What Running for Congress Taught Me About Building a Business

In 2016, I ran for Congress in Wisconsin’s 5th District. Democrat. Deep red district. I lost.

That campaign taught me more about running a business than any MBA program could have. Not in theory. In practice. Every day on the trail was fundraising, team building, messaging under pressure, and absorbing rejection without letting it slow you down. If that doesn’t sound like entrepreneurship, you haven’t started a company.

I’ve since built a commercial roofing operation from $1.5 million to $15 million, helped grow another company past $35 million, and now run four markets for Great Day Improvements. The foundation for all of it got tested on the campaign trail first.

Fundraising Is Sales With Higher Stakes

The average winning U.S. House campaign spent $2.7 million in the 2024 cycle, according to OpenSecrets. I wasn’t raising that kind of money in WI-5. But I was still picking up the phone every single day, calling people I’d never met, and asking them to write a check for something that didn’t exist yet. That’s sales. That’s exactly what starting a business feels like.

Here’s what campaign fundraising teaches you that business school doesn’t: how to handle rejection at volume. I made hundreds of calls. Most people said no. Some said worse. A few hung up before I finished the sentence. You learn fast that the “no” isn’t about you. It’s about timing, priorities, and whether you communicated value in the first fifteen seconds.

When I started Penebaker Enterprises, I carried that skill directly into business development. Cold calling general contractors, pitching roofing projects, chasing bids. The mechanics were the same. You have something to offer. You need to make someone believe in it before they can see it. And you have to keep calling even when yesterday was a shutout.

The biggest difference between political fundraising and business sales? In politics, people judge you before you open your mouth. Your party, your name, your district. In business, at least you start from neutral. After running in a district where the other party held a 20-point registration advantage, selling a roofing job felt like a conversation between friends.

Building a Campaign Team Teaches You About Hiring

According to Gallup, only 33% of U.S. employees are actively engaged at work (Gallup, 2025). Campaigns don’t have that problem. When your team is mostly volunteers working 14-hour days for free, you learn fast what actually motivates people. It’s not a paycheck. It’s belief in the mission.

My campaign team was small. A handful of paid staff and dozens of volunteers. Some had political experience. Most didn’t. What they had was conviction. They showed up at 7 a.m. to knock doors in August heat because they believed in what we were doing. No benefits package on earth generates that kind of effort.

That changed how I hired when I built my company. I stopped looking exclusively at resumes and started paying attention to hunger. Can this person work through discomfort? Do they show up when nobody’s watching? Will they push through a bad week without needing to be carried?

Volunteers teach you something else too. They’ll leave if you waste their time. An employee might stick around for the paycheck even if the culture is bad. A volunteer walks. That feedback loop is brutal and immediate. It forced me to be a better leader, fast. If people aren’t staying, the problem is you, not them.

When I grew Penebaker Enterprises to 50 employees and later managed 180 at Roofed Right America, the principle held. The best people on my teams weren’t just showing up for compensation. They were there because the work mattered and they felt respected. Every time I caught myself over-indexing on credentials instead of character, I thought back to the campaign. The person with the perfect resume wasn’t always the one who showed up at 6 a.m. on a Saturday.

Messaging Discipline Translates Directly to Brand

A Lucidpress study found that consistent brand presentation across all platforms can increase revenue by up to 23%. On a campaign, messaging discipline is survival. One off-message comment. One poorly worded sentence. One moment where you say what you’re actually thinking instead of what you should be saying. Any of those can end a campaign in 24 hours.

I learned this the hard way. Not through a catastrophic mistake, but through the grind of staying on message across hundreds of conversations. Town halls. Doorsteps. Debates. Every interaction is a chance to reinforce or undermine your core message. That pressure trains you to know, deeply, what you stand for and how to say it clearly no matter who’s in front of you.

In business, this is brand consistency. Do your sales team, your project managers, and your admin staff all tell the same story about who you are and what you do? In my experience, most companies can’t answer that honestly with a yes. The CEO has one version. The field team has another. The customer hears a third.

When I built my roofing company, I obsessed over this. Every crew chief, every estimator, every office staff member needed to be able to say what we did, why we did it better, and why the customer should trust us. Same words. Same energy. Same conviction. I got that discipline from the campaign, where one conflicting message from a volunteer could undo a week of door knocking.

Losing Taught Me More Than Winning Ever Could

Harvard Business Review research shows that leaders who’ve experienced significant public failure demonstrate 15-20% stronger resilience scores than those who haven’t (HBR). I believe that. Because nothing in my business career has been as hard as losing an election in front of everyone you know.

Election night is a particular kind of humiliation. The results come in on live television. Your name is on the screen. The margin is public. Your family is in the room. Your volunteers, the people who gave months of their lives to this, are watching. There’s no private failure in politics. You lose in front of everyone.

Here’s what that gives you, though. After you’ve stood in a room full of people who believed in you and said “we didn’t get it done,” after you’ve driven home that night and sat in the dark trying to figure out what comes next, the normal setbacks of business life don’t hit the same way. A lost bid? Fine. A deal that falls through? Next one. A client who picks a competitor? Okay. None of it compares to the exposure of a public loss.

I carried that into everything I built after. When I started Penebaker Enterprises, there were months early on where I wasn’t sure we’d make payroll. There were jobs that went sideways. There were clients who didn’t pay. At Roofed Right America, we scaled to $35 million and still had weeks where everything felt like it was falling apart. But none of it broke me. I’d already had my worst professional night, publicly, at 38 years old. Everything after that was manageable.

This isn’t a motivational speech about failure being a gift. It’s practical. If you’ve never failed at something that mattered, you don’t actually know what you’re made of. And you won’t know how you’ll respond when business gets hard. The campaign gave me that answer before I needed it.

Public Service and Business Leadership Overlap More Than People Think

A 2023 study by the National Bureau of Economic Research found that civic engagement experience correlates with stronger leadership outcomes in private sector roles (NBER, 2023). That matches what I’ve lived. The skills aren’t different. The context is.

In both politics and business, you’re building coalitions. You’re convincing people who don’t know you to trust you with something that matters to them. You’re managing competing interests, limited resources, and unrealistic timelines. You’re making decisions with incomplete information and living with the consequences publicly.

I served as a DNC representative for Wisconsin from 2017 to 2023. That role was pure stakeholder management. Different factions with different priorities, all under the same umbrella, and my job was to find common ground and keep people moving in the same direction. That’s not different from running a multi-market operation where Chicago’s challenges aren’t the same as Milwaukee’s, but the company needs a cohesive strategy across all four.

The leadership lessons I’ve written about before all trace back, at least partially, to this overlap. Whether I was knocking doors in Waukesha County or walking a job site in Minneapolis, the core work was the same: earn trust, communicate clearly, deliver on what you promised.

The Takeaway

Running for Congress didn’t make me a better politician. It made me a better operator. The fundraising built my sales instincts. The team building sharpened my hiring. The messaging discipline became brand consistency. And the loss gave me a resilience that’s paid dividends every year since.

If you’re a business owner who’s thought about running for office, or someone in public service who’s thinking about the private sector, know this: the skills transfer. Completely. The stakes feel different, but the muscle memory is the same.

The best business advice I ever got didn’t come from a book or a conference. It came from losing an election in a district where I was never supposed to win, and discovering that the same stubbornness that made me run in the first place was exactly what I needed to build something worth building.

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Read more about my career background, my advocacy work, or explore the about page for the full story.

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Last updated: March 7, 2026