Lawyers Who Learn

When Jessica left her six-figure government position at the SEC Division of Enforcement, she discovered something startling: she wasn’t the only highly educated lawyer secretly "winging it" with her money, many were carrying financial shame that kept them trapped in unfulfilling careers. Today, she's transformed that revelation into a thriving practice as an Accredited Financial Counselor, helping attorneys break free from golden handcuffs through strategic financial planning. In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, explores Jessica's evolution from Columbia Law graduate drowning in $200,000 of debt to becoming the financial coach who helps lawyers navigate career transitions with confidence. After eight years in Big Law followed by five years at the SEC, Jessica thought she'd leave the legal world behind entirely—until she realized her fellow attorneys needed exactly the kind of support she wished she'd had during her own financial struggles. Jessica's journey took an unexpected turn when her military husband's required financial counseling session introduced her to the Accredited Financial Counselor certification. What started as personal curiosity became her calling when the counselor told her husband, "Your wife should be doing this work." Jessica discovered that while lawyers excel at advising clients, they often lack the foundational money management skills that weren't taught in law school—or anywhere else. Her approach tackles the emotional weight of financial decisions, debunking the myth that legal intelligence automatically translates to financial competence. She offers financial wellness workshops and presentations at law firms and bar associations, but spends the bulk of her time working with individual clients. Through her six-month coaching program, Jessica builds personalized cash management systems for attorneys facing career transitions, helping them calculate exactly what they need to earn to maintain their lifestyle while pursuing more fulfilling work. Her client success stories range from associates leaving Big Law for boutique firms to attorneys launching entirely new careers as astrologers and llama farmers. Jessica's framework addresses the unique financial challenges lawyers face: massive student debt, variable income streams for partners and solo practitioners, and the psychological burden of managing money while working 80-hour weeks. By the end of six months, her clients have the tools and confidence to make strategic career moves without financial fear, proving that with the right planning, attorneys can escape the golden handcuffs and build careers aligned with their values.

Nine years ago, when Tom Martin talked about chatbots and artificial intelligence to lawyers, they dismissed it, saying it sounded like a science fiction novel. Today, his LawDroid platform serves courts, legal aid organizations, and law firms with AI solutions he's been quietly perfecting since that early skepticism—all while remaining bootstrapped and profitable. In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, explores Martin's journey from first-generation law school graduate to legal tech pioneer. Growing up in Los Angeles, California—his father a "philosopher barber" who instilled the belief that "you could do anything you put your mind to," his mother an Avon manager who became number one in the country—Martin's early encounter with an Apple II computer as a preschooler sparked a lifelong fascination with technology. Martin founded a fully remote probate practice in 2006, years before COVID normalized virtual legal work. His LawDroid experiment began when he learned about Joshua Browder, a teenager using chatbots to help people fight parking tickets in London. Martin created his own chatbot to help Californians incorporate businesses, gradually building a sustainable platform serving legal aid organizations that "can't throw enough bodies at the problem." His philosophy of "learning through experimentation" led him to co-found the American Legal Technology Awards after attending a black-tie awards ceremony in London. The event has grown from a virtual experiment to an in-person "law prom" drawing 140 attendees, which Martin still personally organizes despite admitting he's "not the most extroverted person." Martin candidly discusses juggling multiple projects while acknowledging he wishes he spent more time with his daughters, ages 18 and 23. His bootstrapped approach allows him to "place many bets over time" rather than being forced into rigid timelines, adapting organically as AI capabilities evolve at breakneck speed.

Eric Kanefsky took an 85% pay cut to leave BigLaw for the U.S. Attorney's Office, then borrowed $50,000 to start his own firm—transforming from government lawyer into managing partner of a 25-attorney white collar defense powerhouse. In this episode of Lawyers Who Learn, host David Schnurman reconnects with his former college roommate to explore Kanefsky's unconventional reverse path from Temple Law through prestigious firms, federal prosecution, and running New Jersey's Consumer Affairs division with 600 employees. When he and his partner found themselves dreading their planned BigLaw returns, they made a spontaneous coffee shop decision that reshaped their careers entirely. Kanefsky opens up about white collar defense reality: nine out of ten clients genuinely believe they've done nothing wrong, creating heavy emotional tolls when representing people in their worst moments. He discusses how managing Type 1 diabetes since age 23 forced him to prioritize health routines that enhanced both physical stamina and intellectual acuity throughout his demanding career. The episode explores unique challenges of scaling law firms where personal relationships and client trust can't be delegated. Kanefsky candidly addresses his time management struggles and "Pavlovian" addiction to constant action that makes vacation nearly impossible. He shares insights from early desperate months watching Gary Vaynerchuk videos for motivation while sitting in an empty office, wondering if he'd made a catastrophic mistake. Beyond business mechanics, this conversation tackles philosophical questions defining legal careers: maintaining empathy without burnout, when professional success becomes prison, and why lawyers work into their seventies unlike finance professionals. His leadership reflections from managing state employees in his mid-thirties offer lessons for attorneys considering the practitioner-to-owner leap in today's AI-transforming landscape.

What if true transformation isn't about adding more to your life, but deliberately removing what's holding you back? Keith Lee, a partner at Big Law Investor, challenges the conventional wisdom that growth means doing more. His contrarian insight: sustainable change requires sacrifice. Lee's journey from living in a storage closet under a staircase for a year—training in martial arts with nothing but two suitcases—to becoming a partner in a thriving financial education company reveals a pattern most professionals miss. While others chase opportunities, Lee practices "strategic subtraction," deliberately choosing what not to do. As partner at Big Law Investor, Lee tackles the crisis plaguing lawyers who graduate with $167,000 in debt yet receive zero financial education. The platform bridges the gap between law school and financial independence, offering student loan refinancing and JD-specific mortgage programs that save lawyers thousands. Lee applies his "beginner's mind" philosophy to AI and legal technology, revealing how his company literally wouldn't exist without AI tools. He addresses seismic industry shifts: the new $200,000 federal student loan cap, legal deserts in states like Oklahoma, and Hawaii's elimination of bar admission requirements for out-of-state lawyers. This isn't just another productivity conversation—it's a masterclass in intentional living from someone who's consistently stayed ahead of industry curves while maintaining the discipline to remove what doesn't serve his larger vision.

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.