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Career passion vs. economic security trade-off

Discussed in 1 analyzed podcast episode across 1 show

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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

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 College admissions pressure and resume arms race