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Venture with Grace

Caroline Duffy, Partner Cowboy Ventures: Investing in AI & Foundational Tech

24 Sep 2025

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Caroline Duffy is a Partner at Cowboy Ventures. She thrives partnering with ambitious builders reimagining existing categories or creating entirely new ones. She focuses on B2B software and AI, with a particular passion for teams modernizing overlooked, unglamorous industries burdened by outdated tech stacks. It’s never too early to reach out - she’s excited to collaborate with founders from idea inception onwards. Before Cowboy, Caroline was at Construct Capital, where she led investments in a range of technologies transforming real-world industries including supply chain and logistics, manufacturing, and critical infrastructure. Prior, she was building and investing in AI companies with AI pioneer Andrew Ng. Before becoming an investor, Caroline was a management consultant and started her career as an AI researcher at Harvard. Caroline holds an MBA from Stanford and a BA from Dartmouth. She works closely with organizations advancing education opportunities for women and girls in AI and serves on the Board of Access Institute, which increases access to mental health services for under-resourced communities in SF. Topics: Why target the most 'boring' companies everyone else ignoresMost common mistakes B2B AI startups making when targeting legacy industriesFintech, healthcare, logistics: Why these 3 verticals are ripe for AI disruption

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