‘We should have seen the signs’: What’s next for Mike and Annie Cannon-Brookes?
While the separation has blindsided many, real estate sources say there was an inevitability as Annie bought more homes in her name.
Most days, Mike Cannon-Brookes feels like a fraud. It’s called imposter syndrome and he once confessed to feeling way out of his depth in the workplace – and in his marriage too. Always worrying: does he deserve to be here? Will he be exposed? Will his wife wake up one day and wonder what he’s doing on the other side of the bed?
It was a candid, self-deprecating speech the Atlassian billionaire gave at a TEDx talk in Sydney 2017 on the subject of imposter syndrome, connecting it with his business success and the very first accidental meeting with Annie Todd, the woman who became his wife and the mother of their four children.
They were at Sydney airport’s Qantas lounge. He was flying to San Francisco, Annie was on her way home to Michigan.
“A beautiful woman from way out of my league walked into the Qantas lounge and continued walking straight up to me, in a case of mistaken identity,” Cannon-Brookes told the audience.
“She thought I was someone else. So, in this case, I actually was an imposter.’’
He didn’t freeze, as he usually would have done. “I just tried to keep the conversation going.”
Some classic Australian bullshit combined with fake-it-till-you-make-it bravado tipped into the exchange of phone numbers. “And more than a decade later, I’m incredibly happy that she is now my wife and we have four amazing children together,” he said.
But still he had that deep-seated sense of insecurity.
“But you’d think that when I wake up every morning, I wouldn’t roll over and look at her and think ‘she’s gonna say, who are you? And who gave you that side of the bed? Get out of here.’
“But she doesn’t. And I think she sometimes feels the same way. And apparently, that’s one of the reasons that we’ll likely have a successful marriage.”
Thirteen years after their 2010 nuptials, the high profile tie-up between the Atlassian co-founder and his American-born fashion designer wife has collapsed.
Friends and associates circled the wagons this week as the surprise news emerged that the couple was separating, with any questions diligently referred back to the Atlassian public relations team.
Sources say that first signs of a break-up may have emerged when public relations representative made it clear that Annie was buying property in her name – not the couple’s – and point to the very different personalities of Cannon-Brookes, the son of a well-respected English banker, and his outgoing wife, Annie, who has a passion for fashion design and niche interests like the nutritional benefits of dried crickets.
Photographs and past interviews give little away. In his TEDx speech he said he stretched himself to be a better partner than he might otherwise be. “And I think she feels the same way.”
The couple, typically photographed as a loving pair with their arms around each other, have more recently maintained a fierce privacy around their family, particularly when they moved from their $100m Fairwater, from the estate of the late Mary Fairfax, in Sydney’s Double Bay, to the privacy of the Southern Highlands during Covid-19.
Since their fateful Qantas club encounter Cannon-Brookes and his wife have always carved out a very different role in Sydney’s social scene.
Cannon-Brookes has maintained a high profile as a passionate supporter of green energy and issues connected with climate change, including a high-profile raid on gas company AGL last year, and Annie once invited The Australian into the family home, then in Sydney’s Centennial Park, to show themselves as a down-to-earth couple who accidentally got rich.
Questions have arisen as to how the split might affect his shareholding in US-listed tech giant Atlassian, as well as his activist and philanthropic ventures into green energy and environmental projects, and their extensive portfolio of properties.
“We should have seen the signs,” said one observer of the Sydney property scene this week, noting that more properties were being bought by Annie in recent times rather than in the couple’s joint name.
One editor recalled getting a phone call from a public relations woman adamantly insisting that it be made clear in a story that the former Queensland resort, Dunk Island, was bought by Annie and not her husband.
“He likes the Southern Highland and she likes the beach,” said one observer said this week.
“If there is a split of their property this is how it will go.”
The pair’s splurge on property in recent years has included houses in Mackerel Beach north of Sydney and others on the city’s northern beaches.
Atlassian co-founder Scott Farquhar once described his relationship with Cannon-Brookes, which began when they met at the University of New South Wales, as being like a marriage
That relationship, which includes the demanding task of running a US-listed tech company from Australia, continues. However, observers are looking at the increasingly independent role of Annie Cannon-Brookes in more recent times for clues behind the break-up.
The couple recently had a car accident driving back from the Southern Highlands to their Sydney home, although this is not considered a factor.
Observers point to their clear differences, describing Cannon-Brookes as serious and obsessive, likely to make phone calls and tweets late at night, including his famous one to US entrepreneur Elon Musk, while his wife was outgoing and vivacious.
An early interest in fashion design, which included the establishment of the House of Cannon, has been replaced by a passion for buying property and a venture in progress, called Kangaloon Crickets which was set to produce dried powder from crickets – billed as “protein with a purpose” from insects grown on the property they bought on in the Southern Highlands suburb of Kangaloon. A website for the venture describes it as “launching soon.”
One visitor to a dinner when the couple were living in Fairwater recalled her passion for the nutritional benefits of dried crickets which dominated the conversation.
The couple attended the annual Gold Dinner at Fox Studios in 2019 which raises money for the Sydney’s Children’s Hospital, successfully bidding $42,000 for a dinner by celebrity chef Gulliaume Brahimi.
But when the Ireland Funds Australian arm staged its annual fundraising garden party at Fairwater last November, an event long hosted by the late Mary Fairfax at her harbourside home, the event was hosted by Mike’s father, Michael and mother Helen.
Until recently, Cannon-Brookes and Farquhar have enjoyed a dream run of positive publicity off the back of their entrepreneurial success and their high-profile support for green issues.
The two longtime friends have both bought historic houses next to each other from the Fairfax family – Farquhar bought Elaine from John B Fairfax, and the Cannon-Brookeses bought Fairwater from the estate of Mary Fairfax – but their plans to live happily side by side in Sydney’s wealthiest area have not eventuated.
The tide has ebbed a little in recent years, Atlassian’s shares faced a downturn as the tech boom collapsed and the high-flying firm has replaced its frenetic hiring spree of recent years with lay-offs.
The perennially blue-capped CEO, whose unkempt beard and dark hair has resulted in him being sarcastically nicknamed “Jesus of Double Bay” in some Sydney circles, has spent the past two decades building what is now one of Australia’s largest technology firms, while steadily using his wealth to reshape the environmental and corporate sectors through a combination of activist investments and philanthropy.
Cannon-Brookes was born in Connecticut, US, in November 1979 when his father Michael was working for Citibank in New York. He led a global life, going to school for a short time in Hong Kong with his two older sisters, before going to boarding school in England.
When Michael Snr moved to Sydney in the mid-1980s to open the Citibank office, after the Treasurer Paul Keating opened the door to foreign banks, son Mike moved to Sydney, going to the up-market Cranbrook school in Sydney’s east – a school attended by the sons of the city’s wealthy such as James Packer.
(His own sons attended the school before they moved to Tudor House in the Southern Highlands in 2021, a co-ed school where they could attend with their sisters.)
As a teenager, Cannon-Brookes insisted on his parents buying him a computer. He finished near the top of his class, winning a scholarship to the University of New South Wales.
Always entrepreneurial, Cannon-Brookes set up several companies before Atlassian, later inviting fellow UNSW student Farquar to join him in the venture which made their collective fortunes.
‘I’d prefer that tag wasn’t used’
Cannon-Brookes has become arguably Australia’s most successful activist investor but his gamut of extra-curricular activities have left him increasingly stretched.
The executive has an uncomfortable relationship with the media, often shutting down questions he doesn’t want to answer, preferring instead to take to Twitter, where he infamously won a bet with Elon Musk in what eventually became Tesla’s big battery in Hornsdale, South Australia.
He detests the word “billionaire”. “I’d prefer that tag wasn’t used,” he told The Weekend Australian in 2016.
“I don’t think rich lists celebrate the right things … When I think about all the things we are proud of, none of them are dollar-related.”
Annie told the masthead in the same interview that she and her husband had the same goals, in aiming to provide as normal an existence for their four children as possible.
“Our lives are not as crazy as you think. We still have dinner together, Mike or I drop Max off at preschool and Scout at soccer training. We are pretty balanced. We just say no to lots of stuff,” she said.
“In a lot of situations it is easy to outsource your life now, get someone to do the nannying, shopping, cooking. I am really happy that we still do those things like our own grocery shopping.’’
Annie also revealed Farquhar saved her life over a decade ago when she had an anaphylactic reaction after a function while Mike was overseas.
“Scott found me and said ‘You don’t look well’. He literally picked me up, put me in a cab and took me to St Vincent’s (hospital). And if he had not done that, I probably would not have made it there,’’ she said.
Observers this week described the two wives of the Atlassian co-founders as being very different and not close,
Farquar’s wife, Kim Jackson, a former investment banker who runs their own investment company, Skip Capital, is recognised for her work and won the 2019 Veuve Clicquot annual Business Woman Award. She took the title ahead of entrepreneurial business women Adore Beauty founder Kate Morris, Flamingo AI founder and chief Dr Catriona Wallace, Emma Welsh, the co-founder of Emma and Tom’s, and Liven co-founder Grace Wong.
Accepting that award, Jackson said she was “proud to be recognised alongside so many talented businesswomen and am committed to continuing to support big ideas and growing Australian innovation”.
While their wives are very different, the two partners are known to have a rock solid relationship and their unique ties are one of the pillars of the success for their company.
In a 2021 interview with The Weekend Australian, Farquhar said he and Cannon-Brookes had a clause in their early shareholders’ agreement that specified that if they disagreed on a big issue and a mediator couldn’t fix it, it would go to a game of rock, paper scissors.
“I’ve lost 100 per cent of those games with Mike, so that’s not a good spot to be in and I’m heavily incentivised to avoid that,” Farquhar said.
“It’s mostly that if I can’t convince Mike of my opinion then I’ve done something wrong, and vice versa, because he’s a pretty smart guy, right? And we’ve got the same background in that we’ve done the same journey.
“Yet we have different strengths and different ways of looking at the world. And so for us it’s basically saying, ‘well, okay, you’ve got your perspective, I’ve got mine, how do we unify them?’ In most cases, it’s usually different ways of talking about something.
“I think Mike is a bit … Mike is a dreamer. And that has huge benefits and huge, you know, downsides. And I’m probably a realist, and I think that has huge benefits and huge downsides.
“And I think the combination of those two, it makes a pretty potent combo.”
Atlassian shareholders, who will learn the company’s latest annual results next week, will hope the private lives of one of the founders will not spill over into the company as it faces the headwinds of the more challenging outlook for the global tech industry.
Meanwhile, Ireland Funds Australia plans to hold its annual fund raiser this November at Fairwater again.
It will be interesting to see which members of the Cannon-Brookes family attend.
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