This Legal Life: Lessons Learned from a Life in Legal

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 perf...

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 tra...

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 a...

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 d...

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 leg...

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 h...

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 mob...

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 lon...

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...

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 traditi...

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 ma...

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...

In this episode of This Legal Life , host Ben Chiriboga sits down with Tara Young , General Counsel of Spearmint Energy , as she walks us through her remarkable career from a 2008 layoff to navigating private equity pressures and ultimately finding her place as a strategic leader in the fast-changing energy sector. Tara shares how mentors, executive coaching, and learning to be “comfortable being...

In this episode of This Legal Life , host Ben Chiriboga welcomes Tom Martin , founder of LawDroid and co-founder of Vancouver Legal Hackers , for a thoughtful discussion about community and innovation in the legal industry. Tom shares his journey from East Los Angeles to becoming a builder of legal communities, reflecting on the moments that shaped his commitment to connection and collaboration. T...

In this episode of This Legal Life , host Ben Chiriboga sits down with Matthew Korn , Partner at Fisher Phillips and founder of Dad, Esq . , to explore the real meaning of success in today’s legal world. From his first job at McDonald’s to navigating layoffs, in-house roles, and the partnership track, Matt shares an honest account of burnout, resilience, and rediscovering purpose as both a lawyer...

In this episode of This Legal Life , Ben Chiriboga speaks with Charlotte Smith , a UK lawyer turned legal tech founder and executive coach , about the courage it takes to start over. After moving from London to California, Charlotte faced an identity crisis that forced her to redefine success and rediscover her purpose. Through resilience, coaching, and curiosity, she rebuilt her confidence — prov...

In this episode of This Legal Life , Ben Chiriboga speaks with Liz Smith , former legal headhunter and now Head of Talent at Bamboo , about her powerful career transformation and how she’s challenging the traditional model of legal recruitment. After 20 years in the industry, Liz followed her inner voice and made a bold pivot—moving from transactional placements to helping lawyers reimagine their...

In this episode of This Legal Life , Ben Chiriboga sits down with Sarah Cottrell — former BigLaw lawyer turned career coach and founder of The Former Lawyer Podcast . Together, they explore the courage it takes to step away from prestige, perfectionism, and external validation to rediscover what truly matters. Sarah shares her journey through burnout, anxiety, and uncertainty — and why true clarit...

In this deeply reflective episode, Ben Chiriboga sits down with Tony Albrecht , former insurance defense lawyer turned Co-Founder and Creative Director of CONTENDER , to explore how recovery, reinvention, and creativity can redefine success in law. From hitting rock bottom in Guam to helping mission-driven lawyers find their authentic voices on LinkedIn, Tony shares how embracing fear, storytellin...

In this episode of This Legal Life , host Ben Chiriboga sits down with Patrick Patino —attorney, coach, and host of The Newfangled Lawyer Podcast —to discuss what it means to practice law on your own terms. From a poet-turned-lawyer to a founder challenging conventional firm models, Patrick shares how authenticity, creativity, and presence shaped his journey. He reflects on failure, reinvention, a...

In this episode of This Legal Life , Ben Chiriboga sits down with Chad Main , founder of Percipient and host of the Technically Legal podcast , to unpack his journey from commercial litigator to legal tech entrepreneur. Chad shares lessons from building Percipient as an alternative legal service provider, including the persistence and risk-taking required to launch and grow a business in the legal...

Voice is more than sound — it's a leadership tool . In this episode of This Legal Life , Ben Chiriboga sits down with David Pope to explore his journey from BBC studios to coaching law firm partners across Asia and the Middle East. With decades of audio expertise and 30,000 hours in the studio, David now helps lawyers master their vocal presence, command gravitas, and build confidence from the ins...

In this episode of This Legal Life , Guy Alvarez —Founder of Alvarez AI Advisors and former Good2bSocial CEO—joins Ben Chiriboga for a candid conversation about bold reinvention and the evolving role of technology in legal practice. From building one of the first law firm websites in the ’90s, to pioneering digital legal marketing, to now guiding firms through AI-powered growth, Guy reflects on th...

What if legal innovation starts within? In this episode of This Legal Life , Hannele Korhonen joins Ben Chiriboga to share her extraordinary journey from in-house counsel to legal entrepreneur, coach, and PhD researcher in intuition. Through design thinking, radical self-inquiry, and soul-level leadership, Hannele offers a new vision for what legal careers—and legal change—can look like when we st...

In this episode of This Legal Life , Gavin Sharpe —former lawyer, legal recruiter, and now executive coach in Monaco—joins host Ben Chiriboga to share how a personal identity reckoning led him to leave behind external success and embrace his “original child.” From scaling a global business to launching a purpose-driven coaching practice, Gavin discusses the deep work required to lead without the m...