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On with Kara Swisher

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On with Kara Swisher

On with Kara Swisher · Feb 26, 2026

Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley

Career passion vs. economic security trade-off Regulatory capture in tech and venture capital AI disruption and workforce reskilling Silicon Valley's political alignment with Trump administration Peer networks and mentorship as career accelerators