LawNext on Location: the view from Tiburon - A conversation with Pablo Arredondo, Casetext cofounder. - February 24, 2026 Why it matters. The acquisition validates AI's transformative potential in legal services, and CoCounsel's rapid use-case expansion signals a shift toward AI-driven workflow automation across the profession. Key takeaways. * - Casetext launched CoCounsel, GPT-4 AI legal assistant * - Thomson Reuters acquired Casetext for $650 million cash * - CoCounsel identified 74 distinct legal use cases quickly * - Founder now left TR, focusing on personal projects * - Reasoning and agentic AI seen as next breakthrough Pulse analysis. The legal technology landscape has been reshaped by a series of incremental experiments, from crowdsourced research platforms to narrow-purpose analysis tools. Casetext, founded by Pablo Arredondo and Jake Heller, spent a decade iterating on these concepts before securing an early-access license with OpenAI that granted them GPT-4 ten weeks ahead of the public ChatGPT rollout. That early partnership allowed the team to embed a large language model directly into their product suite, laying the groundwork for what would become the first GPT-4-powered AI legal assistant. When CoCounsel debuted on the nationally televised Morning Joe program in March 2023, it instantly demonstrated the scalability of AI in everyday legal work. Within the first 48 hours the founders catalogued 74 separate use cases, ranging from contract review to brief drafting, proving that a single model could replace multiple legacy tools. The rapid validation prompted Thomson Reuters to acquire Casetext for $650 million in cash, a deal that underscored the strategic value of AI-enhanced research platforms for large information providers and signaled broader industry consolidation around generative technology. Looking ahead, Arredondo argues that the next wave will move beyond text generation toward reasoning and agentic AI, where models can autonomously plan, execute, and adapt legal strategies. Competitors such as Anthropic, Google, and emerging specialist firms like Harvey are already training foundation models tailored to jurisprudence, raising the bar for accuracy and compliance. For law firms and corporate legal departments, these advances promise end-to-end automation of routine tasks and smarter decision support, but they also raise ethical questions about accountability and data privacy that the industry must address. Bob Ambrogi As I continue my LawNext on Location series - all recorded live in the San Francisco area at locations of each guest's choosing - he sits down with Pablo Arredondo at his home in Tiburon, a quaint Marin County town with a history stretching from Mexican land grants to naval outposts to a southern railway terminus. From Pablo's home office, the view looks out over Richardson Bay towards Sausalito and, if you look carefully, the Golden Gate Bridge can be seen in the distance. It is a setting that is entirely fitting for a conversation with someone who helped shape one of the more remarkable journeys in the annals of legal technology. (My apologies for the video quality. A videographer, I'm not.) Pablo was co-founder of Casetext, the once-scrappy startup that spent a decade iterating, pivoting and persisting before striking gold with CoCounsel, the first GPT-4-powered AI legal assistant, unveiled on the nationally televised Morning Joe show on March 1, 2023. Just four months later, Thomson Reuters acquired Casetext for $650 million in cash. Now, 2.5 years later, Pablo recently left TR, where he is, as he puts it, building a Lego Death Star with his daughter and finally paying attention to his well-being after 16 years of nonstop pursuit. In this wide-ranging conversation, Pablo reflects on the long road to CoCounsel - from a failed crowdsourcing experiment to CARA's brief analysis tool to the pivotal moment when Casetext signed a $20,000 innovation license with OpenAI and got early access to GPT-4, 10 weeks before ChatGPT's public launch. He describes the surreal experience of those first 48 hours after CoCounsel's debut, when he and co-founder Jake Heller identified 74 distinct legal use cases the tool could handle - any one of which, he says, "would have been a company in the old world." Pablo and I also dig into the bigger questions surrounding legal AI, including whether the field is advancing as fast as he expected; what the foundation models from Anthropic, OpenAI and Google mean for legal-specific AI companies such as Harvey; and why he believes reasoning models and agentic AI represent the next genuinely profound leap beyond GPT-4. Pablo also candidly reflects on the TR acquisition and his work while at TR, and he offers hints on what may lie ahead for him - at least once that Death Star model is done. It is a conversation that is part memoir, part technology seminar and part meditation on what it means to have built something that changed a profession - and his life - all recorded with a sweeping, albeit cloudy, view of the majesty of San Francisco Bay.

He became vice president of Maine Bonding and Casualty Co., which merged with Fidelity & Deposit, where he became Maine branch manager.