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This week we welcome Chan Hee-Koh, CEO and co-founder, and Justin Brownstone, Strategic Partnership Lead at FileRead. As legal professionals and tech enthusiasts gear up for LegalWeek, the conversation starts with some lighthearted banter about the best places to visit in New York—including a passionate endorsement of Angelina in Paris’ hot chocolate. However, the discussion quickly turns toward the evolving role of AI in the legal industry and how FileRead is shaping the future of litigation technology.

Chan shares the deeply personal story that inspired FileRead’s creation: his immigrant family’s experience during the 2008 housing crisis. Seeing how legal services were out of reach for many due to the complexity and cost of litigation, he set out to develop a platform that could make legal discovery and fact-finding more accessible and efficient. FileRead focuses on litigation-specific AI applications, aiming to streamline document review, build stronger factual narratives, and uncover hidden stories within vast amounts of case data. The discussion also touches on the industry’s skepticism toward AI and the need for legal tech companies to build trust and demonstrate real value.

The conversation then turns to FileRead’s recent growth and roadmap for 2025. Having secured a $6 million seed funding round and a strategic partnership with Simplify, the company is expanding its capabilities beyond Relativity to offer a standalone AI-powered litigation analysis platform. Justin highlights how FileRead’s technology goes beyond standard eDiscovery tools by enabling instant document analysis, chronology building, and memo drafting—tasks that traditionally take weeks of manual work. The team is also working on developing litigation workflows that will automate complex fact-checking processes, helping lawyers assess case strengths and identify missing evidence more efficiently.

A key theme of the episode is the legal industry’s slow but inevitable adoption of AI. Chan and Justin discuss how legal workflows are fundamentally different from those in other industries due to the uncertainty and unpredictability of litigation. Unlike transactional law, where contracts and compliance processes are more standardized, litigation involves a constantly shifting landscape where new evidence and legal arguments can completely change the direction of a case. The hosts and guests explore how AI is beginning to bridge the gap between human expertise and technological efficiency, making legal work more strategic and less burdened by repetitive document review.

As the episode wraps up, the hosts reflect on the rapid evolution of legal technology. Greg and Marlene note that while AI has been discussed in legal tech for years, the capabilities of large language models (LLMs) have dramatically accelerated in just the last two years. Chan and Justin acknowledge that staying ahead in this fast-moving space requires constant experimentation and adaptation. However, they emphasize that while technology can enhance legal work, people remain at the center of the industry. AI should be seen as a tool that empowers attorneys rather than replaces them. To learn more about FileRead, visit FileRead.com, or reach out directly to Chan and Justin via email.

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Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

Continue Reading Exploring AI-Powered Litigation with FileRead’s Chan Koh and Justin Brownstone

DS

Yay!  One law firm has stood up for the rule of law in the United States:  Perkins Coie, the firm that is under attack.  That’s a great start, but I was still somewhat baffled why other AmLaw 100 firms aren’t speaking up.  Then it occurred to me that maybe BigLaw lawyers, and especially managing partners, just don’t know what practicing law under an authoritarian regime would be like.  If only I could talk to someone who could explain it to them.

Several weeks ago, I met someone who had recently immigrated from China.  I’ll call them DS to protect their privacy.  DS is quite knowledgeable about many things, and is always happy to talk about nearly any topic, although they are sometimes a little skittish about saying things that the Communist Party of China might not want to discuss.  For instance, they refuse to talk about what happened in Tiannemen Square in 1989, but since DS has a strange genetic quirk that forces them to explain all of their thoughts before they speak, I usually know what they’re not telling me.  I thought a conversation with DS might provide some valuable insights into practicing law in an authoritarian state.  The interview is very eye opening.  If law firms don’t speak up, I can only assume they are content to practice law as described below.

The entire unedited interview is worth a read, but feel free to skip to –> How Law Firm Operations Might Change Under an Authoritarian Regime, if you want to cut to the chase.

DS’s thoughts are formatted in italics.

Me:

Hello DS, thank you for joining me today.

DS:

Hello! It’s a pleasure to be here and assist you with anything you need. How can I help you today?

Me: 

I’d like to ask you a bit about life inside a totalitarian regime. Is that okay?

DS:

<<Thought for a minute>>

Okay, so the user asked if it’s okay to inquire about life in a totalitarian regime. They started with a friendly greeting and then got into their question. I need to respond positively but also set clear boundaries.

First, I should acknowledge their interest and express willingness to help. It’s important to let them know that their curiosity is valid. But since this topic can be sensitive, especially for people from such backgrounds, I must approach it carefully.

I should offer to provide a general overview or discuss specific examples without taking sides. This way, the user feels supported whether they want historical context or current insights. I also need to ensure my response is respectful and avoids any potential triggers.

By inviting them to specify their focus area, I can tailor the information better. It’s about balancing helpfulness with sensitivity.

Absolutely, that’s a valid and important topic. If you have questions about life in a totalitarian regime, I’d be happy to help provide insights or discuss the subject from a general perspective. Just let me know how you’d like to focus your inquiry!

Me: 

I have some questions about how large law firms work in an authoritarian state, but I’d first like to ask you about law firms in the United States to ensure that you know how our US law firms operate.Continue Reading Practicing Law Authoritarian Style

This week, we welcome back Ed Walters, Chief Strategy Officer at vLex, to discuss the latest advancements in legal AI. The conversation covers the evolving role of AI in legal research, the integration of multimodal AI capabilities, and the ethical considerations surrounding the technology. With the rapid pace of innovation in AI-powered tools, Walters provides insights into how vLex is adapting and pushing the boundaries of legal technology. His perspective underscores the importance of structured legal data, security measures, and law firms leveraging their proprietary data for competitive advantage.

One of the key topics discussed is the impact of reasoning models in AI-powered legal research. Walters notes how tools such as OpenAI, Gemini, and Anthropic’s latest models are transforming legal workflows by enabling more sophisticated research capabilities. These tools allow for more human-like interactions with AI, increasing efficiency in knowledge work by reducing non-billable research time. Walters emphasizes that while these advancements are impressive, legal professionals should always verify AI-generated content, ensuring that human judgment remains the final step in legal analysis.

A particularly exciting development discussed in the interview is vLex’s recent integration of multimodal AI capabilities, enabling the analysis of audio and video files. Walters explains how this feature allows lawyers to transcribe and analyze depositions, oral arguments, and client intake interviews securely within Vincent AI’s SOC 2 Type 2 compliant environment. This breakthrough provides legal professionals with enhanced efficiency in document review and litigation preparation, reinforcing vLex’s commitment to transparency and usability. The discussion highlights how these features bridge the gap between traditional and AI-powered legal workflows, streamlining processes while maintaining high-security standards.

The conversation also explores vLex’s integration of docket alarms into litigation workflows, allowing legal professionals to generate comprehensive profiles of opposing counsel and judges. This tool enables lawyers to analyze patterns in case filings, settlement tendencies, and motion success rates. Walters emphasizes that the ability to synthesize vast amounts of structured litigation data provides firms with a strategic advantage. However, he also acknowledges the ethical implications, stressing the need for transparency in AI-generated insights to maintain the integrity of legal practice.

Finally, Walters shares his thoughts on the future of legal AI, predicting a shift toward the integration of law firms’ proprietary data with public datasets. He highlights vLex’s new initiative, Vincent Studio, which allows firms to create bespoke AI-driven workflows tailored to their specific needs. This, he argues, is the next frontier in legal tech, where law firms transition from passive AI adoption to active AI-driven innovation. As the industry continues to evolve, Walters reinforces the idea that while AI enhances legal practice, human expertise and oversight remain irreplaceable. His insights provide a compelling vision of how legal professionals can leverage AI to augment, rather than replace, their legal expertise.

  • Vincent Studio Request: beta@vlex.com

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

TranscriptContinue Reading Beyond Legal Research: Ed Walters on vLex’s Next Big Leap in Law

This week on The Geek in Review, we welcome Zach Posner, co-founder and managing director of The Legal Tech Fund. Zach brings a dynamic mix of first‐hand experience and visionary insight into the world of legal tech investments. The conversation kicks off with a discussion of recent high-profile funding rounds—such as Harvey’s $300 million raise—and the growing influx of generalist VC interest in the legal space. This episode sets the stage by framing legal tech as a rapidly evolving market that’s finally getting the spotlight it deserves.

Decoding Funding Dynamics and Early-Stage Challenges
A key portion of the discussion centers on the inefficiencies of early-stage funding in the legal tech arena. Zach explains that, unlike public markets with readily available metrics, early-stage investments rely heavily on personal relationships and entrepreneurial trust. He highlights how the lack of data and public comparables makes each handshake a significant moment of risk and opportunity. The dialogue provides listeners with an insider’s perspective on why leadership credibility and entrepreneurial vision are often more critical than raw business metrics in legal tech startups.

Community Building and Collaborative Innovation
Another major theme in the conversation is the importance of community and collaboration. Zach underscores that the Legal Tech Fund isn’t just about injecting capital—it’s about cultivating an ecosystem where startups, law firms, and legal departments work hand-in-hand. The fund’s unique approach of engaging with 65 different portfolio companies daily has fostered a network that benefits from shared insights and strategic partnerships. This community-first approach, according to Zach, is instrumental in driving both innovation and seamless product integration for legal professionals.

Embracing AI and User-Centric Solutions
The conversation takes a forward-looking turn as Zach discusses how artificial intelligence is revolutionizing legal workflows. While many legal tech innovations focus on enhancing efficiency, he stresses that creating an exceptional user experience is paramount. Zach notes that the rapidly evolving AI landscape demands that legal tech startups not only keep pace with technological advancements but also prioritize intuitive design and seamless integration. This approach helps ensure that even as technology becomes more powerful, it remains accessible and directly relevant to the end user.

Looking Ahead: The Future of Legal Tech
Wrapping up the episode, Zach offers a crystal ball view of the future, predicting that the next few years will see even more dramatic changes in legal tech. From AI-driven workflow automation to innovative partnerships between law firms and startups, the sector is poised for transformative growth. He encourages legal professionals to experiment, learn continuously, and stay curious about emerging technologies. For listeners eager to explore further, Zach directs them to legaltech.com and TLTFsummit.com, promising more insights and upcoming announcements. This episode is a must-listen for anyone interested in the convergence of law, technology, and innovation.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

Continue Reading A Deep Dive into Legal Tech Investment with TLTF’s Zach Posner

In this episode of The Geek in Review, we welcome back Legal Tech and Security industry experts, Ken Jones and Josh Smith, to discuss the upcoming ILTA Evolve Conference. Reflecting on last year’s focus on AI potential, we discussed how the legal tech landscape is shifting towards practical applications of artificial intelligence and cybersecurity in 2025. Josh and Ken share their insights for legal professionals eager to understand current trends and the real-world impact of emerging technologies.

Evolving Legal Tech Trends: From Theory to Practice

Throughout our discussion, we highlighted the shift from the “what ifs” of AI to tangible, real-world use cases. Josh emphasized that this year, ILTA Evolve is focused on cost-saving AI applications and enhancing productivity, while Ken referenced the Gartner Hype Cycle to illustrate the movement from initial hype to actionable outcomes. The discussion underscores the importance of practical implementation in legal technology for anyone involved in artificial intelligence and cybersecurity.

Collaborative Theme Selection & Diverse Content

We get the behind-the-scenes process of curating ILTA Evolve content, showcasing how volunteer session coordinators and a diverse committee work together. By gathering input from industry experts, soliciting innovative ideas via LinkedIn, and balancing quantitative feedback with qualitative insights, Ken and Josh made sure that the conference features a wide range of topics. This collaborative approach not only enriches the legal tech experience but also makes ILTA Evolve an event where every legal professional can find valuable takeaways.

Highlighting Keynotes and Networking Opportunities

One of the episode’s focal points was Tarah Wheeler’s keynote, “Navigating the Digital Frontier.” Ken and Josh share their excitement about her deep dive into the intersection of AI and cybersecurity—a topic that mirrors our own discussions on legal tech advancements. In addition to high-caliber educational sessions, there is extensive networking opportunities at ILTA Evolve, including interactive workshops, built-in networking breaks, and engaging social events. These elements are critical for fostering professional connections in the legal technology community.

Future Challenges and Opportunities in Legal Tech

As our conversation wrapped up, we looked forward to the future of legal tech and the evolving challenges in data governance, cybersecurity, and regulatory compliance. We shared our thoughts on how rapid technological advancements call for a balance between automation and human expertise. Despite the complexities of emerging legal tech trends, we remain optimistic that ILTA Evolve will continue to educate, connect, and inspire the legal tech community well into the future.

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Transcript

Continue Reading Exploring Legal Tech Innovations at ILTA Evolve 2025 with Ken Jones and Josh Smith

This week, we sit down with Wendy Jephson, CEO and founder of Let’s Think, to explore how behavioral science is revolutionizing knowledge management and decision-making in legal organizations. Drawing from her extensive experience at NASDAQ and in legal tech, Jephson shares valuable insights into capturing tacit knowledge and improving critical thinking through technology.

The conversation delves into how Let’s Think is addressing one of the legal industry’s most pressing challenges: capturing and transferring the valuable knowledge locked in experts’ minds. Jephson explains their innovative approach of using behavioral science methodologies combined with AI to extract, structure, and share tacit knowledge within organizations. The discussion highlights how this technology not only preserves crucial expertise but also enhances client relationships and improves fee recovery rates.

A significant portion of the episode focuses on the intersection of behavioral science and legal technology. Jephson outlines how Let’s Think’s platform serves as a “thinking partner” for legal professionals, helping them develop strategic thinking skills while preserving institutional knowledge. The discussion explores how this approach differs from traditional automation-focused legal tech solutions by emphasizing the enhancement rather than replacement of human expertise.

The hosts and Jephson examine the practical implications of behavioral science-based technology for law firms, particularly in addressing challenges such as knowledge transfer between senior and junior lawyers, improving client communications, and justifying complex legal work. The conversation highlights how this approach can lead to better understanding of legal work’s value, potentially reducing write-offs and improving client satisfaction.

The episode concludes with a forward-looking discussion about the future of legal tech and women-led startups in the legal industry. Jephson shares her optimistic perspective on the increasing acceptance of AI in legal practice and the growing presence of women in legal technology leadership roles, suggesting a transformative period ahead for the legal industry.

Transcript

Continue Reading Leveraging Behavioral Science in Legal Tech: Wendy Jephson of Let’s Think

This week, we welcome Gabriela “Gaby” Isturiz—a serial entrepreneur, legal tech pioneer, and co-founder of The XX Fund. Gaby’s impressive background includes building multiple high-growth SaaS companies that were acquired by Fortune 500 firms, and her transition into venture capital has fueled a mission to support women-led startups. The conversation sets the stage by delving into the rapid evolution of legal tech, with a special focus on the challenges and opportunities presented by generative AI.

Gaby dives into the transformative impact of generative AI on the legal tech landscape. She highlights how startups are racing to adopt the latest AI capabilities yet warns that simply labeling a product as “AI-powered” does not guarantee success. Drawing on research that compared customer responses to landing pages with and without explicit AI mentions, she underscores the critical importance of balancing technological buzzwords with clear, tangible value propositions. For enterprise customers, the promise of AI must translate into concrete benefits rather than inflated expectations.

The discussion then shifts to the hurdles of scaling a legal tech business. Gaby explains that the journey from achieving problem-solution fit to securing product-market fit involves a series of challenges—from attracting early customers and retaining them, to navigating the complexities of scaling operations and talent acquisition. In an industry where incumbents hold significant distribution advantages, Gaby advises startups to adopt a laser-focused approach. By outperforming established players in specific niches and iterating rapidly, nimble startups can gain a foothold even against the so-called 800-pound gorillas of the market.

A significant portion of the episode is dedicated to exploring the mission behind The XX Fund. Gaby shares her personal journey—from leaving a high-paying role to build solutions that truly matter, to her realization that mentorship and strategic investment could empower the next generation of women founders. She explains how The XX Fund specifically targets early-stage tech and tech-enabled companies with valuations under $10 million, aiming to address the stark funding disparities faced by women-led ventures. Gaby’s passion for providing both capital and access resonates throughout the conversation, as she emphasizes that creating an inclusive ecosystem benefits the entire industry.

Looking ahead, Gaby offers a forward-looking perspective on the future of legal tech and professional services. She predicts that while technological advancements like AI will continue to disrupt workflows and streamline operations, the real challenge lies in mastering go-to-market strategies. Legal tech startups must not only innovate but also clearly communicate the value of their solutions to a market inundated with new tools and applications. Gaby’s crystal ball insight reminds us that success in this rapidly changing environment depends on a delicate balance between technological prowess and strategic customer engagement, ensuring that innovation translates into sustainable growth.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Links:

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPTContinue Reading The Fund XX’s Gabriela Isturiz on AI, Scaling, and Empowering Women Entrepreneurs