Navigating Landscape Business Growth

Weller Brothers Landscape Professionals transformed a natural slowdown in market growth into a strategic plan for expansion.

By Jaden Miller
From the October 2023 Issue


When brothers Cole and Brent Weller began mowing lawns as teenagers in 2001, a “strategic growth plan” was the last thing on their minds. One Summer spent working for someone else’s lawn care company had been enough. Armed with entrepreneurial spirit, their Dad’s encouragement, and WordArt posters, the guys began knocking on doors to drum up their own business. “At the time, I was probably thinking I could work less, sleep in more, and make the same amount of money as compared to working for someone else,” Cole jokes.

Twenty-two years later, the Weller brothers are still cutting grass – along with offering full-service landscape design and maintenance. And despite their initial lack of strategy, their company’s growth today has been the epitome of “strategic.” With locations in Sioux Falls, SD; Rochester, MN; and – coming this Fall 2023 – Des Moines, IA, Weller Brothers Landscape Professionals currently employs 150 people and shows no signs of slowing down.

Weller Brothers Landscape Professionals
The Sioux Falls team this past Summer. (Photos courtesy of Weller Brothers Landscape Professionals)


But the growth hasn’t come without challenges, and the leadership team has learned valuable lessons along the way. As they embark on location number three, they’re finally starting to feel they have the whole “strategic growth plan” thing dialed in.

Why New Locations After 17 Years?

After several years of mowing lawns in their hometown of Brandon, SD, Cole jumped into the landscape design program at the local Southeast Technical College in Sioux Falls, SD. Over the next 17 years, the brothers earned the trust of their clients in the Sioux Falls area as they began realizing the potential of their business venture.

First, with Cole’s collegiate experience, they added landscape design to their lawn maintenance repertoire, which they later sold and then reintroduced after the non-compete expired.

Then they grew, and grew some more — and then they reached a slowing point. “We got to a point where, if we wanted to continue to provide growth opportunities for our team, we needed to expand out of Sioux Falls,” Cole explains. “We are not at market saturation yet in Sioux Falls, but we acknowledge it as a real possibility in the next three to five years. We want to be in front of that potential roadblock to growth, and expanding into other markets is one of the ways we are doing that.”

This led to the company expanding into Rochester, MN in 2019. Managed by Brent Weller, that location now employs more than 30 people.

Landscape Business Growth
The September 2023 ribbon-cutting for the Rochester location. Brent Weller is pictured in the center.


The First Expansion

Cole and Brent agree they were in uncharted territory with this first expansion, but quickly identified some strategic moves as they began to lay a foundation for the new location.

1. Community Involvement. The first, Brent says, was finding out where their customers spend time. “For us, joining a private country club has worked well.

These are people who like to spend time outside and typically have a bigger budget. As an owner, you can’t do it all or be at every event, so getting your team involved is always key. We are members of our local chamber and Home Builder’s Association, and we encourage our team to attend the events they put on and get involved.”

2. Hiring To Grow. Brent also credits their hiring strategy as key to the Rochester location’s growth. “Hire to grow; don’t grow to hire,” he says. “Often companies wait until they’re stretched too thin and then decide to hire additional staff. If a great applicant finds your company, hire them. You will figure out how to keep them busy and ultimately help your company grow.”

Making The Move To Location #3

Next up, Iowa. The main factor in selecting Des Moines as the third location for Weller Brothers was simple: great Weller employees wanted to go there. Enter Matt and Anna Stadel.

Weller Brothers Landscape Professionals
Matt & Anna Stadel

After meeting several years ago while both working at Weller Brothers in Sioux Falls, the Stadels married in Fall 2022. Earlier, when Brent launched the Minnesota location, Matt had moved with him and became the landscape production manager. Anna eventually followed and is now a landscape designer at the Rochester location working toward her landscape architecture licensure.

While the leadership team did demographic research and determined Des Moines as a good market, Cole says the research was a far second to knowing they have the right people in place whose hearts are in the expansion.

The Stadels have taken the initiative in driving the expansion into Iowa. Together, with a larger group spearheading the plan – including the leadership team, marketing manager, and HR director – everyone provides input on their respective area of expertise.

With this move, the team now has experience from the Minnesota expansion guiding their strategy. “This article is not long enough to list all of the things that we are doing differently this time around,” jokes Cole. “We are a far more complex organization now than we were in 2019 when we expanded to Rochester. Our advantage going into Des Moines is not only that we have the experience to learn from Rochester, but we have team members in place to improve the process and execute.”

Cole adds that the company is already more prepared for Des Moines than they ever were for Rochester, and he applauds Brent and Matt’s efforts in getting Rochester off the ground. “They were resilient. They dealt with a lot of crap, but they kept grinding,” says Cole. “So, we know that Matt has what it takes to start a branch. He and Anna are going to crush it and do it the Weller Brothers way.”

Advice For Creating A Strategic Growth Plan

When creating a strategic growth plan, Cole encourages other business owners to first identify the “why” behind their business goals. “For us, our why is ‘Creating Outdoor Spaces for Life’s Best Moments,’” comments Cole.

“Whether it’s a new construction project and building a pool and pool house for a customer to enjoy with their family and friends, or a maintenance crew providing services to free up a client’s time to attend their kids’ baseball games or take a family vacation, our team shows up every day knowing that is why we do what we do for our clients.”

Landscape Business Growth
Enjoying their work—literally. The Weller Brothers landscape crew were invited over for a pool party by the customer after the completion of their project.


The Weller Brothers leadership team has hired business consultants in the past, and while Cole says they did a decent job, he believes the company’s best work in strategic planning has come from within.

For example, in 2022, the team developed the following simple strategic plan for the year: • Respect Your Coworkers • Assume the Best • Do the Right Thing.

“Sounds crazy,” Cole admits. “But it worked, and everyone knew the strategy. This was far better than the ten-page strategic plan binder that you get, set on your shelf, and look at on December 15th to see how you did.”

How does he know it worked? While the company hit its revenue targets, Cole says the real measure of success was in how team members showed up for one another. “It’s one thing when you have team members show up because their manager expects them to. It’s a totally different thing when you have a team that shows up for the guy or gal they are working next to each day,” he says. “Everything gets easier when that is the culture. We watched that transformation.”

Asking Hard Questions To Accommodate Big Growth

When it comes to strategic growth, it can be daunting to know how to shift finances, resources, and people. At Weller Brothers, the entire leadership team – comprised of Cole, Brent, the general manager, and CFO Jill Holt– provides input in approaching these decisions.

“Most of our high-level decisions are data- and people-driven,” Cole says. “We have an ‘ace’ for a CFO; Jill is typically the one providing the data, metrics, and financial information. With that information, we consider how it will affect our team, and we decide from there.”

Cole adds that occasionally, he’ll see intrinsic or unquantifiable value in a deal and relies on his gut. “Our CFO doesn’t like this approach as much, but we balance each other out,” he says.

“Your frontline workers are so important. Making sure they are being empowered and motivated by a great manager is so crucial to your business. Earlier in our business journey, we did not put enough emphasis on our people, and it was evident in our culture for a while.”

— Cole Weller

Jill agrees that Cole is more of a “blue sky” decision-maker while she is more analytical and conservative. She points to their honesty and ability to talk frankly about concerns as the key to their success. Often, she explains, they agree about an opportunity being a good fit but may disagree on timing. “Cole wants to move quickly to begin generating revenue and I want to make sure we do our due diligence to mitigate risk as much as possible,” she says.

When faced with a big decision – such as acquisition or expansion – Jill first asks if it aligns with the company objectives. Expansion, she explains, typically does because it aligns with the growth trajectory. Acquisition targets are different because they may be synergistic (similar or complementary services) or they may offer an entirely new service line.

“We then typically discuss all the risks and rewards of the opportunity, which include not only financial risks but also the ‘human’ impact to our employees or the target’s employees,” Jill says. “From a financial perspective specifically, we discuss the expected cost, including upfront cash out and future cash flow.”

Jill then will review the current cash position and projected cash position over the next 12 and 24 months, as well as the existing debt-to-equity position, to determine whether or not they are in a good financial position to proceed. “Cole and I typically land on a compromise that we both feel comfortable with, such as how the deal is structured. It has worked well so far.”

Decreasing Risk & Making Mistakes

As his relationship with Jill proves, Cole points to a primary factor in decreasing risk as a company grows: having the right people in the right positions. And, he says, that goes for everything from mitigating the risk of job site injuries to mitigating the business risk associated with expansion.

Landscape Business Growth
Cole Weller

“When you focus on developing your people and demonstrate that you are invested in them and that you have their back, they will watch out for what’s best for the organization,” Cole says. “When everyone has the greater good of the organization in mind, that is the best type of risk mitigation strategy.”

When Cole looks back on mistakes the company has made over the years, he’s quick to identify that the most impactful ones have been personnel-related. Several years ago, Cole explains, they added some middle managers to the mix without really taking the time to identify what kind of person needed to be hired or promoted to these positions.

“Your frontline workers are so important. Making sure they are being empowered and motivated by a great manager is so crucial to your business,” Cole says. “Earlier in our business journey, we did not put enough emphasis on our people, and it was evident in our culture for a while.”

Cole’s advice to other business owners is to never make a decision without considering how it will impact employees. He says it’s easy to see dollars and overlook the value of investing in and genuinely caring about your team – whether that’s a landscape technician or a C-suite employee. “People first,” Cole reminds. “Profits follow.”

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Cole’s advice to other business owners is to never make a decision without considering how it will impact employees. He says it’s easy to see dollars and overlook the value of investing in and genuinely caring about your team – whether that’s a landscape technician or a C-suite employee. “People first,” Cole reminds. “Profits follow.”

Looking Ahead

It is that “people first” mindset that has driven – and will continue to drive – Weller Brothers Landscaping’s strategic growth into the future. Take acquisition opportunities, for example. Cole is approached frequently by companies looking to sell their business, and he turns many of them down. He explains that while acquisitions are a great vehicle for strategic growth, they are impossible if the people don’t jibe. “Like everything,” Cole says, “the ‘people first’ mindset applies to acquisitions and strategic growth. Not everyone is a fit at Weller Brothers.”

As the Weller Brothers team looks ahead to another 22 years and beyond, they can’t be certain what the next big move or announcement will be. But there always seems to be something big in the works at the company. Just don’t tell teenage Cole and Brent that they probably won’t sleep more and work less in the future, after all.

Weller Brothers Landscape ProfessionalsMiller is the marketing manager for Weller Brothers. In her work, she thrives at the intersection of creativity and data. At Weller Brothers, she enjoys the positive team culture and high standards for exceptionalism. Before joining Weller Brothers, she gained a variety of creative and marketing experience through operating a videography business, doing creative marketing for a non-profit in Uganda, and spending five years in the automotive marketing industry. From South Dakota, she graduated from the University of Sioux Falls with a degree in media studies and journalism. 

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