That background chatter seeped into his blood and in December 1998, he called his first race in Longreach.
He had turned 14 two weeks before.
Less than a year later, after honing his craft at a few more meets, he heard the Birdsville Races - the race that stops the outback - needed a caller.
They called him - and on Saturday, he was set to call his 23rd Birdsville Cup.
Birdsville Race Club vice-president Gary Crook says Mr Fleming has the crucial quality that marks all great sports broadcasters.
"He can impart a story with the call," he tells AAP.
"If you are just calling the race, you might do a fantastic job, but that's all you're doing.
"Whereas Josh, he knows the horses, the trainers, so he can tell a story with the call, with all those snippets and bits of knowledge."
One of those trainers is 81-year-old John Ferguson, who has been a fixture of the Birdsville races for 63 years.
Allegedly, this is his final pilgrimage to the event, racing five-year-old gelding Aussie Adaptor.
But when this is put to him, there's a twinkle: "I've been saying that for a few years," he tells AAP.
He says it depends on his body holding up, holding onto his licence to drive a truck and - most importantly - whether his horse is any good.
Fleming rose to the top of his profession, becoming the voice of horse racing in Queensland for Sky Racing until being unceremoniously dumped in 2025.
Brisbane's winter carnival was about to begin, with many Group 1 races ahead, but Fleming fell victim to the trend towards calling the races off the television.
The day wasn't out before the phone rang, with his services in demand.
He was immediately snapped up as racing and operations manager at the Toowoomba Turf Club.
But Birdsville keeps calling him back, and he can't stay away.
"It's about the people," Fleming told AAP.
"It wouldn't be an easy place to live here, but you know those that do it are here for a reason.
"You're sort of at the mercy of Mother Nature a bit."
That's an understatement.
It'll be 37C on race day, and that's not even close to as hot as it can get.
In 2010, the races were cancelled due to flooding.
On another occasion, in 2016, half the annual rainfall fell the day before the scheduled meet, leaving thousands of revellers stranded.
"Once they removed the road closed signs, it was like the migration of the wildebeest," Fleming remembers with a chuckle.
The Birdsville Races remain one of the biggest weekends on the outback calendar, first run in 1882, raising funds for the Royal Flying Doctor Service.
It's been cancelled on only a few occasions - besides 2010, an equine influenza outbreak canned 2007, while COVID saw off 2020 and 2021.
Fleming has had a break from calling - his last meet was six months ago, near Goondiwindi - and he's a bit nervous.
"Honestly, at that point, I didn't know whether I'd ever do it again, so I was at a little bit of a crossroads," he said.
But, he said, it's like riding a bike, if not a horse, and he's quietly been practising at home, getting himself match-fit for the big one in Birdsville.
"The glasses still work, the eyes still work, the brain still works, so that'll give us confidence that we'll be right to go," he said.
In the end, he couldn't help himself.
"Once the racing bug bites, it never lets go," he said.
AAP travelled with the support of the Birdsville Race Club.
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