When Stephen Lockwood joined insurance company Crombie Lockwood in 1983 he reportedly slept in his car on sales trips because the firm could not afford to put him up in a motel.
But such parsimony paid off because over time it grew into one of New Zealand’s largest insurance providers with annual turnover of more than $100 million.
And when it was sold to ASX-listed conglomerate Wesfarmers in 2006 for an undisclosed sum Lockwood was one of the principal beneficiaries.
As one of Crombie Lockwood’s largest shareholders he walked away with a tidy sum – allowing him to build up a property portfolio worth more than $100m, mostly held in trust arrangements.
Two homes in Herne Bay’s exclusive Cremorne St, the country’s most expensive, have a combined value of about $36m while residential interests include Waiheke Island, Taupo, Papamoa and Lake Tarawera.
There is also the 28ha Motukiekie Island in the Bay of Islands, a $5.1m retreat he bought in 2001 for $2.5m.
More recently Lockwood has been dabbling in commercial and development property.
The jewel in the crown appears to be a significant investment in what was the second stage of Queenstown’s Five Mile development that emerged from the wreckage of Christchurch developer Dave Henderson and Hanover Finance in 2008.
Interests associated with Lockwood and Carl O’Shea, also a former Crombie Lockwood shareholder, are understood to own a 23.3ha development block on the opposite side of Grant Rd, next to Five Mile.
In May 2016, a listed Singapore company snapped up a 3.84ha block on the site for $19.2m.
Lockwood is also active in metropolitan commercial property, with interests in a $27m office block on Auckland’s Queen St and the $20.7m Breakfree Hotel in Christchurch (in conjunction with fellow Rich Lister Brett Russell).
Lockwood’s hobbies include classic cars and last year he bought a 1934 Bugatti Type 57 Gangloff Roadster that once belonged to the late Kiwi engineering legend Bob Turnbull.