This Legal Life: Lessons Learned from a Life in Legal

Nexl
  • 5.0 (5)
  • BUSINESS
  • UPDATED WEEKLY

Join host Ben Chiriboga, Chief Growth Officer at Nexl as he interviews guests to get their lessons learned from a life in legal. From overcoming practice silos to fostering collaboration and battling toxic work environments while building strong client relationships -- This Legal Life leaves no stone unturned.

  1. Bridging the Gap: Why Legal Tech Still Isn’t Reaching Lawyers (and How to Fix It)

    4D AGO

    Bridging the Gap: Why Legal Tech Still Isn’t Reaching Lawyers (and How to Fix It)

    In this episode of This Legal Life, Ben Chiriboga sits down with Ceschino Brooks, founder of The Legal Tech Guide and host of Future of Law Today, to unpack one of the biggest challenges in the industry: why legal tech still struggles to connect with the people it’s built for. Drawing from his journey from Big Law to marketing and legal tech, Ceschino explores the disconnect between innovation and adoption, the rise of the “legal operating system,” and why better information—not more noise—is what the industry truly needs.

    45 min
  2. From Bass Lines to Bottom Lines: Jenn McCarron on Reinventing Legal Through Data and Creativity

    APR 30

    From Bass Lines to Bottom Lines: Jenn McCarron on Reinventing Legal Through Data and Creativity

    In this episode of This Legal Life, Ben Chiriboga sits down with Jenn McCarron, founder of Contracts.ai, to explore a career path that defies convention. From touring musician to legal ops leader at Cisco, Spotify, and Netflix, Jenn shares how blending creativity with technical rigor shaped her approach to transforming legal work. They unpack the evolution of contracts—from static documents to dynamic data—and why the next frontier isn’t CLM, but revenue intelligence. Along the way, Jenn reflects on risk, reinvention, and the power of trusting both sides of your brain in building something truly new

    53 min
  3. From Autopilot to Agency: Rethinking a Legal Career in the Age of AI with Kaj Rozga

    APR 1

    From Autopilot to Agency: Rethinking a Legal Career in the Age of AI with Kaj Rozga

    In this episode of This Legal Life, Kaj Rozga shares his journey from Big Law litigator to in-house counsel navigating the fast-evolving world of legal technology. Sparked by the rise of generative AI, Kaj began exploring how lawyers can move beyond autopilot careers and take ownership of their value in a changing industry. Through launching his podcast Version Up and immersing himself in the legal tech ecosystem, he reflects on building a personal brand, learning in public, and finding clarity in a space full of hype. This conversation is a grounded take on where legal tech is actually headed—and what it means for the future of legal careers.

    36 min
  4. Rethinking the Legal Career Path: Anastasia Boyko on Leadership, Law School, and Reinvention in an AI Era

    MAR 25

    Rethinking the Legal Career Path: Anastasia Boyko on Leadership, Law School, and Reinvention in an AI Era

    In this episode of This Legal Life, Ben sits down with legal futurist Anastasia Boyko for a conversation that goes far beyond career pivots. From emigrating to the States from Soviet Ukraine to navigating Big Law layoffs and personal upheaval, Anastasia traces her own hero’s journey through legal practice, innovation, academia, burnout, and ultimately returning home. Together, they explore what happens when the traditional markers of success fall away and you find yourself in a season without a clear next step, what Anastasia calls “the windless sea”. This episode dives into law school’s hidden rewiring, the pressures of external validation, institutional breakdown in the age of AI, and the hard but necessary work of defining your own North Star.

    48 min
  5. From Wall Street Failure to $1B in Debt Relief: Jonathan Petts on Redefining Legal Impact

    MAR 18

    From Wall Street Failure to $1B in Debt Relief: Jonathan Petts on Redefining Legal Impact

    In this episode of This Legal Life, Jonathan Petts, CEO of Upsolve, shares his unconventional journey from being fired by two Wall Street law firms to building a nonprofit that has helped erase over $1 billion in debt for low-income Americans. Through moments of personal failure, unexpected mentorship, and bold experimentation, Jonathan reveals how rethinking bankruptcy as a tool for economic mobility—not moral failure—sparked a mission to scale access to justice. This conversation explores the realities of building in legal tech, the discipline of product focus, and how technology—especially AI—can unlock opportunity for millions who have historically gone unserved.

    35 min
  6. The Human Side of Law: How Zack Anstett Reconsidered Success in Private Practice

    MAR 3

    The Human Side of Law: How Zack Anstett Reconsidered Success in Private Practice

    In this episode of This Legal Life, Ben Chiriboga speaks with employment lawyer Zack Anstett about how a life-altering medical diagnosis reshaped his perspective on success, ambition, and balance in private practice. Zack shares what it’s like to continue practicing law while navigating serious health challenges—and how that experience changed his relationship with billable hours, titles, and long-term career expectations. The conversation offers an honest look at resilience, flexibility, and the often-overlooked human realities behind legal careers. About Our Guest: Zack Anstett defends Southeast-based employers when the workplace becomes a legal battlefield. On the defense side, Zack has defended hundreds of employment cases in state and federal courts and before investigative agencies such as the EEOC and the Department of Labor. He understands how plaintiff attorneys build their cases because he has spent years strategically dismantling them. On the prevention side, Zack’s litigation experience gives him a clear view of where companies tend to make mistakes that lead to lawsuits. He helps employers make difficult personnel decisions, develop practical HR policies, and draft employment agreements designed to reduce risk and keep disputes out of court. Outside of work, Zack enjoys learning Farsi, cooking with his Persian mother-in-law, and losing at pickleball to his five-year-old daughter—while his three-year-old son and one-year-old daughter cheer from the sidelines with their mom. 🔗 Read Zack’s full bio: https://www.parkerpoe.com/attorneys/zack-s-anstett#tab/overview 🔗 Connect with Zack on LinkedIn: https://www.linkedin.com/in/zackanstett/

    1 hr
  7. A Law Firm Without the Firm: Brian Scherer on Building Leverage, Community, and a New Legal Path

    FEB 27

    A Law Firm Without the Firm: Brian Scherer on Building Leverage, Community, and a New Legal Path

    In this episode of This Legal Life, Ben Chiriboga speaks with Brian Scherer about the pivotal moments that led him from in-house fintech roles to founding Hey Counsel. Brian reflects on the frustrations of Big Law economics, the isolation of solo practice, and the perseverance required to build something entirely new in the legal ecosystem. The conversation explores how technology, community, and intentional reinvention are reshaping what it means to succeed as a modern lawyer. About Our Guest: Brian Scherer is the co-founder of HeyCounsel and a fintech commercial and regulatory attorney. He has worked in-house at fast-growing startups including LendingClub, Opendoor, and Blend. Brian started HeyCounsel to help companies find strong boutique legal support at a lower cost than traditional Big Law. As it evolved, he recognized the bigger opportunity was supporting the lawyers themselves. Today, HeyCounsel is a community and platform where independent attorneys practice alongside one another, share expertise, and build thriving practices. Links: https://heycounsel.com https://www.linkedin.com/in/brianscherer1/

    56 min
  8. Building the Law Firm of the Future: Joe Green on Innovation, Leadership, and Career Pivots

    JAN 15

    Building the Law Firm of the Future: Joe Green on Innovation, Leadership, and Career Pivots

    In this episode of This Legal Life, Ben Chiriboga sits down with Joe Green, Chief Innovation Officer at Gunderson Dettmer, to explore how law firms are evolving — and what it takes to lead that change from the inside. Joe traces his journey from practicing corporate law through legal tech experimentation and his time at Practical Law at Thomson Reuters. He shares how stepping outside the traditional partner track allowed him to develop the skills and confidence needed to return to Gunderson and help shape a future-ready firm. The conversation offers timely insight for law firm leaders thinking seriously about innovation, talent, and long-term strategy. About Our Guest: Joe Green is the Chief Innovation Officer of Gunderson Dettmer. In this role, he leads Gunderson’s innovation strategy to transform the firm's service delivery platform and business model, with a focus on providing a more modern experience for clients, lawyers and business professionals. He was recognized by Lawdragon as one of the 100 leading AI and legaltech advisors. Joe is a Lecturer in Law at Penn Carey Law, where he teaches a course on startups and venture capital. He has authored dozens of articles on startup-related issues, the business of law, legal technology and the future of the legal industry. He speaks regularly on these topics at industry and academic conferences, law firms and law schools, and his academic work has been cited by SEC commissioners and staff in public speeches and reports. Joe was previously a senior associate at Gunderson and left to join Thomson Reuters as a Senior Legal Editor at Practical Law, the premier online legal know-how service for business lawyers. Joe began his legal career as a securities lawyer with Simpson Thacher in New York. Connect with Joe: LinkedIn: https://www.linkedin.com/in/joegreen1/

    25 min
See All (117)

Ratings & Reviews

5
out of 5
5 Ratings

About

Join host Ben Chiriboga, Chief Growth Officer at Nexl as he interviews guests to get their lessons learned from a life in legal. From overcoming practice silos to fostering collaboration and battling toxic work environments while building strong client relationships -- This Legal Life leaves no stone unturned.

Information