Village Talks Ep. 8 — Mark Chassman on Building Places, People, and Pathways

What's up, Village - Damien here!

Episode 8 felt like a beginning. I’m talking new-start energy — and there’s no one I’d rather have on this conversation than my friend Mark Chassman. We’ve known each other for 13 years; he’s been a trusted, life-giving presence in my village. In this episode Mark walks us through why he shifted from a long career in media to working on mission — and how that mission is showing up in North Chicago.

In this episode Mark pulls back the curtain on:

• Why he moved from “working for money” to “working on mission”
• How Transform Capital treats capital as human capital (time, talent, treasure)
• Concrete, relational ways to move families from survival to stability
• A vision for place-based community hubs (sports, recreation, culture) that create pathways for kids and adults alike

Meet Mark: From Media to Mission Mark spent 25 years in entertainment, broadcast, and online media. Around the time we met he began to feel a calling to redirect his gifts toward social and economic challenges — to show up for people who’ve been overlooked. That calling evolved into active work in North Chicago alongside friends and partners committed to rebuilding quality of life where it had frayed.

Why North Chicago? North Chicago is a real city — proximate to the Great Lakes Naval Station — that’s experienced long-term disinvestment. Mark and his partner Paul Hawkinson decided to bring their professional skills and networks to bear: not to parachute solutions in, but to listen, build relationships, and catalyze resources where the community needs them most.

Transform Capital: Capital Reimagined Transform Capital, the nonprofit Mark helps lead, reframes capital away from solely financial terms. Their first move is human capital: who will show up, mentor, open doors, and create demand for local businesses? They mobilize relationships so residents with small, gig-based businesses can actually get customers, grow income, and stabilize family life.

Real, Relational Impact — Stories from the Ground Mark shared tangible examples:

• A gig-economy family juggling DJing, car-detailing, and rental cars — Transform Capital leverages networks to send paying customers their way.
• A local pest-control business that gained clientele from community referrals after receiving mortgage support and trust-building through the organization.
• Homes funded through philanthropic mortgage support coupled with ongoing mentorship, asking families what their next dreams are and helping them pursue them.

The Bigger Vision: Places That Pull People Out of Isolation Beyond housing and business support, Mark’s vision is a physical, place-based hub for North Chicago: recreation, sports, entertainment, and culture programmed year-round. The goal is simple and profound — create safe, vibrant spaces where kids have mentorship and after-school programming, adults find community, and local enterprises can grow. Soccer and other sports are part of it, but the core is building shared space that responds to community needs and can sustain itself economically.

Magic Wand: People, Places, Pathways Given one wish, Mark would want more trusted adults to show up consistently — people who bring time, talent, and treasure to create pathways for others. He believes transformation happens when consistent, honest, sometimes uncomfortable mentorship meets place-based opportunity.

Takeaways for Our Village For funders & leaders

• Fund not just products but people and place-based infrastructure that’s rooted in community needs.
• Recognize that schools, businesses, and neighborhoods need stability and long-term partnerships, not one-off pilots.

For mentors & volunteers

• Show up consistently. Trusted adults over time are the engine of life-change.
• Be willing to sit in friction; deep mentorship often includes tough love and persistent coaching.

For community builders & organizers

• Center local voice. Build hubs that respond to what residents actually want and will use.
• Combine human capital (mentors, networks) with financial capital to create sustainable pathways.

Final Word Episode 8 reminded me why village matters at every life stage. Mark’s work in North Chicago is a model of relational, catalytic engagement — anchoring people, building places, and creating pathways that last. If you can give time, expertise, or connections to help a community design what it needs, this is your moment to step in.

This is Village Talks. Your boy Damien Howard. Peace out.