Brought up on a lifestyle block at Gore, his interest in agriculture was from a young age, with his connection to the land largely through family members farming on the Taieri.
Mr Gregory (23), who now works at Mount Linton Station, spent four years at Lincoln University studying for an agricultural science degree, with honours, with his honours project looking at beef cow efficiency.
Finishing in 2015, he headed to Mount Linton, in Western Southland, for a job as a farm technician on the 12,500ha effective property.
Originally the role was advertised as a genetics intern and one of his passions was genetics. But it was advertised in spring 2014 and he applied, knowing he still had one year left at university.
It was a new position and the station's management was not in a rush to fill it, so Mr Gregory worked in his holidays at Mount Linton until he finished his degree and then started full-time.
Within that time, the farm technician left and the role was split across three people. He also continued with the genetics role, which made up about half his job.
The position also involved doing pasture covers and inputting that information into the feed budget and helping the stock manager with monitoring weights and doing condition scores, and then there was general shepherd work.
Mr Gregory had to build up a team of dogs and the staff at Mount Linton had given him a lot of help with his dog work.
His tertiary studies gave him an understanding of the technical and theoretical side, but it was not until he got to the property that he got a really good practical grounding in large-scale stockmanship and stock skills, he said.
Vice-chairman of Nightcaps Young Farmers Club and also of the Otago-Southland region, Mr Gregory completed his second FMG Young Farmer of the Year regional final this year.
He was fifth last year and fourth at this year's regional final at Roxburgh, so was ''moving in the right direction'', he quipped.
Mr Gregory was keen to take it a step further and win a regional final, enabling him to compete in the grand final, but intended to take a break to gain some more experience.
As a secondary school pupil, Mr Gregory was runner-up in the TeenAg grand final with Richard Gardyne, although he good-naturedly admitted it was somewhat of a sore point, as his brother Robert went one better and won the national title.
In June, Mr Gregory is heading to Scotland to represent New Zealand in a youth competition at the World Angus Forum.
While still at school and through his first couple of years at university, he was involved with showing beef cattle and became involved with the Angus breed. He also did the youth programme Future Beef for about four years.
He had also become a member of Generation Angus, the youth programme for Angus New Zealand, and went to Australia in the summer of 2014-15 on a transtasman exchange, visiting 20 Angus studs in New South Wales, Queensland and Victoria.
All that involvement gave him a strong network in the beef industry and helped him to get his role at Mount Linton.
Competition for selection to travel to the World Angus Forum was ''pretty tough'' and he was the only southern representative in the eight-strong team. Marie Timperley is the only other South Islander.
The event included stock judging, preparation of animal and handler and general farming activities and knowledge.
Several days would be spent at the Royal Highland Show and time with World Angus Forum delegates.
There was a trip planned to Scotbeef, one of the UK's largest privately owned fresh meat companies, and some other farming operations.
Once duties at the forum were completed, he intended attending the International Farm Management Association's conference in Edinburgh.
Short-term, his career plans involved hopefully moving into a stock manager's position and, in the future, looking at operations manager/equity manager roles in order to eventually get into farm ownership.
There were many challenges in the farming sector - ''I'd say there's a lot more than a year ago'' - but it was a matter of working together collaboratively to work against those challenges, he said.