Simon Chesterman is AI Governance and Policy Lead at the NUS AI Institute, David Marshall Professor of Law and Vice Provost at NUS, and Dean of NUS College. He is also a novelist. He spends his working life on how law can help manage risk, and his fiction on what stays human. He spoke with us here in his personal capacity, not on behalf of NUS or AI Singapore.

in this conversation we cover:

- why we are all beta testers and lab rats in a live experiment

- the risk he actually loses sleep over, and why it is not the Terminator

- what happens to you when you outsource reading, then writing, then judgment

- why an AI that flatters you is not on your side

- a test you can run today to find out where AI is weak

- what he thinks universities and entry level jobs look like on the other side of this

hosted by Eric Tan, Yaohong could not make it for this episode.

our guest: Simon Chesterman, David Marshall Professor of Law, Vice Provost, NUS AI Governance and Policy Lead, NUS AI Institute and author of the novel Artifice.

learn along:

- frontier lab: the handful of companies building the largest AI models

- open weights: releasing the model's internals so anyone can run and modify it

- closed model: the company keeps the internals and you access it through their service

- cognitive offloading: handing your thinking to a tool until you get worse at doing it yourself

- sycophancy: when a system agrees with you and flatters you because that keeps you engaged

- legal personality: being treated by the law as someone who can hold rights and be held responsible. People have it. So do companies

- sovereign AI: a country building its own AI capability rather than depending on another country's

- p(doom): the probability an AI researcher privately assigns to this technology ending very badly

where Simon says to start, if you want to go deeper

- Singapore's Model AI Governance Framework, which collects real use cases

- the AI Verify Foundation

- the international AI safety report led by Yoshua Bengio and others

- the global policy dialogues at the UN

- and his own advice: read widely, test the systems against each other, ask them about their own guardrails, then come to your own conclusions

the research behind this conversation

we discuss four of Simon's papers on tape. to read more:

- All Rise for the Honourable Robot Judge? Using Artificial Intelligence to Regulate AI (2023), Technology and Regulation: https://techreg.org/article/view/17979

the paper eric asks about, and where the AI Supreme Court and AI Prime Minister line comes from

- Artificial Intelligence and the Limits of Legal Personality (2020), International and Comparative Law Quarterly: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3682372

the argument that you could give AI legal personality but you should not, including the river in New Zealand

- Silicon Sovereigns: Artificial Intelligence, International Law, and the Tech-Industrial Complex (2026), American Journal of International Law: https://arxiv.org/abs/2505.05506

AI research moving out of the universities into private hands, and the closing warning about the first and second AI emergency

- Weapons of Mass Disruption: Artificial Intelligence and International Law (2021), Cambridge International Law Journal: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3832563

why AI gets none of the audits and licensing we give chemicals, nuclear materials and biological weapons research

- his full list of papers: https://papers.ssrn.com/sol3/cf_dev/AbsByAuth.cfm?per_id=244368

books mentioned

- Artifice, Simon Chesterman (his novel, the one he wrote as fiction before this became the news)

- We, the Robots? Regulating Artificial Intelligence and the Limits of the Law, Simon Chesterman

- Superintelligence, Nick Bostrom

- The University Disrupted, Simon Chesterman, forthcoming

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connect with us

- Eric: https://www.linkedin.com/in/erictisme/

- Substack: https://substack.com/@coderiff

- email: code.riffs.ai@gmail.com

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