The awards aim to highlight the top entrepreneurs from around New Zealand. From hundreds of nominations, 16 finalists are chosen to compete in five categories: young, master, services, products and technology. From here, the winners of each category go on to compete in the finals.
Radcliffe was competing in the young entrepreneur category, having founded IVHQ when he was just 22.
"I was blown away just to win young entrepreneur so when I got told that, I was really stoked. Even at that stage, people down here were stoked with that and really supportive. I guess it's a little bit cliche but it's a nice reward for a lot of hard work over the years."
The four other finalists were BCS Group chief executive Patrick Teo, WhereScape chief executive Michael Whitehead, Vend chief executive Vaughan Rowsell and CBD Goldair chief executive Mark Rice. The five finalists then went through a further examination process to choose the winner.
At a gala dinner at the Langham last week, Radcliffe was awarded the title of Entrepreneur of the Year, taking the win with high scores for national and global impact and for innovation. The awards judge chairman Greg Cross says Radcliffe epitomises the next generation of young entrepreneurs coming through and is almost a prototype of what he hopes they will see more of.
Radcliffe follows last year's winner, Xero chief executive Rod Drury, and says he is thrilled with the accolade, which validates the work his company has done in the seven years it has been operating.
"It's been incredible so far, the type of people I've met and the whole process run by EY has been awesome," Radcliffe says.
After high school, Radcliffe headed to Otago University to do a bachelor of commerce. He enjoyed the experience so much, he stayed on to do his masters. That done, he got a job in a corporate office in Auckland and headed for the big city. Three days in, says Radcliffe, he realised he hated it.
"I just didn't like it. I was there and all I could think was this is terrible, surely this isn't it, this isn't what I've worked towards. So I tried to get a bit of an insight into what I was going to be doing for the next few weeks and months and it didn't look like it was going to get any better so I quit. It went down terribly at the time, but I knew that it wasn't what I wanted to do."
Mid-way through this quarter-life crisis and not sure where he was going, Radcliffe packed up and went to volunteer in Kenya. He spent three months living in a mud hut in a small community, with no electricity or running water, doing volunteer aid work. He attributes a lot of his success with IVHQ to this trip. It was when he returned home and added up the cost of his volunteer work that his years in business studies kicked in and he realised the programme could be done for much less money.
"The seed got planted when I first started looking at options because I was blown away by the cost. I had friends going to Europe at the same time as me who had finished uni and were doing a gap year," Radcliffe says. "Some of them were doing Contikis and travelling through Europe, and I had a chat to them and worked out what they were paying and I realised that I was paying the same and more for the same timeframe. It raised a few question marks for me." From here, Radcliffe started up the company, focused on providing an all-round experience for volunteers but at a much more affordable price. Starting out, he says, his age was his biggest problem. Trying to convince parents to send their kids overseas through his programme, or getting partner companies on board, was difficult.
"When I started the business, it was a pretty sort of grand idea at the time and the things I was doing and trying to set up were pretty large for a 22-year-old to be doing.
"You do question yourself, when you're at the stage of submitting the company registration through to the companies office and you're trying to explain to people what you're trying to do and they're looking at you sideways - having people around you that are supportive is really important."
Despite those hurdles, Radcliffe has managed to build up his volunteer travel company, and with his team of 24 staff in New Zealand and partner teams all around the world, he has sent more than 39,000 volunteers to 27 countries, helping in areas from teaching through to wildlife conservation and medical aid.
While the journey has been hard at times, he says he would not trade where he is now for anything.
"It has definitely not been easy; if you talk to my girlfriend she'll tell you it absorbs my life 24 hours a day. If I'm not on an email I'm thinking about something we're doing or how we can improve it, but it's so rewarding.
"It's rewarding as a business, it's rewarding to get awards like this but I think more than anything else, it's rewarding to see the impact that we can make on a global scale, starting from nothing."