James is the co-founder and Managing Partner of Gutter Capital, with one of the more unusual backgrounds in venture. He holds a master's degree in Computer Science focused on AI, co-founded and served as CTO of a vertical SaaS company, and spent nearly a decade as a professional gambler, building proprietary software and systems that made him one of the biggest winners on DraftKings and FanDuel before retiring in 2020. He has invested in more than 100 early-stage companies as an angel investor.