James Gorman helped wire the early internet, stood in a New York data center turning screwdrivers in the morning and pitched bankers in the boardroom that afternoon, and once told GE's leadership they could own the internet for 30 million dollars. They passed. Now he runs Hard to Hack, an advisory practice that builds security programs for small and mid-sized companies, then trains them up and leaves. He calls his clients graduates. Sam sat down with him to talk cybersecurity, the dot com crash, Y2K, CrowdStrike, AI, and why your network really is your net worth.