Pioneers and Pathfinders

Our guest this week is Gus Neate. Gus is the CEO and co-founder of WilsonAI. WilsonAI, in turn, is a startup using AI to streamline legal operations for businesses. Gus is an Oxford graduate who began his career as an engineer before pivoting to law, working as a private equity lawyer at Clifford Chance. His diverse background also includes co-founding a tutoring company and working in product management at a legal tech startup. As an in-house lawyer, Gus witnessed firsthand the inefficiencies caused by repetitive legal tasks—an experience that continues to inspire his innovative work at WilsonAI. Today, Gus shares how his engineering background shaped his approach to legal problem-solving, the journey of building WilsonAI, and his vision for how AI can empower legal teams. He also offers valuable advice for those entering the legal tech space. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_GusNeate.pdf

This week on Pioneers and Pathfinders, we’re joined by Wendy Jephson, CEO and co-founder of Let’s Think. The company operates in a space they call “behavioral science AI,” which is intended to transform workplace productivity in the legal profession. Wendy brings a rare dual qualification as both a commercial lawyer and a business psychologist, with deep expertise across health care and financial services. Previously, she served as head of Research & Ideation for Market Technology at Nasdaq, where she introduced scientific research methodologies to enhance innovation and development processes. A recognized thought leader, Wendy speaks globally on topics such as AI, surveillance, cognitive engineering, organizational resilience, and the intersection of conduct and culture with technology design. In our conversation, Wendy shares insights into the behavioral science behind legal professionals, the founding story and mission of Let’s Think, and her vision for the future of lawyer training and workplace transformation. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_WendyJephson.pdf

Jack Cushman is the Director of the Harvard Library Innovation Lab and a former software engineer and appellate attorney. He discusses his journey from tech to law, influenced by conflicts like Google Books. Jack shares insights on how libraries adapt in the digital age and their crucial role in community building. He emphasizes the importance of libraries in grounding AI practices and suggests that lawyers develop computational thinking skills. Jack also explores the need for reliable AI systems in legal fields and the evolving benchmarks for measuring their impact.

This week, we’re revisiting our conversation with Leah Molatseli, formerly of Contract Alchemists. Since her appearance on the podcast, Leah has taken on a new role as Country Liaison in South Africa for the legal tech company Saga, where she is still helping lawyers navigate technology, innovation, and more recently AI. In this wide-ranging episode, Leah shares her perspective on the South African legal community, her passion for writing, and the importance of purpose-driven work. It’s a conversation full of inspiration and forward-thinking ideas. Thank you for listening. We will return next week with a new episode. This week, we welcome Leah Molatseli, founder of Contract Alchemists, a company with the goal of modernizing legal teams through legal operations, agile methodologies, and technology. Leah has over 10 years of experience in the legal field, and has a certificate in Entrepreneurship and Innovation from the University of Notre Dame. After practicing for a few years, she co-founded Lenoma Legal, a virtual legal tech startup aimed at helping small businesses in South Africa. Prior to starting Contract Alchemists, Leah was head of business development at Legal Interact, a legal tech company. She is also a speaker, a published author, and a council member at the University of the Free State. Additionally, she recently joined LexisNexis South Africa as an author and became a Voice and Brand Council Member at the Corporate Legal Operations Consortium (CLOC). In today's conversation, Leah discusses the legal community in South Africa, how she approaches her writing, the TV shows that inspired her to become an attorney, and how being purpose-driven shapes her decision-making. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_LeahMolatseli.pdf

Today's guest is Leslie Grandy, an author, speaker, and trusted advisor to CEOs, product leaders, and teams. Leslie's career has taken some fascinating turns—from working in the film industry to guiding major brands on strategy and innovation. She's also deeply committed to education, having taught product leaders through The Product Guild, the University of Michigan Center for Entrepreneurship, and as guest lecturer at the University of Washington's Foster School of Business. Leslie recently added author to her list of accomplishments with the release of her book, Creative Velocity, which explores how to drive better results and better collaboration through creativity and the thoughtful use of generative AI. In our conversation, Leslie talks about the importance of embracing a creative career path and discovering her personal superpower. We talk about her thesis that creativity is a learnable, repeatable system. We also discuss why reframing problems is often the key to solving them, the role of culture and creative problem solving, and her thoughts on how organizations should be approaching AI tools. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_LeslieGrandy.pdf

David Freeman Engstrom, a law professor and co-director at Stanford's Deborah Rhode Center, and Natalie Knowlton, the Associate Director for Legal Innovation, discuss critical regulatory reforms in legal practice. They share insights from their report on the impact of Arizona and Utah's changes, highlighting the promise of legal technology. David reflects on his journey from coaching football to academia, while both emphasize how AI is reshaping the legal field. The conversation reveals the need for law students to adapt to these transformations in practice.

Jason Marty, CEO and co-founder of Lumio, dives into the intersection of law and AI. With a background as global COO at top law firms, he shares Lumio's mission to innovate legal commercial operations through generative AI. Jason discusses the concept of 'service as software' and introduces the 'Rainmaker Companion,' designed to support revenue-generating partners. He also explores the importance of aligning innovation with financial incentives, the unique challenges in legal tech, and how AI is gradually transforming law firm business structures.

Jordan Furlong, a legal industry consultant and founder of Law21, returns to discuss the dynamic intersection of law and technology. He shares insights on how generative AI will transform legal work, suggesting that lawyers will need to adapt and redefine their roles. Furlong emphasizes the importance of balancing commercial pressures with societal duties, urging firms to focus on local actions amid larger issues. He predicts a shift in demand for legal services, highlighting the need for firms to evolve into solution providers and build deeper client relationships.

In this engaging discussion, Jonathan Petts, co-founder and CEO of Upsolve, shares his journey from bankruptcy law to founding a nonprofit that's transforming financial futures. He recounts the pivotal moments that inspired Upsolve, including a crucial pro bono case. Jonathan delves into the challenges of translating legal jargon into user-friendly tools and explores how partnerships enhance their reach. Excitingly, he unveils plans for AI to assist users navigating bankruptcy, aiming to reduce the staggering drop-off rates. His reflections on overcoming fear and embracing failure are both inspiring and relatable.

This week, we’re catching up with Ivy Grey, a legal tech entrepreneur, writer, and longtime friend of the podcast. We first spoke with Ivy three years ago about her fascinating background in anthropology and journalism, as well as her work at WordRake, where she's now chief strategy & growth officer. She also continues as an advisor to PerfectIt, a proofreading tool for legal professionals. In this episode, Ivy walks us through her “sandwich” approach to writing with generative AI, and how new tools in WordRake are helping users write more clearly and confidently. We also talk about staying ethically grounded while using gen AI, and how emerging tech might reshape legal training and apprenticeships. Ivy brings a usual mix of insight, clarity, and energy. Read the full transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_IvyGreyReturns.pdf