Dark clouds flooded the skies over Kansas City as tornadoes threatened to touch down during the VISION Hi-Tech Training & Expo in March, but the employees of Missouri-based Dependable Automotive barely noticed. Instead, their chatter was light and fixated on what was for dinner.

“I think it’s spaghetti night,” someone volunteered. “I can’t remember, but it’ll be good.”

They were there for the same reasons as everyone else—education sessions, fresh ideas, and networking. But instead of a few guys holing up in hotel rooms, their boss, Josh Underwood, brings nearly his whole team of 30 employees every year, rents an Airbnb, and cooks for them every night.

They eat together, learn together, and spend the week like a family. His team isn’t there because they’re required to be. They’re there because they want to be.

That chance encounter with Underwood's team made him the standout choice for our cover contest. Their enthusiasm said it all.

Simple Conversations, Big Opportunities  

Not everything about Underwood’s journey in the industry has been effortless, but his connection with people seems to be. In fact, most of his successes began with a casual conversation with an acquaintance that morphed into a business opportunity.

Take, for example, his neighbor, Ray Forsythe. The duo had an affinity for fixing things in the front yard, which eventually turned into working side jobs together out of Underwood’s minivan. Later on, when times got tough for Forsythe, Underwood hired him to work in his shop.

Mark Cochran was the manager of the O’Reilly Auto Parts store where Underwood frequently purchased parts. Their casual banter went from a customer/manager relationship to Cochran calling on him when other customers needed more assistance than just parts, which ultimately led to an owner/employee transformation.

“Whenever a customer would come in the store and they needed items more than what they could offer at a parts store, (Cochran) would call me and I would go to the store and fix the vehicle right there in front of the store,” Underwood recalls. “I ended up hiring him as my first general manager.”

And then there was Scott Wilson, a business coach from Colorado who started out as “just a customer.” Underwood’s thoroughness on the job as well as his ability to connect with people transformed the men from strangers to friends. Wilson became a general manager and consultant during the early years of Dependable Automotive.

Indeed, Underwood’s natural curiosity and ability to connect with people seemed to catapult him into a career where seasoned veterans insist that fixing cars is secondary to helping people.

“When you go to somebody that is already having a terrible day, they’re interrupted … because their car broke down on the side of the road, or their car’s not working, and they’re trying to get to the next stop, and we show up, get them back on the road, and keep them going, that’s a great feeling to be able to go and help them,” he explains.

His focus was never on scaling, but somehow it just happened until he eventually grew to three operations—two repair shops and a towing outfit.

From a Minivan to Three Locations

Underwood began his stint in the industry at Clear Creek Collision in a position he quickly determined did not suit him.

“I found that I just really didn’t like sanding cars every day, and I really enjoyed doing some of the suspension repairs and that kind of stuff,” Underwood notes. “So, I ventured out on my own.”

On a piece of property acquired through yet another friendly conversation, Underwood knocked down some trees and put up a building shell and laid a concrete pad for parking. He named his first business After-Hours Auto & Marine. For several years, he took in cars and worked on them just as the name implies—after his shift at Clear Creek ended.

Unfortunately, the land was not zoned for his type of business, so when a neighbor complained, the house of cards tumbled quickly.

Lucky for Underwood, he had already secured his next endeavor—a four-bay shop in Camdenton called Dependable Automotive. Ralph May was looking to sell, so the two worked out a deal that put Underwood at the helm in April 2012. May was so thorough in making sure the transition was seamless that he finished every last commitment the shop had by the transfer date.

“Not a single soul came in April 1, and I’m standing there looking around thinking, ‘I’ve got to make some bills. I just took on this big building and big overhead and there’s not a single car in the parking lot,’” Underwood recalls with a laugh.

The second day brought more of the same.

“So, I grabbed my business cards, and I started walking, and I walked from one side of the town to the other side of the town and let (people) know that I had taken over,” he says. “While I was out there, Ralph calls me and says, ‘I need you at the shop right now. We’ve got like 15 cars that just got dropped off.’”

Underwood assured Forsythe everything would be fine and encouraged him to schedule maintenance for all of the vehicles while he finished his pilgrimage. At the last stop, Underwood hit paydirt.

“The last customer I went to was a natural gas company that had a fleet of like 70. I didn’t realize that they had that many cars or trucks, and I met the dad of the owner and we hit it off like nobody’s tomorrow,” he explains with a laugh. “The reason I say this is because I ended up buying their location, and they paid me for all of the maintenance of all of their vehicles—almost $400,000—and I bought the building for 375,000 the following year. So, I ended up moving from a four-bay shop I just bought … into an 18-bay shop.”

Then in 2014, a struggling tow truck driver admitted he could not afford his truck payments. Underwood gave him the money to pay off the truck so long as he agreed to keep towing cars to his lot. The driver worked until he paid off his debt and then some, until one day he stopped answering his phone. 
“Then he finally called me, and he said, ‘Hey, man, I just can’t do it anymore. I left the truck (in the lot), it’s fully equipped and the keys are in it,’” Underwood says. “And I said, ‘Can you at least come and show me how to work this thing?’ I had never worked a tow truck before.”

And just like that—Underwood inherited another business from a man who pledged to help him in any way possible. And he did. When Underwood showed up on his first accident scene—an older woman who drove her car off a two-story embankment—he called the former tow truck driver, who walked him through the right way to untangle the messy scene.

Despite the rapid growth, Underwood rarely talks about market share, expansion plans, or beating competitors. When he acquired another shop in Greenview, Missouri, in 2025, his explanation wasn’t strategic growth—it was helping another owner avoid losing his house.

Building a Family, Not a Workforce

Ask Underwood what matters most in life, and he doesn’t hesitate.

“There are only three things that are important in life,” he says. “Number one is people.”

That philosophy has become the foundation of Dependable Automotive’s culture. While many shop owners talk about employee retention, engagement, or workplace satisfaction, Underwood sees things differently. The people who work in his shops aren’t simply employees—they’re family. And they show up no matter what.

Several years ago, one of Underwood’s employees lost his father unexpectedly in a car accident. Along with the grief came an unexpected responsibility: a herd of cattle and a farm he had never managed. He didn’t know how to operate the equipment, bale hay, or care for the animals.
So, the team showed up.

“We YouTubed it and went down there and figured it out,” Underwood says. “We got it done.”

No one was paid extra. It wasn’t a company initiative or a teambuilding exercise. It was simply a group of people helping one of their own.

“If they called me tonight and they needed something, I’m going to be there,” Underwood says. “If something catastrophic happened at their house, the entire shop is going to be there.”

That commitment extends beyond the walls of the business. Underwood believes one of a shop owner’s most important responsibilities is helping employees navigate life outside of work as well.

“A lot of people don’t realize it,” he says. “The business owner really is a partial counselor.”

It’s a perspective that has shaped the culture at Dependable Automotive from the beginning. The company organizes trips, bowling nights, ax-throwing events, and other outings throughout the year. And every year, Underwood gathers the team at VISION to spend time together.

The goal isn’t simply professional development. It’s connection.

For Underwood, culture has little to do with compensation packages or perks. Those things matter, but they aren’t what keeps people together for more than a decade.

“It’s not all about money because at the end of the day, money is a transactional item,” he says.

Several of his employees have been with him since the earliest days of the business. Others have moved away or pursued new opportunities, but many still call regularly to exchange ideas, solve difficult diagnostic challenges, or simply stay connected.

The result is a network that extends far beyond the walls of any one shop.
“We want to be a team,” Underwood says. “We want to grow as a family.”

It’s a simple philosophy, but after growing from a one-man mobile operation to a company with more than 30 employees, it’s difficult to argue with the results.

 “I will tell you from experience, there’s days where I hate it, there’s days where I love it, and you will have all those days mixed in for the entire time that you own a business," he asserts. "But if you manage your team and you take care of your team, the team will take care of you.”

Lending a Hand While Letting Go

Lending a hand isn’t limited to his own employees. Underwood finds every way to support his community and assist wherever possible. From scouting to being an instructor in the automotive sector at Lake Career & Technical Center in Camdenton, Missouri, to giving the fire department cars to teach extrication training at the local high school, Underwood sees the whole community as an opportunity to get involved.

“I just like to help the community,” he explains. “And that’s why I’m in the field that I’m in because I like to help people.”

He admits his freedom to explore projects comes from his partner, Alyssa, who has kept his personal affairs in order, made sure the financials at the shop were solid, and kept the office humming along. He adds that the time she dedicated to taking care of their kids, now 14 and 11, gave him the ability to expand the business and his team.

“She’s been by my side the entire road, rocky or not. And there’s been a lot of rocks,” he admits. “But she’s my rock, and she’s awesome.”

With so much time dedicated to his profession, Underwood says his success is now measured by his ability to walk away from it—something he finds difficult.

“My success is the time away from the job because my family has struggled through a lot of things without me,” he says. “But realizing that I wasn’t the one that had to do everything, that’s probably my biggest thing to overcome. (It was) that fear of relying on others to do the job that I expected to be done … It’s only going to get as good as you let it.”

Building a Legacy

As for what drives Underwood today, he looks forward to developing young technicians and getting them excited to take on the next round of advancements in the field. As such, he believes in apprenticeship programs that allow high school and technical school students to do more than look through the windows of an auto to get a feel for what the industry entails.

“It excites me to be able to get the kids and get them to really understand that (this job is) not that difficult in a lot of regards,” he says. “I want the guy that wants to go in construction, the guy that wants to be a computer programmer, the guy that wants to do cosmetic repairs, the guy that wants to do the mechanical, or the welding and tell them ‘I need somebody that does all of that.’”

Underwood adds he’s all for giving people a chance to roll up their sleeves and make mistakes because it means they’re trying.

“We’ve got to give the young ones a chance, with the understanding that they’re going to make mistakes,” he points out. "(Because) you can coach people to do the right thing, but you can’t teach the ones that know everything.”

Ultimately, Underwood’s goal remains unchanged—to help people be safe on the road.

“Just being able to help people potentially, that’s my end goal,” he explains. “It’s to make sure that people are taking care of their vehicle correctly and consistently … and keeping everybody safe.”

In other words, Underwood still measures success the same way he did at the beginning—not by the number of bays he owns, but by the number of people he’s able to help.