Josh Canfield, founder, president and CEO of Pinstripe Lawn Care & Landscaping, has been growing his company rapidly, scaling the business up to $6 million in annual revenue in six years, with 90% of the business coming from maintenance and enhancement work.
Canfield’s impressive growth and commitment to innovation in the industry earned him the 2026 Young Professional of the Year award.
“I think it just means that we’ve got the right people around us who pick up on my failures and pick up on downfalls that we have,” Canfield says. “None of this was built by myself. If it was by myself, we would be nowhere near where we are now. It’s just a very surreal moment.”
Canfield originally launched his Guthrie, Oklahoma-based business in 2020 when COVID hit. His wife had just been accepted into graduate school and was pregnant with their first child. He says he started mowing yards as a way to feed his family, but now Pinstripe provides for 40 to 50 families across Texas, Kansas, Missouri and Oklahoma.
He says his proudest achievement is never having laid off a person during the off-season.
“We’ve never had to lay anybody off in the off-season, and that’s been something that, as we grow, gets trickier, but I think there’s a level of commitment that I want to show our guys that they show us in the summertime of working 45-50 hours a week,” Canfield says. “We try to keep our overtime down, obviously. But in the heat of the summer, they’re working and committed to us. How can we be committed to them?”
From the start, Canfield knew he wanted to focus on commercial customers because he could have one contact and take care of multiple properties. As they continued to make these customers happy, they were entrusted with additional sites to care for.
“I think we got into commercial because a lot of it was my sales background,” Canfield says. “I knew how to get in front of them, and I knew that if I called the right person and asked the right questions, then they would get me to the right person.”
Canfield also worked with a developer to create a custom Pinstripe app that their crews, subcontractors and clients use. He says they see their relationships with their commercial customers as a partnership, so each landing page a client logs into on their app has their logo next to Pinstripe’s. They can view photos of job progress, make service requests and more.
“If we have one contact who has 10 sites that they’re in charge of, the selling point in the beginning for us is, ‘Hey, you can’t have eyes on the property at all times, but you can log into our app and see when the last service was and what was done,’” Canfield says.
Canfield credits his company’s rapid growth to them showing up and doing what they said they were going to do. One aspect that Pinstripe is known for their responsiveness.
“I think the bigger thing on how we grew so quick is very early on, I said no if we were full, and I think a lot of companies get that wrong,” Canfield says. “I think they’re just saying yes to everything, and then you look at your schedule and like, ‘How are we going to get any of this done?’ So you either rush through your jobs to try to get to everything, and then no one’s happy, or you can only do half the work, and half your customers are unhappy.”
During his second year of business, Canfield became involved with NALP. He says his company has benefitted from attending events like ELEVATE and Leaders Forum.
Canfield says he has been deliberate about building out his management team and conducting strategic planning from an early stage after attending ELEVATE and talking to Chris Lee and Robert Clickenbeard about it.
“You go to ELEVATE, and you’re like, ‘This is a whole different ball game’” Canfield says. “This is a professional business. It’s not a pickup truck business. Seeing that in Dallas that first year that we went, and I was just like, ‘Okay, this is what I’m looking for.’ But then it’s like, ‘How do we do that?’ And then it was asking questions and talking to Chris and talking to Robert about how do we get there?”
He also credits ELEVATE for how he was exposed to brands like Scythe, which he has been incorporating into his business as a way to help crews visit more properties in a day.
Canfield’s favorite aspect of the business is seeing his vision come to life. For instance, one of his early goals was to have a national account with a dealer.
He knew he didn’t have the volume requirements but reached out to Stanley Black & Decker anyway, sharing their story and their trajectory. Five hours later, they were offered a partnership with Stanley Black & Decker, DeWalt and Hustler, earning huge savings and rebates for the company.
Canfield says they plan to continue to penetrate new markets they’ve moved into and increase their density.
Canfield’s advice to other young business owners in the industry is to follow through and not be afraid to admit to customers when you make a mistake.
“So many people who are probably my age and younger avoid confrontation, and I think it’s so important that you lean into that,” Canfield says. “I don’t think I don’t think you run towards it, but I think you lean into it. Every time we have done that at Pinstripe, our customer appreciates it.”
He also recommends saying no early on when your schedule is full, as you’ll be able to build a better business faster.
Canfield will receive his award during ELEVATE in Tampa, Florida, on Nov. 8-11.
This article will be published in the December/January/February issue of the magazine. To read more stories from The Edge magazine, click here to subscribe to the digital edition.
