“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?
“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.