LawNext

LawNext on Location: Visiting Everlaw's Headquarters For A Conversation with AJ Shankar, Founder and CEO

For the final installment of our LawNext on Location series, Bob heads across the bay, from San Francisco to Oakland, to the headquarters of e-discovery company Everlaw, where he sits down with founder and CEO AJ Shankar for a conversation about technology, AI and being in it for the long game. AJ grew up in Connecticut, came west in 2002 for a computer science PhD at UC Berkeley, and has lived within a few blocks of the Berkeley campus ever since. He stumbled into the legal industry almost by accident — recruited to serve as a technical expert in litigation involving how the internet worked — and quickly realized that the legal world was home to some of the most technically fascinating and underserved problems he'd ever encountered. He never left. AJ had a prior startup, a computer vision company that was acquired, before launching Everlaw in 2011. The company was cloud-native and ML-infused from the start, built on the conviction, AJ says, that there's no single way to find the needle in a discovery haystack, and that building a genuinely useful litigation platform requires solving for collaboration, ease of use and scalability all at once. The bulk of the conversation focuses on generative AI, and how Everlaw has approached it differently than much of the market. Rather than bolting on a chatbot, AJ says, Everlaw embedded AI deliberately throughout the platform — document summarization, coding suggestions, deposition analysis, fact extraction — always grounding responses in the actual documents at hand and citing sources so users can verify the work. The December launch of Deep Dive, which lets litigators pose a question and get a synthesized, cited answer drawn from an entire document corpus in about a minute, is the feature AJ calls a "new era" for discovery — one he genuinely believes represents a categorical shift. As Everlaw continues to grow, it also remains independent, with no private equity and no outside majority owners. As for AJ, he says he is in it for the long game, and has never included an exit slide in a fundraising deck. 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 [https://joinparadigm.com/], home to the practice management platforms PracticePanther [https://www.practicepanther.com/], Bill4Time [https://www.bill4time.com/], MerusCase [https://meruscase.com/] and LollyLaw [https://www.lollylaw.com/]; the e-payments platform Headnote [https://headnote.com/]; and the legal accounting software TrustBooks [https://trustbooks.com/]. * Briefpoint [https://rebrand.ly/briefpoint-lawnext-podcast], eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Chapters 00:00 Introduction and Setting the Scene 03:23 The Journey to Founding Everlaw 08:36 The Evolution of Everlaw's Technology 11:06 Incorporating Generative AI into Legal Processes 14:04 Deep Dive: A New Era in Discovery 19:17 Transformative Experiences in Legal Discovery 22:27 Previewing Innovations at Legal Week 25:03 Understanding AI's Limitations in Legal Contexts 28:11 Navigating Hype in Legal Technology 30:47 The Impact of Foundation Models on Legal Software 34:36 Future Vision for Everlaw and Legal Tech 38:13 Closing Thoughts and Company Philosophy If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

LawNext on Location: At A Sonoma Winery, A Conversation with Briefpoint CEO Nathan Walter about Discovery, Disruption and, Of Course, Wine

Continuing his on-location interview tour of San Francisco, Bob heads an hour north to Santa Rosa to sit down with Nathan Walter, cofounder and CEO of Briefpoint, over a bottle of red wine at Paradise Ridge Winery, a spot literally around the corner from Nathan's house, sitting on the edge of the Mayacamas Mountain Range that divides Sonoma and Napa counties. It is a fitting setting for a founder who grew up in Sonoma wine country, where wine is less a luxury than a way of life, and where his family's most treasured heirloom was a bottle from the year he was born. Nathan's path to founding Briefpoint is an origin story rooted in genuine frustration with the legal system. A U.C. Santa Barbara philosophy major who drifted into law school for lack of better options, he ultimately landed in civil litigation – and grew increasingly disillusioned with how discovery was weaponized to bleed defendants dry financially, even when they had done nothing wrong. After a particularly infuriating mediation where opposing counsel openly admitted the shakedown strategy, Nathan decided to do something about it. He taught himself to code from YouTube videos, built vaporware prototypes, cold-called attorneys to test demand, and eventually found his technical cofounder through a Discord gaming community he had created to build a social life after moving to Orange County. What followed was a years-long grind – including an 18-month stretch working days as an entry-level sales rep at another legal tech company and nights building Briefpoint, until a close acquaintance invested $100,000 of her own money so he could focus full time. Briefpoint launched in June 2022, before the ChatGPT wave, focusing narrowly on automating discovery responses – drafting objections, pulling relevant documents and generating formatted Word documents ready to sign. Nathan talks about the company's deliberate "go deep, not wide" strategy: rather than expanding into motions or other legal workflows to chase the AI hype cycle, Briefpoint is doubling down on doing discovery so exceptionally well that firms will pay for it alongside broader AI platforms, the way teams use Slack alongside the full Microsoft suite. The conversation also covers the threat to legal tech companies posed by foundation models such as Claude and GPT, the psychology behind why attorneys are resistant to automation (Nathan has a theory about "superstitious control" and lucky jerseys), the parallels between winemaking and product development, and the advice he'd give an aspiring founder: burn the ships, go full time and put yourself in a corner with no way out but forward. As for what varietal Briefpoint would be? A Russian River Pinot Noir – not a life-changing Cab, but reliably excellent at exactly what it promises. 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 [https://joinparadigm.com/], home to the practice management platforms PracticePanther [https://www.practicepanther.com/], Bill4Time [https://www.bill4time.com/], MerusCase [https://meruscase.com/] and LollyLaw [https://www.lollylaw.com/]; the e-payments platform Headnote [https://headnote.com/]; and the legal accounting software TrustBooks [https://trustbooks.com/]. * Briefpoint [https://rebrand.ly/briefpoint-lawnext-podcast], eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). * Legalweek [https://rebrand.ly/Legalweek-LawNext-Podcast], 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: 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 [https://joinparadigm.com/], home to the practice management platforms PracticePanther [https://www.practicepanther.com/], Bill4Time [https://www.bill4time.com/], MerusCase [https://meruscase.com/] and LollyLaw [https://www.lollylaw.com/]; the e-payments platform Headnote [https://headnote.com/]; and the legal accounting software TrustBooks [https://trustbooks.com/]. * Briefpoint [https://rebrand.ly/briefpoint-lawnext-podcast], eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). * Legalweek [https://rebrand.ly/Legalweek-LawNext-Podcast], 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 [https://youtu.be/qXo4uLbudlc]. 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 [https://www.linkedin.com/in/alexander-su/], chief revenue officer at Latitude Legal [https://latitudelegal.com/], 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 [https://www.tiktok.com/@legaltechbro], 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 [https://joinparadigm.com/], home to the practice management platforms PracticePanther [https://www.practicepanther.com/], Bill4Time [https://www.bill4time.com/], MerusCase [https://meruscase.com/] and LollyLaw [https://www.lollylaw.com/]; the e-payments platform Headnote [https://headnote.com/]; and the legal accounting software TrustBooks [https://trustbooks.com/]. * Briefpoint [https://rebrand.ly/briefpoint-lawnext-podcast], eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). * Legalweek [https://rebrand.ly/Legalweek-LawNext-Podcast], 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 [https://joinparadigm.com/], home to the practice management platforms PracticePanther [https://www.practicepanther.com/], Bill4Time [https://www.bill4time.com/], MerusCase [https://meruscase.com/] and LollyLaw [https://www.lollylaw.com/]; the e-payments platform Headnote [https://headnote.com/]; and the legal accounting software TrustBooks [https://trustbooks.com/]. * Briefpoint [https://rebrand.ly/briefpoint-lawnext-podcast], eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). * Legalweek [https://rebrand.ly/Legalweek-LawNext-Podcast], 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.