Principal Solicitor
Adrian Cartland
About Adrian Cartland
Adrian “the Taxinator” Cartland’s childhood dream was to become a Transformer (like his hero Optimus Prime). Unable to chart a career path from small human child to giant transforming alien robot, and not being good at maths (to the disappointment of the engineers in his family) he decided instead to pursue commercial law. He achieved good grades at University, despite not doing most of his readings, and overloaded subjects so he could skip a couple of years (not doing most of the work frees up a lot of time). His second lowest grade was tax law. Despite his unimpressive tax law exam results, Adrian found himself reading the Master Tax Guide for fun during the holidays and decided that if this was his idea of fun then he is too odd to do a more normal area of law so he is probably stuck in tax. Plus he wasn’t going to do the readings in the other areas anyway.
Adrian then worked at a number of tax law roles in top tier firms as well as boutique tax practices for about ten years, meeting his billable targets on at least a few occasions. It was then that he began thinking about the future of law and developed an interest in legal Artificial Intelligence, mostly in an effort to find a robot to do the work he was too lazy to do. Deciding that it was best to pursue this expensive and time consuming hobby (er, business) while not on someone else’s timesheet he founded his own firm Cartland Law. Now unemployable, he has run the firm for nearly a decade.
Because Adrian knows very little about other, more normal, areas of law, Cartland Law specialises in and only accepts instruction in tax, trusts and technology. While the engineers in Adrian’s family have constructed many things beneficial to society, Adrian has instead created a number of complex tax and trust structures. He has also created Ailira, the Artificially Intelligent Legal Information Research Assistant and thereby partly contributed to the doom of humanity by AI.
He is the Chair of Society of Trust and Estate Practitioners SA, the Chair of The Tax Institutes State Taxes Committee, was Australia’s funniest lawyer in 2007 and holds the Australian record for fastest MMA knockout at 6 seconds. He used some of the material in this bio to meet his wife on Tinder, and has asked for the remainder to be added to his eulogy if he is ever (accidentally) brutally dispatched (by her).
Adrian Cartland’s Articles
Development Company Structures and Why PCG 2026/D2 Is Wrong
Development Company Structures and Why PCG 2026/D2 Is Wrong In my view the PCG is wrong. It misreads the substantive law. It assumes facts that are not true of the arrangements it targets. It offers an alternative postulate that is not an alternative postulate. This...
Law Firm’s “Charismatic Head of IT” Revealed to Be Technician Least Afraid of Human Interaction
19 May 2026ISSUE NO. 26SYDNEY — Partners at mid-tier firm Ellison, Grant & Wolfe have congratulated themselves on an inspired leadership appointment this week after selecting a “charismatic Head of IT,” later revealed to be simply the technician least afraid of...
AI Is Not a Thing
Or Why Calling Everything “AI” Is Like Calling Every Fight “UFC” That’s UFC There is a certain kind of person who sees a boxing match, a judo throw, and a spinning back kick and says, with great confidence, “That’s UFC.” Anyone who has trained for more than five...
Tax Training – 22/05/2026 – Adrian Cartland: Discretionary Partnerships, s 94 and Partnership Income in a 30% Trust Tax World
This session continues last week's discussion of Harvey v Harvey and s 106-5, and turns to the operation of partnerships as an income-splitting structure in a world where trust distributions are subject to a 30% minimum tax. With the Government's recent announcement,...
Partnership Aspirations Dashed as Firm Introduces Additional “Pre-Partnership” Titles
12 May 2026ISSUE NO. 25HOBART- A boutique commercial law firm has introduced a new seniority classification immediately below partner, citing the need to recognise associate progression. The new title, Managing Counsel, was announced on Tuesday by managing partner...
Tax Training – 15/05/2026 – Adrian Cartland: Section 106-5, Partnership Contributions and the Three Harvey Models
Last week we turned to consider s 106-5 of the ITAA 1997 and the question of what CGT event occurs when a partner contributes an asset to a partnership without transferring legal title, and how the resulting gain or loss is attributed between the partners....
ChatGPT for Lawyers: The Lawyer’s Dilemma in the Age of AI
Another day, another prediction that Artificial Intelligence (“AI”) is going to replace lawyers. As a lawyer who has been building AI for nearly 10 years, it seems proper to comment. In summary, my view is that the prediction that “ChatGPT will replace lawyers” is a...
Why Professionals Aren’t Innovating—And How They Can
Innovation in the professional services sector is often stifled not by lack of opportunity, but by the very nature of the professions themselves. In the tax domain, this challenge is particularly acute. Unlike software development or design, tax is not a skill one can...
Technologists and (Lawyers) Do Not Understand About Legal Services
Document Automation and Client Expectations With Ailira we were able to generate automated documents efficiently and cheaply for clients. They could ask questions, tailor each document themselves, read other information and get all the things they wanted provided...
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