Bill Gurley says that right now, the worst thing you can do for your career is play it safe | TechCrunch

TechCrunch

by Connie Loizos

February 22, 2026

AI-Generated Deep Dive Summary

Bill Gurley, a renowned venture capitalist and general partner at Benchmark, has shifted his focus from investing in startups like Uber and Zillow to pursuing a new mission: writing a book, launching a foundation, and establishing a policy institute. His latest work, *Runnin’ Down a Dream*, argues that pursuing passion is not just romanticized career advice but a competitive strategy, especially as artificial intelligence reshapes the workforce. Gurley challenges the conventional wisdom of "playing it safe" in one's career, emphasizing the importance of taking risks and exploring passions to avoid long-term regrets. Gurley’s research reveals that roughly 60% of people would change their career paths if they could start over, a statistic that shocked him due to its universality across different demographics. He draws parallels to Daniel Pink’s concept of "regrets of inaction," where individuals often feel more burdened by what they didn’t try than by the mistakes they made. This realization inspired Gurley to focus on helping others break free from the constraints of traditional career advice, particularly for those struggling financially. His foundation, the Running Down a Dream Foundation, aims to award 100 grants of $5,000 annually to individuals who

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Originally published on TechCrunch on 2/22/2026