He made his name with the irreverent Mambo surfwear brand he co-founded in the 1980s, but to Dare Jennings, the surf culture was always more than just riding waves.
"I'm a product of the '70s, and in those days if you surfed you had a motorbike those two things just went hand in hand," the 61-year-old entrepreneur says. "So I had this idea of wanting to combine motorcycling and surfing back again."
Having sold Mambo, infamous for its flatulent fidos and beer-loving Australian Jesus artwork, for more than $20 million in 2000 to the giant rag trader Gazal Corp, he eventually revisited those old days - and came up with a new business idea: Deus ex Machina, a business inspired by a time when motorcycles had surf-racks rather than high-tech gimmicks, and their owners would spend their days tinkering and fidgeting in their workshops.
Jennings teamed up with a friend, motorcycle shop owner Rod Hunwick, and graphic designer Carby Tuckwell, in late 2005 to start the fast-growing custom motorcycle emporium operating out of Camperdown. (A fourth partner, racer Nigel Begg, left the business two years later.)
Built around customised motorcycles, surfboards and bicycles, combined with trendy cafes and a clothing line inspired by the rough aesthetic of the motorcycling culture, the company has since branched out to Bali and Los Angeles and grown into a business with more than 130 staff and some $10 million in turnover. Hollywood stars Orlando Bloom and Ryan Reynolds ride Deus bikes, adding to its growing international following.
The inspiration came during trips to Japan when Jennings saw young guys stripping the panels off their bikes to modify and hand-tune them into the machines they wanted, referencing the British cafe racer motorcycle culture of the 1950s in a contemporary way. It was going "back to simple things" in a counter-trend to the motor industry where bikes were becoming ever more powerful and technology-focused, he says.
The romantic notions of "wind in your hair and thunder in your guts", as Deus markets itself, could provide the platform for a combination of profitable businesses, Jennings realised.
He invested some of the millions he made selling Mambo to transform a former factory building on Parramatta Road into Deus's headquarters - a cafe serving barista-made coffee and burgers with an adjacent showroom selling customised Yamahas, Kawasakis and Triumphs, Deus artwork and clothes as engines rev in its workshop at the back.
The company soon also tapped into the trend for single-speed, fixed-gear bicycles, then added surfing products. About 18 months ago, Jennings opened a Deus motorcycle and surfboard compound in Canggu, Bali. Another outlet opened in Venice Beach, California, early this year.
But come on, isn't this all about toys for middle-aged boys, or worse still, boys having a mid-life crisis?
"That really annoys me because it's not like that at all," Jennings says. "If that's all it was, the business wouldn't run like that," pointing to the mums' group, young professionals and artsy types that frequent the Deus cafe during our interview.
The motorcycles, stripped back, then stylishly rebuilt and sold for between $8000 and $50,000, may be at the heart of the business. But in fact, about two-thirds of the turnover is generated by selling T-shirts and other clothing, which is also distributed via licensing agreements throughout countries in Europe, South America, Canada and Asia, emulating the success Jennings had with Mambo.
"We're all kind of one-trick ponies, so we end up doing the same things," he explains. "I'm essentially from the clothing industry and I knew clothing was a scaleable business, whereas modifying motorcycles, while it's fun, it's a business that can't go very far."
Jennings grew up on a farm in Griffith, buying his first bike - a World War II surplus Harley-Davidson - off a "local hoodlum". Escaping to the city to study literature at Sydney University for an "all-purpose arts degree," he soon threw himself into the left-wing scene and anti-Vietnam War movement.
He taught himself how to screen-print T-shirts for his "various enthusiasms - trucks, rock bands and comics", and started running a factory doing contract work for big customers such as Coles in the emerging T-shirt boom.
It was the late 1970s, the days of a burgeoning punk music scene in Sydney. Influenced by his musician friends, Jennings started another business, Phantom Records, an independent music store and label. "We weren't business people, it was just doing it for fun and trying not to go broke in the process," he recalls. Phantom released records for bands such as the Sunnyboys and the Hoodoo Gurus.
Mambo Graphics began life as an after hours project in his screen-printing company, Phantom Textile Printers, seeking to counter the surf giants Rip Curl, Billabong and Quiksilver with a punter-driven, self-deprecating brand "that encompassed everything that my gang felt was important", Jennings says.
As its following grew, he retreated from the music business. Mambo was turned into a stand-alone business by Jennings and his business partner Andrew Rich in 1984. Reg Mombassa, one of the founding members of rock band Mental As Anything, joined as a contributing artist two years later and would help give the label its defining style.
Looking back at his Mambo days, Jennings reckons it's still a miracle how he, as a "radical left-wing, university drop-out, dole-bludging, comic-reading, pot-smoking, surfing, rock'n'roll ratbag with a very short attention span", managed to turn his and his mates' foibles into a global business.
He says the start of Mambo's decline began in the John Howard years, when "dissent and satire sort of went out of fashion, people were more interested in making money". But its terminal problem was the fact that "the new owners didn't respect the importance of the culture they had inherited", managing the brand towards youth-culture oblivion.
The label has since changed hands again and been relaunched to take it back to its surfer roots.
Talking to the self-made millionaire, it's clear Jennings is passionate about his ventures and has little patience for the corporate thinking of business schools and MBAs. He doesn't think much of market research and consultants, banking instead on his instincts of "having an idea and seeing if you can make it fly".
"You can make a business as efficiently as you like, but if it doesn't have a soul, a culture and a tangible purpose, there's not much point to it," he once said in a speech.
Jennings says he sold out of Mambo when he started losing the passion for it.
Starting Deus (pronounced Day-oos), one of the biggest pitfalls was adjusting back to the scale of a small business. Having enough money to go in big, Jennings created a sizeable overhead and then had to wait for revenues to cash up the business.
True to form, he ignored advertising people who said a Latin business name would be detrimental as no one knew how to pronounce it. Derived from Greek theatre, Jennings said he liked "Deus ex Machina" for its literal meaning, "God is in the machine - it's the respect of the machine. And then I realised we could put God on everything, which is pretty funny."
Does he want it to grow into another Mambo? "Like any idea, you would like to see it grow and see where it can go," he says. As the company began expanding, the Deus partners brought the merchant banker Barry Davies, who advised Jennings during the Mambo sale, into the fold. "As things get more complex, you just need a merchant banker hanging around," says Jennings, who owns 55 per cent of the company.
And there are big plans afoot. Deus has attracted the attention of the former Ducati boss Federico Minoli, who has been working on an investor consortium to open a Deus franchise in Milan. The clothing label will be introduced to the Italian market at a menswear trade fair in June.
"They want to do the whole thing, build a restaurant, build motorcycles," Jennings beams.
Yet walking the tightrope between business and passion once again, he's wary of going down the franchise route on a grander scale. "The problem just becomes managing it. Everywhere we've gone so far, it had a reason. As soon as you just start opening them for growth, you lose control of it very quickly."
Now in his 60s, will Deus be his last business venture? He laughs that his last big project will be an action-filled retirement home for men in Indonesia, far away from the peach-coloured safety of Australian nursing homes.
"I spend a lot of time in Indonesia and people just live much more robust lives. It would have things to do and men could be men and fix things, ride motorbikes and hopefully enjoy themselves."