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Chris Castaldo has a fascinating career in cybersecurity. A U.S. army veteran who dabbled in tech during the early 2000s dot-com boom before settling on security, Castaldo is now CISO at Crossbeam and a decision-maker with a bird's eye view into how the should be protected.

Castaldo joins Ryan on the show to talk about his new book on securing the startup, why he's the rare CISO that loves security vendor briefings and demos, and his vision of the CISO's top priorities.