Lawyers Who Learn

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.