nna Guo introduces herself as a wannabe artist who happens to be a lawyer, and that tension runs through her entire story. In this episode of This Legal Life, Ben Chiriboga follows her winding path from a finance degree in China to Duke Law and Big Law in New York, then to Singapore, where she found a startup co-founder on Tinder and built an experiential events company that pivoted into virtual team building for Microsoft and Google during COVID. After selling that business, she drew her next career move out of a hat, went in-house at Alipay and Google, and got early access to GPT when it could barely string a sentence together. Today she runs Legal Benchmarks, the independent platform measuring how AI models and systems perform on legal work. Anna and Ben dig into why benchmarking matters for both buyers and builders, the case for posting things that mean something to you, and how to maximize your surface area for getting lucky.

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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