Lawyers Who Learn

Marc W. Halpert encountered the same paralyzing problem across professions: all struggling to talk about themselves despite extraordinary credentials. The pattern was universal—high achievers frozen by fear, worried about sounding "too out there," dragging themselves through the mud instead of showcasing their value. In this episode of Lawyers Who Learn, host David Schnurman sits down with Marc, a serial entrepreneur turned LinkedIn branding strategist who helps attorneys break free from the psycho-cultural programming that keeps them invisible. Marc's philosophy cuts against conventional wisdom: you're not bragging when you share your expertise—you're serving your future clients by helping them understand why you do what you do. His "know, feel, believe, do" framework transforms LinkedIn from a digital resume into a strategic platform for authentic professional visibility. The conversation reveals why legal professionals particularly struggle with self-promotion, how Marc teaches without slides to promote authentic expertise, and his counterintuitive advice on consistency of original content—post when you have something important to say, not according to arbitrary schedules. From his two published books to teaching at major law firms, Marc demonstrates how authentic visibility creates opportunity without the aggressive selling lawyers fear. For professionals stuck between imposter syndrome and the fear of appearing salesy, this episode offers strategies to finally let your value bubble up.

Fifteen years ago, Richart Ruddie survived on rice and frozen shrimp while working six months without pay, taking out negative equity from ATMs just to get by. Today, after selling his bootstrapped reputation management company for more than competitors who raised $70 million, he's building Captain Compliance—a data privacy software company protecting businesses from costly compliance violations that could mean generational wealth. In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, explores Ruddie's unconventional path from valet parking luxury cars to serial legal tech entrepreneur. After a mentor advised him to intern anywhere during the 2008 financial crisis—even for free—Ruddie spent six months earning nothing while learning digital marketing at a hedge fund's startup. That SEO expertise became the foundation for Profile Defenders, which he launched in March 2011 and grew to $90,000 monthly revenue by December of that year, all while maintaining obsessive client service that included taking 3 AM calls to bury damaging content before morning meetings. Ruddie's approach defied Silicon Valley convention at every turn. He bootstrapped while competitors raised massive funding, prioritized profit over revenue growth, and let efficiency become his competitive advantage—ultimately outperforming venture-backed rivals and achieving a more successful exit despite far less capital. Now with Captain Compliance, Ruddie tackles an even bigger opportunity as privacy laws proliferate beyond California and GDPR. The stakes are higher—he's raising venture capital for the first time while managing two young children—but the market potential is staggering, with competitors selling for nearly $2 billion. His journey proves that grit, efficiency, and customer obsession can beat big budgets every time.

Johnna Story has spent three decades at Finnegan—a remarkably rare tenure in today's legal landscape. But her longevity isn't just about staying; it's about evolving a profession that barely existed when she started. As Director of Professional Development and Wellbeing, Johnna has watched attorney development transform from an afterthought into a strategic imperative. In this episode of Lawyers Who Learn, host David Schnurman explores how Johnna built her 1,700+ day meditation streak using the free Insight Timer app and why she's convinced that wellbeing isn't dessert—it's the main course. Starting as an HR assistant in 1995 at a firm of 120 attorneys where professional development "wasn't really a thing," Johnna grew alongside an emerging profession that truly coalesced in the early 2000s. Today, she supports 350 attorneys at Finnegan, helping them develop the self-discipline, responsiveness, and authenticity that technology can't replicate. Johnna's approach addresses the billing hour paradox directly: taking time for wellbeing means time away from billable work. Her solution involves meeting attorneys where they are—whether through 10-minute tips on the firm's landing page, secondary trauma support for pro bono lawyers, or monthly programming with benefits providers like Cigna and Prudential. She's learned that impacting even one person counts as a win. The conversation turns vulnerable as Johnna discusses losing her mother in September 2025, revealing how complicated grief intersects with workplace authenticity. Her philosophy of "selective vulnerability" offers a framework for bringing your whole self to work while maintaining boundaries—admitting you don't know everything, being willing to learn, and recovering from mistakes. These human skills matter more than ever as AI creates knowledge gaps while demanding different competencies from emerging attorneys.

Jack Newton runs Clio with 2,000 employees and over $300 million in annual recurring revenue, yet he describes his CEO role as "a new job every quarter." His secret to sustaining energy seventeen years into building Clio isn't about winning existing markets—it's about creating entirely new categories of software that didn't exist weeks before. In this episode of Lawyers Who Learn, host David Schnurman sits down with Newton at ClioCon to explore the mindset behind scaling a legal tech unicorn. Newton reveals how humility and continuous learning drive his approach, from seeking mentors among portfolio companies to studying frameworks like Simon Sinek's "The Infinite Game"—which reframes business not as zero-sum competition but as unlimited opportunity creation. Newton's keynote announcement left 2,500 attendees in stunned silence as he unveiled technology that compresses ten hours of legal work into forty-five minutes. The implications are profound: when automation handles routine tasks at scale, it doesn't eliminate lawyers—it creates massive new market opportunities. Newton draws parallels to LegalZoom, where automated forms generate enormous demand for attorney services, demonstrating how giving away commoditized work for free actually expands the entire legal market. Newton balances this demanding role by being fully present at home with his wife of twenty-two years and three teenage children, finding renewal in Vancouver's natural beauty. His philosophy challenges lawyers to stop jealously guarding routine work and instead embrace AI as a competitive advantage that could quadruple market size—transforming how legal professionals deliver value in an automated world.

Four months in a NICU changes you. For Kathryn Marquez, Global Director of Learning and Development at Bryan Cave Leighton Paisner (BCLP), those 120 days watching her three-pound, 14-ounce daughter Evie fight to survive—born with an esophagus that never fully formed—made her a better parent, professional, and leader. The whiteboard goal "to grow strong" wasn't just for her daughter; it became something she carries with her in everything she does. In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, explores Kathryn's journey from a 22-year-old legal personnel assistant at Sidley Austin to her current global role. Taking notes in exit interviews—listening to departing attorneys describe their unhappiness, including one who hadn't spoken to anyone in two days—convinced her not to pursue law school and instead build a career supporting lawyers rather than becoming one. Kathryn shares how BCLP’s learning approach partners with internal practitioners to ensure a pragmatic, targeted experience, rooted in a high-performance culture that emphasizes a client-focused, human-centered, results-focused mindset. Three former high-performing partner leaders bring this approach to life, as they now coach full-time to develop BCLP’s next-generation pipeline. Other in-person programming, including their global sponsorship program, mirrors the firm’s tailored investment in their high-potential talent. The conversation turns vulnerable when Kathryn recalls meeting Dr. Nath, the surgeon who surprised her with his compassion, attentiveness, and skill, beginning that first day when he gave her his cell phone number. She still texts him six years later and uses that story when teaching client service. Drawing on Kim Scott's Radical Candor, Kathryn delivers her core challenge: high care with low challenge—avoiding hard feedback to protect feelings—is inherently unkind. True compassion means having difficult conversations, whether coaching an associate, conducting a layoff, or advocating for your child in a hospital room.

Darshan Kulkarni doesn't believe in meditation, doesn’t have time to read books, and thrives on chaos—yet he's earned six degrees by age 25, founded a law firm, teaches at Drexel, and has recorded thousands of podcast episodes. His secret? "Chase being uncomfortable," he says, and find joy in everything you do. In this episode of Lawyers Who Learn, David Schnurman, CEO of Lawline, sits down with Kulkarni to explore an unconventional learning philosophy that rejects traditional productivity advice. As a sixth-generation pharmacist who added a JD and master's degree to his credentials while still in his twenties, Kulkarni's approach challenges conventional wisdom about focus and balance. Kulkarni's journey began at 15, teaching judo to blind children in India—an experience that taught him about "the tyranny of low expectations." After immigrating to the US at 19, he completed 60 college credits in one year simply because he didn't know it was supposed to be impossible. His learning strategy? Work from 9 AM to midnight daily, pursue 15 projects simultaneously, and outsource everything except what brings genuine joy. "The moment I get comfortable with something, I get bored," he explains. Now focusing on FDA law, life science related privacy and pharmaceutical compliance, Kulkarni is witnessing a seismic shift in healthcare: direct-to-consumer pharmaceutical models that bypass traditional insurance middlemen. From Trump RX to Amazon pharmacy initiatives, he explains how patients are becoming consumers, and why this transformation matters for legal professionals navigating healthcare's future. At Drexel, he's redesigning his courses around AI, asking students to treat artificial intelligence as their boss rather than fighting against its inevitable integration into legal practice.

Anusia Gillespie hasn't applied for a single job since law school, yet she's moved through seven organizations in ten years—all by design. She played pivotal roles in two major legal tech acquisitions, built innovation programs across global law firms, and figured out exactly which parts of work fuel her versus drain her. When the ratio shifts too far, she makes her move. In this episode of Lawyers Who Learn, host David Schnurman, CEO of Lawline, explores this unconventional career philosophy with Anusia Gillespie, Enterprise Lead at vLex and author of the book Soul Toll. Her journey spans BigLaw associate to Global Head of Innovation at Eversheds Sutherland, Chief Strategy Officer at Skillburst (sold to Barbri), and Enterprise Lead at vLex during its billion-dollar acquisition by Clio. Anusia introduces her "soul toll ratio"—measuring how much of your job energizes versus depletes you. She reveals why a hundred percent soul job actually limited her growth at Harvard Law School Executive Education, how a forced meditation experience exposed her complete disconnection from herself, and why she's packaging leadership wisdom in a fiction novel instead of another dry business book. From building AI training consortiums across eleven law firms to landing speaking gigs through simple text messages, she demonstrates how bringing your full self to work creates unexpected opportunities. Her networking advice challenges conventional wisdom: forget sports statistics, find your ballet. This conversation reframes career sustainability for lawyers who suspect they're shutting themselves off to show up—and offers a practical framework for measuring when it's time to make a change.

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.