How did you come to specialise in tax, trusts and technology? 

Tax law appealed to me because of how profoundly it shapes how society actually operates. Many legal and commercial structures don’t fully make sense until you understand their tax function. As a law student, discretionary family trusts initially didn’t make sense compared to direct ownership; once I understood why they exist from a tax perspective, the underlying logic of the system became clear. I then found myself reading the Master Tax Guide on weekends, trying to make sense of as much of the legal world as I could. I come from a family of creatives and engineers, and I’ve always liked building things. Tax gave me a way to do that creatively, by using a deep understanding of law and structure to design systems that work in practice. Seeking understanding led me to the complex law of trusts, and then later into artificial intelligence. 

You were working with legal AI well before the recent surge in interest. What drove that work? 

Once I started thinking about law as a system built on rules and first principles, it was a short step to thinking about automation. In the mid-2010s, I was reading extensively about the future of law and early artificial intelligence, around the time IBM Watson won Jeopardy! Looking at legal work from the inside, I formed the view that much of it is structured and repeatable, and therefore capable of automation. Document templates already existed, but the real opportunity was higher up the chain: automating the professional reasoning that feeds into advice and documents. Tax law, with its rule-based structure, was an ideal place to start. That led me to begin building semantic search and reasoning systems for tax and then applying those ideas more broadly across legal work. 

There’s growing concern about what AI means for junior lawyers. How do you see that playing out? 

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I’m very concerned about the doom-and-gloom narrative being given to young people about the future of law, because it does not reflect what I’m seeing in practice. I use AI at a very advanced level in my tax practice, and over the past few months, I’ve hired more than half a dozen junior lawyers into that practice, with plans to hire aggressively again. That work is supported by a team of experienced specialists embedded in the firm who build and run AI systems for my practice, for clients, and for other tax and legal practices. A good illustration of what AI actually does is an early test of our systems, where a non-lawyer using Ailira, a legal AI that I developed, was able to pass the Adelaide University tax law exam. The point wasn’t that the AI replaced a lawyer, but that it dramatically lifted capability when the work was structured and supervised. In practice, AI reduces the cost and time required to produce legal work, which means more work becomes achievable within real budgets and deadlines. In economic terms, that expands supply and increases the quantity of legal services demanded. All work remains personally reviewed by me, but AI allows juniors to operate at a much higher level much earlier. Used properly, AI does not shrink the profession; it expands it. 

You’ve recently published the Taxinator’s Manifesto on South Australian tax administration. What prompted it? 

It grew out of years of navigating state taxes and repeatedly seeing uncertainty, cost and needlessly difficult disputes driven by administration rather than substance. That contrast becomes especially clear when you work across jurisdictions. I spend a lot of time in federal tax disputes and recently published a book on that process, which forced me to think carefully about how different systems handle audits, objections, review and resolution. Compared with the federal system and other states, South Australia lacks some basic mechanisms that reduce disputes and provide certainty. The manifesto is about adopting those proven approaches so the system works better for everyone involved: taxpayers, their advisors, RevenueSA officers and government. The aim is a more predictable, efficient and cooperative system, without changing tax rates or reducing revenue.

Which proposed reforms would make the biggest difference in practice? 

The most important reform is a hard decision timeframe with a default outcome. If RevenueSA does not decide a matter within six months, it is resolved in the taxpayer’s favour. Reform debates have been stuck for years between criticising inefficiency and calling for more resources. Neither has worked. A default acceptance breaks that deadlock. It clears backlogs for both taxpayers and RevenueSA and creates a clear backstop going forward. 

The second is a formal mechanism to correct genuine taxpayer errors. Many ordinary taxpayers cannot afford detailed advice and make honest mistakes. At present, the system is often too rigid to deal with those fairly or quickly. A structured rectification process would reduce disputes, cost and stress for everyone involved. 

The third is a binding private rulings system across state taxes. Being able to obtain certainty before entering into a transaction is one of the most effective ways to prevent disputes arising in the first place. 

These sit within a broader package of sixteen coordinated reforms, which together form the most comprehensive state tax administration reform agenda developed for South Australia. The opportunity is not to tweak at the edges, but to modernise the system as a whole in a way that benefits taxpayers, advisors, RevenueSA officers and government alike. 

Can you give an example of where the current system creates unnecessary disputes? 

A common cause of unnecessary disputes is delay without consequence. For example, I am aware of a typical Adelaide “mum and dad” couple who applied for a principal place of residence land tax exemption, lodged all the required information, and then waited two years without a decision. When RevenueSA eventually responded, a simple error in the original form meant they were hit with two years of retrospective land tax, interest and penalties. It was an honest mistake that could have been fixed quickly if it had been identified earlier, but the delay turned it into a dispute. 

I have also seen more extreme cases, including a commercial property owner who waited eleven years for a stamp duty issue to be finalised, with significant amounts of money tied up the entire time. Another recurring problem is the lack of any straightforward way to correct genuine errors. In one case, a first-home buyer lost access to a grant because a conveyancing mistake incorrectly put her parents on the title, with no mechanism to fix the error even though she otherwise clearly qualified. These disputes are not about avoidance or bad behaviour. They are created by rigid systems that lack timely decision-making and basic rectification powers.