What Building a $35M Operation Taught Me About Leading People
In 2002, I started Penebaker Enterprises with a truck, a phone, and a willingness to outwork everyone. No investors. No safety net. Just me and a belief that I could build something real.
Over the next several years, I grew that company from $1.5 million to $12 million in commercial roofing and sheet metal fabrication. Then I scaled Roofed Right America to over $35 million in annual revenue across four Upper Midwest markets with 180 employees. After that, I brought that same leadership to Great Day Improvements as Regional General Manager.
Along the way, I learned that building a business and leading people are two very different things. You can grow revenue without growing as a leader. But you can’t sustain that growth without the people around you believing in what you’re building.
Here’s what those years in the field, in the office, and in the trenches taught me about leadership.
1. Nobody Cares About Your Title
When I was running roofing crews in the early days, nobody followed me because of a business card. They followed me because I showed up first and left last. I climbed on roofs. I swept the job site. I did the work alongside them.
That never changed, even as the titles got bigger. The moment you start thinking your position earns you respect, you’ve already lost it. Respect comes from what you do, not what your email signature says.
2. Hire for Character, Train for Skill
I’ve hired hundreds of people over nearly 30 years in this industry. The biggest mistakes I made were hiring people who looked great on paper but didn’t have the right character. They could sell. They could manage a spreadsheet. But they couldn’t show up for the team when things got hard.
The people who built my best teams were the ones who were hungry, honest, and coachable. I can teach someone how to estimate a job or run a sales meeting. I can’t teach someone how to care about the person next to them.
3. Culture Isn’t a Poster on the Wall
Every company talks about culture. Very few actually build one. Culture is what happens when the boss isn’t in the room. It’s how your team treats a customer when nobody’s watching. It’s whether your people feel safe enough to tell you the truth.
At Great Day Improvements, I built culture by being consistent. Same expectations every day. Same accountability. Same investment in people whether we were having a record month or a tough quarter. People don’t need motivation speeches. They need a leader who doesn’t change based on the weather.
4. Growth Breaks Everything (and That’s Normal)
Every time we hit a new revenue milestone, something broke. The systems that worked at $5 million didn’t work at $15 million. The team that got us to $20 million needed different support at $35 million. That’s not a sign of failure. That’s a sign of growth.
The leaders who struggle are the ones who try to hold onto what used to work. You have to be willing to rebuild the plane while you’re flying it. That means new processes, hard conversations, and sometimes letting go of people who were great in one chapter but aren’t right for the next one.
5. Your People Are Watching You More Than You Think
When I was two years old, my mother Joyce completed suicide with a gun. I grew up carrying that loss without fully understanding it. As I got older, I made a choice. I could keep that pain buried, or I could use it to do something meaningful. I chose to become an advocate for gun violence prevention. That decision shaped me as a leader in ways I didn’t expect.
My teams saw that I was willing to stand up for something bigger than business. They saw that I could be vulnerable and still be strong. And that gave them permission to bring their full selves to work. The best leaders I know are the ones who don’t hide who they are.
6. Google Proved What I Learned the Hard Way: Psychological Safety Wins
Years into leading teams, I stumbled across something that put a name to what I’d been doing by instinct. Google ran a massive internal study called Project Aristotle. They wanted to figure out what made their best teams tick. They looked at hundreds of teams, analyzed every variable they could think of, and the answer surprised almost everyone.
It wasn’t about having the smartest people in the room. It wasn’t about seniority, education, or even skill sets. The number one factor that separated great teams from average ones was psychological safety.
Psychological safety means people feel safe enough to take risks, speak up, ask questions, and even admit mistakes without fear of being punished or embarrassed. When your team has that, they innovate. They solve problems faster. They tell you the truth before small problems turn into big ones.
When I think back on the teams I built at Penebaker Enterprises, at Roofed Right America, and at Great Day Improvements, the highest-performing crews always had one thing in common. People weren’t afraid to say “I don’t know” or “I messed up.” And that didn’t happen by accident. It happened because I made it clear, every single day, that honesty mattered more than looking good.
I’ve seen what happens when psychological safety doesn’t exist. People hide problems. They cover for each other in the wrong ways. Small issues become expensive disasters because nobody felt comfortable raising a flag early. In roofing and home improvement, that can mean real safety risks, not just business losses.
Here’s what I took from Project Aristotle that confirmed what nearly 30 years of leading people already taught me. If you want a high-performing team, stop focusing on talent alone. Start focusing on the environment. Ask yourself: can my people disagree with me without consequences? Can they bring a problem to my desk without worrying about their job? If the answer is no, your team will never reach its potential. No matter how talented they are.
The Real Lesson
Building a $35 million operation taught me a lot about systems, strategy, and scaling. But the most important thing it taught me is that none of it matters without the people. Every dollar of revenue, every market we entered, every goal we hit was because someone on my team decided to show up and give their best.
My job was never to be the smartest person in the room. My job was to build a room where the smartest people wanted to stay.
If you’re building something right now, whether it’s a company, a team, or a career, remember that. The numbers will follow if you take care of the people first.
Want to connect? Find me on LinkedIn or check out my experience page to learn more about my journey.