Here’s the gist of it: a retirement home for men in South East Asia stocked with fast motorcycles and classic cars where the nurses are young and beautiful and residents can basically do whatever they want. The idea probably wouldn’t go down well with the tycoons on Shark Tank. But it does have one strong thing going for it: it sprang from the mind of a man who conceived two global lifestyle brands generations apart that together have generated hundreds of millions of dollars in sales.

The first, 1980s surfwear juggernaut Mambo, went from making T-shirts with prints of dogs farting and humping legs to the uniforms for the Australian team at the closing ceremony of the Sydney 2000 Olympics. The second, Deus Ex Machina, founded in 2006, sells clothing and merchandise in the massive crossover space between the surf, skateboard, cycling and motorcycle subcultures. It also builds the finest custom motorbikes on the planet, including Orlando Bloom’s V-Twin and Ryan Reynold’s Triumph Custom Bonneville.

His name is Dare. Dare Jennings. Sixty-seven. Multimillionaire. Father of two. Has no idea how many people work for him. Rides a motorcycle to the office. Well, it’s less of an office and more the embodiment of the man-cave fantasies of every red-blooded male: a slick inner-city Sydney warehouse conversion retrofitted with an open-plan restaurant, bar, function space, design studio, motorcycle workshop cut straight out of the set of Happy Days and a showroom full of shit-hot handmade motorcycles dripping in leather and chrome.

Something in the water

“How on earth did a radical left-wing, dole-bludging, pot-smoking surfer with a short attention span manage to turn his mates’ worst failings into a business?” reads a blurb on a talent website spruiking Jennings’ availability as a public speaker – and his insights on branding and innovation – at $10,000 per appearance.

I ask myself the same question as I chart the course of Jennings’ life. The son of a soldier-settler, he grew up on a farm in Outback NSW in the 1950s and 1960s, in what really was the middle of bumfuck nowhere. But instead of spending the rest of his life as Jennings himself puts it “driving a tractor around in circles”, he becomes a fashion pop-savant with an almost Steve Jobs-like ability to invent – and reinvent – the concept of cool.

I find one clue to the mystery in the writings of his older sister Kate Jennings, an Australian novelist and poet who has won or been shortlisted half a dozen literary awards, including The Man Booker. In 1970, during the height of the Vietnam War, she made her famous ‘Front Lawn’ speech at Sydney University in which she told war protesters they were full of shit because more Australian women were dying in dodgy backyard abortion clinics than soldiers were being killed in Vietnam.

“How many of you would get off your fat piggy arses and protest against the killing and victimisation of women in your own country?” she asked the stunned crowd, before adding: “And to my brothers on the drug scene. Grass is good. But instead of becoming happy and peaceful and oh so motherfucking loving all I can see is you sitting, asserting, even grooving in your maleness, dominating every joint.”

Photo: the man himself, Dare Jennings / Gary Friedland

Was there something in the water at the Jennings farm that turned the kids into agents provocateurs? From an Aussie Jesus who preached against homophobia to a Pauline Hanson-inspired Redneck matchbox design, Mambo’s artwork and Kate’s writing were cut from the same cloth: anti-authoritarian, anti-mainstream and politically incorrect. Yet whereas Kate’s world views were formed reading the works of Gloria Steinem and other literary heroines of the second-wave feminist movement, Dare’s was sparked by something far more elemental: the deep guttural exhaust note of an American chopper.

“I was hanging out with some friends in Griffith when I saw a local hoodlum riding around on a big loud Harley-Davidson,” Jennings tells me. “So I chased him up the road, bought the bike off him and started customising it in the garage. It came easily because growing up on a farm we were obliged to know our way around mechanics.”

After high school, Jennings followed his sister to Sydney University. He spent his time there surfing, skating, farting around on motorcycles, basically doing anything but studying until it became pointless to continue pretending he was working towards a degree.

He spent the rest of the 1970s drifting up and down Australia’s east coast. About the same time he got into screen-printing — first for fun then to make a living, selling T-shirts here and there. Within a few years, Jennings had flipped his hobby into a large screen-printing business that made wholesale fabric prints from a factory near Sydney airport. The business was highly successful, but it didn’t make Jennings happy. “I was a leftie and there I was running a factory, arguing with union reps, stuck in a business I detested when all I wanted to do was surf,” he says.

Rise and fall

Fast-forward to the early 1980s in inner-city Sydney, when live rock had exploded onto the scene. “Every pub had bands playing, everyone went to watch them, and then the whole punk thing happened,” Jennings tells.

Denuded of his soul-sucking screen-printing business, he’d teamed up with Jules Normington, the former manager of cult Australian rock band Radio Birdman, and opened Phantom Records, a record store-cum-record label in the heart of Sydney’s CBD.

“All the big bands, the Hoodoo Gurus, the Sunnyboys, they all used to come in,” Jennings remembers. “Around that time I also became friends with Reg Mombassa. He was playing with Mental as Anything but I just loved his art, crazy stuff like fire-breathing chooks. So I asked him if we could use some it for a [record] cover. That’s how we started the label, by combining the things we loved: music and art.”

That led to another idea: combining art with Jennings’ other passion: surfing. “The idea was to use local artists like Reg to make clothing that was totally different to what the other surfing brands were doing at the time,” he says.

“For them, surfing was an inner sanctum. You were either in or out, their messages were sexist and racist. So Mambo was a chance to take the piss out of the surfing industry and it offended a lot of people. But I’ve found out if you piss off half the people, the other half loves you for it. We were stand-up comedians making clothing with dogs that had musical notes coming out their arses — and it worked. We didn’t need focus groups or marketing managers to tell us what the demographic wanted, because we were the demographic. We were intuitive businessmen. It was an easy model to exploit.”

Jennings rode the crest of Mambo’s wave all the way to the Sydney Olympics. But instead of taking Mambo to the next level, the uniforms created for the closing story became the brand’s undoing. “Getting involved with the Olympics made it mainstream,” Jennings says. “Mambo lost its edge.”

Photo: A Deus Ex Custom motorcycle / Gary Friedland

That same year, Jennings sold Mambo for $20 million. Cashed-up and an expectant father for the first time at the age of 50, he looked like a man on a collision course with retirement. But he continued to travel, studying people and their subcultures while seeking out new ideas.

During a trip to Japan, he came into contact with the ‘bosozoku’ — urban motorbike gangs who dressed like the British rockers of the 1950s and rode around on customised motorcycles and scooters.

“These guys were riding around on vintage bikes and wearing vintage clothes but somehow it all looked contemporary. It looked interesting and new,” Jennings says. “So I came up with the idea to bring it all back with Deus. But I didn’t want it to be one-dimensional like Mambo. I wanted it to be a compendium of all the things I like: motorcycles, surfing, art, music — a brand that was more than the sum of its parts. Today, we’ve got stores in Australia, Bali, the US, Italy and Japan. Global turnover is $30 million or something.”

The Heinrich Manoeuvre

I arrange to catch up with Jennings at Deus Ex Machina’s capacious showroom on Sydney’s Parramatta Road on a dreary winter’s morning. It’s not the first time we meet nor is it my first time in the showroom, which is more of a motochic art gallery — a menage of surfboards, books, prints, paintings, fixed-gear track bicycles, vintage luggage and sunglasses, riding boots, helmets, hoodies, T-shirts and jeans arranged round a chocolate box of beautifully handcrafted motorcycles. But it’s the first time I get to see it all on a private tour with the owner.

Deus motorcycles, Jennings explains, aren’t built from scratch. They are individually handcrafted on the skeletons of popular production bikes like Yamaha’s SR400s and Kawasaki’s W650s – “blank canvasses”, as Jennings describes them, for his wrench-monkeys to do their bidding.

The Jap customs are alluring, as are the odd British and American bikes littering the showroom floor. Yet my eyes are drawn to an infinitely more resplendent machine — a motorcycle so exotic it has its own name.

The Heinrich Manoeuvre is a mongrel dog interpretation of the BMW’s R nineT, a cafe-racer inspired monster with a hand-stitched suede seat, a sexy curve of black glass for an instrument panel and a handmade pearl white fuel tank that’s a work of art in itself.

The Heinrich Manoeuvre costs $60,000 — nearly three times the price of the stock standard BMW R nineT. But it comes with a bloody great story. “BMW gave us this bike to see what we could do with it,” Jennings says. “They invited me to pick it up from the factory in Munich, so I brought along Woolie [Deus Ex Machina USA’s chief mechanic Michael Woolaway] and Woolie brought along Orlando Bloom because he was building a bike for Orlando in LA at the time. They took us very seriously when we arrived.”

When the tour winds up, we retire to the Deus cafe where I spend the next hour quizzing my host on how he came up with his big ideas and the business and life lessons we can learn from his experiences. But a few minutes into the interview, two things become abundantly clear. First, my host has been asked these same questions over and over. And second, he has no place running a business, even one as cool as Deus Ex Machina. Jennings wants out.

Photo: Deus store on Parramatta Road, Sydney / Gary Friedland

In 2015, he told The Australian Financial Review he had “advanced sale negotiations” for Deus with L-Capital, the private equity arm of LVMH Group, oneof the world’s largest luxury goods companies. The first time I met Jennings at a Deus event in Bondi in 2016, he also spoke of his search for investors. And today, no matter what questions I throw at him, his answers gravitate towards plans to hand over the reigns to someone who can take Deus to the next level.

Jennings is an inventor. He exists to make things — new things — and anything else is a waste of his time. Like Mambo and Phantom Records before it, Deus Ex Machina is no longer a crazy idea nor an underdog brand. Deus has gone mainstream. It no longer needs Jennings and Jennings no longer needs it. And when the two finally part company, the market is going to want to know what Jennings is up to next — even if it’s something as ludicrous as age-care for bikies.

“I was going through this period in life when my poor old dad was stuck in a retirement home. Here was this guy who’d led such an active life and now all he could do was sit there because the nurses couldn’t let him go outside and ride his moped,” Jennings says. “So I came up with an idea where the nurses are dusky maidens and patients can do as they please — hopefully drive a motorcycle into a ditch and kill themselves instead of spending the rest of their lives staring out a window.”