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

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.

“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.

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.

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.

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 [http://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