Lawyers Who Learn

Emily Logan Stedman was having full-blown panic attacks on family vacations. Despite making partner track at a prestigious Milwaukee firm—Teach for America, Law Review Editor, clerkship, Big Law success—she was ready to leave law entirely. Then her husband said something that changed everything: "I think you actually like being a lawyer. You might just need a different environment." In this episode of Lawyers Who Learn, host David Schnurman, CEO of Lawline, sits down with Emily, now a partner at Husch Blackwell, to explore her transformation from secretly struggling associate to Big Law's most visible wellness advocate. Raised by attorney parents who joked her birth announcement named her their firm's "newest associate," Emily followed the expected path without questioning what she wanted. Teaching fifth grade in rural Arizona became unexpected litigation preparation—breaking down complex concepts, managing classrooms with precision, and reading people became daily courtroom skills. Emily's breakthrough came when she joined Husch Blackwell with a radical ultimatum: be fully herself, or leave. That authenticity manifested in daily LinkedIn posts about Big Law realities, nationwide mentorship calls, and a systematic approach that "neutralizes" the billable hour by tracking everything like clocking in and out. Her most surprising revelation: adopting an entrepreneurial identity through Coursera business courses, thinking of her practice as "the law office of Emily Logan Stedman" within the larger firm. Emily represents the bridge between generations—an elder millennial who survived the old model and is reshaping it from within, proving strategic time management and authentic self-expression can make Big Law sustainable.

Most law students can argue complex cases but struggle to explain basic legal rights every citizen should know. Marisa Monteiro Borsboom noticed this disconnect and decided to do something radical about it—launching a legal literacy initiative that challenges both how lawyers are trained and how citizens understand their place in the legal system. In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, explores Borsboom's unconventional journey from Portuguese lawyer to quantum computing policy advisor to founder of the Humanity of Things Agency. Licensed since 2004 and splitting her life between the Netherlands and Portugal, Borsboom developed what she calls a "quantum mind"—refusing to see limits between disciplines like law, physics, anthropology, and technology. Her legal literacy initiative tackles a striking paradox: we teach people they need lawyers for everything, yet we never teach them the basic legal toolkit for navigating life—from understanding labor rights to knowing where to go when legal problems arise. Borsboom works with law students who discover they've been trained in complexity but can't explain citizenship in simple terms. Her dream? Integrating this knowledge into K-12 education, creating citizens who understand the legal dimension of their lives from birth to death. Borsboom's philosophy challenges lawyers to go "beyond the commercial pitch" and embrace their role as agents of humanity. She candidly discusses nearly quitting after years of disillusionment, until watching "The Professor and the Madman"—a film about creating the first dictionary—reminded her that transformative work requires relentless devotion, not project management systems. Now juggling quantum computing policy, civil society advocacy, and raising two pre-teens, she argues that waiting for governments to fix education is no longer viable. Civil society must step up, building knowledge infrastructure from the ground up, one community at a time.

What if the reason you struggle with transforming your professional relationships into clients is that you're missing a skill you were never taught? Yuliya LaRoe spent almost a decade in BigLaw before she figured this out. Now, as founder of LeadWise Group, she helps partners at law firms across the country become strategic leaders, master people and practice management, and excel in business development. Her secret to transforming relationships into clients? It's not about networking harder. It's about nurturing smarter - a system she's now sharing in her forthcoming book, The Nurture System: How Smart Lawyers Transform Relationships into Business Development Success. In this episode of Lawyers Who Learn, Yuliya reveals the critical difference between follow-up and nurture, why most lawyers fail at business development (hint: you're trained as tellers, not askers), and the two-word phrase that removes all pressure from nurture conversations. She also shares the single question that uncovers what clients actually need. Along the way, she opens up about building a thriving consulting practice while navigating a cultural gap that started the moment she arrived in the US from Russia at the age of twenty. If nurturing relationships ever felt forced, inauthentic, or impossible, this conversation will change your mind.

Scott Mason spent 25 years building exactly the legal career everyone expected: Columbia Law School graduate, general counsel to the nation's largest domestic violence shelter provider, second-in-command of New York City's court system. When a near-death illness hit in 2023, it didn't introduce a new question. It just made the one he'd been avoiding impossible to ignore: had he become an attorney to meet everyone else's expectations except his own? By then, he'd already launched a transformational coaching practice in 2020, built on an unlikely foundation—Greek mythology. In this episode of Lawyers Who Learn, host David Schnurman, CEO of Lawline, explores why Scott believes ancient Greeks understood something modern coaching ignores. While philosophers like Aristotle rejected mythical thinking, Scott argues they threw out the blueprint. The patterns that trapped Sisyphus in endless repetition, Persephone in darkness, and Prometheus in punishment aren't ancient history—they're operating in law firms today. Attorneys pushing the same rock uphill daily, partners fearing change will destroy them, associates repeating behaviors that stopped serving them years ago. Scott introduces his Five Toxic Myths: tragic origins, social expectations, ritualistic patterns, doomsday thinking, and existential apathy. His solution—stepping into roles of Author, Hero, or Olympian—requires twenty sessions and "radical self-accountability." A remarkable moment arrives when Scott discovers David's son recently studied the exact childhood book that changed Scott's life and led him to identify with Helios, the sun god—proof, Scott suggests, that these archetypal patterns are more universal than we admit. His deliberately bold branding intentionally repels some while attracting his ideal client: the mid-career lawyer sensing greater possibilities but unable to identify the "mist" holding them back.

Claire E. Parsons made equity partner at her first firm, yet found herself paralyzed by a lifetime of fear and perfectionism. Then postpartum depression forced her to try something radical: one minute of daily meditation. That single minute grew into a 30-minute practice that didn't just change her mental health—it transformed her entire career trajectory. In this episode of Lawyers Who Learn, host David Schnurman explores how Claire evolved from a civil rights attorney afraid to speak about her meditation practice to a mindfulness teacher with over ten speaking engagements scheduled for Q4 alone. Now Of Counsel at Bricker Graydon, Claire represents school districts in high-conflict special education disputes while teaching meditation and wellness courses on Lawline. Claire's journey reveals a counterintuitive truth: she didn't overcome fear by eliminating it, but by accepting it. As an introvert who loves teaching but hates networking events, she discovered that authentic expertise creates its own opportunities. Her approach to combining ancient mindfulness practices with modern legal challenges offers a blueprint for attorneys navigating emotionally charged cases. Whether dealing with angry parents in special education disputes or difficult opposing counsel, Claire demonstrates how seeing adversaries as human beings rather than enemies can actually make you a more effective advocate. This conversation offers practical strategies for legal professionals struggling with anxiety, perfectionism, and the fear of putting themselves out there—while showing how wellness practices can become both a personal refuge and a professional differentiator in an increasingly divided world.

"Are my best days behind me, or are my best days ahead of me?" It's the question that haunts successful professionals in midlife—one they often can't even verbalize. David Schnurman, CEO of Lawline, faces this internal struggle daily, driven by Abraham Maslow's warning: "If you deliberately plan on being less than you're capable of being, you'll be unhappy for the rest of your life." In this unprecedented episode of Lawyers Who Learn, David steps away from the host chair to become the guest, guided through a live coaching session with Kara Hardin, CEO and founder of The Practice Lab. Hardin, a former practicing lawyer turned registered psychotherapist who specializes in high performance and mental health, creates a rare moment of vulnerability as David confronts the painful gap between his potential and his current reality. David achieved everything he visualized in his twenties—the Brooklyn townhouse, the successful company, the family life he dreamed of. But now, without a clear vision for the next twenty years, he feels his soul "crying to be used" in ways he can't yet articulate. Hardin expertly unpacks the paradox plaguing high achievers: the very strengths that propelled them to success often become barriers to their next evolution. This condensed seven-minute session from a thirty-five-minute coaching conversation reveals how the skills that got us here won't get us there. Hardin challenges David—and every listener facing their own midlife inflection point—to examine their deepest fears and strongest protections, showing how true growth requires embracing the opposite of what once made us feel safe. For legal professionals questioning whether their peak performance days are over, this intimate dialogue offers both mirror and roadmap for navigating the complex terrain between past achievement and future potential.

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.

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.

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.

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.

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.