Team-building tips for work and play

Published on December 29th, 2022

The Winning name is well-known in Australian 18-Skiff racing, but their lease of the 100-f00t Comanche maxi racer earned them the elapsed time win of the 2022 Sydney Hobart Race. Skipper John ‘Herman’ Winning Jr explains how as chief executive of his fourth-generation family company, he combines sport and business.


As the 38-year-old retail boss who just won line honors with his crew on board Andoo Comanche in the Sydney to Hobart yacht race, he says analyzing data is crucial to his success in sailing and business.

Race authorities handed Winning and his crew a magnum of champagne after they crossed the finish line in the early hours of Wednesday morning. They sprayed half of it over the boat and each other before drinking the rest.

Winning was aboard Perpetual LOYAL when she won line honors in 2016, but this was his first success as skipper. He sailed alongside his father, John Winning Sr, who won Sydney to Hobart line honors in 1976.

Sail GP

“It was really incredible,” Winning tells The Australian Financial Review. “My Dad said he was ‘tickled pink’, which sounds like something an old man would say. It was a special moment and I got to stand at the helm across the finish line. I was almost in tears.”

About six months out from the race the younger Winning, who is chief executive of the century-old family business Winning Group that includes Appliances Online, Winning Appliances, and online shopping website Andoo among others, took two apps from his business world into sailing. – Full report


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The 628 nm Rolex Sydney Hobart Yacht Race is the 77th edition in 2022 and had a fleet of 109 boats for the start on December 26. One hundred fifty seven teams set off in 2019, but since then the 2020 race was cancelled due to the pandemic with 88 entries in 2021.

From the start in Sydney Harbour, the fleet sails out into the Tasman Sea, down the south-east coast of mainland Australia, across Bass Strait (which divides the mainland from the island State of Tasmania), then down the east coast of Tasmania. At Tasman Island the fleet turns right into Storm Bay for the final sail up the Derwent River to the historic port city of Hobart.

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