This Legal Life: Lessons Learned from a Life in Legal

por Ben Chiriboga

Temporada 4

The artist, the lawyer, and the founder: three acts of Anna Guo

nna Guo introduces herself as a wannabe artist who happens to be a lawyer, and that tension runs through her entire story. In this episode of This Legal Life, Ben Chiriboga follows her winding path from a finance degree in China to Duke Law and Big Law in New York, then to Singapore, where she found a startup co-founder on Tinder and built an experiential events company that pivoted into virtual team building for Microsoft and Google during COVID. After selling that business, she drew her next career move out of a hat, went in-house at Alipay and Google, and got early access to GPT when it could barely string a sentence together. Today she runs Legal Benchmarks, the independent platform measuring how AI models and systems perform on legal work. Anna and Ben dig into why benchmarking matters for both buyers and builders, the case for posting things that mean something to you, and how to maximize your surface area for getting lucky.

T4 · E13

10 ago 2026

48:36

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.

T4 · E12

29 jul 2026

46:01

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.

T4 · E11

14 jul 2026

54:22

“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.

T4 · E10

21 may 2026

45:19

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.

T4 · E9

14 may 2026

38:40

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.

T4 · E8

7 may 2026

44:34

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

T4 · E7

30 abr 2026

53:16

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.

T4 · E6

1 abr 2026

35:45

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.

T4 · E5

25 mar 2026

48:15

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.

T4 · E4

18 mar 2026

35:25

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