Why 95% of AI Pilots Fail and How to Build a Business You Can Sell, with Ted Wolf

The Operating System Show · Jul 28, 2026 · 30m

Ted Wolf started at IBM in the 1970s, built an IT services company to 650 people with his brother, and sold it to Iron Mountain in 2018. Now he runs GuideWise, helping founders put agentic AI into the machinery of their business without the hype. He also wrote a book, The Intelligent Business Equation, a formula for turning a people dependent company into one you can actually sell. In this conversation Ted and Matt get into what it really feels like to scale to 650 people (and scale back down through four recessions), why most AI pilots fail, and the five moves that make a business…