Ignite VC: Shaping the Future of Startups and Venture Capital with Kirby Winfield of Ascend VC | Ep41

Ignite: Conversations on Startups, Venture Capital, Tech, Future, and Society

In this episode of the Ignite podcast, Kirby Winfield, founding general partner of Ascend VC, shares his journey from a marketing executive in early internet startups to a seasoned venture capitalist. Kirby's narrative begins with his roots in Seattle, detailing his initial foray into the startup world with GoToNet and his subsequent ventures, including Marchex and Dwellable, highlighting the lessons learned from each. He candidly discusses the challenges and personal sacrifices involved in the startup ecosystem, such as the impact on his health and family life, which led to a significant personal and professional recalibration. Kirby's transition to venture capital was marked by a desire to leverage his extensive experience to guide new founders. His story reflects a deep understanding of the intricacies of building and scaling companies, as well as the importance of adapting to the ever-changing tech landscape. The discussion also delves into his investment philosophy, emphasizing the value of engaging with founders and the dynamic nature of the venture capital industry. Kirby’s insights into the Seattle venture scene, his strategic approach to investment, and his reflections on personal growth and work-life balance provide valuable lessons for entrepreneurs and investors alike. His journey from a startup executive to a venture capitalist illustrates the evolution of a career driven by passion, resilience, and a continuous quest for learning and impact. Outline 00:00 Introduction and Background 00:43 Early Career and Startups 02:09 Venture Capital and Selling Companies 03:00 Life Reset and Self-Reflection 05:09 Discovering Passion for Working with Founders 07:34 Realizing the Importance of Personal Fulfillment 09:20 Transitioning to Angel Investing 11:58 Raising a Venture Capital Fund 13:38 Portfolio Construction and Investing in Seattle 15:20 Diaspora of Unicorn Creation 17:32 Increasing Volume of Swings for Outlier Success 19:26 Finding Alignment in Work and Skills 20:59 Outsourcing Tasks and Focusing on Strengths 22:22 Pursuing Childhood Dreams 24:11 Shared Love for Hip Hop 28:14 Overcoming Unhealthy Habits 32:35 Finding Balance Between Work and Family 39:33 Ideal Startup Profile 45:06 Trends in AI Investing