The Shepherd Doesn’t Run Ahead with Josh Menold

Josh Menold grew up on a farm in Illinois. His dad ran the operation, his uncle had a construction company, and his grandfather had a habit of writing on things. On the side of a grain bin, in orange marker, were the letters I-T-A-B-W-O-D-I. It stood for a question the older man asked constantly: Is there a better way of doing it?

Josh is now the CEO and owner of CHE Companies, a 68-person exterior construction platform serving the Carolinas and Virginia. He has held CFO roles, done nonprofit leadership work in the Dominican Republic across three languages, earned an MBA from Campbell University, and acquired his company through a management buyout. He is also, somehow, building 15 AI-powered apps on the side.

The grain bin question became the name of his parent company. It also became, as he explained in a recent episode of The Entrepreneurs Blueprint, the organizing logic behind how he approaches every day.

How He Got Here

The path from farm kid to CFO to business owner is not a straight line, and Josh does not pretend it is. What ties it together is a thread he can only see in retrospect.

“I always had an entrepreneur itch,” he said. “I always felt like God calling me to branch out and do my own thing. I just didn’t know how to get there or what to do.”

His route was through finance. Watching what a CFO actually does, the operational breadth of it, the proximity to decisions that matter, he saw a path. He spent years learning the role and eventually doing it for other organizations, including a nonprofit in the Dominican Republic.

That season was not glamorous, and he does not dress it up. “Some days I don’t know if it helped me out,” he said. But what it did teach him was listening. Managing across three languages forces you to separate what someone says from what they actually mean. It sharpened something that has become central to how he leads now.

The acquisition itself happened through a relationship. He went to the owner asking how he could help, not asking to buy in. “It wasn’t necessarily I want to buy you out,” he said. “Obviously, I told him my big vision is I wanted to buy an owner out. But yeah.” The deal came together as a management buyout. CHE has been his since.

What He’s Actually Most Proud Of

Given the financial background, the MBA, and the track record, you might expect the thing Josh leads with to be a number. It is not.

“What’s most exciting for an organization is for people to grow, to come in, be super excited, and then to grow as a person, as an individual.”

He hires for what Patrick Lencioni calls hungry, humble, and smart, a framework from the book Advantage. He has watched it play out over 20 years. “If one of those things is off, it makes it difficult. And normally they don’t fit where the vision of where I want to go.”

What he is looking for is not a finished product. He is looking for someone he can understand fully enough to connect what they do at work to who they actually are. “A lot of people separate the personal life and the business life. In reality, who you are at home is who you are at work.”

When people leave CHE, he stays in touch. He keeps checking in. Their growth does not stop being interesting to him just because they are no longer on his team.

ITABWODI as Operating System

The acronym is not a brand play. It is not a marketing decision. It is genuinely just the thing his grandfather wrote on the grain bin.

“It doesn’t feel like a big deal or a brand,” Josh said. Growing up on the farm, if a piece of equipment needed a new part, the answer was not always to order one. The question was whether you could fix it with something else. Resources were limited. Creativity was required.

“I didn’t appreciate it until I got older. And I realized I was thinking that way and other people weren’t.”

The question became uncomfortable for people who were not raised with it. When Josh asked teams why they did something a certain way and whether there was a better way, it read as criticism to people with 20 years of history doing it their way. He has had to learn to hold the curiosity while accounting for how it lands.

But the curiosity itself is not something he is willing to set aside. He connected it directly to his faith. “Every day is okay, what do we have today? Just because yesterday was this, what will today bring? And it’s exciting to walk into every day curious.”

AI, Apps, and Stewardship

This is where the conversation took a turn that surprised even Courtney. Josh has built 15 AI-powered apps. His team at CHE now has a field tool, built internally, that outperforms anything available on the market. Field workers take out their phones, talk to the app, and AI guides them through the work while connecting directly to CHE’s ERP system. The goal: fewer clicks, less data entry, more time actually doing the job.

It started with a small group scheduling tool. He needed a better way to coordinate his church small group, texting was disjointed, GroupMe was not cutting it, so he built something. Someone in his small group who worked at Nvidia looked at it and told him, politely, that he thought he could do it better. The result was something genuinely useful.

With 15 apps in various stages, the obvious question is how he decides what to prioritize. His answer is stewardship.

“What has God placed before me? And it’s CHE and the CHE companies. The other stuff is cool and fun and maybe I can make that work. But first and foremost, I’m focused on CHE.”

The side exploration feeds the main work. He is learning, staying curious, developing skill. But he is not letting enthusiasm for new things pull resources from the responsibility already in front of him.

He also offered a perspective on AI that Courtney said she had not heard from anyone else yet. Rather than framing it as a job-elimination threat, he sees it as a vehicle for creating opportunity. “The way of stewarding AI so that I can provide jobs for people, not so that I can have this great company. It’s how am I empowering others and what opportunity am I giving to other people?” The caveat he added was worth noting: “If the wrong people control it, it will take over. The opportunity is who’s gonna take over.”

The Leader Who Stopped Driving Hardest

For most of his career, Josh said, he believed the job of a leader was to outwork everyone in the room. That belief has changed.

He now thinks about a shepherd. A shepherd does not run to the next water source and leave the sheep behind. The shepherd makes sure everyone gets there, including the ones moving slowly, the ones who need more help, the ones who are still catching up.

“Don’t run forward, but wait for everyone and shepherd everyone to get there.”

He is honest that this is harder than driving hard. He told on himself in the conversation, describing a recent stretch where he was moving too fast at CHE, working on a field app and a management app simultaneously while starting other things. He pulled back. He apologized to his team. He refocused. “I changed my behavior so that way I can build that trust and make sure I pull some people along that are straggling.”

He was also candid about the fact that people will say they are keeping up when they are not. Part of leading slower is being willing to look closely enough to notice.

What He’s Talking to God About

At Summit Church in Apex, when someone is baptized, they are asked two questions: Are you willing to go and do whatever God calls you to do? And do you believe Jesus has done everything to save you?

Josh started asking himself both questions every morning.

“Is my posture today going to be towards that of trusting God in everything? Because it’s super hard when you’re looking at cash, you’re looking at family issues, you’re looking at everything coming at you.”

He described the weight entrepreneurs carry, and said something that landed clearly: “What God has shown me lately is just the weight we feel is the absence of letting Him in.” When there is no room left for God in the operation, the pressure accumulates without relief. His daily practice, imperfect and ongoing, is to create that room before the day starts and to return to it when the overwhelm hits.

He wrote a blog post about pulling weeds. A moment in the garden became an encounter with God, and he processed it in writing. That kind of reflection, the willingness to find God in the ordinary and mundane, is part of what keeps his faith integrated with his work rather than sitting adjacent to it.

To the founder who is pretending to have it together, he said this: “You align your feelings with truth rather than let your truth fall in line with feelings.”

And to the Christian business owner who is still unsure how much of their faith to put on the table publicly, he was direct. The enemy wants you quiet. That is not a reason to be.

Where to Find Josh

Everything Josh is building lives at ITABWODI.com, including his blog, his ventures, and a way to reach him directly.

Courtney Cook is the founder of Monarch COO and the host of The Entrepreneurs Blueprint. You can find her at www.monarchcoo.com and on Instagram at @monarchcoo.