Views on the Ground: Scenes from Our Chicago Founder Fly-In

Portfolio company leaders from across the country touched down in the Windy City to connect with fellow Rise of the Rest-backed founders on tactical tools for turbulent times. VP of Platform and Portfolio Success, Amira Ouji, and Head of Community, Liz Westhouse, recap the event below.

If you’re building a company in 2025, the headlines are loud: market whiplash, trade realignments, AI acceleration, geopolitical shockwaves. Scaling is hard enough on its own. Finding product‑market fit, raising a round, and keeping a team motivated gets even harder (and, too often, lonelier) when the external noise piles up. Sometimes, just stepping into a space with people who understand that weight can make all the difference.

At Rise of the Rest, we aim to meet founders where they are — on the ground in their communities, and in a mindset shaped by real constraints, not blind optimism. Pulling founders into one physical room has always been a powerful tool for clarity, camaraderie, and the occasional course correction. Last week, for 24 focused hours in Chicago, that power was on full display.

After the team touched down in Chicago, we brought together founders, funders, and friends of the ecosystem for dinner at Chicago Winery, our home base for the Fly-In. David Hall opened the evening with a reflection fit for a room that’s seen more than a few cycles: “To be and invest in entrepreneurs, you have to believe in a better tomorrow.” That outlook shaped the conversations that followed.

We kicked off our full day of programming as we so often do: with a grounding in place. Phil Clement, President and CEO of World Business Chicago, joined us to share why the Second City is a first-rate place to build, and to remind us of its grit and global reach. In his words, “everything dope, now including the Pope, comes from Chicago.”

From freight dominance at O’Hare to Chicago’s grand stakes in quantum computing, Clement made a compelling case for the city that’s never done, and never outdone.

Whitney Capps, founder of RootWorks, took the mic next to turn the lens inward, examining why we’re hardwired to go into firefighting mode and how to recognize and break the cycle. Some highlights from her playbook: start by noticing whether you’re “above or below the line” (operating from a place of curiosity versus threat), and when tension spikes, pause for three deep breaths and a step back to remember the long goal.

Before lunch, we mixed founders with Chicago’s civic, academic, and financial leaders — including former Google exec, Ted Souder, J.P. Morgan’s Kim Patel, 1871’s Betsy Ziegler, the Polsky Center’s Samir Mayekar, and The Economic Club of Chicago’s David Snyder. The discussion ran the gamut from local engagement and alternative financing to treasury market tremors and trade realignments, with one steady throughline: how founders can turn shifting macro forces into tailwinds.

Smart (and memorable) advice from Samir on building mutually beneficial, enduring relationships with ecosystem players: “Be a local champion, not a local extortionist.”

After debriefing over tacos, founders split into two working sessions — one on practical ways to integrate AI into day-to-day operations, the other on navigating culture and change. Both sessions offered space for honest reflection, with insights straight from the trenches.

Key threads from the rooms:

• AI-native is a culture, not a birthdate. Early adopters who use proprietary data to solve real problems are the ones who turn experimentation into edge.
• Teams absorb the founder’s mindset. Show panic, get panic. Show curiosity, get solutions.
• Peer feedback > guru advice. Nothing beats troubleshooting and pressure‑testing with fellow founders.

Peer-to-peer breakouts ran long (in the best way), full of the kind of off-the-record candor no agenda can really plan for. Despite storm clouds rolling in, Chicago’s broader startup community packed the evening happy hour — proof that momentum here doesn’t mind a little weather.

Some things we took home that won’t fit in our carry-on:

• Policy is more than a backdrop, it’s a lever — but only if you’re in the room.
• Conscious leadership isn’t a luxury; it’s a prerequisite for resilience.
• AI is only as powerful as the problem it actually solves.
• Peer insight beats theory, especially when the stakes are real.

Getting the portfolio together — and then getting out of the way to let the dialogue flow — always fills our cup. Huge thanks to every entrepreneur, partner, and Chicago champion who made 24 hours feel equal parts breezy and consequential.

See you back on the road.