The years since have seen massive changes in the sector. While many point to the growth of online retailing, Wilkinson says that's just one factor, with changes also in consumer patterns and behaviour. Reduced discretionary spending has also vastly altered the landscape.
The growing pace of technological change is a topic on the lips of everyone in business these days, but those conversations began much earlier in some sectors than others.
Wilkinson says his involvement in the photographic industry, among the earliest sectors disrupted by digital technology, offered him insights he was keen to take into consultancy.
"Photography was one of the first sectors that transitioned with new digital technology, before books or even CDs ... That's really helped us understand how sectors can change and how to manage those changes properly, so we've developed a bit of a speciality in working with sectors going through extreme change."
Wilkinson says his ambitions are now focused on building the resilience of the business.
Currently about half of First Retail Group's business comes from overseas - primarily the UK, the Pacific Islands and Australia - and Wilkinson says he sees this as a key measure of the company's success.
"I feel very successful travelling around the world seeing our clients in action. I feel a tremendous amount of success putting my suit on in the morning and going to work in a different country."
Wellington's growing reputation as a hub for technology companies means the firm is often exposed to new ways to employ technology in its operation. A lot of the company's work overseas is carried out remotely from the capital. Wilkinson says this is key to maintaining a good work/life balance, which he cites as another measure of his success.
Given so much of the firm's work is relationship-based, says Wilkinson, getting the right people to maintain those relationships has been the biggest challenge.
"So it's about keeping the team small," he explains, "and not chasing all the work that's out there. Naturally, commercially, you want to pick up every piece of business but we've realised that it's like a marriage, where we want to have clients that we love and we want them to love us."
Running your own business can also be a lonely road but Wilkinson says he's developed a strong peer network to share successes, challenges and ideas.
Having started in business at a young age, Wilkinson says it's a pattern he's keen to continue. One thing is for certain, change will be a constant. "The big question we get from businesses is, 'When is everything going to stop changing?'," he says. "Well, it won't - but that's what I think is so exciting."
ASB Ambition
Part two of a Business Ambition series in partnership with ASB, based on a survey conducted over the past six weeks and giving insights into the ambitions, concerns, wants and needs of NZ businesses.