LawNext

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, 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). 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.

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, 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.

Pablo Arredondo, legal technologist who co-founded Casetext and led development of CARA and CoCounsel. He recounts the long road from early product failures to getting GPT-4 access and launching CoCounsel. He describes the frantic first 48 hours after launch, why Thomson Reuters bought Casetext, and his reflections on legal AI, competition, and what comes next.

Alex Su, chief revenue officer at Latitude Legal and former lawyer turned legal-tech executive, shares his nonlinear career path and rise to social media notoriety. He talks about his favorite Alameda restaurant, the shift from BigLaw to ALSPs, the TikTok moment that changed his reach, and how AI and flexible legal talent are reshaping law firm hiring and workflows.

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.

Winston Weinberg and Gabriel Pereyra, co-founders of Harvey, transitioned from roommates in a San Francisco apartment to leaders of an $8 billion legal AI powerhouse. They share their unique journey, including the challenges of gaining traction with law firms and the pivotal role of GPT-4 in enhancing their platform. They discuss the complexities of scaling infrastructure while ensuring data security and ethical compliance. Additionally, they highlight their ambitions to create an essential AI operating system for the legal industry and plans for future growth in corporate legal teams.

In a dynamic discussion, Reagan Attle, Clio's CMO since 2017, reveals how the landmark $1 billion vLex acquisition is reshaping marketing strategies and enhancing customer focus. She emphasizes the complexity of growth and the delicate balance between guiding and responding to client needs, especially with AI in play. Joining her is A.J. Axelrod, VP of Payments, who unveils innovative financial products like Pay Later and Clio Capital, aimed at providing law firms with fast funding and seamless client payment options, while hinting at exciting fintech expansions ahead.

The biggest deal of 2025 – in fact, the biggest deal ever in legal tech – was legal tech company Clio's acquisition of vLex for $1 billion. A global legal research company founded in Spain, vLex had, just two years earlier, merged with the U.S. legal research company Fastcase, and the union of those two companies – which also included the Docket Alarm trove of court docket data – had further accelerated the development of Vincent, vLex's generative AI technology. Now, with Clio's acquisition of vLex, comes a combustible combination that has the potential to unify the fuel of all that vLex legal research and docket data with Clio's cloud practice management technology to create an unprecedented, AI-driven platform that unifies both the business and practice of law. Against this backdrop, I sat down with Ed Walters, the founder and CEO of Fastcase, during ClioCon in October, to discuss the acquisition and its implications for the legal industry. Walters cofounded Fastcase in 1999 along with his former Covington & Burling colleague Phil Rosenthal. After Fastcase merged with vLex, he became vLex's chief strategy officer. Since the Clio acquisition, he is now Clio's vice president of legal innovation and strategy. Note: As of this recording, Clio had not yet closed its acquisition of vLex. The deal did finally close on Nov. 10. 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.

For legal technology company Clio, this was a particularly significant year, marked by major announcements – including its $1 billion acquisition of vLex – that many saw as transformative for the company. This was on full display at the company's ClioCon conference in October, where CEO Jack Newton gave a keynote laying out the company's vision for a new era of AI-driven legal work in which Clio becomes an "intelligent legal work platform" that serves not as a system of record, but as a system of action, powering lawyers through their workdays by automating much of what they do. In today's episode, recorded live at ClioCon, host Bob Ambrogi sits down with the two key executives leading Clio's product and technology vision: John Foreman, who joined as chief product officer in May, bringing experience from major SaaS companies including MailChimp and Podium, and Jonathan Watson, the chief technology officer who's been with Clio for eight years. They explore the company's ambitious vision to develop AI and expand into larger law firms, discuss how vertical software creates advantages for AI implementation, and explain why understanding the complete client journey enables more powerful automation. Foreman and Watson share insights on moving beyond simple chatbots to AI that can actually take action, the challenges and opportunities of expanding into the enterprise market, and what's next as they work to "finish drawing the owl." "We've started to draw the owl for folks," Foreman says, "and we're going to finish drawing the owl, and it's going to be a beautiful owl." Note: As of this recording, Clio had not yet closed its acquisition of vLex. The deal did finally close on Nov. 10. 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.

Join Adam Borgman, a litigation expert at Vorys, Julie Brown, the firm's Practice Technology Director, and Joshua Schnoll, Everlaw's CMO, as they dive into how law firms are reimagining litigation through AI. They discuss the crucial step of mapping existing workflows before adopting AI tools, sharing insights on Everlaw's Deep Dive feature that uncovers hidden evidence. Expect fascinating stories, including a surprising Tums revelation, and key considerations such as trust, cost-effectiveness, and the future of legal jobs in an AI-enhanced landscape.