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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

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

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

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

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…

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…

This week I got to spend time with a few of my peers from other law firms in lovely Fort Lauderdale, Florida. We talked about the actual effects of new technology on the legal information industry, and the wins, losses, and draws when it comes to adoption to these new tools within their firms. It…

I hope everyone bagged enough Halloween candy last night to last them through to the US Thanksgiving dinners. Hard to believe it is November, but apparently I say that every year.

This week in legal tech news had some interesting acquisitions like Harbor acquiring Ascertus, as well as new partnership announcements like Spellbook using Thomson…

Lots of travel on my part this week, and I’m happy to be in New York at the KM&I conference with a few hundred of my closest KM friends.

Here’s a few things that I ran across this week in legal technology news.

Remember, you can track these stories with the AI Lawyer Talking Tech…