Lawyers Who Learn

#61 AI Is Forcing Lawyers to Rethink Who They Are

In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Anastasia Boyko, Legal Futurist and Product Evangelist at Filevine and host of PLI's "How to Navigate Law School" podcast. Anastasia shares her remarkable journey from fleeing Ukraine at age eight to becoming a pioneering force in legal education and innovation, earning her self-described title as the "Goldilocks" of career pivots.
The conversation centers on Anastasia's passion for transformation in the legal profession. She argues that AI is forcing a fundamental rethinking of who lawyers are and what they do, moving beyond efficiency improvements to questioning the core purpose of legal practice: helping people navigate complex systems and resolve conflicts. Drawing from her experience building Yale Law School's leadership program from scratch, Anastasia advocates for a more holistic approach to legal education that includes financial literacy, professional skills, and ethical decision-making.
Anastasia discusses her innovative work creating comprehensive programming at Yale without budget or structure, developing everything from negotiation intensives to cross-disciplinary AI courses. She emphasizes the critical need for lawyers to develop self-awareness and operate from clear values, particularly as traditional legal models face disruption. The conversation explores why law schools still teach using 1970s methods and how institutions must evolve to prepare lawyers for an AI-driven future.
Through her PLI podcast and various roles spanning BigLaw, legal tech, in-house, and academia, Anastasia demonstrates how continuous transformation and deep self-reflection can lead to more fulfilling careers and better client service, ultimately addressing both the access to justice gap and the mental health crisis in the legal profession.

#60 Why Law Firms Finally Embrace Personality Training

In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, reconnects with Rob Toomey, co-founder of TypeCoach, for a wide-ranging conversation that begins with their shared experience meeting while living in Barcelona and evolves into a deep dive on personality types, AI, and the future of interpersonal competence in legal practice. Rob shares insights from his journey from BigLaw attorney to building a 20-year-old business that revolutionizes how teams understand and interact with each other. Unlike traditional Myers-Briggs assessments that leave people wondering what to do with their four-letter code, TypeCoach creates practical "instruction manuals" for working with colleagues based on personality combinations. Their platform provides specific, actionable advice like "how to give feedback to Sarah" or "how to influence Mark" without requiring users to master complex personality theory. The conversation explores how AI is reshaping the skills that matter most in legal practice. As technical competencies become baseline expectations accessible to everyone, Rob argues that "interpersonal competence" becomes the new differentiator. He discusses TypeCoach's integration of AI through their "Ask Rob" avatar feature, which provides personalized coaching advice in real-time using their proprietary content library. Rob explains why law firms initially resisted personality-based training 20 years ago but are now embracing it as they adopt more sophisticated business models. The discussion covers practical applications like helping teams navigate stress and change management, understanding client personalities, and why certain personality types thrive during disruption while others struggle. This episode offers valuable insights for legal professionals looking to enhance their interpersonal effectiveness in an AI-driven world.

#59 The Foundation You Don't See: A Lawyer's Inner Work

In this deeply personal episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Somya Kaushik, Associate General Counsel at Mitratech, who reveals the foundation behind her diverse legal career: a lifelong practice of meditation, yoga, and self-empowerment rooted in her cultural heritage. This conversation explores the intersection of ancient wisdom and modern legal practice, showing how inner work creates outer success.
Somya opens up about her non-traditional career path from corporate litigation to founding a legal tech startup (Esq.me) to her current in-house role, but emphasizes that her professional achievements stem from decades of meditation and yoga practice inherited from her family. She explains how these practices help lawyers manage the high-pressure demands of legal work by teaching self-awareness, emotional regulation, and the ability to lead others through chaos while maintaining equanimity.
The discussion provides practical guidance for stressed legal professionals, including specific breathing techniques, the importance of being a witness to your thoughts rather than fighting them, and how movement helps release tension stored in the body. Somya shares her morning routine combining yoga's sun salutation with meditation, and recommends transformative books like "Radical Acceptance" by Tara Brach and "Autobiography of a Yogi."
As a mother of young children who works remotely, Somya demonstrates how to integrate these practices into a busy life while maintaining authenticity. She also reveals her side project authoring a children's book called "You Yes, You" through her company The Veda Club, designed to teach self-awareness concepts to young minds. This episode offers a blueprint for combining ancient practices with modern legal careers to achieve both professional success and personal wellbeing.

#58 Ancient Stoicism Meets Modern Legal Practice

In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Maria Yiannitsarakos, a practicing real estate attorney turned confidence coach who brings ancient wisdom to modern legal practice. Maria shares her remarkable journey from working at a law firm to building her own practice while raising three children, driven by her need for freedom and the stoic principle of controlling what you can control.
Maria opens up about her personal transformation, including her decision to reconnect with her father after 15 years and how sharing her life journey publicly on LinkedIn has become a way to empower others. Her approach combines stoicism, strategic influence, and practical negotiation skills, drawing from philosophical texts like Marcus Aurelius' Meditations and modern works like Robert Greene's 48 Laws of Power and Chris Voss's Never Split the Difference.
The conversation explores how stoic principles can reduce stress in the legal profession by helping lawyers focus on what they can control rather than external events. They discuss practical frameworks from Dale Carnegie's How to Stop Worrying and Start Living, including the powerful three-step formula for handling any crisis: identify the worst-case scenario, accept it, then work to improve the situation.
As an empty nester entering a new life phase, Maria embodies the philosophy of being "all in" on using modern tools like AI and social media to create the quality of life she wants, demonstrating how ancient wisdom and contemporary opportunities can lead to both professional success and personal fulfillment.

#57 Why Law School's Third Year Should Be Eliminated

In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Jordan Furlong, founder of Law21 and one of the legal profession's most influential voices on reform and the future of lawyering. This conversation tackles the fundamental questions facing legal education and the profession itself: Why do we have lawyers? What value do they provide? And how should we form competent practitioners in an AI-driven world? Jordan challenges the core assumptions of legal education, arguing that law school has become nothing more than an expensive credentialing institution that fails to prepare lawyers for actual practice. He advocates for eliminating the third year of law school entirely, describing it as a "massive waste of time" that adds unnecessary debt without educational value. Drawing from successful models in England and Wales, Jordan envisions a system where students can become lawyers without traditional law degrees, focusing instead on competency-based assessment and apprenticeship-style learning. The discussion explores the coming identity crisis for the legal profession as AI reshapes what lawyers do day-to-day. Jordan predicts that most traditional legal work will be automated, forcing lawyers to redefine their value proposition around human connection, judgment, and trusted guidance rather than document production and analysis. The conversation also examines unauthorized practice of law as a "protectionist scam" that AI will render obsolete, emphasizing the urgent need to shift from lawyer-centric to client-centered service delivery.

#56 From Classrooms to Courtrooms: AI Adoption Reality

In this fascinating episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Conor Grennan, Chief AI Architect at NYU Stern and founder of AI Mindset, who brings a unique perspective on how AI will fundamentally reshape education and work. The conversation begins with an inspiring story about Conor taking his 16-year-old son to Nepal to teach AI to NGOs, revealing how the next generation naturally understands and adopts AI technology.
Conor challenges conventional thinking about education, discussing how the current educational system needs to evolve in the AI era. He explains why students adopt AI faster than employees - it's all about incentives - and shares his vision for reimagining classrooms where students use AI to learn faster, then teach others without technological assistance. The discussion explores the fundamental shift from information consumption to human-centered skills like public speaking and authentic communication.
The conversation delves into practical AI adoption challenges, drawing parallels between the "tapping problem" (where experts assume others understand what they're communicating) and how organizations struggle with AI implementation. Drawing from his extensive work with law firms and major corporations, Conor explains why being an early adopter is crucial, the reality of AI agents, and why understanding large language models now is essential for managing AI employees in the future. He reveals that despite the legal industry being perfectly positioned for AI transformation, adoption rates aren't necessarily higher than other industries. The episode concludes with insights on creating authentic content using AI tools like Claude and building sustainable practices in an AI-driven world.

#55 From 10,000 Doors to 25 Keynote Topics

In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Kendra Brodin, whose unique background as an attorney, social worker, and wellbeing coach led her to become CEO of Esquire Well. This conversation explores the fascinating intersection of law, social work, and entrepreneurship while diving into the real challenges of building authentic expertise and overcoming imposter syndrome.
Kendra opens up about her unconventional journey from first-generation college student to running for public office with a newborn baby, sharing how knocking on 10,000 doors taught her invaluable lessons about resilience and business development. She candidly discusses her first business failure from 2008-2011, emphasizing how that painful learning experience shaped her eventual success in relaunching Esquire Well in 2021. The conversation reveals her struggles with imposter syndrome as someone from rural Illinois navigating elite educational and professional environments.
The discussion takes a practical turn as Kendra shares insights from building a speaking business with over 25 different keynote topics, explaining how she structures presentations, works with instructional designers, and prices her services. She reveals the business psychology behind offering both high-end keynote speaking and accessible online content, demonstrating how different price points serve different needs without cannibalizing each other. David and Kendra engage in real-time coaching around overcoming barriers to building a speaking career, covering everything from content creation to closing deals while balancing entrepreneurship with motherhood and personal wellbeing.

#54 How Being Ahead in Cloud Computing Changed Everything

In this episode of Lawyers Who Learn, host David interviews Niki Black, one of legal tech's most influential voices and employee number one at MyCase. This conversation goes beyond the typical career overview to explore the learning journey behind building authentic expertise in a rapidly evolving industry.
Niki opens up about her transition from practicing criminal and civil law to becoming a legal tech evangelist, starting with her early advocacy for cloud computing when it was considered "blasphemous" for lawyers to use. She shares how a chance encounter with Richard Susskind changed her career trajectory, leading to her first book collaboration on social media for lawyers and eventually her groundbreaking work on cloud computing. The discussion reveals how she impressed MyCase founders with her cloud expertise, and how her role has evolved through multiple acquisitions into her current position as Principal Legal Insight Strategist at AffiniPay.
The conversation explores her unique approach to building a massive LinkedIn following (206,000+ followers), launching a newsletter that gained 27,000 subscribers in just months, and her weekly Friday calls with legal tech journalists. Niki discusses how AI tools like ChatGPT have transformed her content creation process, allowing her to maintain authentic expertise while scaling her output. This episode offers valuable insights for legal professionals looking to build thought leadership, transition into legal tech, or simply understand how to leverage technology authentically in their practice.

#53 From Plane Crash to Rainmaker Coach

In this compelling episode of Lawyers Who Learn, host David interviews Steve Fretzin, one of the legal industry's most respected business development coaches and author of five books on legal rainmaking. This isn't your typical business development conversation - it's a candid deep dive into the mistakes and transformative moments that shaped a coaching empire.
Steve opens up about his journey from underachiever to serial entrepreneur, starting with how a devastating 1996 plane crash became his turning point. He shares the costly lesson of running four separate companies simultaneously with $35,000 in monthly overhead, revealing how "shiny penny syndrome" nearly derailed his career before teaching him the power of focus and specialization. Listeners will discover why Steve now intentionally limits himself to just 20 clients per year despite having triple the demand, and his philosophy on what truly defines a "rainmaker."
The conversation explores Steve's innovative approach to content creation, including the fascinating story behind his AI-powered book "101 Top Rainmakers’ featuring podcast interviews, and why having 101 co-authors became a marketing masterpiece. Steve discusses his personal growth journey, the life-changing impact of "Getting Things Done" by David Allen, and how undiagnosed ADHD shaped his entrepreneurial path. This episode offers rare transparency about choosing lifestyle design over maximum profit, perfect for legal professionals, entrepreneurs dealing with scattered focus, and anyone interested in intentional business design.

#52 The Legally Speaking Story: 400 Episodes Across 6,500 Cities

In this episode of Lawyers Who Learn, David Schnurman speaks with Robert Hanna, founder of KC Partners legal recruiting and host of the Legally Speaking podcast, one of the legal industry's most successful shows with nearly 400 episodes across 6,500+ cities worldwide.
Robert shares his journey from working at traditional legal recruitment firms to building his own company and becoming a digital media powerhouse. He reveals how testing content on LinkedIn in 2019 led to creating the Legally Speaking podcast as a business development tool – a strategy that transformed both his recruiting business and personal brand.
The conversation explores Robert's innovative approach to podcasting, where instead of cold calling for clients, he invites law firm partners to be guests, providing them with valuable marketing assets while building relationships that convert to business. This "give first" mentality helped him land a major sponsorship deal with Clio in 2021, just two years after launching.
Throughout the discussion, Robert shares personal insights about his grandfather's legal legacy and how it drives his mission to "build a kinder, more collaborative, future-proof legal community." He emphasizes the importance of finding your "why" – noting that "your why should make you cry" – as the foundation for persevering through business challenges.
The episode concludes with practical advice on building a personal brand, the power of creating mini-series content, and why "the magic you're looking for is in the work you're avoiding" – particularly when it comes to embracing AI and digital transformation in the legal industry.