Chuck Eesley
Blog - ai
    ARR Is Not the Problem. The Institutional Vacuum Around It Is.

    ARR Is Not the Problem. The Institutional Vacuum Around It Is.
    SUBSTACK

    On the Cluely confession, AI-era revenue metrics, and what would actually fix the measurement problem in private markets.

    entrepreneurshipventure capitalai
    The Operator Was the Last to Know

    The Operator Was the Last to Know
    SUBSTACK

    On what the July 2026 Hugging Face incident, Bainbridge's 1983 paper on the ironies of automation, and our 2024 Nature audit of programmatic advertising suggest about governing AI agents.

    aigovernanceautomation

    Proxy-Expert Practice: Teaching a Skill You Can Only Learn From an Expert
    NEWS

    A Stanford Accelerator for Learning grant funds work on expertise-gated skills — the ones you can only practice against someone who knows enough to refuse a shallow answer.

    entrepreneurshipaiteachingresearch
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Chuck Eesley
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