This Legal Life: Lessons Learned from a Life in Legal

Nexl

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

    1 APR

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

    25 MAR

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

    18 MAR

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

    3 MAR

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

    27 FEB

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

    15 JAN

    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
  7. Starting Over in Law: How Dana McKenna Built a Modern GC Career

    08/12/2025

    Starting Over in Law: How Dana McKenna Built a Modern GC Career

    In this episode of This Legal Life, Ben Chiriboga sits down with Dana McKenna to unpack how a collapsing startup led her to rebuild her legal career from the ground up. Dana openly discusses juggling uncertainty, discovering fractional GC work, and confronting internal barriers like imposter syndrome and people-pleasing. She highlights why today's companies need strategic legal partners who can manage risk, lead proactively, and simplify complexity. An inspiring conversation for lawyers designing a career that fits their strengths—and their life. About Our Guest: Dana McKenna is the Founder of Align General Counsel, a fractional GC practice built on one core belief: high-growth companies deserve legal leadership that operates in true alignment with how their business actually runs. With more than 18 years of legal experience, Dana began her career in BigLaw litigation before moving in-house, where she spent over a decade advising Fortune 5 corporations, mid-sized businesses, and scaling startups. She has served as General Counsel, Chief Legal and People Officer, and trusted advisor to founders, boards, and executive teams—bringing a rare blend of legal strategy, operational insight, and business pragmatism. Dana’s background spans tech, staffing, marketplaces, retail, and consumer brands. She specializes in employment law, California and multi-state compliance, commercial contracting, and litigation strategy. Over her career, she has led organizations through complex restructures, PAGA litigation, high-stakes internal investigations, M&A activity, and evolving regulatory environments. Known for her practical and people-centered approach, Dana focuses on the intersection of legal, HR, and company culture. She partners closely with leadership to deliver guidance that is clear, candid, and designed to keep the business moving forward—without slowing growth or creating unnecessary friction. Connect with Dana: Website: https://www.aligngeneralcounsel.com/ LinkedIn: https://www.linkedin.com/in/danabethmckenna/

    33 min
  8. Soul vs. Toll: Anusia Gillespie on Courage, Career Reinvention & Finding Your Light

    01/12/2025

    Soul vs. Toll: Anusia Gillespie on Courage, Career Reinvention & Finding Your Light

    In this episode of This Legal Life, Ben Chiriboga sits down with Anusia Gillespie, legal tech executive and author of Soul Toll, to explore the inner work behind career reinvention. Anusia shares how meditation, misalignment, and seven roles in ten years shaped her understanding of the “soul toll” we pay in our professional lives. She explains why trusting yourself matters more than mentors when your path is still unpaved, and how her debut novel blends leadership lessons with fantasy storytelling. A thoughtful, powerful conversation for legal professionals navigating change, ambition, and authenticity. About Our Guest: Anusia Gillespie is a lawyer turned novelist and RYT 200 certified yoga instructor whose debut contemporary fantasy, Soul Toll, blends corporate ambition with personal awakening. Her writing is shaped by a career at global law firms, legal tech companies, and Harvard Law School Executive Education, offering a sharp, insider perspective on high performance culture and the personal cost of chasing success. Well known in the legal industry for her insight on leadership and transformation, Anusia now channels those themes into fiction that invites readers to question the lives they have been told to want. In Soul Toll, a high achieving attorney’s search for clarity pulls her into a hidden world, and a battle for something far more meaningful than success. Anusia holds a JD and MBA from Boston College and a BS in Management from Tulane University. She lives north of Boston with her husband, young son, and old dog. https://www.amazon.com/Soul-Toll-Anusia Gillespie/dp/B0FN9PSS2N/ref=tmm_pap_swatch_0 www.anusiagillespie.com https://www.instagram.com/anusiagillespie/ https://www.linkedin.com/in/anusiagillespie/

    38 min
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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.

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