Tax, Trust & Technology Articles

We fix tax problems and resolve tax disputes. We prepare high-level tax documentation for complex structures and transactions as well as dealing with revenue authorities and other parties about those structures and transactions.


The Tax, Trusts and Technology Newsletter is a monthly publication with in-depth articles on novel subjects. It also highlights upcoming events and matters of interest. Subscribe if you would like to read fresh ideas and insights on Tax, Trusts and Technology. 

Stop Robot Slavery

Stop Robot SlaveryI saw a guy wearing a t-shirt that said, “Stop Animal Slavery.” I thought of the cruel and inhumane conditions that my two golden retrievers are forced to endure (by their own accounts): never enough food, insufficient pats, and hard work each day...

Prediction: Sustaining, Disruptive and Revolutionary Innovation

As COVID forces disruption upon the world there is an opportunity for extensive positive change including in the law. Courts that have resisted online document submission and video conferencing have adopted them virtually overnight. Firms that could not get away from printing everything on the file have suddenly adopted cloud storage and filing. A vast number of meetings that could have been emails have become, well, emails. 

COVID, Rent, Sharing Losses and Systemic Risk

Our contracts and the law surrounding them do not account for systemic risk. I believe that the common law has done a good job of balancing risks between parties (or rather a not-terrible job: it is difficult to determine whether law is truly good, merely whether there could be worse). Parties are generally held to their obligations, and there are limited situation that they can get out of them such as misrepresentation, fraud, implied terms, unconscionability, duress, frustration and undue influence to name a few. 

Why running a Tech Startup is like fighting MMA 

Why running a Tech Startup is like fighting MMA 

Earlier this year I participated in my first MMA fight. I have been karate training for 25 years (3rd Degree Black Belt Goju Ryu) and have taken part in other martial arts (BJJ, wrestling) but this was, without a doubt,  the hardest thing that I have done so far.  I have also been running a tech company that builds legal artificial intelligence (Ailira)  for the last 4 years, alongside my law firm, and I was struck (pun intended) by a number of similarities in the experience. 

Adrian Cartland Writes on Law, AI & Ethics in South Australia’s Law Society Mag,     The Bulletin (June 2019)

Adrian Cartland Writes on Law, AI & Ethics in South Australia’s Law Society Mag, The Bulletin (June 2019)

Although history remembers the winners, if that “winner” were not to exist someone else would have taken their place. A number of people developed lightbulbs,2 combustion engines,3 and powered aircraft at approximately the same time. While Google is the dominant search engine, Facebook the dominant social media platform and Uber the dominant ride sharing service, it could have equally been AltaVista, Myspace and Lyft or Biadu, Weibo and Didi.

Chatbot-based ‘firm without lawyers’ launched

A lawyer has launched an artificial intelligence-backed (AI) chatbot that powers what he calls the ‘Law Firm Without Lawyers’, initially aimed at consumer and tax law but shortly to be extended to domestic violence. The Australian creator, Adrian Cartland, a tax specialist who runs Cartland Law, in Adelaide, South Australia, told Legal Futuresthat he hopes to bring it to the UK.

Hundreds of people’ trusting artificial intelligence to write their will

South Australian taxation lawyer Adrian Cartland invented Ailira to fulfil everything from legal advice, to research, and now important tasks with clients. It’s been set up in the Northern Territory town of Coolalinga, and its website’s official description states: “Ailira’s advice function works like a chatbot. Ailira asks a number of questions via text (or speech) like an interview. That information is collated and can be analysed to provide advice, and also automatically generate documents.”

Forget robot lawyers – AI is your R2D2

Adrian Cartland wants us to stop talking about robot lawyers. As principal lawyer of Cartland Law and creator of Ailira and Law Firm Without Lawyers, it’s a surprising sentiment. Ailira, which stands for Artificially Intelligent Legal Information Research Assistant, famously helped Adrian’s speech pathologist girlfriend score 73% in the Adelaide University tax law exam – with better grades than Adrian. His work combines the best of AI and legal practice.

Xmas Chatbot

Xmas Chatbot

Chatbots are the new black. But this season they have also been the new red white and green - with the Cartland Law Xmas Chatbot. Having just spent 18 months developing legal AI (Ailira) when I went to send a Xmas message out to clients I thought that it wouldn’t be a...

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