How I built an AI chief of staff for $25 a day

For 20 years, I built my career on the business side of startups: sales, marketing, customer success, operations—areas where I never needed to learn coding or build something myself. That changed this year. My CEO role grew beyond my domain of expertise to span the company’s full operations, and I needed a way to keep up. After using Claude for almost a year, I started with Claude Code and realized I could replace the traditional functions of a human chief of staff with an AI solution. I built my own agent, turning memory and previous sessions into durable skills that help me gather intelligence across the business, connect dots I couldn’t see, and free me up for the decisions only I could make. Within the first week, it was already handling roughly half the workload of a full-time chief of staff, running meeting prep, gathering company updates, and drafting strategy memos. A few months later, I now use it daily, and it costs no more than $25 in tokens on a given day. That’s less than 5% of what a full-time hire would cost. It’s taken quite a bit of iteration to get there. Agents have limits, and I learned that the hard way. Early on, I asked for an account summary ahead of a cust…