Wednesday, February 25, 2026

LawNext on Location: The View from Tiburon – A Dialog with Pablo Arredondo, Casetext Cofounder

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As I proceed my LawNext on Location sequence – all recorded stay within the San Francisco space at places of every visitor’s selecting – he sits down with Pablo Arredondo at his residence in Tiburon, a quaint Marin County city with a historical past stretching from Mexican land grants to naval outposts to a southern railway terminus. From Pablo’s residence workplace, the view appears to be like out over Richardson Bay in the direction of Sausalito and, in case you look rigorously, the Golden Gate Bridge could be seen within the distance. It’s a setting that’s solely becoming for a dialog with somebody who helped form one of many extra exceptional journeys within the annals of authorized expertise.

(My apologies for the video high quality. A videographer, I’m not.)

Pablo was cofounder of Casetext, the once-scrappy startup that spent a decade iterating, pivoting and persisting earlier than putting gold with CoCounsel, the primary GPT-4-powered AI authorized assistant, unveiled on the nationally televised Morning Joe present on March 1, 2023. Simply 4 months later, Thomson Reuters acquired Casetext for $650 million in money. Now, 2.5 years later, Pablo lately left TR, the place he’s, as he places it, constructing a Lego Demise Star together with his daughter and eventually being attentive to his well-being after 16 years of nonstop pursuit.

On this wide-ranging dialog, Pablo displays on the lengthy street to CoCounsel – from a failed crowdsourcing experiment to CARA’s transient evaluation instrument to the pivotal second when Casetext signed a $20,000 innovation license with OpenAI and received early entry to GPT-4, 10 weeks earlier than ChatGPT’s public launch. He describes the surreal expertise of these first 48 hours after CoCounsel’s debut, when he and cofounder Jake Heller recognized 74 distinct authorized use circumstances the instrument might deal with – any one in all which, he says, “would have been an organization within the outdated world.”

Pablo and I additionally dig into the larger questions surrounding authorized AI, together with whether or not the sector is advancing as quick as he anticipated; what the muse fashions from Anthropic, OpenAI and Google imply for legal-specific AI firms reminiscent of Harvey; and why he believes reasoning fashions and agentic AI characterize the following genuinely profound leap past GPT-4. Pablo additionally candidly displays on the TR acquisition and his work whereas at TR, and he provides hints on what could lie forward for him – at the very least as soon as that Demise Star mannequin is finished.

It’s a dialog that’s half memoir, half expertise seminar and half meditation on what it means to have constructed one thing that modified a occupation – and his life – all recorded with a sweeping, albeit cloudy, view of the majesty of San Francisco Bay.

Pay attention right here:

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