Adrian Sanabria sits down with Hadar Krasner, Co-Founder and CPO of Bold Security, for a dive into the history of data security and why it has always been such a hard problem to solve. Hadar tells the Bold origin story: the founders ran a cloud data security company, kept getting asked what happens once data leaves the cloud, and found there was no real answer for the endpoint. From there the conversation turns to why DLP has disappointed a generation of security teams, with Hadar naming noise, configuration complexity, and the missing piece underneath both of them, context. Adrian backs it up from his own assessor years and names the failure mode he sees across dead security categories: the customization tax, or how much work the customer has to do to make the product work at all. Thirty minutes in, they had barely scratched the surface, and a return visit is already on the table.