Photo of Mike Cannon-Brookes of Atlassian in a fireside chat with Matthew Panzarino of TechCrunch

Mike Cannon-Brookes ⇨ the nous of a billionaire imposter ⇦

Mike Cannon-Brookes is a 38-year-old Australian self-made software billionaire. His real time net worth at the time of publication is estimated to be $3.5 Billion — #10 in Australia's 50 Richest, #973 in the world — (Forbes 2017). He is the co-founder of Atlassian, a software–as–a–service company that makes collaboration tools for teams of all sizes. Atlassian provides products well-known to the software industry like Jira, Bitbucket, Confluence, and Trello.

I was at the Unconventional TEDxSydney this year where Cannon-Brookes delivered his charming and non-chalantly Australian talk about his Imposter Syndrome. He started with the origin story of Atlassian. He said that when he started the company with his friend Scott Farquhar straight after university they didn't have any grand plan. Not having any prior business experience to start with, their goals then were simply not to have to get a real job and to not have to wear a suit to work everyday.

Cannon-Brookes talked about how even with the success Atlassian has achieved, most days he still feels he doesn't know what he's doing. He talked about feeling out of his depth like a fraud that guessed/bullshitted his way through the situation, and petrified that at anytime someone was going to call him out on it. He gave humorous examples: (1) having to interview their first HR Manager when he himself has not worked in a company that had an HR department; (2) attending board meetings in a T-shirt surrounded by suits, acronyms flying around, feeling like a five year old surreptitiously writing them down so he could look them up in Wikipedia later; and (3) in the early days when people would call up and ask for accounts payable, he would freeze and think wait, are they asking for money or giving it to us? He would cover the phone and pass it to Farquhar so that Farquhar could pretend he was in the accounts department.

He said with Imposter Syndrome: internally one feels that one is not skilled enough, not experienced enough, or not qualified enough to justify being in the position, yet one is already in the position. And one has to figure a way out because one can't just get out. To him it's not a fear of failure or a fear of not being able to do it. It's more a sensation of getting away with something. A fear of being discovered. Cannon-Brookes told stories about how the Imposter Syndrome is not all bad. Stories about how the blessings he's had came from being able to stay with the discomfort of feeling like an imposter yet still going thru with it. He discovered that the feeling doesn't go away with succees. Most successful people he met have it. And it equally applies to personal life not just business.

I learned that one of the attributes of the most successful relationships is that when both partners feel that their partner is out of their league. They feel like imposters. And if they don't freeze and they're thankful, and they work harder and stretch to be the best partner they can, it's likely to be a very successful relationship.

—Mike Cannon-Brookes

Cannon-Brookes' pre-disposition to the Imposter Syndrome may have even catalysed the solution to South Australia's renewable energy power crisis. The Tesla battery deal emerged from a bout of late night tweeting with Elon Musk back in March this year.

Ever since I discovered the work of Nassim Nicholas Taleb—after I randomly found his book Fooled by Randomness on the business shelf of an airport bookstore — I've made it a practice to be wary of being tripped by cognitive biases. One of these biases I'm on the watch out for is the Halo Effect. It was first named by Edward Thorndike in the 1920s. It's the effect that after seeing a person first in a good light, it is much more difficult to darken that light and vice versa. It can manifest in this phenomenon: one assumes that a person who is good at doing A will also be good at doing B, C or D. And the reverse.

An example of the bright halo effect. Stephen Hawking became well-known in making some theories in physics which experiments have verified. Because of this, many people are likely to agree with his view that artificial intelligence (AI) is an existential threat to humankind. When in reality, he may not have the necessary domain knowledge on what's really going on in the field of AI. He may well have or maybe not. It's not clear. But because of the Halo Effect, many would be inclined to think he has.

I am not capable of avoiding being the fool of randomness; what I can do is confine it to where it brings some aesthetic gratification.

—Nassim Nicholas Taleb

An example of the dark halo effect: many—especially those who profess to be on the left of the Americal political spectrum— would likely discount what Peter Thiel says about globalisation, and technological stagnation simply because Thiel is an out and out supporter of Donald Trump. Thiel has in the past been a few times successful in recognising the success of early stage technology businesses early on in their lives. Yet many in the Silicon Valley scene appear to have thrown out insights from this expertise because Thiel does not conform with their political views. Even though one's political views may have nothing to do at all with one's ability to recognise technological business breakthroughs before they happen.

In Cannon-Brookes' case, he may be very good in leading a company that makes collaboration software for teams but he may not be that necessarily good in knowing which superannuation newcomer would be good for milliennials for example (Yoo 2017). But because of the Halo Effect, many are most likely to ascribe that skill to him.

The Halo Effect also manifests in the phenomenon encapsulated in the saying: first impressions last. I was very much impressed with Cannon-Brookes' TEDxSydney talk. To practice empirical skepticism, I had to proactively counteract this first impression. For example by noting to myself that a lot of these TED talks are rehearsed to death. They've been coached on how to deliver the sound bite, the story to get that TED effect. The slick packaging may not necessarily reflect the goods inside.

It was therefore good for me to see Cannon-Brookes again live in a fireside chat with Matthew Panzarino, editor-in-chief of TechCrunch. This was during the first TechCrunch Startup Battlefield Australia held at the Australian Technology Park in Eveleigh last Thursday, 16 November 2017. It provided me with another data point to consider.

Overall, I found Cannon-Brookes to be a level–headed guy who knew when to weigh in or pull back on complex issues. He was asked to weigh in on the changes happening in Silicon Valley to combat harrassment and to improve poor working conditions. He was asked what advice he would give to someone like Dara Khosrowshahi—the new CEO of Uber— who needs to refactor that company's culture. Instead of launching into a tirade of ready-made solutions as many trigger happy pundits are apt to do, Canon-Brookes pulled back to acknowledge that Khosrowshahi is far more qualified to do that than he was, and that from the outside it sounds like a complicated issue to unpick. He then proceeded to give a simple level-headed pragmatic advice that made a lot of sense to me.

I think you got to start with core values. You got to make sure you've got the right people on the bus. Get rid of the wrong people as quickly as you can if they're toxic to the culture, or to the environment or what you're trying to achieve. It's not rocket science but it's hard to do on a continual basis. We've always said it's a marathon not a sprint. Too many start-ups think if you sprint long enough, you can kind of achieve something. You just run out of energy and the whole thing blows up.

—Mike Cannon-Brookes

With the follow-up question on building the right culture of a start-up early on in it's history, Cannon-Brookes again characteristically admitted that Atlassian did a lot of correct things without forethought. They did not plan a great culture. Both the founders simply had a strong sense of ethics and values which they tried to imbue in the business. They had an early rule that they wanted to build something where they'd want to come in to work everyday. They had simple rules of thumb that served them well that become a lot more refined over time. For example he said one has to be careful not to water down investment in people and culture as the company scales up in size.

When asked about diversity and inclusion in Atlassian as a global company, Cannon-Brookes said that one must obviously be sensitive to the different geographies one is in. He went further to ever so astutely point out that their primary goal was always to achieve diversity of thought. The reason they want to achieve diversity is to build the best products for the biggest audience. That is to have all the different viewpoints, experiences, and thoughts that come together. And that necessarily usually requires them having men and women, younger people and older people. He said Atlassian has a very open culture which is fantastic but can also be at times difficult. He gave the example of the same sex marriage debate and plebiscite in Australia recently. They had to question (internally and externally) should they be supporting same sex marriage as a company? From the founders' point of view it was a definitive Yes! But internally there are employees who are going to vote in all ways. And they have to support people's rights to a personal choice in having their own vote and their own opinion. Cannon-Brookes again astutely mentioned that there were also a lot of people in Atlassian personally affected by that vote. It was a tough time for LGBTI people to hear all the debates happening around them.

Cannon-Brookes said that working openly is such a big thing in Atlassian's products, company, and culture with all its ramifications. One of these ramifications is to have an open way of being. Being able to bring one's true self to work is incredibly important to them as a business.

You don't want to have a home self then turn it off and turn up to work with a work self. At work you're expected to be a certain way. You're expected not to have emotions, feelings, or interests. That doesn't make sense to me.

—Mike Cannon-Brookes

In contrast to the financial runway given to venture-backed start-ups, Atlassian has been profitable for 15 years without needing outside money. This according to Cannon-Brookes has given them a long term view on the business. He said the company and the founders are still young. In ten or twenty years they'll still be doing this. So he said if he was going to be working at Atlassian for the next twenty years—he may not be able to tell us what products they'll have—but he can certainly tell us how he would want the company to feel like, to be like. Being profitable has given them the control of being patient in allowing the things they want to happen. Cannon-Brookes said that patience over time mixed with growing ambition has for them been a powerful combination.

He said that until the IPO, Atlassian has not taken any institutional capital into the balance sheet. They did two rounds of venture capital. In both instances, the money raised all went to the employees and not into the business. At no stage did the company needed cash from the public. Cannon-Brookes said that the IPO did not really affect how they run the business. The business was culturally ready and they have already been running the business as a public company for at least two years before the IPO. They wanted the IPO to simply be a continuation. He said that Atlassian has a flywheel, high–velocity business and nothing about that business they wanted to change in going public. That was what the investors were valuing. And that's what they're going to continue to do for a very long time.

Canon-Brookes said that as Australians, they've always been kind of under estimated. That's fine. He said Atlassian's investor relations formula is very simple: they say what they're going to do and they go do it.

When asked about if the future would be about distributed companies, Canon-Brookes said his guess is that it could be more of a hybrid. He said he doesn't think there's going to be one way of doing it. One can make everything work. He said that Atlassian has a series of models internally. He said that Atlassian basically has one product in every city. Sydney, Mountain View, San Francisco, Austin, and New York have a different product each with platform teams that run across the whole thing. He said that they made a different T-shirt for each city. Then the remote employees said “what about us?” so they made a separate T-shirt for the remote team. They've since learned to treat remote employees as one of the offices. He said one has to be aware of the model. One cannot make a hybrid model work without being thoughtful about it.

Cannon-Brookes said that they're largely pragmatic and not dogmatic. They are thoughtful in whatever model is chosen for the team, unit or group to make it work. He said there's always pros and cons, and investments have to be made on whichever model is chosen. For example, the remote team spend less on offices but has to spend to get the team together regularly and also to train new people. He said the worst thing is to think that one can get remote working for free without any cost.

When asked how Atlassian handles the pressure of launching a new product, he said that they spend a lot of time talking to customers about what works and what doesn't work. They've always focused heavily on actual active usage, customer satisfaction, and other metrics. Then they let the business side take care of itself over time. He said they're very patient. He said the worst thing to try to do in tech is to win the war in a year. It's not going to happen. Wars are won in decades.

Lastly he said that the competitive advantage that Australian entrepreneurs have over their Silicon Valley counterparts is the Australian ability to make most out of very limited resources. He said Australians are good at getting the juice out of whatever we have. Canon-Brookes said this is the natural psyche of being on the far side of the planet with a lot of rocks and not a lot of water. That's why the successful Australian tech companies build scalable, global, and profitable businesses.


  1. Atlassian Corporation Plc 2017, Atlassian, website, viewed 21 November 2017, <>.
  2. Forbes Media LLC 2017, Forbes Profile, magazine, viewed 21 November 2017, <>.
  3. Taleb, N. 2004, Fooled by randomness. The hidden role of chance in life and in the markets, 2nd edn, TEXERE Thomson Corporation, New York.
  4. TEDxSydney 2017, Imposter Syndrome | Mike Cannon-Brookes, video recording, YouTube, viewed 21 November 2017, <>.
  5. Escher, A. 2017, Fireside Chat with Mike Cannon-Brookes (Atlassian), video recording, TechCrunch Startup Battlefield Australia, viewed 22 November 2017, <>.
  6. The Economist 2009, 'The halo effect', The Economist Idea, magazine, viewed 21 November 2017, <>.
  7. Yoo, T. 2017, 'Millennial superfund Spaceship just removed Atlassian co-founder Mike Cannon-Brookes from its marketing' Business Insider Australia, blog, viewed 21 November 2017, <>.