An AI like ChatGPT struggles to provide tech support for its own features because the product changes too rapidly. The web content and documentation it's trained on lag significantly behind the current software version, creating a knowledge gap that doesn't exist for more stable products.

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People struggle with AI prompts because the model lacks background on their goals and progress. The solution is 'Context Engineering': creating an environment where the AI continuously accumulates user-specific information, materials, and intent, reducing the need for constant prompt tweaking.

Despite access to state-of-the-art models, most ChatGPT users defaulted to older versions. The cognitive load of using a "model picker" and uncertainty about speed/quality trade-offs were bigger barriers than price. Automating this choice is key to driving mass adoption of advanced AI reasoning.

Generative AI tools are only as good as the content they're trained on. Lenovo intentionally delayed activating an AI search feature because they lacked confidence in their content governance. Without a system to ensure content is accurate and up-to-date, AI tools risk providing false information, which erodes seller trust.

In the current AI landscape, knowledge and assumptions become obsolete within months, not years. This rapid pace of evolution creates significant stress, as investors and founders must constantly re-educate themselves to make informed decisions. Relying on past knowledge is a quick path to failure.

Even professionals who use ChatGPT daily are often unaware of its most powerful "reasoning" capabilities, like Deep Research. This pervasive knowledge gap means users stick to basic tasks like writing, missing out on the profound strategic value these advanced features offer for complex problem-solving.

A paradox of rapid AI progress is the widening "expectation gap." As users become accustomed to AI's power, their expectations for its capabilities grow even faster than the technology itself. This leads to a persistent feeling of frustration, even though the tools are objectively better than they were a year ago.

Unlike deterministic SaaS software that works consistently, AI is probabilistic and doesn't work perfectly out of the box. Achieving 'human-grade' performance (e.g., 99.9% reliability) requires continuous tuning and expert guidance, countering the hype that AI is an immediate, hands-off solution.

Unlike traditional SaaS, AI applications have a unique vulnerability: a step-function improvement in an underlying model could render an app's entire workflow obsolete. What seems defensible today could become a native model feature tomorrow (the 'Jasper' risk).

For consumer products like ChatGPT, models are already good enough for common queries. However, for complex enterprise tasks like coding, performance is far from solved. This gives model providers a durable path to sustained revenue growth through continued quality improvements aimed at professionals.

An AI tool's quality is now almost entirely dependent on its underlying model. The guest notes that 'Windsor', a top-tier agent just three weeks prior, dropped to 'C-tier' simply because it hadn't integrated Claude 4, highlighting the brutal pace of innovation.