In 2022 Jeff McMillan joined Invisible Machines as Head of Firmwide AI at Morgan Stanley—months before ChatGPT rewrote the public conversation. The episode documented an early mover partnering with OpenAI when the work was still curated, cautious, and legally scrutinized.
This article summarizes that first visit. It is not a transcript. For the operational curation story with David Wu, see Curating Knowledge Before RAG; for the 2026 agent-scale checklist, see Knowledge Before Agents.
Before ChatGPT
McMillan described building with OpenAI when the interface was still a controlled experiment—not a consumer phenomenon. Leadership buy-in mattered because payoff was slow and the work was unglamorous: legal and compliance from day one, not bolted on after a pilot embarrassed someone on CNBC.
Curated Content, Not Volume
The through-line even then was garbage in, garbage out. Financial services could not afford a document dump into a model and hope for the best. Content had to be selected, governed, and maintained—the same lesson McMillan would later sharpen with Wu when vector stores became fashionable.
Prompt Engineering as New Literacy
Before “agentic AI” was vocabulary, advisors needed to learn how to ask. McMillan framed prompt craft as a literacy problem for knowledge workers—not a developer-only skill. That seed grows into the 2024 prompt-coaching operations and the 2026 insistence on explicit iteration and golden-source testing.
Hackathons and Young Problem Solvers
The episode celebrated internal hackathons and young creative problem solvers who could bridge business pain and model capability—provided someone senior protected the foundation work from being dismissed as “just knowledge management.”
Why It Still Matters
Read alongside McMillan’s later visits, S2E22 is the early-mover chapter: partnership appetite, compliance-first delivery, curated corpora, and the intuition that the model is not the product. By 2026 the stakes are agent count and accountability—but the stack he describes in the latest episode was already implicit in the first hour.