Ruppert Landscape Co. owner Craig Ruppert grows thousands of trees on hundreds of acres. The trees in the background are Armstrong maples. (Susan Biddle/For the Washington Post)

You can trace the Ruppert Companies’ success to the yard where the golf caddies waited for their assignment at the exclusive Chevy Chase Club in the 1960s.

Back then, caddy Craig Ruppert would sit for hours on end and watch the social and economic dynamic play out as 50 or 60 other caddies, young and old, black and white, working class and poor, waited their turn — based on seniority — to carry golf bags for the club’s august membership: senators, attorneys, admirals, CEOs, doctors, diplomats, small-business owners.

“That caddy yard was a great mixing bowl,” said Ruppert, who grew up one of eight kids in a house that was about one long tee shot from the club. His family were not members, but the Chevy Chase Club is where Ruppert learned the people skills, patience and grit that have served him in his successful business career.

Caddymaster Jim Hardy’s calming presence and quiet leadership helped ennoble a young, ambitious caddy to become a prominent businessman.

Doesn’t everybody remember a first boss or someone who set an example to follow?

Workers at Ruppert Landscape Co. prepare to load a weeping willow on the truck for delivery to a home in Libertytown, MD on October 26, 2012. Ruppert grows thousands of trees on hundreds of acres. (Susan Biddle/For the Washington Post)

“I learned to appreciate how he handled himself,” said Ruppert, who commands a group of businesses with $90 million a year in revenue.

Like Hardy all those years ago, Ruppert now supervises hundreds of employees with diverse social and economic backgrounds.

“It gave all of us who had that experience . . . a broader understanding of the world at a young age and how to deal with all kinds of people while at the same time mixing it up with the Alan Greenspans of the world.”

He realized how to manage people and the importance of treating them with respect.

An array of businesses

The Ruppert Companies is a mini-conglomerate of Montgomery County-based businesses that handle work as diverse as landscaping, electrical contracting and managing giant warehouses. Ruppert even owned a bus company in Poland at one time.

The conglomerate’s flagship is Ruppert Landscaping, where Craig is chief executive. It is a $70 million, 700-employee, privately held firm, with three divisions: building commercial landscapes (Martin Luther King Memorial, World of Coke in Atlanta), maintaining commercial properties (Bethesda Row, Six Flags in Prince George’s) and growing trees.

I have been following Ruppert for about a year and recently visited him at the company’s 600-acre nursery in Laytsonville, where the 59-year-old gave me a tour on an all-terrain vehicle, through miles of rows of trees.

Ruppert is one of those successful businessmen who flies under the radar. His aw-shucks modesty is disarming, but it belies a fierce, single-minded discipline. The guy has grit.

Some of it came from St. John’s College High School, the northwest Washington Catholic prep — run by the Christian Brothers — that has graduated some of the most successful businesspeople in the Washington area, including Under Armour founder Kevin Plank, sports team owner and venture capitalist Raul Fernandez and the late financier and philanthropist Joe Robert.

Add Ruppert to that list.

He, his brother Chris and childhood chum Chris Davitt caught the entrepreneurial bug early. They caddied. They peddled newspapers. They launched a lawn service while in their teens. In less than three decades, they grew it from the Ruppert family garage into a 900-employee business with approximately
$45 million in revenue. They sold Ruppert Landscape Co. to Servicemaster in 1998.

After they cashed out, the antsy bunch — too young to retire — launched other ventures, including a satellite communications company and an electrical company, and bought up warehouses. That’s when they bought that bus company in Poland.

In 2003, after a noncompete agreement with Servicemaster had expired, Ruppert and Davitt decided to pull their old landscaping team together. They reclaimed the original company name and built a new landscaping company, piece by piece.

Today the sprawling business has branches and maintenance depots stretching from Philadelphia to Atlanta. There are 223 vehicles, including everything from flatbed trucks to tree diggers to lawnmowers.

The company even has a fleet of 40 hybrid Camrys for its managers.

The importance of people

The common denominator running throughout all of Ruppert’s enterprises, including the flagship landscaping business, is the ability to find good people and manage them.

The company employs a rigorous recruitment process in the search for good managers, drawing from 14 colleges and universities with top horticulture programs, such as Cobleskill, Mississippi State and Virginia Tech.

The sifting process for potential leaders starts with summer internships. About half of the interns return to the company after graduation.

The training process includes nine days of intensive instruction a year, and managers are given wide experience throughout the company as they move up.

“Attracting, keeping and growing good people . . . is the secret to our success,” Ruppert said. “We take good care of our people, and they are the ones who make us successful.”

Ruppert, who quit the University of Maryland in his second year, fosters a humble company culture. (He even asked me to focus the story on his employees and to leave him out.) The headquarters are airy and functional. Everyone wears the same company uniform. Bureaucracy is almost non-existent.

Ruppert Landscaping has no human resources department. Instead, every manager is accountable for his or her employees.

“It’s everybody’s job to be a member of the human resources department,” Ruppert said.

Employees must enjoy working outdoors, work hard and stay positive. Ruppert has no time for gloomies. “We are demanding of our people,” Ruppert said. “It’s a hard place to work because expectations are high.”

Everyone gets a bonus, from $80 for a recently hired field worker to $80,000 for a top performing manager (Ruppert doesn’t like the word “executives”).

Loyalty is rewarded. Long-term employees get goodies such as limo and helicopter rides to review their projects. They also get anniversary dinners, trips to ball games and even commemorative coins.

The big prize: Key managers get ownership stakes.

Ruppert said the respect accorded employees gives the company an edge over the competition because employees work harder and stay longer, keeping down turnover costs.

Word of mouth generates an endless supply of hard-working employees, who are about 50 percent Latino.

Ruppert Landscaping has profit margins estimated at
5 percent to 12 percent a year. Profit varies, but I estimate it runs from $3 million to $9 million, based on industry standards.

Employees know the math so that they can help move the numbers — and move up in responsibility and pay.

“We want everyone to know the score,” said Ruppert, who earns a low-six-figure salary. “If the branch is doing well or the company is doing well or not doing well . . . they have access to it all.”

Ruppert is nuts about his business. He spends weekends tooling around the nursery in Laytsonville, where 60,000 trees are in various stages of growth. His house is on a hill in a corner of the sprawling farm.

As we toured the spread, Ruppert said he golfs only a couple of times a year.

He told me the only relationship he has had with a country club is working at one.

It sure paid off.

For previous Value Added columns, go to business.