatory after-after party where we closed out the night at Electric Shuffle with a few founders. 

Thank You to Our Sponsors

A huge thank you to our 2025 sponsors—Ark, Banc of California, Gunderson Dettmer, Northern Trust and Riviera Partners—for making this year’s Summit possible. Your support helps us bring together the best of the best to Chicago each year. 

About M25: M25 is an early-stage software-focused venture firm based in Chicago, investing solely in tech startups headquartered in the Midwest. Since launching in 2015, M25 has become the most active investor in the region, quickly becoming the preferred seed investor for the next generation of Midwest unicorns. Portfolio companies include Kin Insurance, Loop Returns, Astronomer, Branch Pay, Authenticx and more. For more information, please visit www.m25vc.com