Closed Transaction: The CTO's Perspective

Doug Hathaway is the Co-founder and CTO/CPO of LawFi, a legal fintech platform that helps consumers and small businesses finance legal services. With over 20 years of experience in software engineering, he co-founded DadeSystems, a SaaS platform for Fortune 500 enterprises and top banks, which was acquired by Versapay, where he led its Cash Application platform. In this episode… The journey from startup to profitable exit is rarely a straight line, and the twists often reveal the most valuable lessons. How did a decade of persistence, pivots, and near-misses lead to the right acquisition at the right time? Co-founder and CTO/CPO of LawFi, Doug Hathaway, discusses building and selling his company after 11 years of growth. With host Todd Taskey, Doug talks about navigating investor influence, managing shifting board dynamics, and handling the emotional swings of a deal that nearly collapsed before closing.