Seasoned coach

Jason Cupp spent the bulk of his career building a landscaping business in Kansas City, Kansas, but his biggest passion is helping other business owners succeed.

After growing and managing a landscaping business for 20 years, Cupp resolved to give back to others in the industry by volunteering time to industry associations and starting a consulting service. He began his consulting business about 10 years ago, and today he helps hundreds of clients across the U.S., many of which are in the green industry.

Even though Cupp has developed an extensive client list, colleagues describe him as personal and down-to-earth with everyone he helps. Julie Farrow, founder and president of Plantscapers – an interior plant design firm in Irvine, California – attributes her business’ growth to Cupp’s consulting work.

“Without his prodding and strategy, we would have kept dragging our feet (on a decision),” Farrow says. “I think we’ve grown 45 percent with his leadership. His level of consulting is something you don’t see in the green industry a lot. He’s reasonable and passionate about his clients and what he does – it’s infectious.”

Unintended career path.

Cupp first landed in landscaping almost by accident at 12 years old. “My dad was doing some part-time real estate at the time, and he had two relocation properties that needed to be mowed,” he says.

Cupp spent his weekends mowing two properties for about $100 per week. What started as a weekend job eventually turned into a business. Cupp officially launched The Kincaide Company in 1986 to service customers in Kansas City.

Cupp didn’t plan on pursuing a full-time career in landscaping. When he graduated from high school, he went to the University of Kansas to study advertising while working at The Kincaide Company on the side.

However, halfway through college, he received a job from a homebuilder that would generate about $1 million in annual revenue by itself. He says that job opened his eyes to the possibilities he had with his business.

“I started to see opportunity in landscaping,” he says. “I had clients who believed in me, and I saw myself making money and building careers for other people around me.”

Cupp received his bachelor’s degree and decided to focus full-time on growing his company.

Donating time back.

Cupp never received a formal education in landscaping or business, so he credits a lot of what he learned to trade publications and associations. In particular, he learned a lot from industry leaders involved in the Associated Landscape Contractors of America, today known as NALP. Cupp says he connected with many industry leaders who came before him – Jim McCutcheon, Ron Kujawa and Frank Mariani, to name a few.

In 2004, after a few years of learning from these leaders, Cupp signed up to be on the association’s board of directors. Cupp joined ALCA’s board at a challenging time.

Dan Foley, the president of DHCC Management Corporation, says the association was going through a merger with PLCAA, the national lawn care association. The two groups officially merged in 2005 and were renamed the Professional Landcare Network.

“It was an interesting time for the national association,” Foley says. “There were two national associations that got together and a whole group of people coming together – doubters, believers, old-timers and new-timers. (Jason) continued a legacy of leadership in an important time. He (took) his role as a leader with extreme responsibility to the point where I think sometimes he cared more about the association at times than for himself or his own business.”

Sabeena Hickman was also joining the association around that time as its new CEO. The association was in the process of moving and merging its national education event, now called LANDSCAPES, into the Outdoor Power Equipment Institute’s GIE+EXPO show. She says Cupp helped to organize and develop what the event has turned into today.

“I know he was spread thin, but I feel like he never showed it,” she says. “He gave 100 percent to everything, which says a lot about his character.”

Coaching others.

As Cupp led PLANET, he also realized he had a passion for consulting work. Cupp received Kolbe Index certification in 2006 to improve hiring in his own business. The Kolbe Index measures people’s natural instincts to help business owners understand their employees better. After receiving the certification, colleagues began asking Cupp about the Kolbe Index for their own companies, including Foley for his business. When Cupp administered the Kolbe Index training at Foley’s business, he says he had the “most satisfying day of work” ever.

“I remember getting into the car and thinking about the long-term impact that day would have on (Foley’s company), their employees, their finances,” he says. “It was the first time in my life that I felt like I had worked, but I didn’t really work.”

At that point, Cupp refocused his career on building his consulting business. In 2009, he officially informed employees of his plans to shut down his business. He sold off some assets and then closed the doors in November.

“Jason has always been one to help others thrive, whether it be through peer groups, his consultancy or helping out a friend,” Hickman says. “He has touched and improved so many businesses, caring for them as if they were his own.”

Since then, Cupp has been fully dedicated to consulting other businesses. He tries to meet with clients in person as much as possible, so he estimates he takes about 140 plane rides each year.

“He does traditional Kolbe certification coaching, but he works with teams on more than that,” Foley says. “He turns different scenarios into coachable moments.”