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In this OODAcast, Chris Wysopal, co-founder of Veracode, reflects on his journey from hacker to cybersecurity pioneer, emphasizing the evolution from vulnerability research to comprehensive application risk management in the age of AI-driven development. He highlights the dual-edged impact of generative AI—boosting development speed while increasing security risks—and advocates for embedding automated security tools into the software lifecycle. Wysopal also draws parallels between successful hackers and entrepreneurs, noting their shared traits of creativity, grit, and persistence.