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
Hallucinations Are a Model T Crash
When cars first appeared on public roads, they were genuinely dangerous.They crashed. They frightened horses. They injured pedestrians. They broke down constantly. People died. Newspapers ran moral panics about the recklessness of motorists and the irresponsibility of...
New TV Show Claims To Portray “Real Life In An Australian Law Firm” — Nation Horrified
14 January 2026ISSUE NO. 8SYDNEY — Australian audiences are this week grappling with the release of Billable, a gritty new workplace drama marketed as “the first TV show to accurately depict what it’s really like to work in an Australian law firm.” Far from the...
Tax Training – 16/01/2026 – Adrian Cartland: Fletcher v FCT and the Limits of Deductibility
This session examines Fletcher v Federal Commissioner of Taxation and its place in the deductibility framework under s 51(1) of the ITAA 1936 (now s 8-1 ITAA 1997). Building on Ronpibon Tin and Ure, the case addresses how deductibility is assessed where the outgoing...
HR Christmas Spirit Tested by Kris Kringle Gift from Sex Shop Nobody Can Explain
17 December 2025ISSUE NO. 7SYDNEY — The People & Culture team at Harrington, Lowe & Myers has confirmed it is unable to determine whether a Kris Kringle gift purchased from a sex shop breaches firm policy, pending clarification of what the item is actually...
Firm Generously Gives Staff Mandatory Employment Entitlements for Christmas — Except for Urgent Matters
10 December 2025ISSUE NO. 6SYDNEY — Staff at Whitlam, Grange & Phelps have expressed gratitude after the firm announced it will be “generously” allowing employees to take their mandatory Christmas employment entitlements this year, subject to the minor condition...
New “Lawyer Flexitime” Lets Staff Work Whenever They’re Already Miserable
3 December 2025ISSUE NO. 5SYDNEY — In a bold step toward modern workplace reform, Cartwright & Dull LLP this week proudly announced the introduction of “Lawyer Flexitime,” a program designed to let staff work whenever they are already at their lowest ebb...
Government Employee So Busy They Don’t Even Have Time For Standard 90-Minute Lunch Break
26 November 2025ISSUE NO. 4Chaos has erupted in the Department of Administrative Processing this week, after one mid-level public servant was reportedly forced to complete nearly a full day’s worth of work, leaving no time for the traditional staring out the window or...
Tax Training – 21/11/2025 – Adrian Cartland: Consultation on 16 Proposals for Reforming SA State Taxes
This session presents a draft set of 16 proposals for State Taxes reform, circulated for discussion and practitioner feedback before being finalised. These reforms aim to modernise South Australia’s tax administration by drawing on proven ATO systems and best...
Bendel May Be More Interesting Than It Appears – Clarifying Present Entitlement
Bendel is one of the most anticipated tax cases of the past couple of decades. Simply put, whether UPEs trigger a Div 7A deemed dividend is a matter that is consequential to every tax advisor in the country. In my opinion, the High Court may make Bendel even more...
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