James Everingham, former head of engineering at Instagram, shares his unconventional career journey from being kicked out of college and getting an FBI visit as a teenage hacker, to working at pre-IPO Netscape during the browser wars, leading Instagram Stories development, heading Meta's Libra/Novi cryptocurrency project, and now founding Guild, an AI agent management platform. Key lessons include: building relationships over networking, why small focused teams outperform large ones, the difference between CTO and VP of Engineering roles, thinking about your career like an investment portfolio, and how failure often leads to better opportunities.
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