Lessons from Investing Through Bubble Regimes with Andy Constan

First Principles with Andy Constan launches with a deep dive into market bubbles, AI, semiconductor stocks, and the financial conditions that can turn powerful technological change into a dangerous investment regime. Andy explains how bubbles form, why they are almost impossible to time, how today’s AI boom compares to past episodes like 1987, the dot-com bubble, housing, and the bond bubble, and what investors should watch as expectations, financing, and FOMO build.Andy Constan on Xhttps://x.com/dampedspringDamped Spring Advisorshttps://dampedspring.com/Topics covered:Why bubbles are easy to identify in hindsight but nearly impossible to define in real timeThe difference between an expensive market and a true bubble regimeHow new technologies, easy money, regulation, and exogenous shocks can create bubble conditionsWhy AI may rhyme with the internet boom without being an exact repeatThe role of ChatGPT, Microsoft’s OpenAI investment, and semiconductor earnings expectationsWhat the 1987 crash, Japan, housing, bonds, and dot-com bubble can teach investors todayWhy human nature, FOMO, and “keeping up with the Joneses” make bubbles so powerfulHow the late-1990s Fed response to Long-Term Capital Management helped fuel the final phase of the tech bubbleWhy tech’s current size in the economy and market may limit how far the AI boom can growHow AI capex, hyperscaler spending, buybacks, debt issuance, and IPO supply could determine what happens nextTimestamps:00:00 Intro and the challenge of identifying bubbles04:32 Expensive markets vs true bubble regimes09:57 The five bubble episodes Andy compares to today14:35 Root conditions, escalation events, and the peaking phase19:20 Why the 1987 crash may also have been a bubble24:25 The late-1990s setup and the Netscape Navigator moment28:00 Crisis analogs, easy financial conditions, and today’s AI parallels32:20 Long-Term Capital Management and rocket fuel for the tech bubble36:11 Why tech’s market share matters more today than in the 1990s43:18 Policy mistakes, subsidies, and how governments feed bubbles47:42 Semiconductor earnings expectations and valuation risk53:45 The AI capex chain and where the money has to come from58:42 IPOs, corporate debt, and the financing risk behind the AI boom01:02:27 What investors should do differently in a bubble regime