What Running for Congress Taught Me About Building a Business

In 2016 I ran for Congress in Wisconsin’s 5th district. I was 38 years old. I had already built and run a commercial roofing company for nearly a decade. I had managed crews, P&Ls, client relationships, and more than a few crises. I thought I understood pressure and I thought I understood leadership.

The campaign taught me I was right about some of it and badly wrong about the rest.

What follows are not lessons about politics. I’m not making a political argument here. These are lessons about building organizations, managing people, making decisions under pressure, and leading through failure. The context happened to be a congressional race. The applications are universal.

You will hire people who believe in the mission before they believe in you

When I grew Penebaker Enterprises to 50 employees, most of my team came through referrals, job boards, and the normal channels of construction industry hiring. They took the job for the paycheck and the work. That’s fine. That’s how most businesses work.

The campaign was different. The people who showed up to volunteer, to knock doors, to make calls, weren’t there for a paycheck. They were there because they believed in something. That changes the dynamic completely. You can’t manage mission-driven people the way you manage transactional workers. They need to understand the why behind every decision. They need to feel like their contribution matters to the larger goal. They will stay late without being asked, but they will also walk away without warning if they lose faith in the direction.

I learned to carry this back into my business life. The best hires I’ve made since 2016 are people who are motivated by something beyond the paycheck. They care about the work, the team, the impact. And they require a different kind of leadership to keep. Not harder. Just more intentional.

Speed matters more than perfection

BLS data shows that about 45 percent of new businesses don’t survive the first five years. In a congressional primary, the window is even shorter. You have weeks, not months, to make decisions that a business might spend quarters deliberating. You have to decide on strategy, messaging, resource allocation, and coalition building simultaneously, in real time, with incomplete information.

The campaign trained me to make faster decisions. Not reckless ones. But I stopped waiting for perfect information before acting. A 70 percent confident decision made this week beats a 95 percent confident decision made next month if the opportunity has passed. I carried that principle into every business leadership role I’ve had since. Waiting for certainty is usually just fear dressed up as diligence.

Your personal story is a leadership asset, not a liability

I lost my mother when I was very young. She died by firearm suicide. That loss shaped how I think about vulnerability, about what people carry quietly, about the difference between strength and stoicism. Before the campaign I kept that part of my life mostly private in professional settings. It felt like a personal matter, not a business matter.

Running for Congress changed that. When I spoke about my mother, something happened in the room. People stopped listening the way you listen to a stump speech and started listening the way you listen to someone telling the truth. The vulnerability didn’t weaken my message. It grounded it.

I brought that lesson back to the business world. The leaders who earn deep loyalty aren’t the ones with the most impressive credentials. They’re the ones who show enough of themselves that their team understands what they stand for and why. Authenticity is a differentiator in business the same way it is in politics. People can tell the difference between a leader who is performing and a leader who is real.

Coalition building is just stakeholder management with higher stakes

Winning a political campaign requires building a coalition of people who don’t always agree with each other. Labor and small business. Urban and suburban. Longtime activists and first-time voters. You have to find the common ground, articulate a vision that speaks to all of them, and manage the friction that comes from bringing different groups under one tent.

That’s the same skill as stakeholder management in any large organization. Whether you’re managing across departments, building community support for a new facility, or negotiating a contract with a general contractor who has competing priorities, the ability to find shared interest and hold a diverse coalition together is the difference between leaders who move initiatives forward and leaders who don’t.

The campaign didn’t teach me a new skill. It sharpened one I already had and showed me where it applied beyond the business context I’d been using it in.

Losing teaches you more than winning does, if you let it

I lost the primary. And for a period afterward I processed it the way most people process public failure: quietly and not particularly well. The instinct is to minimize what you learned from it or to tell yourself the narrative where you would have won if only one thing had gone differently.

Gallup’s research on what separates high-performing teams consistently points to psychological safety: the belief that you can be honest about failure without being penalized. I had to build that for myself after the campaign before I could build it for others.

The most useful thing I did in the year after the race was to write down honestly what I would do differently. Not to beat myself up. To learn. I identified three decisions I made early that compounded into problems later. I identified places where I had the right instinct and ignored it. That exercise produced more leadership growth than most things I had done in the previous decade.

Failure is data. But only if you’re willing to read it honestly.

What came next

After the race I went back to building businesses. I served as a DNC Representative for Wisconsin from 2017 to 2023. I kept working on gun violence prevention, the cause that drove my candidacy in the first place. And I carried every one of these lessons into the multi-market leadership roles I’ve held since.

The campaign didn’t break me. It clarified me. And that’s the best thing any hard experience can do.

If you want to understand more about how resilience shapes leadership, that’s where I’d point you next.

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Last updated: June 28, 2026