In this episode of Shift AI, Kirby Winfield General Partner at Ascend.vc shares his journey from founding multiple successful startups to becoming a leading AI investor and outlines lessons learned, insights on the Seattle startup ecosystem, and his optimistic yet pragmatic views on generative AI and the future of work. Summary of topics covered: Background and early career: Kirby gained experience as an entrepreneur early in his career through founding multiple companies. Transition to Venture capital: Looking for a new challenge, Kirby leveraged his experience operating startups to co-found Ascend and advise other founders. Investment thesis and framework for evaluating AI opportunities: Kirby evaluates AI opportunities through the lens of whether they present applied or foundational uses of the technology. Portfolio companies: Two of Ascend's portfolio companies applying AI in novel ways are Overland for autonomous vehicles and Clarity for detecting deepfakes. Incumbent tech companies and AI: Kirby believes startups should focus on radically improving problems rather than competing directly with incumbent features to succeed against large companies. Seattle's potential as a tech hub: Seattle is poised to become a major tech hub to rival Silicon Valley as its startup ecosystem matures and attracts more founders and engineers. Mentors and influences: Guidance from mentors like John Keister and Oren Etzioni helped Kirby navigate different stages of his career in startups and investing. Future of work and AI: Kirby is optimistic AI could automate drudgery and unleash human potential but acknowledges change will be gradual and new challenges will emerge. Connect with Kirby Winfield ⁠Twitter⁠ ⁠LinkedIn⁠ Connect with Boaz Ashkenazy ⁠Twitter⁠ ⁠LinkedIn⁠ Email: ⁠[email protected]⁠ --- Send in a voice message: https://podcasters.spotify.com/pod/show/shift-ai/message