In this episode of "The Free Lawyer," host Gary interviews Ben Chiriboga, a former maritime litigator turned legal tech executive and co-founder of Nexl. Ben shares his journey from traditional law to legal technology, discussing the challenges of overcoming fear and imposter syndrome. Together, they explore the importance of authenticity, redefining success beyond financial gain, and building meaningful client relationships. The conversation highlights how technology, personal growth, and connection can help lawyers find fulfillment and adapt to the evolving legal industry.Ben is a former practicing lawyer turned legal tech executive. He is the founding team member of Nexl, one of the fastest growing companies in APAC (Financial Times). He is also the host of This Legal Life, where he interviews legal professionals on how they built their careers.

Ben’s Legal Career and Hero’s Journey (00:02:24)

Maritime Law Practice (00:03:06)

Stirring for Change and Discovery of Legal Tech (00:05:12)

Transition to Legal Tech and Nexl (00:07:16)

What is Nexl? (00:09:13) E

How Nexl Works (00:10:39)

AI, Automation, and Data Accuracy (00:12:26)

First-Party vs. Third-Party Data (00:13:30) C

Transition Challenges: Imposter Syndrome (00:15:55)

Transferable Skills and Leadership (00:16:28)

Leadership Traits and Inner Work (00:20:31)

Fear, Authenticity, and Lawyer Challenges (00:22:38)

Managing Uncertainty and Mindset (00:23:51)

Traits of Fulfilled Lawyers (00:26:14)

Redefining Success and the Hero’s Journey (00:29:18)

Values-Based Practice and Intentionality (00:31:45)

Trends in Legal Careers and Fulfillment (00:32:56)

Connection and Combating Isolation (00:36:26)

Advice to Younger Self: Risk and Instinct (00:37:15)

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