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In this special year-end episode of The Geek in Review, Greg Lambert takes listeners on a unique journey through the past year’s 50 episodes, all with the help of Google’s NotebookLM audio overview tool. Inspired by Josh Kubicki of the Brainyiacs Newsletter, Greg experiments with this cutting-edge AI tool to synthesize and discuss the key themes, guests, and topics covered throughout 2024. The result is an innovative meta-conversation between Greg and AI-generated co-hosts, offering insights into the future of law and legal technology.

Key Themes from 2024:
The episodes this year highlighted critical shifts in the legal landscape, from the integration of generative AI to the rise of client-centric practices. Technology’s impact on efficiency, mental health, and the evolving role of lawyers emerged as recurrent topics. Discussions also included the push for ethical AI adoption, flat-fee models, and the importance of balancing professional and personal lives, particularly in the “Love and Legal Tech” series. NotebookLM reflected on these trends, offering a synthesized perspective on how the legal industry is adapting to innovation.

Generative AI and Legal Tech:
Generative AI dominated discussions, with guests exploring its transformative potential and the skills needed to leverage it effectively. While some feared job displacement, most viewed AI as an augmentation tool, enabling lawyers to focus on higher-value tasks. Leaders like Dr. Megan Ma and Conrad Everhard shared groundbreaking projects, such as an M&A negotiation simulator, exemplifying AI’s capabilities. The conversation underscored the necessity for prompt engineering skills and ethical considerations in AI deployment.

Data Management, Security, and Transparency:
The importance of robust data management and security was a consistent theme, with experts like Kelly Griswold emphasizing it as a foundational business function. Conversations also explored “garbage in, garbage out” scenarios, the need for explainable AI, and maintaining client trust through transparency. These discussions highlighted how firms must prioritize governance to ensure responsible and effective AI use.

Collaboration, Social Impact, and Access to Justice:
The legal tech community’s collaborative spirit shone through in initiatives like Baker Donelson’s Legal Design Lab and Tom Martin’s LawDroid, which aim to make legal services more accessible. Guests celebrated the social impact of innovative tools designed to reduce barriers to justice and foster inclusivity. These efforts reflect a broader commitment to using technology to address systemic inequities in the legal system.

Looking Ahead:
Wrapping up the year, Greg revisits the podcast’s hallmark “Crystal Ball” question, noting common predictions for the next two to five years. From AI’s continued evolution to shifts in pricing models and the rise of emotional intelligence in leadership, the future of law promises to be dynamic. This episode not only recaps a transformative year but also sets the stage for the challenges and opportunities ahead.

Tune in to this engaging recap as Greg Lambert merges legal innovation with AI technology to reflect on an extraordinary year for The Geek in Review. Happy Holidays and Happy New Year!

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

TRANSCRIPT

Continue Reading 50 Episodes of Legal Innovation and a Chat with Google NotebookLM

In this year-end episode of The Geek in Review, hosts Marlene Gebauer and Greg Lambert are joined by legal tech experts Niki Black, Principal Legal Insight Strategist at AffiniPay, and Sarah Glassmeyer, Director of Data Curation at Legal Technology Hub, to recap the top stories of 2024. From the evolution of generative AI in legal tech to groundbreaking acquisitions, the conversation delves into the successes and challenges that shaped the year in the legal industry.

The discussion kicks off with a look at AI’s growing role in legal research and practice management. Greg recalls the controversial Stanford report that questioned the reliability of AI tools marketed as hallucination-free. The guests explore the importance of unbiased evaluations, the complexity of defining legal research, and the rapid pace of AI development that often outpaces regulatory and academic studies. Sarah highlights the need for peer-reviewed analysis to guide the effective use of these tools, while Niki emphasizes the user-friendly interfaces that generative AI brings to legal software.

Marlene shifts the conversation toward the challenges of integrating AI into law firms’ existing frameworks. The hosts and guests discuss the hesitancy of document management systems to adopt generative AI due to trust and security concerns. Niki and Sarah examine how firms are adapting to AI by organizing data more effectively and addressing client expectations. They also reflect on the potential of AI to bridge access-to-justice gaps, with tools that empower self-represented litigants and underserved communities.

The episode takes a closer look at notable mergers and acquisitions in 2024, such as Bloomberg’s acquisition of Dashboard Legal and Thomson Reuters’ purchase of SafeSign Technologies. Sarah raises concerns about the consolidation of the legal tech market, warning of diminished innovation and competition. Niki observes how cloud-based technologies have facilitated these integrations, making it easier for companies to offer comprehensive solutions that touch multiple aspects of legal practice.

Wrapping up, the group forecasts trends for 2025, including regulatory developments around AI and shifting priorities within law firms regarding tech adoption. While some predictions are cautious, like Sarah’s concern over the impact of external political factors on the tech workforce, others remain optimistic about the growing sophistication of legal tech. The episode concludes with reflections on how the industry can better prepare junior lawyers and law students to navigate an increasingly AI-driven landscape.

Join Marlene, Greg, Niki, and Sarah for this insightful look back at 2024 and an exciting glimpse into the year ahead. As always, we thank our listeners for tuning in, and we encourage you to share this episode with colleagues and connect with us on LinkedIn or Blue Sky!

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠

Twitter: ⁠⁠⁠⁠⁠@gebauerm⁠⁠⁠⁠⁠, or ⁠⁠⁠⁠⁠@glambert
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPT

Continue Reading Sarah Glassmeyer and Niki Black on Legal Tech in 2024 – Highlights, Hiccups, and Hopes for 2025

This week on The Geek in Review, we sit down with Mark Doble, Co-Founder and CEO of Alexi, to discuss the state of AI-driven tools in the legal industry and how they are evolving to meet the needs of modern litigation practices. The conversation begins with a timely debate on measuring productivity in remote work settings. Doble, coming from a background in both law and software engineering, draws intriguing parallels between how legal services and software development measure output and efficiency.

Moving on to Alexi’s core offering, Doble delves into how the platform is currently being used by litigators. He explains that Alexi’s AI technology not only handles the tedious work of research and memo drafting but also provides opportunities for lawyers to explore creative, strategic approaches to cases. By automating routine tasks, Alexi empowers attorneys to focus on high-level legal reasoning and client goals, rather than sifting through mountains of documents.

A key aspect of the discussion centers on the ways in which AI tools, like Alexi, can transform junior associate work. Instead of solely performing rote research or document review, younger lawyers can now leverage these tools as teaching aids, accelerating their path to deeper legal understanding. Doble emphasizes that as automation becomes more sophisticated, the human lawyer’s role in guiding strategy and exercising judgment grows ever more critical.

Doble then addresses concerns around data security and confidentiality. He reiterates that while the underlying technology is evolving, core principles of security remain the same—encrypting data, controlling access, and ensuring that information is never inadvertently trained into the model’s outputs. He acknowledges emerging questions around work product and privilege but sees them as part of the natural adaptation cycle in adopting new technology.

Finally, looking ahead, Doble hints at a significant upcoming announcement from Alexi early next year. He suggests that this new release will push beyond current capabilities, bridging the gap between mere information retrieval and genuine “legal reasoning” support. While keeping details under wraps, Doble leaves listeners with a vision of AI as a true partner in litigation, promising exponential improvements that will redefine how attorneys practice law.

Links:

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Twitter: ⁠⁠⁠⁠⁠@gebauerm⁠⁠⁠⁠⁠, or ⁠⁠⁠⁠⁠@glambert
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPT

Continue Reading Harnessing AI for Litigation: Mark Doble on Alexi’s Next Evolution

If you’ve been around the legal tech block a time or two, you’ve probably noticed a familiar pattern: We deploy technology to better understand and streamline the law as we know it. Legal analytics platforms sift through case law, AI-driven tools tackle contract review and due diligence, and blockchain-driven “smart contracts” hold the promise of self-executing agreements. But here’s a shift you might not have considered: It’s not just about making sense of the legal texts we already have. It’s about the laws themselves evolving to fit the tools we’re building.

Most of us think of legal technology as something that reacts to what Congress and courts produce. But what if tomorrow’s legislative drafters start structuring statutes—right from the get-go—in a code-like, machine-friendly manner? Over time, lawmakers might take their cues from how AI and automated reasoning systems process text. They could craft statutes with hyper-structured logic, standardized definitions, and reduced interpretive leeway. This would be more than just a stylistic choice: it could fundamentally reshape the balance of power among the branches of government and the role of agencies.

Courts and the Waning Ambiguity
Traditionally, the courts have a big job: interpret ambiguous statutes, reconcile conflicting provisions, and apply legal canons to unpack what Congress might have meant. If laws read more like neatly organized code—complete with precisely defined triggers, conditions, and outcomes—the courts’ interpretive heavy lifting could be significantly reduced. Judges would still have their constitutional role: to say what the law is and to apply it to specific facts. But if there’s less wiggle room, their work might look more like verifying whether the facts meet the clearly stated criteria, rather than engaging in lengthy interpretive gymnastics. While that doesn’t strip the courts of their authority, it does streamline their function. They become less about discovering meaning and more about confirming that a given scenario fits the predetermined parameters.

Agencies and the Loss of Regulatory Latitude
This shift could also ripple through the administrative state. Right now, agencies benefit from statutory ambiguity to interpret and fill in the gaps. They set rules and policy through their regulatory authority, often receiving deference from courts in recognition of their expertise. But if statutes are drafted with fewer interpretive grey areas—each statutory provision carefully defined and logically consistent—agencies may find themselves with less room to maneuver. The “we’ll fill in the details” model of agency rulemaking loses steam when Congress provides the details up front.
Continue Reading When Law and Legal Tech Start Writing Each Other’s Code

This week we welcome Jane Oxley, Chief Revenue Officer at Smokeball, to discuss the pivotal role of communication in legal organizations and how AI is transforming legal practice management. While normally in Australia, we were lucky enough to find Jane while she was working in Chicago, Jane shares her global perspective on communication challenges, bridging time zones, and the creative ways Smokeball leverages technology to streamline law firm operations. Co-host, Greg Lambert kicked off the show by introducing the concept of “Lambert’s Law,” highlighting that “all problems are communication problems,” setting the tone for an insightful discussion on organizational efficiency.

Jane explains how effective communication structures can reveal the health of an organization, whether through Slack’s rapid exchanges or more traditional law firm channels like email and face-to-face meetings. She notes the unique challenges faced by smaller firms, particularly their focus on casework over internal collaboration. Smokeball addresses these needs by integrating AI tools that help firms manage cases, streamline communication, and reduce administrative burdens, allowing lawyers to feel more in control of their workflows.

Jane Oxley and Marlene Gebauer also discuss the role of AI in enhancing productivity and profitability. Jane describes Smokeball’s AI tool, Archie, which helps automate document creation, email drafting, and summarization tasks. With AI handling routine work, lawyers can dedicate more time to client interaction and higher-value tasks. This shift not only increases efficiency but also helps smaller firms bill more accurately for their time—a long-standing challenge in the legal industry.

Addressing the potential impact of AI on the billable hour, Jane shares her perspective on the slow but inevitable shift toward value-based billing. She emphasizes that while AI enhances efficiency, widespread change in billing models requires education and a mindset shift. Some firms have begun experimenting with alternative billing structures, but the transition is gradual and nuanced, varying by practice area. Ultimately, AI tools empower firms to deliver better client service and justify their fees confidently.

Finally, the discussion highlights ethical considerations in adopting AI, particularly regarding client data privacy and regulatory compliance. Jane advises firms to be vigilant in choosing trusted AI providers and implementing safeguards. She predicts that AI will amplify client expectations for efficiency and responsiveness, but the human side of law—empathy, communication, and trust—will remain irreplaceable. By embracing AI to manage routine tasks, firms can focus on delivering exceptional client experiences, making the human element the true winner in this evolving landscape.

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Twitter: ⁠⁠⁠⁠⁠@gebauerm⁠⁠⁠⁠⁠, or ⁠⁠⁠⁠⁠@glambert
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPT

Continue Reading Communication, AI, and the Human Side of Law: Insights from Smokeball’s Jane Oxley

This week, we talk with Elena Tsalanidis and Justin Hansky, co-founders of Deeligence, a revolutionary due diligence workflow tool. Hailing from Australia, this dynamic duo delves into the challenges of traditional due diligence processes and how their AI-powered platform aims to streamline and optimize legal workflows for greater efficiency and accuracy.

Elena Tsalanidis and Justin Hansky share their personal journeys that led to the creation of Deeligence. From Elena’s background in human rights litigation and her experience working at Buckingham Palace, to Justin’s tenure as an M&A lawyer, their combined expertise and insights have laid the foundation for an innovative solution in legal tech. Their unique approach to addressing inefficiencies in due diligence is rooted in their deep understanding of both the practice and business of law.

The hosts and guests explore the skepticism surrounding generative AI in the legal field, including transparency and the accuracy of outputs. Elena and Justin emphasize that Deeligence prioritizes clarity and user trust by integrating human oversight into the process. They outline how their platform simplifies document review, reduces the need for exhaustive scoping, and enables legal professionals to identify key contract provisions quickly and confidently.

Implementing new technologies in law firms often encounters resistance due to entrenched practices and security concerns. The Deeligence team discusses their strategies for encouraging adoption, from ensuring ease of use to providing verifiable results. They also highlight the importance of fostering internal champions who recognize the value of modern tools in enhancing legal service delivery and client satisfaction.

Deeligence challenges the traditional billable hour model by enhancing the efficiency of tasks like due diligence. The platform allows firms to offer fixed-fee models without compromising the quality of their work, enabling them to surface critical issues across all documents instead of relying on selective reviews. This shift promotes more comprehensive client outcomes and cost predictability, marking a significant transformation in how legal services are delivered.

Looking ahead, Elena and Justin discuss their aspirations for Deeligence, including expanding into international markets like the US and UK. They express their commitment to staying at the forefront of legal tech innovation, continually improving their platform to meet evolving industry needs. Their insights underscore a broader trend of specialized, user-focused AI solutions redefining the legal landscape.

Listeners are invited to connect with Elena and Justin to learn more about Deeligenceand its impact on legal workflows. This episode provides a compelling look into how technology and a fresh perspective can address long-standing challenges in the legal profession.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠

Twitter: ⁠⁠⁠⁠⁠@gebauerm⁠⁠⁠⁠⁠, or ⁠⁠⁠⁠⁠@glambert
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPT

Continue Reading Revolutionizing Due Diligence: Elena Tsalanidis and Justin Hansky From Deeligence

Once again, hallucinated citations are not just for lawyers. A recent Minnesota case highlighted the issue of GenAI hallucinations when it come to making up things to fit the narrative of its users. In this situation, a prestigious Stanford University Professor, Jeff Hancock, founding director of the Stanford Social Media Lab submitted an affidavit…

[Ed Note: We were holding off on publishing this episode because we were waiting on the official announcement that Kara Peterson and Rich DiBona of Descrybe.ai were the Silver Anthem Award winners in Best Use of AI from the International Academy of Digital Arts & Sciences! Congratulations to Kara and Rich for the prestigious award! – GL]

In this episode of “The Geek in Review,” we welcome Kara Peterson and Richard DiBona, the dynamic married duo behind Descrybe.ai. Descrybe is an AI-powered legal tool aimed at democratizing access to legal information, particularly by providing summarized legal decisions that make case law more accessible to everyone. The conversation centers around how Descrybe was created, its mission, and the challenges and opportunities involved in developing a legal tech tool that truly serves its users.

Kara and Rich share the story of how Descrybe began as a personal project sparked by a challenging legal issue they faced themselves. Rich, a software engineer, started experimenting with AI summarization of judicial opinions and was struck by how well it worked. Over time, this experiment evolved into Descrybe—a platform that not only delivers quick case law summaries but also enhances accessibility through simplified language and multilingual support. They delve into the technical challenges of managing massive datasets of judicial opinions and ensuring that their platform remains accurate and reliable.

The development of Descrybe has been heavily influenced by user feedback, which Kara and Rich emphasize throughout the episode. They explain how advisory feedback has been instrumental in shaping key features, such as Spanish translations and simplified summaries, which make the platform more accessible to non-native English speakers and those with varying levels of reading proficiency. Their genuine commitment to evolving the product based on user needs is a core aspect of Descrybe’s mission to democratize legal information.

A particularly intriguing segment of the episode focuses on Rich’s perspective on the legal tech market and his skepticism regarding companies that label their offerings as “LLMs” (large language models) without meeting the threshold of a true LLM. Kara adds her insights on the broader mission of Descrybe: not only to innovate within legal tech but also to address access to justice as a public health issue. They both underscore the importance of responsible AI development, ensuring that new technology genuinely benefits society rather than exacerbating existing inequalities.

Towards the end of the episode, Kara and Rich discuss the future of AI in the legal industry and the role Descrybe aims to play. They express optimism that AI can be a powerful force for improving the legal system, especially if it is used to automate lower-level tasks and free up lawyers to focus on more impactful work. They also highlight the potential for AI to facilitate alternative dispute resolutions, diverting some cases from the courts altogether. Kara concludes on a hopeful note, emphasizing that if the right choices are made now, AI could be a driving force for positive systemic change within the legal field.

This conversation with Kara Peterson and Richard DiBona offers a candid, behind-the-scenes look at building Descrybe—a legal tech solution driven by a mission to improve access to justice. Their commitment to making complex legal information understandable for everyone shines through, making this episode a must-listen for anyone interested in the intersection of technology, law, and social good.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠

Twitter: ⁠⁠⁠⁠⁠@gebauerm⁠⁠⁠⁠⁠, or ⁠⁠⁠⁠⁠@glambert
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠

TRANSCRIPT

Continue Reading Democratizing Law with Descrybe.ai’s Kara Peterson and Rich DiBona

Another week, another round of travel. This time to rainy and cold Raleigh, NC. It’s a beautiful city… when it’s not cold and damp. But, I still had a great time with a number of law librarians and KM attorneys reviewing some new information tools on the market.

A lot of tools now are focusing…