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Noah Waisberg left Weil Gotshal without a company, without a plan, and without knowing if the technology would work. For two and a half years, the AI kept failing. There was zero revenue, a newborn at home, and mounting financial stress. Then his co-founder finally cracked it. They bootstrapped to 100 employees before raising $50 million, then pulled off one of the most creative exits in legal tech by selling while keeping 30 people and launching a new company as a spin-out. In this episode of Lawyers Who Learn, host David Schnurman explores Noah's philosophy that you become your best self through challenge, not comfort. As a junior associate at Weil, Noah watched lawyers bill hundreds of dollars an hour for repetitive contract review work they hated and weren't particularly good at. He saw an opportunity for disruption even before legal tech was a defined category. Noah shares the brutal reality of those early years: meeting four computer science PhDs at a Starbucks, choosing his co-founder, then watching month after month as their AI simply didn't work. His candor about going from a well-paying BigLaw job to financial stress with a newborn offers a rare glimpse into what bootstrapping actually costs. The conversation reveals how Noah became an expert at selling efficiency technology to hourly billing lawyers, navigating the paradox that making lawyers faster doesn't automatically reduce client bills. Whether discussing his children's book on AI, his Wall Street Journal bestselling book, or his creative deal structure, Noah proves that challenging yourself and being willing to face years of uncertainty can lead to outcomes you never imagined. 00:00 Introduction and Guest Welcome 00:50 Noah's Career Journey and Achievements 01:45 Kira Systems and Legal AI 03:50 Challenges and Growth in Legal Tech 08:24 The Future of Legal Tech and AI 12:41 Starting a Legal Tech Business 16:13 Building Kira Systems 21:42 Scaling and Success of Kira Systems 24:31 Efficiency in Legal Tech 25:48 Demonstrating Value and Realization Rates in Law Firms 27:38 The Unexpected Sale of the Business 29:01 The Spin-Out Deal and Its Aftermath 36:13 Writing and Promoting an AI Children's Book 41:39 Health and Wellness as an Entrepreneur 45:27 Recommended Reads for Entrepreneurs Links • Connect with David Schnurman (Host) - / davidschnurman Connect with Noah Waisberg (Guest) - / noahwaisberg Visit Our Website: https://www.lawline.com/podcast/lawye... Follow Lawyers Who Learn: https://linktr.ee/lawyerswholearn Lawline: https://www.lawline.com/ More About Lawyers Who Learn • Exploring how lifelong learning empowers attorneys' growth. Tune in for inspiring journeys and insights to elevate your legal career!