HeyJaredThis Legal Life: Lessons Learned from a Life in Legal
Join host Ben Chiriboga, Chief Growth Officer at Nexl as he interviews guests to get their lessons learned from a life in legal.
- Indexed episodes, last 90 days
- 4
- Latest publication
- Aug 18, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 14, 2026
Latest episodes
Authorize yourself early: Quentin Solt on four decades of legal innovation and the age of abundance (opens the original)
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Quentin Solt was preaching commoditization to law firms in 1997, decades before Harvey and legal AI made it fashionable. In this episode of This Legal Life, Ben Chiriboga sits down with the veteran UK solicitor and writer behind the Facts Are Friends Substack to trace a remarkable career: from typing out Eliza on a BBC Micro as a boy, to running deal negotiations live on a laptop when opposing counsel could barely believe it, to founding a venture fund that once held patents on intelligent agent
The artist, the lawyer, and the founder: three acts of Anna Guo (opens the original)
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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 c
From 0.3 hours to recurring revenue: Mathew Kerbis on subscription legal services (opens the original)
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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
Building What Matters: Horace Wu on creation, AI, and going against the crowd (opens the original)
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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 t
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