The right questions

After 40 years of operation, Dupper Landscape rebranded to reflect the partnership between the father and son that have turned the company into a $45.7 million business. It ranked No. 70 on Lawn & Landscape’s 2024 Top 100 list.

Today, Dupper Landscape employs 220 people and focuses on landscape maintenance and construction, but back at its inception in 1983, Russ Dupper was just looking for a way to make a living for his budding family. He and his wife, Patti, already had a two-year-old and another child was on the way.

VIDEO BELOW: Russ and Josh Dupper talk family business

The father-son duo explain how they've kept faith and company culture at the forefront of their business as they grew their business into a Top 100 company.

Russ couldn’t have known this child, Josh Dupper, would grow up to be his partner. Russ had grown up on a 2,300-acre farm in rural South Dakota, and when it came down to which of the four kids would own the farm one day, Russ drew the short straw. So, he borrowed some money to go to college and moved out to Phoenix to be with Patti. After working for another landscaper, Russ decided he wanted to launch his own company.

Learning on the fly

Years later, Josh would spend his days in the company warehouse over spring and summer breaks, learning anything from pulling parts to job estimating. After earning an accounting degree in school, Josh approached his dad about joining the business.

When the Great Recession hit in 2008, Josh told Russ he thought they were in trouble. At the time, they primarily offered landscape construction, so Josh pitched the idea of instituting a landscape maintenance division as well.

There was a learning curve: Josh says he didn’t know much about maintenance from the jump.

“The first job I bid, I thank the Lord I actually bid it to a very gracious property manager, because she called me up knowing us from our construction relationship,” he says. “She said, ‘Hey, do you want to go to lunch? Because you’re about three times what the price should be.’”

It’s been smoother sailing since then. Josh now runs that division full-time while Russ runs construction, and they both share administrative duties once Josh was promoted to business partner.

After years of operating at RH Dupper, the company rebranded as Dupper Landscape to reflect the familial partnership.

“It’s been all organic growth through an amazing team. It’s been quite the journey,” Josh says. “The last 40 years was an amazing ride, and I’m hoping to carry the legacy on and continue what Russ started for the next 40 years.”

The Duppers believe the organic growth comes from a strong pool of employees. The company’s still privately held and family-owned, but they’ve grown the company so much by selecting employees carefully. Russ says that when they interview an employee, they tell them that there’s two things they’re trying to discover together — does the opportunity fit your passions, and do your personal values match our company’s core values?

“If we match those two things, you’re going to like Monday morning and you’re going to like being on our team,” Russ says. “If we miss on it, you’re going to leave or we’re going to ask you to.”

Russ says the company asks questions aimed at feeling out what those personal goals might be. For instance, he says they’ve asked candidates to describe a time when their personal values or integrity were violated and what that situation was like. How did they handle it?

Alternatively, they might ask a candidate to talk about a time their values differing from those at a previous companies, and then they’d ask how they handled that situation. Or they’ll ask what they liked at their last company, and if they had the ability to change one thing in that company’s culture, what would it be?

Josh adds that they’ve asked questions like “describe your best boss and describe your worst boss, without naming those individuals.”

“We get a lot of insight into what they value and how they like to be treated,” Josh says.

Genuine partnerships

And sure, the labor pool’s tight — that’s why they use H-2B and have helped workers become permanent citizens. They also have strongly incentivized their referral program because Russ believes those employees will already have the values your company seeks.

“Your people will find like-minded people,” he says. “The employees who are with us will already know what’s required.”

Of course, it helps reinforce the strong company culture when the two partners are so close. Russ and Josh acknowledge that some family businesses become contentious due to personal drama, but that hasn’t been the case at all here. Josh says the pair are best friends and do a lot outside of work together, including bass fishing. They’re also faith-based, which they say has helped them forge a strong vision for what the company should be.

Russ says that when disagreements do come up, it’s Dupper Landscape’s goal to arrive at the best solution for all of the teammates. Keeping that humility has helped the company retain its company culture even as it has grown.

“When you work together with family or anyone, you’re going to have different points of view, and you’re going to have disagreements,” Russ says. “How you view different points of view or disagreements are really a big factor in making you successful.”

The author is an associate editor with Lawn & Landscape magazine.