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

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

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

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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. A business that has been built over 8, 12, or 20 years has accumulated decisions. Some were brilliant at the time. Some were necessary at the time. Some became habits. Software often falls into that last category. A system gets bought. The team adapts. The business grows around it. The contract renews. The pain becomes normal. Then one day the business is paying thousands, sometimes tens of thousands, for a platform that no longer creates the value it once promised. Why This Matters Now AI is not just changing the tools leaders use. It is changing the value structure underneath software itself. Reuters reported in February 2026 that U.S. software and data services companies had lost roughly $1 trillion in market value over a week as investors worried that fast-moving AI tools could disrupt the sector. The same report noted pressure on major names like ServiceNow, Salesforce, and Microsoft during that selloff. (Reuters) That does not mean traditional software disappears. It does mean the market is asking a harder question. What part of the software stack is still defensible? The answer may be uncomfortable for some vendors. AI is beginning to move into functions that used to be sold as expensive modules. Reporting. Search. Drafting. Analysis. Knowledge retrieval. Support. Internal workflow. A company that once charged a premium for a specialized layer may now be competing with an AI-supported tool that does 70% of the job for a fraction of the cost. For leaders, that is not a theory. That is a margin opportunity. The Economy Is Adding Pressure This is happening while the broader economy remains uneven. The Bank of Canada has described the Canadian economy as growing at a moderate pace while adjusting to U.S. tariffs, with inflation pressures affected by higher oil prices and global conflict. (Bank of Canada) Statistics Canada reported that real GDP declined 0.2% in the fourth quarter of 2025 after growth in the previous quarter. (Statistics Canada) That matters because software companies are not immune to the same pressures their customers face. When buyers get more cautious, sales slow. When investors expect the old growth curve, pressure rises. When AI begins replacing pieces of the value proposition, sales teams miss quotas. Then customer success teams get stretched. Support gets thinner. Implementation gets slower. Product teams rush to add AI features. Customers feel it as friction. The vendor may still have a good product. The people may still care. The system may still matter. But pressure travels. Eventually, it lands on the customer. The Common Mistake Most leaders look at AI as a productivity tool. They ask if it can help write emails, summarize meetings, draft proposals, or speed up marketing. Those are useful questions. They are not the biggest questions. The bigger opportunity may be hiding in cost structure. Govindh Jayaraman makes the point clearly in this episode: the opportunity is not to chase AI because it is new. The opportunity is to use AI as a lens to see what has become bloated, stale, or unexamined. That is a very different posture. It is not reckless replacement. It is disciplined attention. The proven entrepreneur cannot afford chaos. There are real teams, real customers, real workflows, and real consequences. But that same entrepreneur also cannot afford to treat old decisions as permanent. AI Is Not the Spine. It May Be the Layer Around the Spine. Some systems are still essential. They hold customer records. They manage billing. They connect field operations. They track inventory. They support ...
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