The Yardstick: Q&A With Craig Ruppert, Ruppert Landscape

From mowing neighbors' lawns in the 1970s to one of the most iconic names in the industry, Craig Ruppert tells his story.

By Jessica Schwartz & Christine Menapace
From the June 2023 Issue

The Yardstick

A Timeline Of Accomplishments


Craig Ruppert, Ruppert Landscape

Craig Ruppert
CEO & Founder
Ruppert Landscape
Laytonsville, MD

1. When, why, and how did you start your business?

I grew up in a large family and was one of eight kids. We were all motivated to work in order to have spending money and to help pay for our schooling. My sisters and brothers all worked to earn money by babysitting for neighbors, delivering newspapers, and shoveling snow.

When I became old enough to use a push mower (in the early 1970s), I began asking my neighbors if I could mow their yards. Within a few years’ time, with my parents’ garage as home base, my neighborhood yard business grew. I was even able to expand my services and hire a few employees, including my brother, Chris. I also started to learn more about horticulture, the fundamentals of running a business, and how to manage employees and customers.

In 1976, we incorporated and became Ruppert Landscape Company. The first ten years progressed slowly. There were many challenges and we made plenty of mistakes along the way.

Like many young entrepreneurs, we started developing processes and systems that gave us the ability to scale our business. Our company evolved and we gradually learned how to adapt and lead in order to meet the needs of our company.

As we grew, we realized that our success was tied to two simple values: work hard and be fair with our employees and customers. Over the next 50 years, the projects we undertook grew in scale and complexity.

Craig Ruppert
Click image to enlarge.

2. Please describe your business now.

Today, Ruppert Landscape is a trusted name in the Industry, providing customers with high-quality commercial landscape construction and management services. Headquartered in Laytonsville, MD, the company employs nearly 2,000 people and serves customers from 31 branches in nine primary markets: Philadelphia, Baltimore, D.C., Richmond, Raleigh, Charlotte, Atlanta, Nashville, and Houston.

We pride ourselves on providing high-quality workmanship in all phases of landscape construction and maintenance. The culture and values that helped us grow and evolve are still a key part of our company today.

Landscape Company
Ruppert has approximately 2,000 employees today. (Source: Ruppert Landscape)

3. What is your educational background or skill set? Is there a degree, continuing education class, or skill you recommend for success?

Like many people in our Industry, I didn’t have a lot of formal education. I went to a great high school and completed about a year and a half of college, but never finished. In many ways, learning on the job was a lot easier for me and I feel like I received a lot of firsthand lessons that I probably couldn’t have gotten in school.

Eventually, I followed the recommendation of a friend and, in my 50’s, completed some more structured learning through the Harvard Business School’s Owner/President Management (OPM) leadership program. The program gave me a broader, more global perspective, a deeper understanding of operations and IT, and greater insights into leadership. I found it valuable and over the years, five of our senior leaders have also completed the program.

4. What do you see as the main reasons why your business grew successfully?

Perhaps like many in our Industry, I enjoyed working and I had a healthy fear of failure that tended to drive me. Over time, I found that what it really comes down to is surrounding yourself with good people who share your values.

It took us quite a few years in business before we could even articulate our core values. But once we did, it really helped us define who we were, convey what we expected from ourselves and others, and enabled us to share that information more broadly, which in turn helped us grow.

We were also fortunate to have had a lot of support and guidance along the way. We developed a network of people that we could ask for advice and rely on, including business and Industry professionals, associations like the National Association of Landscape Professionals (NALP) and Associated Builders and Contractors (ABC), and trusted advisors. They all permitted us to see our strengths and challenges and make better informed decisions as we grew.

Craig Ruppert

TOP: Training on the Caterpillar 262D skid steer loader. Ruppert’s safety practices were profiled in the Turf April 2022 edition.
MIDDLE: Field Day 2021 at Children’s National Hospital in Washington, D.C. Field Day is a long-standing, philanthropic—and fun—Ruppert Landscape tradition.
BOTTOM: A morning team huddle of Ruppert Landscape employees. (Source: Ruppert Landscape)

5. How did you set yourself apart from competition?

In the early days, our strategy was to make up for what we lacked in experience by just out-hustling our competition. We just tried to work harder, faster, and smarter where we could.

We’ve spent a lot of time over the years watching and learning from our competition and there are many great companies that we’ve admired. Every competitor we have does something better than we do— so we are still watching and learning!

6. What was your best business decision?

In 1998, we sold the business during a period of Industry consolidation. In 2003, we decided to start our business over again. We’d received feedback from old customers and employees who were interested in working with us again, so we decided to give it another go. I was 49 at the time and it certainly wasn’t something that we were planning to do. Now 20 years later, I can look back and realize that it worked out well for us and it was probably one of the best decisions I have made.

7. What was your worst business decision?

There were many along the way, and I probably made more mistakes than most, so pinpointing just one is difficult. But what I learned is that failures provided us opportunities to learn what not to do going forward. By analyzing what went wrong and considering what could have been done differently, it helped me avoid making the same mistakes again. And as you may know, part of life is making the best decisions we can with the information we have and then learning and growing from those decisions, whether they turn out good or bad.

All business owners and entrepreneurs have different strengths, ambitions, goals, and desires. They have different lifestyle aspirations and family considerations, all factoring into decisions about growth. These factors help determine how fast to grow and how big you want the company to be.

What I learned is that if you want to grow, you need more processes and systems in place and you need to rely on—and trust—others. It took me a while to realize this, and to be able to give up my control carefully, while I gradually built trust in others around me. This became a little easier once we had good processes and systems of measurement in place.

Craig Ruppert

Landscape Truck

Six Flags
TOP: Ruppert Landscape won an NALP Gold Award for its work at The Boro, a 17-acre mixed-use development in Tysons Corner, VA.
MIDDLE: A revamped truck representing Ruppert’s original truck with a misspelled sign.
BOTTOM: Ruppert employees spread mulch at Six Flags America. (Source: Ruppert Landscape)

8. What was your funniest business experience?

When we bought our first truck, we got a magnetic sign that would help us look more professional. Unfortunately, we were driving around with the word “maintenance” spelled wrong for several months before someone finally pointed it out!

9. What’s your favorite piece of equipment/landscaper tool?

I’m usually never without my pruners as I like hand-pruning. When I’m in the field or visit jobsites, I always try to remember my pruners. It helps me lead by example, because they are part of our uniform, and occasionally I’m able to give our team pointers on how to prune better.

But I also enjoy doing work on our farm. Whenever possible, on weekends and when I’m not in the office, I spend time at our tree-growing nursery using the skid steer, loader, tractor with a bushhog, and a chainsaw. These are the tools and equipment that I’m familiar with and can safely operate.

10. What is your advice to others? What do you wish you had known?

Work hard is the first thing I always think of. People often laugh when I say, “We’re not just looking for the A and B students at Ruppert—we’re looking for the C students who have a strong work ethic and enjoy working hard.” That example comes to mind because I was the C student in many cases. I excelled in some areas, but not in others. I didn’t always apply myself if it was not my favorite subject or one that I didn’t have a particular interest in. But I always enjoyed working hard— and what I lacked in knowledge, I tried to make up for in effort. (P.S. We still have plenty of room for the A and B students here at Ruppert!)

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Be responsible with your money. One of the best pieces of advice I ever received was from my father-in-law who said, “Keep your wants simple.” That always stuck with me and was a good reminder to be content with what you have.

Also, I’m from a big family, so I learned early on how important it was to watch the pennies, live within your means, and pay as you go to avoid debt.

Stay humble. Over the years, I’ve been lucky to have been around some very successful people from many different industries. The people that I admired the most all had a sense of humility. They tended to be the ones who were down to earth and didn’t feel the need to emphasize their own accomplishments. Instead, they let their actions speak for their ideals.

11. What is your plan for the future of your business?

I’m very excited about the future of our company. We are entering a new phase in our evolution with our recent strategic partnership with capital investment firm, Knox Lane. This partnership will enable us to continue to grow at a faster pace than we have historically, which will in turn provide even more opportunities for people.

I’m excited that our team will have a greater ability to try new positions, learn new things, move to new locations, take on more responsibility, move up, and earn more—all of which will help them achieve their personal and professional goals. In my mind, our future is bright.

For more on Craig Ruppert, see the Ruppert Landscape website.

For more from Turf, read: Ruppert Landscape Gives Employees $28M In Appreciation Bonuses

Would you like your business to be considered for a Yardstick profile or know one who should? Email the Editor at


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