Josh Diamond is the General Partner and founder of Walkabout Ventures. See sector focus, stage focus and contact routes.
Josh Diamond is the General Partner and founder of Walkabout Ventures, a Los Angeles-based seed fund he launched in 2019 after serving as a Principal at Clocktower Technology Ventures and earning a JD from UCLA School of Law. His investment thesis targets early-stage financial services and fintech startups, specifically focusing on B2B “picks-and-shovels” infrastructure that modernizes back-office operations for banks and insurers rather than consumer-facing apps. Walkabout typically invests $100,000 to $500,000 per deal and prefers to lead pre-seed and seed rounds. Notable portfolio companies include Advisor.com, which received a $9M led seed round from Walkabout in October 2025, as well as Barker (invested November 2025), Themis, and Functional Finance, where Diamond serves on the board. Diamond’s distinctive point of view centers on filling an underfunded gap in very-early-stage financial services infrastructure, leveraging his legal background to navigate regulated markets. He has not published public writing, but his firm’s thesis explicitly prioritizes technical solutions over consumer fintech.
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