Shepherd has always been a keen sportsman although his rugby days ended when he moved to Hamilton Boys' High School and found himself "getting pushed around" when he weighed only 34kg.
Hamilton Boys' rowing coach Glenn Ross eyed Shepherd for the coxswain's seat and he quickly enjoyed the new sport, buoyed by early success. He was part of the under-15 crew that won plenty of silverware that year as he came to grips with the vagaries of the role.
"Some might say I am a yappie bloke but I wouldn't say so," he said.
"The main priority for a cox is to steer the boat on a straight course. I have to convey the tactics to the crew, make the technical calls and provide the motivation."
Success continued in bucket loads for Shepherd at Hamilton Boys', including the famed Maadi Cup-Springbok Shield double in the eights and fours respectively in 2010, earning him the trophy as leading coxswain.
That year he was selected for the New Zealand juniors, finishing sixth in the coxed four at the worlds and second the next.
Shepherd advanced to the under-23 national team in 2012, winning a bronze medal in the coxed four. He moved to the under-23 eight in 2013 which won the gold medal at the world championships, a feat they repeated at Varese in July.
"That was so much pressure. Having won it the year before, we felt the pressure to repeat it."
Coxswains keep an eagle eye on steerage and the speed of the boat, before conveying the pre-arranged team tactics to the crew. Sometimes a different call is needed on the water.
"We were set to make our move at the 900m mark in the final at Varese. But at 750m we had moved to the lead and I decided to make that move early, so we could bust the race wide open and control it in the second half. It worked out perfectly."
After their success Shepherd headed to Belgium to join the elite team, and the daunting task of coxing for Bond and Murray. The duo is famous for being unbeaten for several years in the coxless pair, but wanted to add the coxed pair to their CV.
"I was so focused on the under-23 eight I did not think about the pair until I went to Belgium. I was a bit overawed at first. I had only been approached a few weeks before going away," said Shepherd.
"I was actually quite relaxed on race day. After all, I had Eric and Hamish behind me who are the best in the world. I just had to do a good job for them.
"I've not had a chance to really take it all in yet. My focus right now is very much on this weekend's Gallagher Great Race."
The novel river race will demand plenty of Shepherd, navigating under three bridges, steering around the bends and ensuring the crew last the longer 3.8km distance.
"I know the river well from training days at Hamilton Boys'. I just have to remember."
The Gallagher
When:
Today, 8am to 4pm - Corporate and schools competition.
Tomorrow, 10am - Corporate and schools finals; 11.30am - Haka performance; 12.20pm - Women's race; 1.25pm - Men's race.
Where: On the Waikato River based at Grantham St.
Entry: Free.
Online: www.thegreatrace.co.nz
