LawNext

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

As Bob continues his 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. Pablo was cofounder 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 cofounder 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 Bob 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.    Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.   Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City.   If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.  

LawNext on Location: Lunch with Alex Su of Latitude Legal In Alameda, Calif.

This episode is recorded live, and is best enjoyed on YouTube. Watch the episode here.   While Bob is visiting San Francisco for two weeks, he is sitting down for conversations with legal tech innovators and entrepreneurs "in their natural habitats" – places in the Bay Area they consider special. Today, in the first in this series, Bob sits down for lunch with Alex Su, chief revenue officer at Latitude Legal, over Thai iced tea and tofu dishes at Phnom Penh House, a Cambodian restaurant in Alameda that Alex considers something of a personal institution, frequenting it for both family meals and business meetings.   Alex's career path is anything but linear. He started as an associate at Sullivan & Cromwell in New York, clerked for a federal judge in Chicago, then drifted through a plaintiff's firm, a brief solo practice, and ultimately a leap of faith into legal tech sales – joining e-discovery company Logikcull in 2016. From there, he moved to Everlaw, then to Ironclad, where he served as head of community development, building a reputation that spread well beyond any job title.   That reputation was shaped in large part by TikTok, where Alex's comedic, self-effacing videos skewering law firm culture – partners, associates, privilege logs and the absurdities of BigLaw – earned him more than 100,000 followers, got shared inside Ironclad's internal Slack, and ultimately helped land him his next job. It's a story of accidental virality and deliberate reinvention that mirrors the broader shifts he sees in the legal profession.   Now at Latitude Legal, an ALSP providing on-demand legal talent to law firms and corporate legal departments, Alex represents a kind of poetic symmetry: a lawyer known for championing "alternative careers" working at an "alternative legal services provider" — a label he thinks has outlived its usefulness, given how mainstream flexible legal talent has become.   Bob and Alex also dig into the current state of legal AI – what's overhyped, what's underhyped, and why the pandemic was arguably a bigger inflection point for legal tech adoption than generative AI. Plus, Alex and Bob reflect on Bob's three decades of covering legal innovation, the stubborn persistence of the billable hour, and why the justice gap remains stubbornly wide despite all the talk of disruption.   It is a wide-ranging and candid conversation – one you may want to watch on video instead of just listening to the audio.    Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City.   If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.   Chapters 00:00 Intro to Today's Lunch: A Special In-Person Series 04:45 Career Transitions: From Law to Legal Tech 23:27 Going Viral: The TikTok Journey 25:10 Balancing Humor and Professional Identity 26:54 Redefining Career Paths for Lawyers 28:39 The Evolution of Legal Careers 30:35 Innovation in Legal Practice 34:07 The Impact of the Pandemic on Legal Technology 34:28 The Future of Legal Technology and AI 38:10 Navigating Uncertainty in Legal Services 40:18 The Ongoing Relevance of Traditional Legal Models 42:11 Personal Reflections and Future Outlook  

From Customer to Acquirer: Filevine's Ryan Anderson and Pincites' Sona Sulakian on Building AI Contract Intelligence

In this episode of LawNext, we talk with Ryan Anderson, co-founder and CEO of Filevine, and Sona Sulakian, former CEO and co-founder of Pincites, about Filevine's acquisition of the AI-powered contract redlining company. The deal, which closed in December, marks Filevine's second major AI acquisition of the year. Even more notably for this traditionally litigation-focused company, it represents a significant strategic expansion into the corporate and transactional legal market — a segment where Filevine saw 120% growth in 2025. What makes this acquisition particularly compelling is its origin story: Filevine was actually a customer of Pincites before acquiring the company. After Filevine's legal team became early adopters and enthusiastic users of the product, Anderson and his team recognized that Pincites' Word-native contract intelligence platform filled a critical gap in their offerings. The acquisition brings aboard sister co-founders Sona and Mariam Sulakian and their team, who will continue developing what Filevine now calls "LOIS for Word" — a drafting and redlining tool integrated directly into Microsoft Word. Along with host Bob Ambrogi, they discuss how the Sulakian sisters identified the market gap that led them to build Pincites, why they chose to build directly into Word rather than create a standalone platform, and what attracted them to Filevine among multiple suitors. Anderson shares his vision for building a comprehensive Legal Operating Intelligence System (LOIS) that connects contracts, depositions and all legal work into a single unified platform. They also explore the broader implications of AI for legal practice and access to justice, and how tools like Pincites and Filevine are transforming the way legal work gets done.   Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.   Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City.   If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.  

From Roommates to Billionaires: Harvey's Founders Gabriel Pereyra and Winston Weinberg on Building AI Infrastructure for Law

Gabriel Pereyra and Winston Weinberg started legal AI company Harvey in 2022 as roommates in a San Francisco apartment. Pereyra had been working on AI research at Meta and Google, while Weinberg was a first-year litigation associate at O'Melveny & Myers. Today, they still share that same apartment, but their company has grown into a global enterprise serving more than 1,000 law firms and corporate legal departments and valued at a whopping $8 billion. In this episode of LawNext, Pereyra and Weinberg take us back to Harvey's earliest days, when they were sending thousands of LinkedIn messages trying to get anyone to look at their product. They share the pivotal moment when early access to GPT-4 transformed what they could build, the breakthrough that came when Allen & Overy became their first major client, and how they have evolved from building an AI assistant for individual lawyers to constructing what they call "essential infrastructure" for legal work. With host Bob Ambrogi, they discuss Harvey's vision for becoming an AI operating system that integrates across the entire legal tech ecosystem, their focus on memory and agentic AI that can handle complex multi-step workflows, and the massive infrastructure challenges of deploying AI at scale across global law firms while maintaining ethical walls and data security.  Pereyra and Weinberg also reflect candidly on how two founders with no management experience have learned to scale a company now employing hundreds of people — more than 20 percent of whom are lawyers — and what it is like to go from struggling startup to being featured in The New York Times as AI billionaires while still sleeping on a mattress on the floor.   Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.   Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Eve, taking care of the tasks that slow you down so you can operate at your highest potential   If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.  

Clio Doubleheader: CMO Reagan Attle and VP of Payments A.J. Axelrod

In the last in a series of interviews recorded during the ClioCon conference in Boston in October 2025, we bring you a doubleheader – two interviews with two of the legal tech company's key executives.  In the first, LawNext host Bob Ambrogi speaks with Reagan Attle, chief marketing officer at Clio since 2017. In a year in which Clio made the biggest acquisition in legal tech history with its $1 billion purchase of vLex, and in which Clio is aiming to dramatically expand its market and its use of AI, what are the challenges and opportunities for the person tasked with leading the company's global brand and marketing strategy? One thing for sure, Attle says: It makes her job more complex. Listen to the interview to hear Attle's perspective.  In the second interview, Ambrogi sits down with A.J. Axelrod, who joined Clio in November 2024 as vice president of payments and financial services. He fills us in on the two financial products unveiled at ClioCon: Clio Capital, a capital-advance program offering law firms fast access to funds for growth or cash-flow management, and Pay Later, a financing option for law firm clients to pay their legal bills in installments, while the firm gets paid up front. He also talks about what else may be on the horizon for fintech at Clio.   Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Eve, taking care of the tasks that slow you down so you can operate at your highest potential   If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.