This week's major theme: AI is disrupting the enterprise software model and the build vs. buy calculus with it. PE firms that paid 20x+ revenue multiples for niche software companies are stuck with leveraged portfolios losing value. $2 trillion wiped from software market cap. The big infrastructure players (Salesforce, Oracle, ServiceNow) will survive, but the mid-market squeeze is real.
Also in this issue:
- The Wire — 96% of companies miss AI ROI by spending 80% on tech and 20% on people instead of the reverse. Mercor's $2B AI agents failed at real consulting work. Marketing teams pivoting to optimize for ChatGPT, not just Google. And Toto (yes, the toilet company) is an AI stock.
- Quanta Lab — The token bill is the new cloud bill: hitting Anthropic Max limits within days, testing local model offloading. Plus why AI chatbots surfacing your old content is a governance problem nobody owns yet.
- After Hours — Catching up with the 28 Days/Weeks/Years Later series before The Bone Temple drops.