Day 246: Todd Connor

The Veteran Building Bridges in a Divided Nation

There’s a particular kind of courage that doesn’t involve jumping on grenades or charging into enemy fire. It’s the courage to step into the space where everyone is shouting past each other and say: “There has to be a better way.”

Todd Connor has made that his mission.

From Service to Building Builders

After serving in the U.S. Navy and working as a management consultant, Todd Connor could have settled into a comfortable corporate career. He had the credentials—a BA from Northwestern, an MBA from the University of Chicago. He had the experience. He had every reason to follow the traditional path.

Instead, in 2014, he founded Bunker Labs in Chicago with a different vision: helping military-connected Americans start and grow businesses. Not just teaching them how to write a business plan, but creating an entire ecosystem of support, mentorship, and community for veteran entrepreneurs.

Could you think about what that addressed? Veterans come out of military service with incredible skills—leadership, discipline, problem-solving under pressure, and the ability to execute complex missions with limited resources. But they often lack the networks, the business knowledge, and the startup capital that others take for granted. They’re trained to accomplish the mission, but not necessarily to build the company.

Todd saw that gap and built a bridge across it.

A Network That Transforms Lives

Bunker Labs didn’t just stay in Chicago. It grew to over 40 chapters across the United States, creating a national network of veteran entrepreneurs supporting veteran entrepreneurs. In 2024, it was acquired by the D’Aniello Institute for Veterans and Military Families at Syracuse University—a testament to both its success and its sustainability.

But here’s what makes this exceptional: Todd didn’t build an organization that needed him to run forever. He built something that could grow beyond him, be institutionalized, and serve veterans long after he moved on to the next challenge. That’s the mark of a trustworthy builder—creating something that outlasts your direct involvement.

And what did Todd do after successfully building and scaling Bunker Labs? He started another organization tackling an even more complex problem.

Taking On Political Polarization

In an era when most people avoid politics at family dinners, Todd Connor co-founded Veterans for All Voters to address political polarization head-on through election reforms and innovations. This isn’t about picking sides in partisan battles. It’s about fundamentally reimagining how our democratic systems work.

This is where the adversity really shows. Political reform is thankless work. Both sides of the partisan divide often resist changes to systems that they think benefit them. The incentives are all aligned toward maintaining the status quo. People are tribal, defensive, and suspicious of change.

And yet, Todd is leading an organization that gives voice to the military-connected community on these issues. Why veterans? Because they’ve sworn an oath to the Constitution, not to a party. Because they’ve served alongside people from every background, every political persuasion, every part of the country. Because they understand that mission success requires putting aside differences and finding common ground.

Veterans for All Voters represents a bet that this community—which has learned to work together despite differences—can model a way forward for the rest of the country.

The Adversity of Bridge-Building

Here’s what people don’t always appreciate about being a bridge-builder in 2025: you get attacked from both sides. When you’re trying to reform systems, the people invested in those systems see you as a threat. When you’re trying to find common ground in a polarized environment, both extremes see you as the enemy.

Todd Connor operates in that uncomfortable middle space. He’s not trying to make everyone happy—that’s impossible. He’s trying to make things better, which often means making people uncomfortable. It means challenging assumptions. It means proposing changes that threaten existing power structures. It means weathering criticism from people who profit from the current dysfunction.

And he does this while also running The Collective Academy, a leadership development consulting firm, and Emerson House, a retreat venue in Indiana. While teaching as an Assistant Adjunct Professor of Strategy at the University of Chicago Booth School of Business. While serving as lead faculty for the President George W. Bush Veteran Leadership Program. While serving on multiple boards.

That’s not padding a resume. That’s someone who can’t stop building, teaching, and serving.

Why This Matters Now

We’re living in a moment when American institutions feel fragile, when polarization seems insurmountable. When cynicism about democracy is rising, especially among younger Americans. When it’s easier to tear down than to build up.

Todd Connor is a builder not just of businesses, but of systems, networks, and pathways that make democracy work better. He’s using the skills he learned in the Navy—mission focus, strategic thinking, building effective teams—to tackle problems that most people think are unsolvable.

He wrote a book called “Third Shift Entrepreneur” about building businesses while working full-time. But in a larger sense, Todd’s entire career is a “third shift” project—doing the extra work that nobody asked him to do, tackling problems that aren’t his responsibility, building solutions because he sees the need and has the skills to address it.

Living the Values

Todd lives in Hyde Park, Chicago, and Northwest Indiana with his husband, Andrew, and their son, Jasper. In a political environment where LGBTQ+ veterans still face discrimination and challenges, Todd’s openness about his family is itself a quiet act of leadership—showing younger veterans that you can serve your country, build successful organizations, and live authentically.

He’s been recognized as a Presidential Leadership Scholar and a Presidio Fellow. He serves on boards ranging from the National Civic League to First Women’s Bank. He’s a venture partner with the Academy Investor Network, helping fund the next generation of veteran entrepreneurs.

But the recognition and the titles aren’t what drive him. What drives him is the belief that things can be better—that veterans can build thriving businesses, that democracy can function less dysfunctionally, that leadership can be taught and learned, that bridges can be built even in divided times.

The Bigger Picture

As we count down to America’s 250th birthday, Todd Connor represents a particularly American form of exceptionalism: the refusal to accept that problems are unsolvable. The belief that if the system isn’t working, you can build a better one. The commitment to service that doesn’t end when you take off the uniform, but continues in whatever arena where you can make a difference.

He faces the adversity of swimming against powerful currents—the inertia of established systems, the polarization of modern politics, the challenge of scaling solutions to national problems. He does it not because it’s easy or glamorous, but because he sees gaps that need to be filled and has the skills to fill them.

Todd Connor didn’t just thank veterans for their service and move on. He built Bunker Labs to give them the tools to succeed. He didn’t just complain about political polarization. He co-founded an organization to address it. He doesn’t just talk about leadership. He teaches it, models it, and builds institutions that develop it in others.

That’s what doing the right thing looks like in the face of systemic challenges. That’s what service looks like when it becomes a way of life rather than a phase. That’s what exceptionalism looks like when it’s focused not on personal achievement, but on building the platforms that help others achieve.

And he keeps building, one organization, one student, one veteran entrepreneur, one democratic reform at a time.

That’s 4 down, 246 exceptional Americans to go. The countdown continues.