Why I resigned from a $35M company I helped build

There is a specific moment I can point to when I knew it was over. Not the first argument. Not the first time something felt off. The moment was quieter than that. I was sitting in my truck in the parking lot of a company I had helped build from almost nothing to over $35 million in revenue, and I could not make myself walk through the door.

180 employees. Trucks with our logo rolling through neighborhoods across the region. A business that by every external measure was working. And I was done.

Resigning from something you built is one of the hardest decisions you’ll ever make. Not because the decision is wrong, but because it forces you to separate who you are from what you created. And sometimes those two things have gotten so tangled up that you can barely tell where one ends and the other starts.

TL;DR: I helped grow a roofing company to $35M in revenue with 180 employees, then resigned due to a breakdown in the partnership. Leaving a business you built is genuinely painful. Here is what the experience taught me about partnerships, identity, and knowing when to go.

What we built

Before I get into the leaving, you need to understand what we built. Because resigning from something small is one thing. Resigning from something that works is something else entirely.

I came into this with experience. I had already founded Penebaker Enterprises, a commercial roofing and sheet metal company that I grew from $1.5 million to $15 million with about 50 employees. I knew the industry. I knew how to sell. I knew how to build teams. I knew the technical side, from EPDM and TPO to GAF products and ANSI/SPRI standards.

When the opportunity came to partner up and build something bigger, I went all in. It worked. We took the company past $35 million in annual revenue. We had 180 people on payroll. The growth was real, and I’m proud of what we accomplished.

But revenue is only part of the story. It never tells you the whole thing.

The warning signs I ignored

Looking back, the signs were there early. I just didn’t want to see them.

The first red flag was how we handled disagreement. In a healthy partnership, you hash it out and move on. In ours, disagreements started feeling like power struggles. It stopped being about what was right for the company and started being about who had the final say.

The second was the culture shift. When you build a company, you set the tone. How people are treated, how problems get solved, how the team operates. I started noticing things that didn’t match what I thought we were building. Small things first, then bigger ones. Standards I believed were non-negotiable turned out to be negotiable for everyone but me.

The third flag was my own behavior. I was shorter with my kids. Distracted at home. Waking up at 3 AM running through conversations that hadn’t happened yet. My body was telling me something my brain wasn’t ready to accept.

What made it harder was that this wasn’t just a business partnership going sideways. This was a friendship. Someone I considered a real friend. Watching that change, watching the dynamic shift from genuine alignment into something I didn’t recognize, that’s a different kind of loss than most people talk about when they describe leaving a company. It’s grief on two levels at once.

I’ve talked to enough business owners to know the pattern. The partnership starts strong. You’re both hungry, both aligned, both pulling together. Then success changes the dynamic. The assumptions you made about how you’d operate together, the things you never put in writing because you didn’t think you’d need to, those gaps become cracks. And cracks become breaks.

The decision to resign

This wasn’t quick. It was months of back-and-forth in my own head. Conversations with people I trust. Long drives trying to figure out if I was being unreasonable or if the situation was actually as bad as it felt.

Here’s what made it hard: I wasn’t failing. The company wasn’t going under. If this had been a simple case of a business not working, the math would have been easy. But resigning from something profitable and growing, something that looks successful to everyone on the outside, that’s a different kind of hard. People don’t understand it. They think you’re crazy, ungrateful, impulsive.

But I had already built and closed one company. I knew what healthy looked like, and I knew the difference between a rough patch and a fundamental misalignment.

The other piece was simpler. Josie, Kyan, and Sydney deserve a father who is present, not someone coming home every night carrying the weight of a broken partnership. I had already given this company years of my life. I wasn’t going to give it my family too.

So I made the call. And I resigned.

What the aftermath actually looks like

Nobody prepares you for what comes next. The business books cover building and scaling. They don’t cover the silence that hits when you are no longer part of something you poured years into.

The first few weeks were disorienting. My phone stopped ringing with the daily problems I had been solving for years. The team was still there. Projects I had started were being finished by other people. The company kept going. That is both the sign of a well-built organization and a gut punch to the ego, and both of those things are true at the same time.

I went through a period of questioning everything. Did I make the right call? Did I give up too soon? Should I have stayed for the employees who counted on me?

Those questions don’t have clean answers. What I can tell you is that the relief came slowly, then all at once. About two months after I resigned, I realized I hadn’t woken up at 3 AM in weeks. I was present at dinner. I was sleeping. I felt like myself again.

That was the answer.

I also want to be clear about something I believe and mean. I miss my friend. Not the business disagreements, not the hard conversations, but the friendship we had before all of that. That part is a real loss and I don’t pretend otherwise. Whatever paths life takes us on from here, I’m rooting for him. I want nothing but success for him, for the team still there, and for the company we built together. Those are real people with real families depending on that business. The problems were in the partnership, not with them. I hope it grows. I hope they win. That has never been complicated for me.

What I’d tell someone in the same situation

Put everything in writing before you need to. An operating agreement is not distrust. It is professionalism. Define roles, decision-making authority, and exit terms while the relationship is good, because by the time you need those terms, it’s too late to write them fairly.

Separate your identity from the company. This was the hardest one. When you build something from the ground up, your sense of self gets wrapped into it. The company’s wins become your wins. Its reputation becomes your reputation. That’s dangerous, because when the company and your wellbeing are in conflict, you can’t think clearly if you believe leaving means losing yourself. I had to learn, the hard way, that I am not the company I helped build. I’m the person who built it, and I’m also the person capable of building something else.

Revenue is not a reason to stay. $35 million sounds impressive. It is impressive. But money is a terrible reason to stay in a situation that is damaging your health, your relationships, and your judgment. I’ve met too many business owners who stayed in bad partnerships because the money was good. Every one of them paid for it somewhere else.

The people around you see it before you do. Anne would tell me I was different when I came home. My kids felt the distance. Close friends were asking if I was okay in the way that means they’re actually worried. Listen to those people. They don’t have the financial stake or the ego investment clouding their view. They just see you.

Resigning is not the same as giving up. I didn’t give up on the work, the industry, or the people. I made a deliberate decision that the partnership was no longer workable and that staying would cause more harm than leaving. There’s a difference between quitting because something is hard and resigning because something is broken. I know hard. I built two companies. Broken is a different thing entirely, and no amount of effort fixes a foundation that has cracked.

Where I am now

I started at Great Day Improvements in December 2025 as a Regional General Manager, overseeing the Upper Midwest across Chicago, Madison, Milwaukee, and Minneapolis. It’s a different kind of role than running your own company. Larger scope in some ways, more structured in others.

What I’ve found is that the skills transfer. The sales instincts, the team building, the operational discipline, the ability to read a P&L and know exactly where the problems are. None of that stayed in the parking lot of my old company. It’s mine. It came with me.

I’m also in a better place. Healthier. More present for my kids. Anne and I are planning our wedding for November 2026. I sleep through the night. I have the mental bandwidth to be a good father, a good partner, and a good leader, not just a stressed-out operator running on fumes.

That doesn’t mean any of this was painless. Resigning from something you built with someone who was once a real friend, watching a partnership and a friendship dissolve at the same time, that’s a loss. It’s okay to call it that, because that’s what it is. Some days it still sits heavy.

But it was the right decision at the right time. And I made it with my eyes open.

The question worth asking

If you’re reading this because you’re in a similar place, ask yourself this: not “Can I fix this?” but “At what cost?”

Because you probably can fix it. You’re the kind of person who builds things. You can grind through almost anything. But grinding through a broken partnership costs you time with your family, your health, and eventually your ability to lead at all.

I spent years trying to fix something that wasn’t fixable. Those years taught me things I couldn’t have learned any other way. But if I’d been honest with myself earlier, I’d have gotten here sooner.

You don’t owe a company your whole life. You owe it your best work while you’re there. When the situation makes that impossible, you owe it to yourself to find somewhere it’s possible again.

That’s not walking away. That’s making a decision.

Last updated: March 25, 2026