"At 17 years old I was snatched up by the Auckland Warriors and went on to play for the NZ Sevens side at the Coca-Cola World Sevens in Sydney," he said.
"From there the St George Illawarra Dragons signed me up and I moved back to Australia as a 19-year-old. The rest is history."
Cullimore then went on to play for a variety of rugby and rugby league teams.
"I was a rugby league player to start with. I had stints with Auckland Warriors, Illawarra Steelers & Manly Sea Eagles," he said.
"I then went on to play for the Junior Kiwis and NZ Maori Sevens. But then I switched to union where I got my start with NSW 21s. From there I went on to Australian Barbarians, Aussie Sevens and Super Rugby's NSW Waratahs."
But after a long time as a professional rugby and league player he called it quits, citing that he "lost the drive".
Following this, a chance encounter with a sevens teammate turned him to the sport of bobsledding.
"I got through to the top eight out of 50 hopefuls at the national trials and made the squad to go to the Olympic training centre at Lake Placid, North America," he said.
Unfortunately I snapped my Achilles three months out from Vancouver. So it was game over for me and my Olympic dream. That was a tough one to deal with."
For most people, the journey would have stopped there. But Cullimore turned to another sport: MMA. He credits this as the sport that made him continue his sporting journey.
"It truly shows how mentally strong you actually are," he said.
"That changed a lot about my outlook on life and that I still had a fire burning inside to compete at a high level. That sport helped me get back on track again."
Now Cullimore is putting himself through a new challenge - bodybuilding.
"I loved Mr Olympia and Arnold Schwarzenegger, but it just wasn't possible as a footballer," he said.
"So when I got the opportunity and time, I found ex-Waratah player Kevin O'Kane, who was the coach of Ryan Laos who is the first Australian natural BB world champion. I thought he'd be able to get me looking like a body builder. And that was it."
Still a relative novice in the sport, Cullimore has his eyes firmly set on world titles.
"Mr Versatile" finished third in the International Natural Bodybuilding Association Australian Pro qualifier, which gives him entry into next year's Mr Natural Olympia.
But it hasn't been smooth sailing for him.
"My posing was rubbish, my coach pushed me hard to practice but I thought you just go out and flash your body with a few flexes. Boy was I wrong," he said.