"It's a rare trade. You tackle something different every day."
The business was founded by Winter, Barry Shane Richards, and Te Riaki Hawira, with Dominic Rogan and Harry Josephs coming on board to form a five-man crew.
While Treestylers is a new venture, they bring over 30 years of experience to the operation.
"We can do it all - pruning, tree dismantling, stump removal, the works," Winter said.
"We'd like to venture into the schooling side of things, and show rangitahi out there that this is a good career path to head down.
"In a year or two it would be awesome to be able to run a training facility of some sort."
Winter said building a client base and getting solid contracts was the next step for the business.
"We are getting all our staff fully qualified. We'll keep ticking all the boxes in terms of health and safety as well.
"You need to do a three-year apprenticeship, which gets you a national certificate in arboriculture."
Dominic Rogan said he and Winter had been working together for 17 years.
"We are tree doctors, really," Rogan said.
"I started arboriculture way back in the day with Treeco, working for Michael Hussey.
"I guess you could say we are the kaumatuas around here."
Another of Winter's passions is competitive tree climbing.
He's been crowned regional champion seven times, placed second in the national competition, and has represented New Zealand in the Asia Pacific and World championships.
Winter said he hoped to pass the torch to another member of the Treestylers crew soon.
"There's a few lined up, they've just got to put the hard work in themselves.
"I'll help them out where I can."
Like Winter, Barry Shane Richards said he fell in love with arboriculture immediately.
"I started by doing a course down here in Whanganui for thoughtplanters," Richards said.
"From there I worked for a couple of companies, and now we've got one of our own."
Winter said work had continued to come in, despite Treestylers doing little in the way of advertising so far.
They have released an inspired, "Freestyler" themed promotional video sung by actor Tammy Davis, however.
"When Te Riaki Hawira started this up I was a stay at home dad," Winter said.
"He needed a hand on quite a big job so we helped him get set up. It's been all go since then.
"Money grows on trees, they say."
