Lawyers Who Learn

What happens when a successful attorney has not one, but two midlife crises and emerges as a leading voice in cybersecurity? Yan Ross, editor-in-chief of Cyber Defense Magazine and author of "The vCISO Playbook," shares his unconventional journey from Washington D.C. banking law to running a ranch in Arizona while protecting small businesses from cyber threats. Ross's story begins with a pivotal 1980 bank merger case that led him to abandon his D.C. life for the mountains of Utah—his first midlife reinvention. Twenty years later, another crisis pushed him to leave traditional law practice entirely, launching him into identity theft protection, privacy law, and ultimately cybersecurity consulting. Today, he runs Cyber Risk Management Associates, a veteran-owned small business, helping both for-profit and non-profit organizations navigate the existential threat of cyber attacks. The conversation reveals startling statistics: over a third of America's 32 million small businesses have suffered damaging cyber attacks in the past five years. Ross explains why traditional security measures like passwords are becoming obsolete in the age of AI, and why the human element remains the biggest vulnerability. He breaks down the security-convenience spectrum that every business must navigate and shares practical steps firms can take immediately. Beyond cybersecurity tactics, Ross offers a masterclass in career reinvention at any age. Working entirely with remote teams he's never met in person, Ross co-authored his book and built a business with less than $1,500 in cash investment, proving that passion and expertise can trump traditional business models. This episode offers both a cybersecurity wake-up call and inspiration for lawyers considering their own professional pivots.

In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, interviews Caitlin Vaughn, Managing Director of Learning and Professional Development at Goodwin, who shares her remarkable journey from practicing attorney to innovating legal education. Caitlin's story begins with an unexpected twist during the 2008 financial crisis when Goodwin created the "Make a Difference Fellowship," allowing half their incoming class to work with nonprofits for a year instead of laying them off. Caitlin opens up about her transition from practicing law to discovering her true passion in learning and development, revealing how she loved everything about practicing law except the actual practice itself. The conversation explores Goodwin's progressive approach to career paths beyond traditional equity partnership, including their flex work program and professional track roles that redefine success in BigLaw. The centerpiece of the discussion is Caitlin's groundbreaking eight-week training program for new associates, which represents a fundamental rethink of how law firms onboard talent. This comprehensive bootcamp combines technical legal skills with business acumen, innovation challenges using generative AI, and crucial professional skills like communication and relationship building. The program reflects a shift from information-heavy training to focusing on skills that AI cannot replicate - judgment, discernment, and human connection. The episode concludes with insights on the future of legal education and how law firms must evolve their training models to stay competitive in an AI-driven world.

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.

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.

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.

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.

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.

Conor Grennan, Chief AI Architect at NYU Stern and founder of AI Mindset, shares his insights on AI's revolutionary role in education and the workplace. He recounts a transformative trip to Nepal with his son to teach AI, illustrating the generational ease with technology. Conor discusses the urgent need to reform educational practices, highlighting the difference in AI adoption between students and employees. The conversation also emphasizes the importance of public speaking and human-centered skills in an AI-driven world, while urging organizations to embrace early AI adoption.

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.

Niki Black, Principal Legal Insight Strategist at AffiniPay and a pioneer in legal tech, discusses her fascinating journey from traditional law practice to advocating for cloud computing. She shares how her passion for tech transformed her career, influenced by a pivotal meeting with Richard Susskind. Niki reveals her strategies for building a massive LinkedIn following and leveraging AI tools like ChatGPT in content creation. The conversation shines a light on the ever-evolving intersection of law and technology, offering invaluable insights for legal professionals.