Where he has risen to the challenge, however, it is through his willingness to try almost anything, his dogged refusal to give up and his creativity in finding solutions to sticky problems.
Throughout his 50-year career, Yealands has been a mechanic, industrial painter, fisherman, fencer, shearer, hay contractor, coal merchant, paver, builder, mussel farmer, timber exporter, deer farmer, developer and, finally, a winemaker.
Some of his career choices, such as rabbit farming, were understandably short-lived.
Others, such as deer farming and aquaculture, he pioneered, making it up as he went along with his number-8-wire, can-do approach.
In the past two decades he has become an environmental champion, and Yealands Estate was certified CarboNZero at its inception.
"We are approaching self-sufficiency here. The goal is to eventually sell power back to the grid," says Yealands.
Among the usual carbon reducing initiatives such as wind turbines, solar panels and a vehicle fleet run on biofuels, are some of Yealands' own ideas, such as the Babydoll sheep, a small breed that keeps the grass between the vines mowed but cannot reach the grapes, and boilers, which burn vine prunings to heat the winery's water.
Regularly making the New Zealand rich list, Yealands has been critical of the reporting.
"When they said I had assets of $70 million, I probably had closer to double that, but unless I'm mistaken and I hope I'm not, they can't know the specifics of your bank debt."
The book also traces the spat between himself and wine baron Jim Delegat over Yealands' attempted takeover of the Oyster Bay vineyard in 2005.
Yealands believed that Oyster Bay, which had an exclusive deal to supply all of its grapes to Delegat's Group, should have been more profitable.
He made himself unpopular by asking questions about the price Oyster Bay was receiving for its fruit.
A bidding war ensued which was won by Delegat's but overturned in the High Court, sparking another round of share-price one-upmanship.
Legal issues persisted throughout 2009 and, finally, the matter was settled out of court in 2010, with Delegat's increasing its shareholding to a 54.9 per cent majority and later taking full ownership through a takeover.
Yealands says he is content at the winery, but insists he has plenty of other ideas.
"Whether I'll get them done I don't know.
"The way I look at it, the day I run out of ideas, I might as well die."