Deeply Chicago
A Tuesday Tech Book Club Peer Accelerator
For leaders who want to understand Chicago more deeply — and shape its future with intention.
Chicago is one of the most complex, diverse, and quietly powerful tech ecosystems in the world. Yet many leaders work in Chicago without fully working with Chicago — its history, its neighborhoods, its civic fabric, and the forces shaping the city's next era.
Deeply Chicago is a Tuesday Tech Book Club accelerator for tech leaders who want to go beyond headlines and networking events to understand the city they’re helping shape. It’s for people who are passionate about Chicago as a place to live, build, invest, raise families, and drive change — and who want to anchor their leadership in a deeper sense of place.
Across six Tuesday sessions, a small, fixed cohort of twelve participants meets for book-anchored discussions exploring Chicago’s identity, inequities, creativity, resilience, and tech-driven transformation. Media will span biography, history, sociology, innovation, science, and civic design — giving participants space to reconsider what it means to build in Chicago today.
Each session is hosted by a Chicago tech or civic leader who welcomes the group into their workspace. These conversations move beyond professional roles into questions of responsibility, belonging, and what it means to lead in a city undergoing profound change.
This is a place-based leadership accelerator — designed to help tech leaders deepen their connection to Chicago, learn from its complexity, and build relationships across sectors that strengthen both their work and the region.
Whether you’re new to the city, returning to it, or ready to engage with it more intentionally, Deeply Chicago offers a rare space to think, reflect, and explore what it means to contribute to a city you love and are actively helping to shape.
Program Details:
Tuesdays · 12:00–2:00 PM · February–December 2026.
Location: Hosted by fellow tech leaders, each session will occur in or nearby Chicago’s Central Busines District.
Lunch: Everything is better with food and fellowship.
Application Deadline: December 15, 2025. Reviewed and accepted on a rolling basis.
Pricing: $1,450 + optional add-ons
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Co-facilitator, AI for Executives
Founder and CEO, Intentional Gravity
Director of Plafform, PACE Healthcare CapitalI’m an executive and entrepreneur with a two-decade track record of building companies, organizations, platforms, and catalytic communities that bring together the people shaping the future of innovation - entrepreneurs, scientists, innovators, corporations, investors, operators, and civic leaders.
Trained as an economist and grounded as a creator and connector, I’ve worked across industries—from biotech to fintech, food innovation to climate tech. I specialize in seeing patterns others miss, bridging siloed spaces, and helping individuals and organizations make intentional choices to create new value and shift their trajectories.
I’ve held senior leadership roles across the private and nonprofit sectors, including founding Intentional Gravity to advance people-centered tech; helping scale Portal Innovations into a national biotech venture platform; leading strategic programs at the University of Chicago’s Polsky Center; and positioning the Kauffman Foundation as a global leader in innovation. My work has been featured in The New York Times, The Wall Street Journal, and other national outlets.
Today, I focus on coaching leaders, advising organizations, and designing communities where deeper connection fuels meaningful progress. I’m especially drawn to smaller, trusted groups, spaces where people can be honest about hard choices, map out their next moves, and support one another with clarity and courage.
I often work with explorers: the curious, mission-driven professionals navigating complex systems and building what’s next. My role is part coach, part strategist, and part mission control - helping gather the right people, tighten their orbits, and gain velocity for change and impact.
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Deeply Chicago is for tech leaders who want to feel more connected to the city they call home — whether you’ve lived here for decades, just arrived, or telecommute from a neighborhood you’re still getting to know.
Participants come from across the innovation economy — product, engineering, science, design, venture, data, civic tech — but share a desire to understand Chicago more intentionally and to build relationships with others who care deeply about the city’s future.
This is a program for the curious and committed — for people who want to explore Chicago not just as a backdrop for their work, but as a place they live, contribute to, and help shape.
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Chicago is always evolving, industries shifting, and civic challenges and opportunities abound. It’s a city filled with talent and possibility, but also inequity and untold stories.
Tech leaders have a growing role in shaping what comes next — yet most have few places to pause, learn, and reflect on Chicago beyond their daily work.
Deeply Chicago offers:A grounded sense of place — understanding the forces that shaped the city
A space to reflect on responsibility — how your work intersects with civic life
A trusted network — a bench of peers learning alongside you in real time
A way to belong — to step into Chicago’s next era with more context and intention
Leaders build better organizations when they understand the city they’re building them in.
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Deeply Chicago meets six times across 2026, each session anchored by a single book or media piece that illuminates an aspect of Chicago — its culture, innovation, communities, inequities, or evolution.
Here’s how it works:
One small cohort of twelve tech leaders commits for the year
Book-anchored discussions offer shared context without heavy homework
Sessions are hosted in or near downtown, each with an outside guest speaker
Conversations stay confidential under Chatham House rules
Place-based learning connects professional leadership to the city’s story
By the end of the year, participants won’t just know more about Chicago — they’ll feel more connected to it and more equipped to lead within it.
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Book-anchored Learning — Each session is built around a thoughtful piece of media connecting to the city from different perspectives.
Cross-industry Cohort — Perspective from other leaders in tech.
Confidential, Closed-door Environment — A trusted space to compare approaches and discuss challenges openly.
Built-in Peer Bench — A curated group of tech peers passionate about exploring the city.
Hosted across Central Chicago — Accessible, consistent, and anchored in spaces where real transformation is happening.
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1:1 Coaching
Members of Tuesday Tech Book Clubs get an additional 10 percent off all IG coaching rates.
Personalized coaching is not included in the program but is available at a discounted, additional rate.
Priority Booking for Gravity Unplugged Events
Early access to supplemental private events.
Gravity Unplugged salons bring guest leaders across tech, science, and civic innovation together in small, private settings.
Access to Specialized Workshops
Reserved or discounted entry for standalone workshops from Intentional Gravity.
