“It was pivotal in that it somehow made sense of everything.” Dare Jennings is remembering the moment in 2004 when he was captured – in board shorts, a guitar in his lap – for the cover of The Australian Financial Review Magazine. Fresh from flogging his iconic surfwear label Mambo four years earlier, Jennings was the poster boy for a story on a generation of entrepreneurs, from David Smorgon to Laurence Freedman, who had cashed in their empires and were eyeing the horizon.

It was the early days of a new millennium. Business’s old order – gold watches, captains of industry, stable, lifelong careers – was passing. For most, the future had yet to announce itself, though. And for Jennings, it suddenly looked a lot like that cover, which would play, he now reveals, directly into his next big move, Deus Ex Machina, the international bike-and-fashion brand he launched 18 months later.