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Showing posts from November, 2026

The Solopreneur AI Team Illusion: Four Colleagues, Eight Jobs, One Neck in the Noose

The easy story goes like this: hand one experienced person a few AI agents and she becomes a company. As we discussed in our recent CRMKonvo with Kristy Tupper , founder of OCSI and a business, product and AI strategy advisor, the capacity half of that story holds up. The company half does not. What Kristy has built is disciplined, and the discipline shows why it is not a company. TL;DR If you want to watch the full CRMKonvo, please go ahead here (optimized for smartphones) or here (optimized for tablets/computers). Else, be my guest and continue to read. Or do both … A Division of Labor Is Not a Delegation of Judgment Kristy's roster reads like an org chart. Chad (ChatGPT) runs marketing. Claude is research assistant, junior business analyst and admin. Phil (Perplexity) is the deep research department. Gemma (Gemini) is the graphics department and the second reader, provided she gets a very long prompt. Doing all of this without AI, Kristy says, would take five or six peo...