This week we welcome Raghu Ramanathan, President of Legal Professionals at Thomson Reuters, for an insightful discussion on the profound impact of Artificial Intelligence (AI) on the legal industry. Raghu shares why he believes the legal sector, alongside healthcare, stands at the forefront of the AI revolution. His journey into the legal tech world, driven by the transformative potential of AI, sets the stage for a deep dive into current trends, future predictions, and the strategic initiatives shaping the future of law.

Central to the conversation is Raghu's updated perspective on the evolution of law firms, revisiting predictions he first made in 2017. He outlines a compelling framework describing "three waves" of AI adoption currently underway. The first wave, "Optimization," which many firms are experiencing now, focuses on using AI to enhance existing workflows, making tasks faster and more efficient. The second wave, "Re-engineering," involves fundamentally rethinking processes, staffing models (including the traditional pyramid structure), pricing strategies, and the very nature of legal work to leverage AI's capabilities more deeply. Looking further ahead, the third wave anticipates the emergence of entirely "New Business Models."

Thomson Reuters is actively navigating and shaping this transformation, particularly through its AI platform, CoCounsel. Raghu highlights the rapid evolution of CoCounsel, emphasizing the continuous development of new "skills"—capabilities ranging from summarization and research to drafting and complex analysis like the innovative "Claims Explorer." He explains TR's strategy involves integrating proprietary data (like Westlaw), client-provided documents, and public information, leveraging advancements in Large Language Models (LLMs) from various providers to deliver comprehensive and powerful AI assistance. Prioritizing new skill development involves balancing significant client value with technical feasibility, constantly informed by close collaboration with innovation-focused customers.

Beyond law firms, the conversation explores the crucial role and adoption of AI within the court system. Raghu notes a surprising enthusiasm among courts, driven by the urgent need to address growing case backlogs and enhance access to justice within tight budgets. He points to Thomson Reuters' significant partnerships, including a major agreement to deploy AI tools across the US federal courts and ongoing collaboration with the National Center for State Courts (NCSC), which is fostering education and policy discussions among judges and court staff nationwide. Complementing product innovation, TR's expanded "Customer Success" initiative underscores the importance of user adoption, providing dedicated resources and best practices to help lawyers and legal professionals effectively integrate AI tools into their daily workflows, ensuring technology translates into tangible value.

Raghu anticipates that smaller and mid-sized law firms may initially leverage AI more aggressively as a competitive equalizer, pushing larger firms to make bolder, more strategic moves beyond simple optimization. He stresses that the ultimate differentiator for success in the AI era will likely be less about the technology itself and more about effective change management. The rapid pace of AI adoption already witnessed in the legal sector signals that this transformation is not a distant prospect but a present reality reshaping the industry at an unprecedented speed.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

In this week’s Geek in Review, we sit down with Patrick Waldo, CEO of Unicorn Forms and proud Houstonian, to explore the intersections of data, document automation, and legal tech innovation. From the vibrant startup culture at Houston's ION and the Capital Factory's SXSW House event to the regulatory grind of form design, Waldo shares how his journey—from working in compliance-heavy industries to launching a playfully named but technically serious platform—is reshaping how we think about document-driven workflows.

Waldo pulls back the curtain on Unicorn Forms’ approach to digitizing and structuring data trapped in PDFs. With a background in regulatory intelligence, he understands firsthand how critical, yet painfully inefficient, static documents can be. Unicorn Forms aims to transform the “eight-and-a-half-by-eleven world” into structured, field-driven digital tools. By mimicking the look and feel of familiar e-sign interfaces while embedding structured fields and integrations like Calendly or Stripe, the platform bridges the gap between legal formality and technical interoperability.

Security and compliance are at the heart of the conversation as Waldo outlines the different levels of electronic trust, explaining how Unicorn Forms distinguishes itself with hashed documents, timestamp authorities, and encryption standards that exceed many traditional e-signature solutions. He highlights how many professionals—especially in legal, healthcare, and finance—aren’t aware of the risks they take when using non-secure PDFs for sensitive data like social security numbers or payment details.

The episode also dives into the often-overlooked role of data ontologies in making government and enterprise forms interoperable. Waldo describes the complexity behind something as seemingly simple as a name or address field and how lack of standardization leads to inefficiencies and errors. By applying his years of ontology-building experience, Unicorn Forms aims to enable more intuitive, human-readable, and system-compatible data capture, with real-world use cases already in place—like improving film permitting processes for the Houston Film Commission.

From a startup perspective, Waldo gets candid about fundraising challenges, the paradox of needing metrics to raise money and needing money to build metrics, and how early-stage companies must balance marketing, sales, and product development. He emphasizes the value of angel investors and local ecosystems like the ION and the Canon, while acknowledging the rising bar of investor expectations in today’s post-2023 funding environment.

Finally, Waldo shares his philosophy behind the Unicorn Forms brand—born as an April Fool’s joke but grown into a conversation starter and signal for early adopters. With Party City swag, a pink logo, and a message that draws in the curious and the creative, Unicorn Forms is redefining legal tech not just through software, but through an intentional, approachable identity. As Waldo looks ahead, he sees opportunity in pairing strong data engineering with AI tools—not just to automate, but to make legal and regulatory processes smarter, faster, and more human-centered.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

This week, we sit down with Sam Flynn, COO and co-founder of Josef, to separate substance from hype in the rapidly evolving world of legal tech. Sam shares his passionate stance that “RAG is not dead,” defending Retrieval-Augmented Generation (RAG) as a foundational and still deeply relevant method for deploying AI in the legal industry—despite the flashy allure of agentic AI. His nuanced take reminds listeners that success in this space depends not only on the sophistication of the technology, but on doing the “boring” foundational work: ensuring data integrity, context-aware chunking, and responsible workflows.

Throughout the discussion, Sam champions the idea that great legal technology should not just enhance expert workflows but make legal information accessible to non-experts. With examples from Josef’s clients like L’Oréal, Bumble, and Bupa, Sam illustrates how Josef’s tools allow legal departments to offload routine work through reliable self-service systems—freeing up time for more strategic thinking while improving speed, compliance, and consistency across organizations. He makes the case that empowering end users with trustworthy tools isn’t just good tech—it’s a new model for scaling legal and compliance services.

A key highlight is Josef’s Roxanne project, developed in collaboration with Housing Court Answers and NYU. Roxanne is an AI-powered tool designed to help tenants in New York navigate the complexities of housing law. Sam outlines the safeguards that ensure Roxanne’s answers are accurate and compliant, such as closed-domain data sources, human-in-the-loop validation, and smart escalation workflows. The conversation touches on the broader access to justice (A2J) implications of this technology—arguing that when designed carefully, AI can amplify the reach and impact of legal aid organizations by orders of magnitude.

The episode doesn’t shy away from the tensions legal professionals feel when automation enters their domain. Sam offers a powerful reframing: instead of seeing these tools as a threat, lawyers should view them as opportunities to offload low-value tasks and expand their influence. The goal, he says, is not to cut jobs—but to redefine the kind of work legal professionals do, making space for more proactive, strategic, and meaningful engagements within organizations and communities.

As the conversation wraps, Sam shares his optimism about the future—tempered by a clear-eyed understanding of the human factors that will determine success. While the technology is ready, the question is whether legal professionals will step up and take the lead. His call to action is clear: focus less on the hype, and more on the systems, safety, and trust that make tech transformative. Whether you're a legal technologist, innovator, or cautious observer, this episode offers a grounded and inspiring look at what it takes to build legal tech that actually works.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode. 

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

This week we sit down with Sean West—co-founder of Hence Technologies and author of Unruly: Fighting Back When Politics and Law Upend the Rules of Business. Together, they explore the shifting fault lines where law, technology, and geopolitics collide. From the growing reliance on generative AI in legal work to the erosion of rule of law and the emerging threats (and opportunities) facing knowledge workers, Sean offers a strikingly global—and at times unsettling—view of the legal profession's next frontier.

The conversation kicks off with a discussion on the Law360 survey showing that 62% of lawyers are using ChatGPT in some aspect of their work. Sean explains the popularity of general-purpose AI tools over legal-specific ones as a matter of price, accessibility, and perceived innovation. While lawyers trust themselves to edit AI outputs, Sean warns that this passive use of AI could slowly and invisibly displace traditional legal roles, without firms consciously realizing what’s been lost.

The discussion deepens as Sean introduces the idea of passive job displacement—where tasks once assigned to junior lawyers, interns, or external vendors are quietly absorbed by AI tools. He likens it to carrying "a quarter of a human brain in your pocket" for $20 a month. What starts as convenience becomes infrastructure, and over time, demand for human input declines. He also questions the long-term viability of legal tech products that can’t clearly outperform generalist AIs like ChatGPT or Claude.

Sean then draws on his geopolitical expertise to underscore the urgent need for situational awareness in law firms and businesses alike. He explains how political volatility—from China and Taiwan to Europe’s regulatory tactics—can suddenly reshape the legal landscape. Rather than relying on traditional prediction models or complex advisory plans that get shelved, Sean emphasizes proactive legal scenario planning. His new product, Hence Global, offers a “geo-legal” lens on global news, customized for specific legal practice areas to help firms act instead of react.

We push further into the implications of “front-stabbing” politics, where once-hidden power plays are now openly transactional. Sean describes a world where AI-driven lobbying, mass arbitration spam, and “robot lawyers” can reshape public policy or flood companies with legal claims at scale. He argues that when the rules are ambiguous, large players will push boundaries—and smaller players may get squeezed out. In a world without a clear referee, the game favors those who can afford better tools and faster moves.

Finally, Sean challenges legal and corporate leaders to stop avoiding the hard conversations. Whether embracing AI to boost productivity or choosing to protect jobs, organizations must be transparent. “Let’s front-stab about it,” he says. Make your commitments public—whether you're retraining your workforce or doubling down on AI-driven efficiency. Because in a world where legal, political, and technological lines blur, silence isn’t just unhelpful—it’s a risk.

Links and Mentions:

• Learn more about Unruly and Sean’s work at https://hence.ai

• Subscribe to Sean’s newsletter: https://geolegal.substack.com

• Try Hence Global with a discount: global.hence.ai – use promo code GEEK for one-third off

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

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.
Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

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: [email protected]

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Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

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

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠ Transcript

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.

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.

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.

One of the episode’s focal points was Tara 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.

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.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Evolving Legal Tech Trends: From Theory to PracticeCollaborative Theme Selection & Diverse ContentHighlighting Keynotes and Networking OpportunitiesFuture Challenges and Opportunities in Legal TechBlue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠ Transcript

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.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠Transcript

This week, we welcomeGabriela “Gaby” Isturiz—a serial entrepreneur, legal tech pioneer, and co-founder ofThe 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.

Links:

• Customers don't care about your AI feature
• The Fund XX
• Gaby's LinkedIn Newsletter (Build Legal Tech)

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPT