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Paper Napkin Wisdom · Leadership & Entrepreneurship Insights for Founders and Executives

[EON] Hiding in Plain Sight: AI and Software Costs | Paper Napkin Wisdom

Paper Napkin Wisdom · Leadership & Entrepreneurship Insights for Founders and Executives · 2026-06-01 · 25 min

Episode notes

Some of the biggest opportunities in business do not look like opportunities at first. They look like invoices. They look like renewals. They look like software platforms everyone complains about, but nobody questions anymore. That is the tension at the center of Episode 368 of Paper Napkin Wisdom, which is also #39 in the Edge of the Napkin series. In this solo episode, Govindh Jayaraman explores a shift that every proven entrepreneur should be paying attention to now: AI is starting to expose the cost and fragility of expensive enterprise software. Not all of it. Not the mission-critical spine of the business. But the extra layers. The add-ons. The reporting modules. The document tools. The workflow pieces. The customer communication functions. The things that used to cost a lot because, at the time, there was no other way to get them. The Real Question Leaders Should Be Asking The question is not, "Can AI replace my software?" That question is too broad. The better question is: What are we still paying for because five years ago there was no other way to get it? For a proven entrepreneur, that question has weight.

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