He’s auctioned thousands of homes. So what’s it like to sell to a famous billionaire?

The following article about top Sydney auctioneer Damien Cooley contains accounts of assault, the killing of a deer and Lachlan Murdoch. But something tells me, Cooley doesn’t like giving people spoiler alerts. He prefers to keep everyone guessing.

You might be familiar with Cooley from his regular appearances on reality television program The Block but thousands more would know the Double Bay-based auctioneer if they simply turned up at a Saturday morning auction – he has conducted thousands of them.

Auctioneer Damien CooleyCredit: Edwina Pickles

I have asked Cooley for lunch because he is somewhat of an auction king in a city obsessed with real estate. And if real estate agents might be collectively loathed for their underhand tactics, might auctions be the antidote to behind the scene deals, where the market alone dictates the price? Not necessarily so when Cooley, 43, is holding his hammer, generating the anxiety and excitement that might just translate into a buyer paying more than they expected.

“One of the great arts to being a great auctioneer is the momentum, the urgency, the auctioneer’s voice, and the speed at which they call and the tones which they use in their voice to extract the bid they want to extract,” Cooley says.

He recalls an auction while he was in his early 20s and already working as a junior auctioneer, which would influence the rest of his life. “I can’t remember exactly what I did during that auction, but I remember there was a Telegraph journalist who was there,” he says.

Cooley’s surname was misspelt, but the story, splashed across the paper the next day was clear: he had committed a cardinal sin in real estate, indicating the property was on the market and was going to be sold before it had reached its reserve. His bosses read it too, and the next day was told he would be demoted back to managing rental properties. Cooley decided he was too good for that, and quit.

Damien Cooley in full flight.Credit: Peter Rae

“I remember sitting on my girlfriend’s bed at the time, literally in tears, thinking what am I going to do, life’s over.”

It forced him to start his own business, which would eventually become Cooley Auctions, from the loungeroom of his share flat, where, dressed in a suit, he handwrote notes to agents or would cold call them, hoping to get work. Success slowly followed, and his business has since conducted more than 75,000 auctions. The fees for hiring an auctioneer range from $695 for a junior up to $2200 for Cooley.

For this interview, I asked Cooley to nominate his favourite eastern suburbs’ venue. He replied: “How about lunch at my restaurant?”

Sella Vinoteca in Randwick isn’t normally open for lunch on Friday so it’s empty when I arrive and Cooley arrives five minutes late. I don’t care what we eat, and he suggests we order dishes which will photograph well for this article. Who could begrudge him some self-promotion at a time when so many restaurants are closing down? We both drink sparkling water – Cooley is driving to Wollongong for auctions before returning to Sydney later in the evening to run a Roosters’ charity auction.

“How about lunch at my restaurant?“: Cooley at Sella Venetica in Randwick.Credit: Edwina Pickles

Some might assume eastern suburbs real estate identities own restaurants for tax purposes, but that’s not the case for Cooley. He established it with Fabio Dore after striking up a friendship with the Italian migrant years earlier at Limoncello in Double Bay where Dore worked as a waiter. Cooley practiced his Italian, Dore worked on his English and a long friendship began. Cooley was the best man at his wedding.

Cooley’s auctioneer origin story began on the other side of a Sydney in Campbelltown at St Gregory’s College. He had grown up in Rosebery and attended eastern suburbs schools but wanted to be a boarder like his older brother. “I liked the idea of going and meeting the country boys and meeting people who had farms and motorbikes,” he said.

He joined the Catholic school in year 8, excelled at public speaking, debating and even beat the country kids at their own game: winning the national junior fleece judging championship. “A lot of the country kids could judge the fleece really well. I think where I excelled was the ability to stand up in front of an audience and speak about why I had put four fleeces in a particular order,” he says.

As he’s talking about sheep we are both graze on a selection of cured meats – Cooley’s favourite is Lardo – a fatty layer of pig attached to the pork rind. Fried octopus, agliata sauce, and crispy potato soon arrives.

He dreamed of being a lawyer like his father but when he graduated from high school in 1998 he didn’t quite get the marks, so enrolled in an arts degree instead. Cooley lasted a week at the University of Sydney before dropping out. “I thought I was back at school,” he said. He decided to try real estate.

“It was a nervous conversation for an 18-year-old boy coming home to his father to tell him he’s dropping out of university and the significant investment in private school education, for want of a better word, has gone down the drain for real estate.”

His father took it well, his mother helped organise him a first job, he did the course to get his real estate licence. But why real estate?

“People see real estate agents now as young guys and girls in flash suits, nice clothes driving fancy cars and being all spivvy, and standing out the front of a house, and it’s all showmanship. It is something which appealed to me at the time.”

He was excited about the expensive cars and the suits but in the years since has realised they were nice byproducts of success – not key performance indicators.

Fregola, cuttlefish, calamari, prawn ragú, mussels.Credit: Edwina Pickles

“Some people measure success by what car they drive, what suit they wear and what expensive watch they have. And I don’t even own a watch.”

At this point, I peer past Cooley’s Burberry cufflinks and I confirm the absence of a Rolex. In its place is a tattoo. Cooley is freshly inked, with the name of his new partner.

Cooley, like many, bought a farm in the Southern Highlands during the pandemic and also separated from his wife two-and-a-half years ago. As he’s telling me this, we’re eating a spatchcock with crispy kale. It feels downright rude to prod at what triggered the end of his marriage. Instead, I ask what he has learnt from it.

“Peppi and I were married for, I am going to say 16 or 17 years, we have three beautiful children together. Even when we got divorced, I continued to make mistakes after that divorce because there is a lot of anger and animosity between two people if it is not an amicable separation.

“You try not to hate, you try and understand. Something I have really worked a lot on myself, [is] to put myself in the other person’s shoes and think about things from their side of the story.

“For me personally, it is about getting on with the next stage of life. I feel like my focus is laser beam right now, both in my business and my personal life.”

And how does the auction king stay at the top of his game and stay hungry for success after more than 20 years? “I do get my haircut every week, I get my car washed at least two to three times a week, I polish my shoes twice a week … If I feel good about myself, I auction better,” he says.

Cooley wakes up anytime between 4.30am and 6am and trains at the gym twice a week with his personal trainer Sam Karam. Cooley weighs 80 kilograms, he came 122nd in the 100km Ultra-Trail Australia race and has placed in the top 150 in the City 2 Surf. He’s also run two ironman races and multiple marathons. When Cooley trains better, he auctions better. And what does Cooley look like on the floor of an auction at the top of his game?

Fried octopus, agliata sauce, crispy potato.Credit: Edwina Pickles

“As an auctioneer, sometimes I am putting more pressure on a buyer and other times I am taking the pressure off. Sometimes I am really hammering them to try and get an increased bid or, if I can see they’re about to snap, I just back off. Sometimes I walk closer to a buyer, not to intimidate, but to influence them the way they feel. Because as somebody gets closer, your anxiety goes up a bit more. If someone walks away, it takes the pressure off.”

Most high-end trophy homes sell via private treaty and Cooley’s biggest home sale in Sydney was for $23 million, the former French consulate in Bellevue Hill in 2009. The purchaser was billionaire Lachlan Murdoch. I invite Cooley to give him a performance review. “Great bidder, walked in and just owned it. That was an exciting auction, at the time that was an Australian record for the highest price paid at auction,” he says.

I imagine home buyers might not like Cooley hovering over them, with the intense stare of his blue eyes, his resonant voice could easily go from charming to unrelenting. “In my 20 years of auctioning, I have never had anyone punch me, but I have had a few threats. I have had one of my auctioneers double pumped in the chest.”

In these high-pressure situations, it might be easy to hate Cooley, and it turns out some people really do – but not for anything he’s done at an auction.

In 2022, he posted a photo of himself on Instagram, which was then featured in The Daily Mail. ”A five-time winning auctioneer on The Block has been criticised for killing a deer and posting a celebratory photo of the hunt on Instagram,” the article read.

He explained to the reporter that he respected animals but was genuinely proud of killing a feral pest and that his family enjoyed eating venison and many other animals like rabbits, and pigs. But defending his actions against internet trolls was futile.

The bill, please. Wine bar and restaurant Sella Vinoteca in Randwick.Credit: Sella Vinoteca.

“What I underestimated was the amount of backlash that I would get from people who don’t like hunting, don’t believe in culling animals, don’t believe what goes on in our world every single day,” he said.

The Daily Mail called a second time and Cooley gave another interview. “I made a phone call to a certain PR person, I said, ‘I need your advice’. She said to me, ‘do not say another word about it’. I will probably get in trouble for talking to you about it right now.”

“I do auctions sometimes where people love the auction that I do, and other people absolutely hate the auction I did … [but] the things that I have had sent to me about that post is just unbelievable – death threats, hate mail, unbelievable.”

After one and a half hours sitting with him, something tells me that these days a wiser Cooley is a little more judicious about what he says and what he posts on the gram. And clear about what matters in life. “Kids change everything. They bring you a lot of joy, they present you some challenges that you need to overcome, as all kids do, but at the end of the day, really what it boils down to is your family, the lifestyle you have, the legacy you have with your kids and the lessons you try to teach them.”

And it’s not difficult to be sold on that.

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