David Umansky is the CEO and co-founder of Civic Builders, a nonprofit organization that designs, finances, and builds public charter schools in underserved communities across the United States. Since its inception in 2002, Civic Builders has helped create over 65 schools serving more than 30,000 students. But David’s impact goes far beyond buildings. He is an architect of opportunity, an operator of systems change, and an advocate for equity through infrastructure. 

In this episode of Paper Napkin Wisdom, David shares a deceptively simple message: "Be bold!" — a two-word command that reads like a whisper and hits like a thunderclap. But what does it really mean to be bold in a world driven by constraints, compromise, and compliance? 

For David, boldness is not just about bravery. It’s about designing for transformation. "If you want to solve big problems, you can't nibble around the edges," he says. "You have to get comfortable with discomfort — that's where the real change happens." 

Building More Than Buildings 

David opens up about the origin of Civic Builders and how a personal dissatisfaction with conventional impact pathways led him to pursue a model that merges public good with private execution. "We saw a gap. Charter schools were doing great work — but they were stuck in basements and old churches. The facilities were holding back the promise." 

Rather than waiting for someone else to step in, David co-founded Civic Builders to solve a systemic failure: infrastructure as a barrier to educational equity. “We didn’t just want to help a few schools. We wanted to build a machine that could support thousands.” 

De-Risking the Impossible 

What makes Civic Builders unique is their ability to de-risk bold ideas for others. “We operate like a nonprofit, but we think like investors and developers. We make it easier for school founders and funders to say yes.” It’s a kind of courageous humility — removing the heavy lifting so others can lead. 

But this isn’t about playing hero. David frames his work as a team sport — one that requires long-term partnerships, shared vision, and the ability to thrive inside constraints. “Real impact isn’t about throwing money at a problem. It’s about putting in the time to understand systems and then doing the hard work of redesigning them.” 

When Bold Means Listening 

Boldness, for David, doesn’t always mean shouting louder — sometimes it means listening better. He shares the story of how Civic Builders adapted its approach after deeply engaging with the school leaders and communities they serve. “It’s easy to come in thinking you know what’s best. Boldness is admitting you don’t.” 

This humility-led design thinking — something David calls “mission with feedback loops” — is what sets Civic Builders apart. Their work evolves with every conversation, every school opening, and every challenge faced. 

 

🖐 5 Key Takeaways from My Conversation with David Umansky 

1. Boldness Is Not Recklessness — It’s Purpose in Action 

"Being bold doesn't mean doing something risky for the sake of it. It means aligning your courage with something meaningful." 

🧭 Take Action: Identify one area in your work where playing it safe is no longer serving the mission — then ask, “What would boldness look like here?” 

 

2. Infrastructure Can Be a Lever for Equity 

"The physical environment where learning happens directly impacts what’s possible." 

🧭 Take Action: Audit the systems, spaces, or tools your organization relies on. Are they holding people back? If yes, what can you redesign? 

 

3. Build the Machine That Scales Good 

"We didn’t want to build one school — we wanted to solve the problem of building schools." 

🧭 Take Action: Think beyond the one-to-one solution. How can you build processes or models that enable others to succeed at scale? 

 

4. Be the Calm Inside the Chaos 

"Leaders are most valuable when they can steady the ship — even if they’re paddling like crazy below the surface." 

🧭 Take Action: In moments of uncertainty, pause and model presence. Boldness often looks like stillness amid noise. 

 

5. Feedback Isn’t a Threat — It’s Fuel 

"Every critique is a window into a better version of what we’re building." 

🧭 Take Action: Create a mechanism in your business or team for gathering real feedback. Don’t just listen — build with it. 

 

David Umansky’s napkin reminds us that boldness is not a slogan. It’s a muscle — developed through intention, action, and reflection. Whether you’re building a business, a school, or a movement, being bold means owning the moment where courage meets design. 

📝 What’s your bold move? Draw it out. Post it. Share your #PaperNapkinWisdom with the world. Let’s build better — together. 

 

Connect with David Umansky 🔗 LinkedIn 🌐 Civic Builders