Stepping Back to Level Up: How Chris di Stefano Grew a Multi-Million Dollar Landscaping Company

Chris di Stefano (President of di Stefano Landscaping) has been connected to the natural environment for as long as he can remember.

As a kid, he grew up in an entrepreneurial family that owned a Christmas tree farm and nursery. That business grew rapidly and eventually expanded to include ornamental trees and shrubs, as well as some landscaping. When di Stefano’s father passed away in 1990, his mother carried on the business and leaned on her two sons to help her keep it going. Reflecting back on this time, di Stefano says he didn’t realize at the time how much he was learning just growing up in the trade.

He also says he learned around this time that he didn’t want to be a farmer because, “it’s lonely being out on a tractor by yourself all day and there’s not a lot of human interaction.” That desire for connection (and both his parents’ backgrounds as teachers) drove him to go to college to possibly become an educator.

After college, and over the course of a variety of non-teaching jobs, di Stefano’s desire for human interaction in his work really began to crystalize and pull him back into the natural environment. For extra money, he started doing landscaping work on the side, and pretty quickly he found himself at a crossroads.

“I was able to sell and interact with clients, which I loved, and I was also making more money on the weekend than I was making a week in my day job. And then I had a crazy idea. I kind of had a big calling to carry forward my dad's legacy and quickly decided to quit my day job.

“I got a $10,000 loan. I bought a $6,500 truck. I had an old beat up trailer that I fixed up, bought a little mower and some hand tools, made some flyers, and off to the races I went.”

Di Stefano says he was “blown away” by the $80,000 in revenue he made his first year, which only fueled him to keep going. He expanded services from just maintenance to also include installation and “didn’t really say no to anything” as he operated the business out of his two-bedroom apartment for the first few years.

“I would like, bring the weed whackers into the kitchen at the end of the day and my partner at the time, she really loved that,” he jokes while reflecting on his company’s humble—but promising—beginnings.

Growing Pains

Not long after, the company really started experiencing growth. Di Stefano was selling more work than they could produce, so he had to hire some staff, but still found himself “doing it all” - a sentiment many landscape business owners are all too familiar with.

“It was somewhat directionless,” he says, explaining his approach to managing the chaos of a rapidly growing small business. “I was just so busy working nearly 80 hours a week - trying to do the jobs in the field and then coming home in the evening to do the estimates, the billing, the accounting and all that stuff.”

Around the 3rd or 4th year in business, di Stefano says he realized how he was operating wasn’t sustainable and something had to change.

“I needed to either scale back a bit and become an owner/operator and maybe have one or two staff... or grow a real enduring business that could be sustainable for not just myself, but also for my clients and my employees,” he said before adding, “And that would mean growing it up to that next level.”

Stepping Back to Level Up

Di Stefano points to three things he did at that turning point that would allow him to successfully scale the business over the next decade.

Spend Time ON the Business, not IN the Business

One decision di Stefano made early on was to spend time learning about parts of the business he didn’t know as well. He realized there was always something that needed to be tended to (broken machines, client inquiries, materials for jobs, etc.) but that it wasn’t always the best use of his time to focus on those things—especially when he had others in the company who were (mostly) capable of handling those issues on their own (more on that in a minute).

So he started reading books, attending conferences and networking events, and joining trade associations like the NALP. Eventually, as he was approaching the million dollar revenue mark, he hired a business coach (Jeffrey Scott) who helped him level up the business yet again.

When pressed to pinpoint how he knew it was time to make those investments, and exactly what investments to make, di Stefano says it was less about the amount of time they’d been in business and more about the amount of work they were doing… and his continued involvement in that work.

“I was still hands-on on all the projects, working on Saturdays, and missing out on a lot of personal stuff. I was thinking, ‘If I do this for another three years, I'm gonna be dead. Or the business is gonna fail.’”

So he put more levels of management in place to take some of the day-to-day off his plate in order to free him up to spend more time on the business, instead of in the business.

Learn to Let Go

Initially, as he started to step back from operations, di Stefano says he got pushback from some of his more tenured employees who were used to him being so hands-on and particular about the way the work was done. But—however difficult the change was for both him and his staff—di Stefano knew it was the right move for the next chapter of his company’s growth.

Citing advice he once heard from a successful business owner, he said “When you're hyper-focused on a goal and you're clear on what that is, you have to get comfortable with the fact that things are going to kind of get messy. You have to stay focused on that one important thing that's going to drive your business forward. During that process though, you're going to drop some balls and you won’t get to certain things and you might let some things slide that you wouldn’t otherwise.”

When he decided to make that shift, di Stefano says he really had to coach himself to learn to let things go.

“I couldn't just be half in/half out. It was either, I was going to be real mental about exactly how that wall was built and exactly where it was and how it was communicated to the client, or I was going to be totally out and I was going to let somebody else do it. And they were going to make mistakes and things were going to happen. But ultimately in the big picture, it was going to be okay.”

The coaching didn’t stop with himself, either. Clients were used to dealing with him directly. Employees were used to working by his side. And things did get messy before they got better. But, di Stefano says, that’s just part of growing, and it never goes away.

“It happens at different stages, too. Different level, different devil. You get to a different spot and things get messy in a different way again. You have to recalibrate and shift as a leader and figure out how you fit into the whole picture again. There's even days now where I find myself getting pulled into something and have to ask myself, ‘Is it really the best use of my time? Is it really serving my overall company in the best possible way?’ And, sometimes the answer is no, and I just have to walk the other way.”

Take Care of the Staff

The fact that some of di Stefano’s employees have been with him for 10-14 years speaks volumes about the company culture he’s cultivated. At the heart of that culture, and what di Stefano points to as a key motivator to stay with his company, is their ability to continuously provide opportunities for employees.

Those opportunities go far beyond surface level benefits like new equipment and frequent staff parties—although those things are excellent, and certainly help! Ultimately, and perhaps somewhat paradoxically, di Stefano believes that the organization’s relentless focus on profitability is what has allowed him to continuously create new opportunities for his employees so that they can grow in lockstep with the company.

“If you come into our yard, you’ll see on a huge sign that profitability is one of our core values. Because we strive to make a good profit, we’re able to take care of our customers and our team. We can throw parties. We can have nice equipment. We’re able to say no to crappy clients and jobs. We’re able to focus on safety. We can pay out a profit share. We can take a day off to go see the eclipse. We can do things like that because we’re profitable.

“I’ve just made it so that ‘profit’ is not a dirty word around here.  We talk about it all the time. In order  for this company to continue to operate the way that it's been—to pay the highest wages, to have lots of benefits, to work on the coolest stuff, to have innovative equipment, all these things—we've got to make a profit.”

Looking Ahead

Unsurprisingly, di Stefano is currently engaged in planning for his company’s next major milestone: a new satellite office that will allow him to test the branch model for expansion.

“I realized a couple years ago that we were going to max out our relatively small local market pretty quickly. I didn’t want our growth to become stagnant, so I identified a new market and we’re laying the groundwork right now for a new, small facility. The goal is to be up and running by 2025.”

It’s a perfect example of how business growth can compound quickly when the right elements are present. Center your team around profitability, and you can reward them with a share of those profits. Take care of your employees, and they’ll commit to your organization for years to come. A strong, committed team allows you to take on more business, further compounding profits, fueling growth, and creating new roles within the organization—which keeps everyone excited, motivated, and energized for the future.