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
Firmwide ALL CAPS Email Confirms Ageing Consultant Hit Pub for Lunch
8 April 2026ISSUE NO. 20SYDNEY — A firmwide reply-all email sent mid-afternoon has confirmed that former equity partner turned consultant Michael Reeves, 72, attended the pub for lunch, consumed approximately six glasses of red wine, and then attempted humour in...
LinkedIn Thought Leader Confirmed to Speak Exactly Like His Posts
1 April 2026ISSUE NO. 19Queensland — A reporter attempting to interview a prominent LinkedIn thought leader this week has confirmed that the distinctive tone and structure of his posts appear to be an accurate transcript of how he actually speaks. Mark Delaney, who...
Tax Training – 27/03/2026 – Adrian Cartland: Sun Newspapers and the Capital vs Revenue Distinction
This session examines Sun Newspapers Ltd v Federal Commissioner of Taxation (1938) and its role in determining whether an outgoing is on capital or revenue account under s 51(1) (now s 8-1). Please see below link to case materials which is assumed reading in order to...
Accounting Tech CEO Explains Why Every LinkedIn AI Discussion Is Really About Their Product
25 March 2026ISSUE NO. 18Melbourne — A Melbourne accounting technology founder has clarified that most discussions about artificial intelligence on LinkedIn are, when examined carefully, actually about his company’s product. Lachlan Reeves, chief executive of...
Lawyer “Humbled and Surprised” to Receive Prestigious Industry Ranking Firm’s Marketing Department Paid For
18 March 2026ISSUE NO. 17PERTH — Commercial lawyer Daniel Whitaker says he is “deeply humbled and genuinely surprised” to have been named one of Australia’s Recommended Lawyers – Commercial Litigation in this year’s Australian Legal Industry Rankings (ALIR), following...
ATO Data-Matching Reveals Handwritten Signs Strongest Predictor of Tax Evasion
11 March 2026ISSUE NO. 16CANBERRA — The Australian Taxation Office has announced a new data-matching initiative after internal analysis revealed that handwritten cardboard signs are the strongest statistical predictor of undeclared income in the Australian economy....
Tax Training – 13/03/2026 – Adrian Cartland: Socratic Questioning, Intellectual Dominance, and Bullying in Professional Discourse
This session examines whether rigorous questioning can cross the line into bullying in professional environments. Using Plato’s Hippias Minor as a case study, the discussion considers Socrates’ method of questioning the sophist Hippias and whether the exchange...
Lecturer Begs Students to Skim Read AI-Generated Assignments Before Submission
4 March 2026ISSUE NO. 15ADELAIDE — An Administrative Law lecturer has appealed to students to “at least skim read” their AI-generated assignments before submission, following what she described as “a semester of entirely avoidable errors.” Dr Eleanor Grant, who...
New Legal AI Platform Revealed to Be One Man’s ChatGPT Login, Raises $42 Million Anyway
25 February 2026ISSUE NO. 14SYDNEY — A newly launched “agentic legal workflow platform” has raised $42 million in seed funding despite quiet industry recognition that the product is, in substance, founder Lachlan Reeves’ personal ChatGPT login with several dropdown...
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