1871

This year taught me something unexpected: Sometimes healing looks like a walk. So I’m going to spend the next year walking 210 miles around Chicago—with other people. 210 miles. No rush. I’ve been thinking a lot about how to mark this moment. Finishing chemo. Getting a clean marker. Turning a page. I’ll 100% mark it in a few different ways. But one thing feels very clear: I want to keep leaning into the lesson this year taught me. In my last post, I wrote about how much joy exists in the “between.” Not the milestones. Not the announcements. Not the big wins. But the walks. The conversations. The laughter around the table. The people who show up beside you. Charlie and I made a very conscious decision early on that we would not wait for joy to return. We wanted to live inside our lives while they were happening. A walk can matter. A few miles beside someone can matter. Not doing hard things alone can matter. So this is one small way I want to carry that forward. Over the next likely year (my endurance will get better!), I’m going to walk the 210-mile Outerbelt around Chicago — a continuous loop connecting parks, river paths, forest preserves, and neighborhoods most people never see. The route was created by the OUTERBELT ALLIANCE NFP, a nonprofit working to connect these spaces into one continuous experience around the city. There are guides that map it as a 19-day, 200+ mile thru-hike. This is not that version. 🙂 This is my version: Shorter walks. Over time. Together. A way to celebrate recovery. A way to celebrate Chicago. And a way to spend more time inside this extraordinary city with other people. Starting in mid June: • 2–3 miles to begin • Building gradually • ~30–40 meetups to complete the full loop This is not a race. We’ll walk slow. We’ll stop when we want. We’ll explore neighborhoods, trails, river paths, forest preserves, public art, hidden corners, and all the little things that make Chicago feel like Chicago. Bring your kids (strollers welcome). Bring your dog. 🐕🦺 Come for one walk or twenty. Walks will be announced as they’re scheduled — you can join whenever it fits. And fair warning: 📸 there will absolutely be selfie moments. 👉 If you want to join a walk, sign up here: https://lnkd.in/gj3XRayb Chicago is a city of builders. 🏙️ 🏗️ This year reminded me that one of the most beautiful things we can build is community around ordinary moments. So I’m building this one step at a time. Would love to have you with me. ❤️ 210 miles. No rush.

Over the past few years, one thing has become increasingly clear to me: The old leadership playbook is breaking. For decades, leadership advantage came from access to information. Today, leaders face the opposite problem: Too much information. Too much noise. Too many competing narratives. Too much pressure to react faster than they can think. AI. Emerging technologies. Shifting institutions. New risks. New expectations. New operating models. And one thing I hear constantly is some version of the same question: How do you stay on top of everything? What are you paying attention to? What are you reading? Who do you listen to? What trends actually matter? What questions should leaders be asking right now? That realization is what led us to create the 1871 Leadership Network. The network is built around a simple belief: In periods of massive change, leadership advantage comes from better signal. Not networking. Not collecting contacts. Real conversations. Trusted relationships. Pattern recognition. The ability to see around corners. And honestly, some of the most important conversations are the ones you never could have planned for: The dinner where someone from a completely different industry changes how you think about AI. The founder who sees a shift before everyone else does. The operator asking a question nobody else has thought to ask yet. Those moments matter. As CEO of 1871, I have the privilege of sitting at the center of thousands of conversations each year across founders, Fortune 500 executives, investors, universities, policymakers, and emerging technology leaders. For a long time, I’ve been thinking about how to create a more intentional environment for those conversations, relationships, and perspectives to deepen. The 1871 Leadership Network is designed for leaders who want to think better, see earlier, and navigate change alongside other ambitious builders, operators, executives, investors, and civic leaders. The goal is not scale. The goal is signal. Applications are now open: https://lnkd.in/gDPmyWna

Momentum is building. Nominations for the 2026 1871 Momentum Awards open May 25. Each year, we recognize the founders and startups shaping what’s next for Chicago and beyond. Mark your calendar and get ready to nominate the leaders moving Chicago forward. Learn more: https://lnkd.in/gy_pCwpF

Exclusive for 1871 Emerging Tech Summit attendees👇 Learn to build your own AI efficiency tool with Claude Code, led by Amie Ninh, Chicago Regional Co-Lead of Women Defining AI. No technical jargon, just real actionable solutions using Claude Code on Thursday, May 28. Attendees leave with: → A working tool you built yourself → A framework for high-impact use cases → Strategies to scale faster and leaner Spots are limited to summit attendees! 🎟️ https://luma.com/8j2l4k9p Supported by: Microsoft, BMO U.S., CCC Intelligent Solutions, Bosch, Polsky Center at the University of Chicago, United Airlines, Neal & Leroy, LLC, Deloitte, DeVry University, Convergence: Technology Policy Institute, Aon, AI 2030, & CGI.

AI. Quantum. Web3. Emerging tech isn’t coming. It’s already here. Before the Emerging Tech Innovation Summit comes the policy conversation shaping it. Join Convergence: Technology Policy Institute on May 27 for a deep dive into the systems, regulation, and global shifts redefining AI, blockchain, and quantum technologies. May 28 at Hyde Park Labs, we’re bringing founders, investors, and operators into one room to show what’s actually working and what breaks when you try to scale it. This is where policy meets production. Where Chicago builds what’s next. Register now: https://luma.com/uoyi50gg Policy Summit May 27: https://luma.com/9wtswisc

The 10th Annual ScaleUp was more than just another tech conference. We brought together 150+ growth and late-stage founders to share real-world tactics, strengthen industry ties, and gain direct access to world-class experts. Missed out this year? Stay in the loop so you don't miss the next opportunity to be in the room. Supported by BMO U.S.

Legalization opened the door but building in cannabis still means navigating a complex landscape. Join 1871 and Dentons on May 19 for a conversation built for founders, operators, and investors navigating what it really takes to build in the Illinois cannabis market. Hear from Eric Berlin and Amy Rubenstein of Dentons as they break down what legalization changes, what it doesn’t, and what founders need to know about operating within Illinois’ cannabis framework. Attendees will also have the opportunity to sign up for pro bono legal office hours with Dentons following the event. Register: https://luma.com/9gbl28qm

If you’re building in AI, Quantum, or Web3, the biggest risk to your roadmap isn't the tech, it's the regulation. Don’t miss Day 1 of the Emerging Tech Summit, where we’re diving deep into the policy shifts that will define the next decade of innovation. 5.27 Tech Policy Summit: https://luma.com/9wtswisc 5.28 Emerging Tech Summit : https://luma.com/uoyi50gg Built w/ Convergence: Technology Policy Institute

Most founders don’t fail because they run out of ideas. They fail because they run out of runway. And in today’s market, too many entrepreneurs believe the only way to extend that runway is to give away more of their company. But the best capital is always the capital you don’t have to give equity away to get. That’s why I want to spotlight someone from the 1871 community who saw a real problem founders were facing — and decided to do something about it. When I met Sam Shanley and heard his story, one thing really stuck with me: He told me he gets “mad” knowing there is money out there for founders that so many entrepreneurs simply don’t know exists. That frustration became a mission. So Sam build FundingTrail — a platform designed to help founders and small business owners discover grants and non-dilutive funding opportunities without spending endless hours digging through fragmented websites, outdated databases, and hard-to-navigate government resources. And there is far more funding available than most people realize. Today Sam sent out his longest email ever with opportunities! FundingTrail typically tracks 500–600 active grants at any given time, many of them available to for-profit businesses — not just nonprofits. What I also love about this story is how Sam built it. He is not a traditional developer by background, but he used tools like Gemini and Claude to help bring the platform to life. It’s such a powerful example of what becomes possible when someone deeply understands a problem and is determined to solve it. That is the builder mindset. See the gap. Refuse to ignore it. Build something useful. Help other people win. This is exactly the kind of practical innovation we love seeing at 1871. Because founders need more paths to survive long enough to scale. If you’re building a company, I’d encourage you to take a look: www.thefundingtrail.com Because sometimes the capital you need already exists. You just need someone committed enough to help you find it. 🙌