March 18, 2026

This piece is sponsored by the Prairie Family Business Association.

Shortly after Stuart Stein joined his family business, he did what many next-generation members likely have contemplated.

“I made a list of things I would do differently as owner,” said Stein, third-generation leader of Watertown-based Stein Sign Display and its wholesale manufacturing division, Esco Manufacturing.

“There were 57 items on it.”

That was in 2019. Not long ago, he pulled up that list and gave it another look.

“I’ve only done 16 of those things I thought I would do different,” he said. “I couldn’t help but think of how the job might look easy from the outside, but until you’re in the shoes with all the information and knowing causes and effects and pros and cons, you shouldn’t judge.”

Stein Sign Display will mark 75 years in business next year and is approaching the one-year anniversary of its decision to expand to Sioux Falls.

“This company is a true multigenerational success story,” said Mason Van Essen, assistant director of the Prairie Family Business Association. “Their intentional approach to transition and next-generation leadership is a model for others, and their business continues to evolve to meet changing market needs.”

From neon shop to industry leader

The company’s roots trace back to 1952 when Stein’s grandfather Clint Stein began working at a neon shop called Ralph’s Neon after serving in the Air Force during World War II.

Clint Stein had worked as a mechanic testing military aircraft and found a fit in the emerging sign electronics industry of the time.

“We believe through family stories that he ultimately bought out Ralph’s to form Hi-Way Sign Co.,” Stein said.

While neon signs were cutting edge at the time, the industry evolved into fluorescent tubes and lamps and then LED.

“We still have customers who want neon signs or want them repaired, and we have a source for that, but it’s not the bread and butter it used to be,” Stein said. “We used to have nine neon benders; now we don’t have any.”

Even some of the company’s earliest manufacturing innovations eventually became obsolete.

Esco Manufacturing was founded in 1965 and centered around a patented machine called a roll former that turned single sheets of steel into rectangular sign cabinets.

“That machine he founded the company on — it existed for about 25 years,” Stein said. “We no longer use that either, so there have been interesting evolutions of the company.”

Generational transitions

Stein’s father, Mark, was one of six kids and one of two who worked in the family business. He spent 40 years with the company and intentionally set his retirement date for Feb. 4, 2020 – the date of his 40th anniversary.

“That was definitely by design,” Stein said. “He chose that day at least a year in advance, which allowed us to work backwards from there. We shared it with the staff, so everyone was on the same page.”

As the third generation, Stein committed to the family business later in his career. He grew up working part time in a variety of roles, from scraping off metal in the prep department to working in advertising for the billboard division.

After graduation, he spent nine years in retail banking with Wells Fargo before coming to Stein Sign Display as a general manager in 2014.

“I knew the family business would always be an opportunity, but my dad was adamant about me going to work somewhere else to gain real-world experience, and I applaud him for it,” Stein said. “To work at a multibillion-dollar company and get to see structure and policy and procedures was invaluable.”

Over time, he was drawn to continue the family business legacy.

“It felt like the right time, and I’m grateful I was able to share with my grandpa in the last month of his life that I was going to come to the family business and it was going to transition to the third generation,” he said. “He was probably more interested than anyone what my path was going to look like, so to share that with him was special to all of us.”

He worked side by side with his dad for about six years. As the transition neared, Stein would sit in on weekly meetings with his dad’s direct reports.

“What worked so well was when my dad walked out the last time, he was done,” Stein said.

“There was no coming back to check on a project – it was a clean cut. With my grandpa, he would come back into the office, and then people didn’t know who to go to.”

But while his father wasn’t visible in the office, he didn’t disappear.

“My dad always told me, ‘I’m retiring from the business, but I’m not retiring from you,’” Stein said. “And those two things have been such a blessing. He’s a trusted resource, and I can call him for advice, but he’s not in the business unless he’s stopping by for a free meal at a company potluck.”

Growth and national reach

Two weeks into his role as president, on Feb. 20, 2020, Stein called a companywide meeting to roll out one of the most important items on that original list of changes he wanted to make: implementing companywide core values and a vision statement, which is “Creating wow experiences for our team members, customers and communities.”

Along with it, he gave everyone two $20 bills –“the timing worked great on 2/20,” he said. “One was for them and one was to pay it forward and go live our vision to create that ‘wow’ experience for the community and then report back, so it was a fun way to kick off things.”

Today, the 135-person company operates across two divisions.

Stein Sign Display focuses primarily on retail sign sales, installation and service across South Dakota and the surrounding region, while Esco Manufacturing produces signs for other sign companies nationwide.

“Our customer base for Esco is some very large sign companies across the country but largely family-owned sign companies that we manufacture and ship signs to,” Stein said.

The company’s work appears in high-profile venues through a relationship with Daktronics.

“When Daktronics sells a sign package to places like Madison Square Garden, Met Life Stadium or Little Caesars Arena, many times we’re blessed with the opportunity to create the signs that go around those message centers,” Stein said.

 The retail sign division has expanded from four people when Stein began leading it to 19 today.

“I’m very proud of that, and it’s largely due to our team’s passion and drive for servicing all of South Dakota,” Stein said.

April will mark one year since Stein committed to the Sioux Falls facility near 12th Street and Interstate 29 at 4430 W. Crossroads Place.

“So far, it’s going really well,” he said. “We’re past the hard part — is there a market, are people going to buy from us, are they going to give us a chance? The answer is yes, yes, yes.”

The Sioux Falls location launched with four employees and already has grown.

“We started with four in the Sioux Falls market, we’re up to six now, and we’ll likely be at eight by the end of 2026,” Stein said. “We surpassed sales expectations in year one, and we were profitable in year one.”

The next phase of growth includes bringing manufacturing capabilities to the Sioux Falls facility.

“We’ve renovated the entire building and have space now,” Stein said. “One of the next things we’ll focus on is bringing some manufacturing into the Sioux Falls plant.”

Learning alongside other family businesses

As Stein navigates leadership of the third-generation company, he has found support through the Prairie Family Business Association.

The company recently joined the organization, which connects family-owned businesses across the region and even nationally, providing ongoing resources to help them thrive across generations.

“It’s opened some doors with different relationships and connections,” Stein said.

“The transition planning strategies and speakers have been really helpful.”

He has enjoyed attending the PFBA Annual Conference and recently joined an Affinity Peer Group.

“It’s gone really well,” he said. “And I know it will help us effectively navigate transitions.”

While his father’s succession was relatively straightforward, Stein knows the future could be more complex.

“My dad had three kids, and only one was interested,” he said. “I have four kids, so that transition and estate planning could be a very complex decision.”

Having a network of family business leaders to learn from provides reassurance, he added.

“I know Prairie Family Business will be a tremendous resource to lean on,” Stein said.

His own next generation includes four kids, age 14, 12 and 9-year-old twins.

“I can’t say for certain one way or the other who might be interested, but I’ve always shared my vision is to grow the business and not plateau it,” he said. “I’d like to give our kids every opportunity to get involved with the business, and hopefully I can do that.”

To learn more about positioning your family business for multigenerational success, connect with the Prairie Family Business Association at fambus.org.