The son of a tradesman and an executive assistant, Drury credits his interest in technology to one of his teachers at Napier Boys' High School.
"[He] was getting computers into the classroom - this was back in the eighties. That was where my passion came from, being able to take computers home and play with them, learning to programme and all of those things. It really goes back to sixth and seventh form," he said.
From high school, he went on to study Commerce and Administration at Victoria University of Wellington.
He then worked at accounting firm Arthur Young, which became Ernst & Young after a global merger in 1989.
In 1995 Drury co-founded the software firm Glazier Systems, which sold four years later for $7.5 million.
His next project, AfterMail, was bought by California-based Quest Software for an amount thought to be as high as US$65 million ($85 million).
His latest venture, online accounting software company Xero, began in 2006 and is listed on the NZX.
Xero replaces software-in-a box with a service running over the internet. It is payable by subscription and has processed more than $50 billion of customer transactions.
The company was named as New Zealand's fastest growing exporter in the Deloitte 2011 Fast 50.
If he didn't move into business, Drury reckoned he would have ended up as a professional skateboarder.
"That would be my dream job," he said. "I was into board sports so after university I did a ski season down in Queenstown, right when snowboarding was first starting. It was either do a ski-instructor's course, or go and work for Arthur Young in Auckland and, actually, I was really interested in business so I went and did that," he said.
Drury said he still enjoys both surfing and skateboarding in his spare time.