Analysts say Rural Portfolio Investment's problems stem from taking on too much too soon.
After Mr Norgate left Fonterra in 2003, he and the McConnons set about reshaping agriculture through PGGW investments in the ailing wool and velvet sectors designed to change their business model.
Both investments have yet to pay a dividend.
Mr Norgate tried to do the same with the meat industry, entering a partnership in 2008 with Silver Fern Farms in a deal which would have cost PGGW $220 million for a half share in the Dunedin meat company.
The deal was never completed due to the economic recession, and eventually cost PGGW $42 million for failing to settle the partnership.
Baird and Alan McConnon got their start turning a small Otago dairy-processing business started in 1954 by their father Peter, into an exporter with reported annual turnover of $700 million.
It was bought by Fonterra in 2006 and the Dunedin factory closed with the loss of 130 jobs, but Fonterra kept the brand, and Mainland dairy products are still sold throughout New Zealand and Australia.
In 2004, the McConnon family were new entrants in the National Business Review Rich List, with a fortune estimated at $70 million.
After selling Mainland, the McConnons formed a family investment company, Aorangi Laboratories, which has investments and the McConnons' directorships in Sabcon Ltd, Lifevent Medical Ltd, Vinpro, Mt Difficulty Wines, Innovative Learning, engineering firm DC Ross, 45-South Exports and 45-South Management.
The McConnons had dealings with Mr Norgate, who as chief executive of Kiwi Co-operative Dairies bought a cornerstone stake in Mainland.
In 2001, Mr Norgate became Fonterra's founding chief executive but that ended in 2003 after a dispute with chairman Sir Henry van der Heyden.
Mr Norgate then joined forces with the McConnons to form RPI.
The New Zealand Herald reported yesterday Mr Norgate may head offshore.
"I do feel as though I've done everything I can to New Zealand agriculture. Even [in] the areas that there might be unfinished business, people know exactly what needs to be happening.
"It's 25 years I've been involved here now and I don't feel as though there's that much new I've got to offer. So you can take it from that that I will be considering other things," he was reported as saying.
