An Interview with Bill Gurley About Runnin’ Down a Dream

Stratechery

by Ben Thompson

February 26, 2026

AI-Generated Deep Dive Summary

Bill Gurley, the renowned retired venture capitalist, shares his insights in a recent interview about his new book *Runnin’ Down a Dream*, which focuses on building a career that aligns with one's passions and values. Known for his early investment in Uber, Gurley discusses the challenges of scaling innovative companies, the evolving landscape of venture capital, and the importance of purpose-driven work. His reflections offer valuable lessons for entrepreneurs and professionals seeking to create meaningful careers in tech. Gurley emphasizes the significance of passion in professional success, drawing parallels between his experiences at Amazon and as a VC. He highlights how aligning personal values with career choices can lead to greater fulfillment and sustained motivation. Gurley also delves into the state of venture capital, addressing changes in funding models and the rise of new players challenging traditional norms. His perspective provides a comprehensive view of the industry's dynamics and future trends. The interview underscores the importance of resilience and adaptability in both personal and professional growth. Gurley’s insights on Uber, particularly its early days,

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Originally published on Stratechery on 2/26/2026