My second conversation with Christina Cacioppo (@christinacaci), Vanta's cofounder and CEO. Charlie Songhurst says the best returns come from companies that are highly boring and highly complex, because fewer founders want to build them. Vanta is one of those companies. When we first talked five years ago, Christina told me about building the first version of Vanta in Excel. Since then she has turned it into the category leader in security compliance. Now she is rebuilding it around AI. We discuss: - Why great software businesses got cheap - Why Vanta eats the cost of AI instead of marking it up - Why comp for top people is up 10X in five years - What is over/under hyped in AI - How AI attackers are changing security - Vanta marketing + billboards - Building trust in an era of low trust Enjoy! TIMESTAMPS 0:00 Intro 4:17 Surviving the SaaSpocalypse 9:40 The AI Pricing Trap 16:17 Rebuilding Software for AI 22:43 Silicon Valley's Talent Wars 31:57 What's Overhyped in AI 38:39 Security at Machine Speed 47:16 Reinventing Software 55:37 The Billboard War 60:38 Rebuilding Trust in Technology