Shawn Chan contrasts a polished AI demo with an investment memo that must withstand questions before money moves. Fluency and confidence are not enough when source documents disagree, numbers change across pages and readers need to trace each claim back to evidence.
Chan identifies six recurring trust failures: treating sources as equally reliable, inconsistent figures, hidden contradictions, guesses presented as facts, claims without quick source access and decisions without a responsible human. He illustrates the risks with examples from finance and other high-stakes uses, but the individual incidents and figures are not independently verified by this review.
Chan proposes sentence-level source links with source quality, a visible distinction between facts and estimates, automatic number checks, surfaced conflicts and a logged human approval gate. He says founders pitching an AI finance product face similar scrutiny because an investor will turn their deck into an internal decision memo. The transcript ends before the four further investor lessons he introduces, so none are inferred here.
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