Gregor Watson

Gregor Watson I’m a founder and operator focused on building scalable, technology-enabled platforms in asset-heavy and operationally complex industries. I’m the co-founder and CEO of Chisel Industries, a holding company acquiring and modernizing skilled-trade and home-service businesses across the U.S., including roofing, HVAC, plumbing, and pools. I apply data, process discipline, and AI to improve unit economics, professionalize operations, and create durable enterprise value in fragmented local markets. I also co-founded 1Sharpe Capital, a San Francisco–based investment firm that has invested over $15B across real estate credit, private equity, and venture capital strategies. Across cycles, my work has centered on identifying overlooked opportunities and pairing them with operational rigor and technology to drive durable, risk-adjusted returns. Previously, I founded 643 Capital Management and co-founded Roofstock. Collectively, these platforms participated in the acquisition, financing, and operation of 20,000+ single-family homes nationwide, providing deep experience at scale. I’ve also co-founded Vellum, an AI-powered reinsurance platform, and Dwell Finance, a single-family rental lender la

Career