managing the risks of societal collapse

what's next - part 1

Work-email refresh anxiety was the first thing to disappear. Then, the night sweats. After years leading the team responsible for conceptualizing and coordinating the cyber activities of the U.S. government, on the National Security Council Staff, I had become accustomed to the foreboding morning-email-check: North Korean spear-phishing critical infrastructure companies! A global Russian ransomware campaign that has locked down thousands of hospitals! Hackers associated with the Chinese government are conducting global intellectual property theft campaigns! If not woken by the Situation Room, I would tap out a quick email with the latest information I could collect from various resources (human or digital), then roll into work. “What’s the best part of your job?” people would ask. Jokingly, I would answer: “My [White House] parking spot.”

For nearly a year leading up to my departure I had been thinking about what to do next. Distilling everything I had learned on the NSC Staff, as an active duty military officer with multiple deployments to Iraq, at a YCombinator-backed cybersecurity startup, and even founding a few small businesses, I wanted to start another company. I huddled with friends and colleagues, and eventually came to an initial thesis: why not build a boutique insurance practice that specializes in risk mitigation for companies with significant industrial control systems (ICS) infrastructures?

It sounded great, but the idea only lasted for a few weeks. As we say in the military, “no plan survives first contact.”