This Legal Life: Lessons Learned from a Life in Legal

Ben Chiriboga

Join host Ben Chiriboga as he interviews guests to get their lessons learned from a life in legal.

  1. Jul 29

    From 0.3 hours to recurring revenue: Mathew Kerbis on subscription legal services

    What happens when a lawyer logs 0.3 hours for a phone call with his own dad? For Mathew Kerbis, it sparked a question that would reshape his entire career: is there a better way to practice law? In this episode of This Legal Life, Ben Chiriboga sits down with the attorney known across the industry as the Subscription Attorney to trace his journey from billing hours at a litigation firm to founding a practice built entirely on recurring fixed fees. Mathew shares the pricing and packaging lessons that doubled his business two years running, why retention matters more than acquisition in a subscription model, and his advice for lawyers ready to burn the boats and start their own firm. He also previews Practi, his new software company helping solo and small firm lawyers build recurring revenue of their own.

    From 0.3 hours to recurring revenue: Mathew Kerbis on subscription legal services

  2. Jul 14

    Building What Matters: Horace Wu on creation, AI, and going against the crowd

    What does it take to build something meaningful in an industry obsessed with the next big thing? In this episode of This Legal Life, Ben Chiriboga sits down with Horace Wu, founder of Cynthia, to explore the journey from corporate lawyer to legal tech entrepreneur. Horace reflects on leaving private practice, the lessons learned from an early startup that was eclipsed by Google and Facebook, and why he believes the best founders solve real problems instead of following market trends. Together they unpack the evolution of legal AI, why today's conversation has become overly focused on products instead of problems, and where Horace believes the next wave of innovation will come from. Along the way, they discuss bootstrapping, creativity, listening to customers, and why building something truly useful often means going against the crowd. Whether you're a lawyer, founder, or simply curious about the future of AI, this conversation is a thoughtful reminder that lasting innovation starts by listening before you build.

    Building What Matters: Horace Wu on creation, AI, and going against the crowd

  3. May 21

    “Just Go for It”: The Mindset Behind Modern Legal Business Development with Robin van Keeken

    Legal business development often stays stuck in planning mode—but Robin van Keken took a different approach: just start. In this episode, he shares how a “try it and see” mentality helped him carve out a new kind of role at BUREN, one focused on connection, experimentation, and results. From building communities to creating opportunities out of conversations, this is a story about action over perfection—and why that matters more than ever in legal.

    “Just Go for It”: The Mindset Behind Modern Legal Business Development with Robin van Keeken

  4. May 14

    When the Ground Shifts: Helping Lawyers Trust Themselves Again

    In this deeply reflective episode of This Legal Life, Ben Chiriboga speaks with Elena Deutsch, founder of WILL (Women Interested in Leaving Law), about what it really feels like when your career no longer fits. Drawing from her own journey and years of coaching women lawyers, Elena explores the moment when “something isn’t right,” and how that internal signal can become the starting point for transformation. From burnout and anxiety to clarity and agency, this conversation is a powerful reminder that change isn’t failure—it’s information.

    When the Ground Shifts: Helping Lawyers Trust Themselves Again

  5. May 7

    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.

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

  6. 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

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

  7. 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.

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

  8. 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.

    Rethinking the Legal Career Path: Anastasia Boyko on Leadership, Law School, and Reinvention in an AI Era
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Join host Ben Chiriboga as he interviews guests to get their lessons learned from a life in legal.

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