Lawyers Who Learn

Steven Harber's path to legal tech started in an unexpected place: selling Japanese robots to automotive factories in 1985. Fresh out of Bucknell with an East Asian studies degree and zero job prospects, he stumbled into a role that taught him the power of eliminating waste from processes. That lesson from Toyota's manufacturing philosophy would later become the foundation for three successful legal technology companies. In this episode of Lawyers Who Learn, host David Schnurman explores Harber's journey from New York Law School graduate to serial legal tech entrepreneur. After practicing law for barely a year, Harber raised his hand when his small firm needed someone with sales experience to commercialize their early document scanning technology. That decision launched a 30-year career, though not without self-doubt about whether he was pivoting because he wasn't good enough at law. Harber's philosophy challenges the Silicon Valley playbook. He calls himself a conservative entrepreneur who built profitable services businesses solving real problems rather than chasing unicorn status. But the journey was far from smooth.Navigating through the Lehman bankruptcy and dealing with challenging owners made for some very long days Today, as Executive Chairman of Cimplifi, Harber is pushing the industry toward fixed-fee AI review. His core belief, drawn from The Old Man and the Sea: you don't have to go out too far to succeed.

Matthew Galando never intended to build a 23-year career at one law firm. As a college student interning at K&L Gates, he quickly realized that while practicing law wasn’t his path, the legal industry itself was. What began as a legal administrative assistant role evolved into leading professional development for a global team of 13—shaping lawyers’ growth from a perspective grounded in strategy, talent, and organizational leadership. In this episode of Lawyers Who Learn, host David Schnurman explores how Matt's unexpected journey shaped his leadership philosophy at K&L Gates. His approach centers on compassionate leadership, a concept that might seem counterintuitive in the legal world, but one Matt believes is essential because "the hardest lawyer is still a human being at the end of the day." Matt's transformation evolved by overcoming his default response of "no" after learning more about growth mindset. Now he approaches requests with "what if" thinking, opening possibilities while maintaining thoughtful boundaries. His work spans leadership development programming at every level, from high-potential managers to lateral partners, always emphasizing strategic relationship-building and fundamental skills enhanced by humanity. Drawing from his lifelong music career as a trumpet player who sits first chair in musicals and ensembles, Matt applies performance lessons to professional development: teamwork, adaptability, and the pursuit of polish – knowing that precision matters most when the spotlight is on. Whether he's reading Adam Grant or Kim Scott, his message remains consistent–lead with compassion, default to possibility, and remember that caring for your team comes first.

At 40, Chris Keefer had everything lawyers are supposed to want: partner track, jury trial wins, Indiana Supreme Court experience. He also had something else—a growing certainty that litigation was slowly crushing him. When the celebration after his biggest courtroom victory felt hollow, he knew something had to change. So he made a decision that seemed crazy to everyone around him: sell the house, move his family of five to Oregon, and spend 18 months earning a master's degree in sports product management. In this episode of Lawyers Who Learn, host David Schnurman explores how Chris discovered that law school never taught him the one thing he needed most—how to be an entrepreneur. His journey from the University of Oregon back to legal practice wasn't a straight line. It included living apart from his wife Garetta and three young kids for a year, sitting face-to-face with her in a WeWork fishbowl managing a fledgling solo practice, and experiencing panic attacks while their savings dwindled. The turning point came from a couple unexpected sources: a coffee meeting with a colleague trying to understand the types of services Chris was providing, and then a book called Toothfish that taught him to stop competing in crowded markets and create his own. Those insights led Chris to "preventive law"—a framework for helping businesses peek around corners before legal problems materialize. But his real breakthrough was realizing that entrepreneurs who need legal help most can't afford traditional hourly rates. His solution became The Legal Wellness Kit, an Amazon #1 new release and bestseller that delivers hundreds of hours of practical guidance for the cost of a brief phone call with a big firm attorney. Today, as Associate General Counsel at Pacific Seafood and principal of Keefer Strategy, Chris continues building his practice while eyeing his next chapter: more writing, more teaching, and paying forward the knowledge he wished he'd had at the start. His story reveals that mid-career reinvention requires more than courage—it demands partnership, resilience, and the willingness to get comfortable being uncomfortable even when everything feels uncertain.    

Stacey had it all—managing $300-500 million brands as a marketing and advertising executive, traveling the world, leading teams. Then in her mid-thirties, she walked away from that successful career to attend law school full-time. Her colleagues thought she was crazy. For Stacey, law school felt like a vacation compared to her 80-90 hour work weeks. In this episode of Lawyers Who Learn, host David Schnurman explores Stacey's journey from brand management executive to founder of Kalamaras Law Office and later as creator of Trademarkabilities, a practical trademark training academy that has served over 200 attorneys. After working with trademark lawyers in her corporate role, Stacey realized she agreed more with the attorneys than her marketing colleagues, a revelation that sparked her midlife career pivot. Stacey's path wasn't linear. She started her first firm in 2009 after being laid off during the recession, moved in-house, then returned to Big Law again before finally restarting her firm intentionally in 2018 when her mother needed more care. The turning point came when her practical, business-focused teaching style on Lawline attracted thousands of lawyers, and clients started reaching out saying, "My attorney told me I had to watch your course." Her philosophy centers on one powerful truth: "No one is coming to save you." Whether you work for yourself or someone else, you must be your own cheerleader and self-promoter. Stacey reflects that losing two jobs in three years might have broken her at 29, but by her 40s, the business experience she gained earlier in life helped her rebuild her legal career with confidence—and with a strong sense of how to serve clients and their brands.

Steve Gluckman, a pioneer in legal e-learning, discusses his journey from PwC to founding SkillBurst Interactive. He reflects on the importance of timing in business innovations and the emotional journey of entrepreneurs post-acquisition. Gluckman shares insights about building customizable e-learning solutions for law firms and how he navigated the challenges of identity after selling his company. The conversation also touches on leadership, work-life balance, and the evolving landscape of legal education, highlighting the need for adaptability in today's market.

Amy Woods failed her very first IOLTA audit. Fresh out of school with a master's in accounting, she thought she had everything in order for her lawyer client, until an auditor named Bruno sat her down and explained she was looking at trust accounts like an accountant when the bar wanted something entirely different. That moment of failure became the foundation for a 20-year specialization in an area where 99% of law firms aren't in full compliance. In this episode of Lawyers Who Learn, host David Schnurman explores how Amy transformed repeated failures into expertise, building IOLTA Consulting to help attorneys navigate trust account regulations that weren't taught in law school. Working across multiple states, Amy has never walked into a single law firm doing everything correctly—not one. From real estate wire fraud to simple recording errors that snowball into thousand-dollar problems, she's seen how easily well-intentioned attorneys can face suspension or worse for mistakes they didn't know they were making. Amy's vision extends beyond compliance fixes. She's building a team to provide coast-to-coast support while she travels to speak and educate, turning a niche accounting service into a scalable business model with monthly subscriptions and strategic growth plans. The conversation takes a vulnerable turn when Amy shares why she recently shifted her two youngest children from homeschooling to traditional school—her husband's epilepsy diagnosis and the need to prepare financially for an uncertain future. Her story demonstrates how personal challenges can sharpen professional focus, transforming specialized knowledge into both security and service for an underserved legal community.

Kenton Brice sits at the center of what he calls "a massive Venn diagram"—law libraries, legal technology, higher education, and the practicing bar—and from that unique vantage point, he sees something most people miss: law schools have zero incentive to change. With three powerful forces keeping the status quo locked in place (U.S. News rankings, ABA accreditation, and unlimited student loans), traditional legal education persists even as the profession transforms around it. In this episode of Lawyers Who Learn, host David Schnurman explores Kenton's vision for reimagining legal education at the University of Oklahoma College of Law, where he directs the law library and runs the Digital Initiative—a 12-year experiment in building technology competencies outside the required curriculum. Through Tuesday and Thursday lunch-and-learns, conference trips, and hands-on workshops, Kenton prepares students for a profession where managed service organizations are disrupting traditional firm structures and AI is forcing a complete rethinking of legal service delivery. The conversation moves from practical questions about preserving legal materials in a digital age to provocative ideas about trashing the bar exam entirely. His blueprint for building a law school from scratch prioritizes design-oriented curiosity over doctrinal mastery, AI-infused hybrid learning over traditional lectures, and two years of intensive study over three years of diminishing returns. But Kenton's real passion emerges in his vision for the "holistic lawyer." Beyond competencies and technology, he wants lawyers who see themselves as protectors of democracy, not just service providers. When 78% of people can't access the civil justice system and a single mother facing eviction can't find representation, Kenton asks the fundamental question: can we make money and serve people at the same time? His answer, drawn from his men's reading group discussions of Man's Search for Meaning and his weekend woodworking projects, is an emphatic yes—if we're willing to reimagine the profession entirely.

When Jennifer Rakstad's firm surveyed their associates, the feedback was clear: traditional training wasn't having the impact they wanted. As Senior Manager of Learning and Development at White & Case, Jennifer worked hand in hand with a committee of partners to lead the creation of Momentum—a three-day immersive program that's already reached 350 lawyers. What makes it different: every session is designed and taught by the firm's own partners and senior associates, for a true “lawyer-led” experience. In this episode of Lawyers Who Learn, host David Schnurman explores Jennifer's path from litigation to professional development. After applying to 200 judges for clerkships with over a dozen interviews and receiving zero offers, Jennifer regrouped with a targeted approach that landed her a federal clerkship in Puerto Rico. Seven years into litigation practice at Mayer Brown, a colleague noticed her passion for firm initiatives and recruiting work, asking if she'd consider pivoting entirely. That conversation led to her becoming one of the first ICF-certified coaches in a law firm. The Momentum program represents a major investment, taking associates offsite for three days with full partner faculty involvement. The program creates cohort experiences where associates learn from partners who've been in the trenches, with plans to have participants eventually teach each other. Jennifer also shares how a fractured ankle during a family trip to Japan transformed her perspective on accessibility challenges. Despite doctors suggesting she fly home, she completed two more weeks in Japan on crutches, followed by two months in a wheelchair. That experience reinforced the empathy that drives her work developing lawyers.

Sarah Ennor spent years as a securities lawyer at major banks, excelling at sophisticated legal work but challenged by corporate politics and what she sometimes thought was lack of motivation and discipline. In 2015, she left corporate law, traveled to Sri Lanka for a 10-day silent meditation retreat, worked and lived on a New Zealand winery, and returned to launch her own legal practice. But running a solo practice without corporate infrastructure proved unexpectedly overwhelming, until a stranger at a cocktail party asked if she had ADHD. In this episode of Lawyers Who Learn, host David Schnurman explores Sarah's journey from that eye-opening conversation to formal diagnosis, and ultimately to becoming a sought-after speaker who makes ADHD "human and profitable" for law firms and their attorneys, and corporations. Sarah reveals why lawyers are drawn to the profession's constant urgency and novel problems (the very dopamine hits that ADHD brains crave) while also explaining why law firms often punish the behaviors that come with the condition. When she finally tried medication, the fog lifted and she realized she'd been working ten times harder than necessary. She now helps firms move beyond surface-level awareness to create genuinely supportive environments through curiosity and outcome-focused thinking. This conversation goes beyond the "ADHD as superpower" narrative to honestly address the disability many face and the transformative power of self-compassion over discipline. These insights resonate deeply even for those still navigating their own undiagnosed experiences.

Yeve Chitiga immigrated to the United States at sixteen with clear goals shaped by hope and determination: college, law school, becoming an attorney. She followed that path, working in banking in London and later as a corporate lawyer at a top firm, reaching milestones that surpassed her wildest dreams. Along the way, a quieter inner question began to surface about meaning, contribution, and alignment. In this episode of Lawyers Who Learn, host David Schnurman explores Yeve’s journey from financial services attorney to career transition coach for high-achieving professionals in demanding environments. Raised in Zimbabwe, Yeve grew up in a culture rooted in connection where there are no strangers, only extended family. That deep belief in belonging now shapes the heart of her coaching work. Rather than one dramatic turning point, Yeve’s story is marked by a series of moments that invited reflection and realignment across different chapters of her life. Each asked the same essential question: What kind of impact do I want to make? Over time, the answer softened and clarified—meaningful, human-scale impact through one-on-one connection. Motherhood deepened this shift, reshaping success into presence, listening, and moments like when her little one says, “Mommy, I love that you just listened to me.” Then a career shift allowed her to fully embrace pivoting from law to coaching. The conversation weaves through boundaries, faith, cultural expectations, and Yeve’s vision for an intimate retreat at Victoria Falls, one of the world’s most awe-inspiring natural wonders. With its rising mist, roaming wildlife, and expansive sunsets, Victoria Falls becomes both a setting and an invitation: to slow down, reconnect, and rediscover parts of ourselves often lost in the pace of everyday life.