Jack Newton runs Clio with 2,000 employees and over $300 million in annual recurring revenue, yet he describes his CEO role as "a new job every quarter." His secret to sustaining energy seventeen years into building Clio isn't about winning existing markets—it's about creating entirely new categories of software that didn't exist weeks before.

In this episode of Lawyers Who Learn, host David Schnurman sits down with Newton at ClioCon to explore the mindset behind scaling a legal tech unicorn. Newton reveals how humility and continuous learning drive his approach, from seeking mentors among portfolio companies to studying frameworks like Simon Sinek's "The Infinite Game"—which reframes business not as zero-sum competition but as unlimited opportunity creation.

Newton's keynote announcement left 2,500 attendees in stunned silence as he unveiled technology that compresses ten hours of legal work into forty-five minutes. The implications are profound: when automation handles routine tasks at scale, it doesn't eliminate lawyers—it creates massive new market opportunities. Newton draws parallels to LegalZoom, where automated forms generate enormous demand for attorney services, demonstrating how giving away commoditized work for free actually expands the entire legal market.

Newton balances this demanding role by being fully present at home with his wife of twenty-two years and three teenage children, finding renewal in Vancouver's natural beauty. His philosophy challenges lawyers to stop jealously guarding routine work and instead embrace AI as a competitive advantage that could quadruple market size—transforming how legal professionals deliver value in an automated world.

#77 Playing the Infinite Game in Legal Tech's AI Revolution