Lawyers Who Learn

#125 From Yale Law to Legal Tech Startup: A Philosopher's Bet on Someday

Sam Davidoff spent twenty years mastering the art of litigation at one of Washington D.C.'s most elite firms — but the kid who taught himself to program at 15 never fully let go of his first love. When he finally told his wife, she'd seen it coming long before he had, and that was all he needed. That conversation became the catalyst for Align, a digital binder platform built to move trial lawyers off paper and onto their iPads.
In this episode of Lawyers Who Learn, host David Schnurman, CEO of Lawline, traces Sam's unlikely path from St. John's College, where he spent four years wrestling with Plato and Aristotle around a seminar table, to Yale Law, to a partnership at Williams & Connolly, to first-time founder. That unconventional philosophical education gave him something most lawyers never develop: the habit of stopping to examine how he works, not just what he's working on.
Sam opens up about the brutal realities of legal tech sales, how convincing a partner isn't enough, how institutional inertia can bury even an obvious product, and why building a startup feels exactly like a home renovation that costs twice what you budgeted. He also shares the practice that keeps his small team sharp: every other Friday is a mandatory no-product professional development day, where learning anything — watercolor painting included — is fair game.
For lawyers and entrepreneurs alike, Sam's story is a reminder that "someday" has an expiration date, and that the examined life doesn't just make for good philosophy — it makes for better decisions.

#124 How a Wake-Up Call at age 43 Sparked 25 Years of Reinvention

Barry Seidel was at the peak of his success—running a thriving personal injury practice while building a lucrative per diem business, which was featured on the cover of the New York Law Journal. Then, at 43 years old, he had a heart attack—one his doctors called a "no-risk-factor" event, apparently triggered by anger and stress. What followed was a complete reimagining of how he approached law and life.
In this episode of Lawyers Who Learn, host David Schnurman explores Barry's transformation from an angry, stressed attorney to someone who has embraced the ongoing process of learning to manage the emotional aspects of law practice and life. After a year away from practice, Barry pivoted from personal injury law to probate and estate administration, continuing to practice for another 25 years while developing new skills for handling stress.
Barry's journey includes starting his own practice straight out of law school. His recent book, "Evolutions of a Law Practice, How I Opened My Own Practice Right Out of Law School….and lived to tell about it" captures his non-traditional path through multiple career evolutions. In this episode, Barry discusses how staying curious and adaptable can transform adversity into opportunity. Now at 69 and transforming his practice to semi-retirement mode, he's focused on writing, speaking, and helping others navigate legal practice challenges—proof that even the most difficult moments can become the foundation for a life without regrets.

#123 The Power of Mastering One Niche: Built by Saying No

Most lawyers chase growth through more clients and more cases. Michelle Itkowitz built her practice by doing the opposite.
After her first five years as a lawyer, Michelle realized that saying yes to everything was burnout waiting to happen. She narrowed her focus to landlord-tenant law in New York City, committed to mastering the niche, and built a boutique practice rooted in intentional selectivity. Today, she fields hundreds of inquiries each year and accepts only about 20 cases, guided by three non-negotiables: she must add real value, the client must be able to pay her rate, and the relationship must work.
In this episode of Lawyers Who Learn, host David Schnurman explores how Michelle transformed deep subject-matter expertise into authority and impact. For decades, she has read the appellate decisions in her field, taught extensively, and created content that sharpens her thinking. Her podcast, Learn to Live Better: A Housing Law Podcast, serves New York’s vanishing middle class, people who fall between legal aid and high-end representation. In each episode, she distills complex cases into practical takeaways, then makes something clear: the show is not a funnel, and listeners shouldn’t call her for representation.
Drawing on Essentialism and legal project management principles, Michelle front-loads every engagement with a detailed written analysis outlining options, costs, timelines, and likelihood of success. The result is clarity, aligned expectations, and virtually no unhappy clients.
Her story is a reminder that real growth in law isn’t about expansion, it’s about refinement.

#122 Why Teaching What You Learn is the Ultimate Law Practice Growth Engine

Patrick McCormick didn’t start his career as a renowned international tax expert; he built that reputation by systematically teaching every complex concept he encountered. From nearly dropping out of law school after a grueling first year to authoring a treatise for Thomson Reuters, Patrick discovered that the fastest way to master a niche is to explain it to others. Today, he manages a high-level book of business at a multinational firm, proving that visibility is the byproduct of continuous, public learning.
In this episode of Lawyers Who Learn, host David Schnurman sits down with Patrick to explore the "market what you learn" strategy that transformed his practice. They discuss Patrick’s journey from a suburban New Jersey boutique to Ramon Law, a firm spanning 12 countries, and how he uses speaking engagements at Lawline and other providers to stay ahead of seismic shifts in tax law. Patrick reveals the "small but significant" changes in the latest tax legislation and why he still reads hundred-page bills from cover to cover to maintain his edge.
The conversation highlights why specialization, particularly in underserved areas like international and state-and-local tax, is the key to long-term security in an evolving legal market. Patrick offers a roadmap for attorneys looking to transition from "backroom work" to industry leadership through publishing and mentorship. As the legal landscape becomes more complex, Patrick’s story serves as a masterclass in turning specialized knowledge into a scalable professional brand.

#121 From Bollywood to AI: Reinventing Legal Leadership

Pralika Jain has built her career on bold pivots—from Bollywood media and entertainment in India to health tech, Twitter during Elon Musk’s acquisition, and now leading legal at an AI data company in New York. But her real transformation isn’t about industries. It’s about mindset. After years of watching lawyers chase perfection, Pralika embraced a different philosophy: stop taking yourself so seriously, stay curious, and build as you go.
In this episode of Lawyers Who Learn, host David Schnurman sits down with Pralika to explore her journey from Georgetown LLM student learning to code to becoming the first Head of Legal at Hex, an AI analytics data platform. She shares what it was like to be the sole lawyer at a 160-person  SaaS startup, how she navigated the chaos of Twitter’s acquisition, and why sitting quietly in product meetings as a “fly on the wall” made her a better business partner. Pralika explains how she uses AI tools like Claude and Slack integrations to build internal playbooks, triage legal requests, and operate as a one-person legal team without burning out.
Throughout the conversation, she challenges the legal profession’s obsession with perfection. Working hard isn’t enough. Growth requires agility, experimentation, and the courage to show up authentically—even if you don’t fit the traditional mold.
For lawyers navigating AI disruption, in-house pressure, or career pivots, Pralika offers a powerful reminder: you don’t need to know everything to lead. You just need to stay curious, stay flexible, and keep building

#120 How a Health Crisis Turned a Corporate Partner Into a Lawyer Coach

After 18 years in corporate finance law, Heather Moulder had built exactly what success was supposed to look like — partner at Greenberg Traurig, thriving book of business, career on track. Then a breast cancer diagnosis at 38 forced her to stop and ask a question most high-achieving lawyers never let themselves ask: Is this actually the life I want?
In this episode of Lawyers Who Learn, host David Schnurman, CEO of Lawline, sits down with Heather to unpack a journey that started long before the diagnosis — the burnout four years into her career, the perfectionism, the people-pleasing, and the feeling of succeeding at something that was slowly draining her.
Her return to the firm after treatment looked like a comeback. It was actually the beginning of something else. She spent years quietly reevaluating her values, training as a coach, and building a practice on the side before finally making the leap. She initially avoided working with lawyers — then found herself almost exclusively coaching them. Today, she works with attorneys on both mindset and business development, grounded in the belief that you simply cannot separate the two.
Heather's story is a powerful reminder that burnout isn't weakness — it's often the clearest signal pointing toward the work you were always meant to do.

#119 The Recruiter Who Talks Rainmakers Out of Switching Firms

Jennifer Gillman built her recruiting career by doing something most recruiters avoid: telling lawyers not to leave. When partners complained about being underpaid, she dug into the numbers—sometimes discovering they could dramatically increase compensation elsewhere, and other times realizing they were already better off staying put. Same frustration. Completely different reality. That instinct to prioritize long-term happiness over short-term commission checks eventually reshaped her entire business.
In this episode of Lawyers Who Learn, host David Schnurman sits down with Jennifer, founder of Gillman Strategic Group and author of The Happy Rainmaker, to explore her evolution from management-side employment attorney to trusted advisor for high-performing rainmakers. After 12 years in practice—and barely seeing her young child awake during the week—Jennifer made a bold pivot into recruiting. What started as a search for flexibility became a mission: helping lawyers avoid moves that create more stress, more friction, and less control.
Now working with partners who can choose almost any firm, Jennifer focuses on one question: will this move actually improve your life? Through her Six Pillars framework, she challenges the assumption that more revenue equals more fulfillment. Instead, she argues that the happiest rainmakers build business intentionally, set boundaries confidently, and design careers that are both profitable and sustainable.

#118 Building the Lifelong Learning Vision That's Transforming Legal Education

Lucie Allen's journey through legal education started with an accidental entry into IP protection during the dot-com boom and evolved into a leading growth strategy at one of the industry's most recognizable names. As Chief Growth Officer at BARBRI, she's helping transform a company known primarily for bar prep into something much bigger, a lifelong legal learning platform where bar prep no longer represents the majority of revenue.
In this episode of Lawyers Who Learn, host David Schnurman explores how BARBRI is building what Lucie calls a "lifelong legal learning continuum" through strategic acquisitions like West Academic, Quimbee, Skillburst, and Stratford. The conversation reveals how the company is reimagining legal education from LSAT preparation through late-career professional development, operating in both mandatory CLE markets in the US and the UK's professional development landscape where continuing education isn't required.
Lucie shares insights on navigating the AI revolution in education, including BARBRI's decision to hire its first Head of AI, a role dedicated largely to external innovation and improving how clients experience their products. She discusses the challenge of operating in "Horizon Two"—that experimental space between maintaining daily operations and pursuing an uncertain but necessary future. With refreshing honesty, she talks about the unique pressures women face in professional growth, from proving yourself in male-dominated sales environments to managing career ambition alongside motherhood, and even navigating menopause.
The episode touches on everything from early sales training with video feedback to cold plunging in a garden tub, from Microsoft AI partnerships to Simon Sinek's infinite game philosophy. Lucie offers a candid look at the opportunities, challenges, and strategic thinking required to stay relevant when technology is reshaping everything.

#117 From Law Firm Attorney to Building a High-Stakes Translation Business

Sarah Dray took a sick day from her Tel Aviv law firm to complete a freelance translation project, not because she was ill, but because that single job would pay more than her entire week's salary as a junior attorney. That pivotal moment crystallized a truth she'd been avoiding: the practical career path she'd followed since age 18 was leading somewhere she no longer wanted to go. In this episode of Lawyers Who Learn, host David Schnurman explores Sarah's journey from studying law in Hebrew, to building a thriving translation business that now handles high-stakes legal and financial documents for publicly traded companies. After immigrating to Israel for what was supposed to be a gap year, Sarah navigated law school while ultra-Orthodox and married at 19, juggling cultural expectations with an independent streak inherited from her Moroccan immigrant parents. Sarah's entrepreneurial evolution didn't stop with translations. During COVID, she co-founded a seven-figure e-commerce business selling VR headsets on Amazon, a venture born from scrolling TikTok while trapped at home. Her translation business has weathered AI disruption by pivoting from routine litigation work to complex financial documents that still require human expertise and formatting precision. Now, as she considers her next chapter, Sarah's contemplating a new mission: helping women entrepreneurs make the leap from zero to one, drawing from her own unconventional path of building multiple businesses while navigating motherhood during wartime in Israel.

#116 The Navy JAG Who Teaches Lawyers to take a low-key approach in Court

Brendan Horgan learned a counterintuitive lesson as a young Navy judge advocate: the most effective arguments aren't delivered with fire and brimstone. Standing before decorated military officers as a third-year JAG, he discovered that matter-of-fact credibility beats theatrical passion every time, a principle that now guides his employment law practice at Hofheimer in Richmond, Virginia.
In this episode of Lawyers Who Learn, host David Schnurman explores Brendan's evolution from University of Connecticut Law graduate who "just jumped in" to active duty JAG service, through five years prosecuting and defending courts martial, to building a thriving private practice while serving as a Navy Reserve judge advocate. After graduating in 2012 into a challenging legal market, Brendan took a recruiter's pitch and found himself in Newport, Rhode Island, preparing for a career he'd never considered—one that would give him courtroom experience most attorneys never achieve.
Brendan's litigation philosophy rests on two principles: assume mistakes before malice, and find the hidden leverage point in every case that goes beyond the legal arguments. By giving people the benefit of the doubt and avoiding aggressive posturing from the start, he achieves faster settlements in employment disputes. His JAG experience,prosecuting service members with clean records while rotating between prosecutor, defense counsel, and advisor, taught him a crucial lesson: clients' problems are his to solve, not to carry on his shoulders.
Beyond the courtroom, Brendan candidly discusses the "starfish method" of balancing work, family, and public service while coaching his kids' sports teams and maintaining his reserve commitment. His message: even with three children and a demanding practice, there's always room to serve—you just have to intentionally choose which areas get your focus at any given time.