A founder's real boss is their customer base. While keeping a board happy is important, some CEOs become so consumed with managing up that they lose sight of the product and customer needs, ultimately driving the company off a cliff despite running perfect board meetings.

The most common failure mode for a founder-CEO isn't a lack of competence, but a crisis of confidence. This leads to hesitation on critical decisions, especially firing an underperforming executive. The excuses for delaying are merely symptoms of this confidence gap.

Technically-minded founders often believe superior technology is the ultimate measure of success. The critical metamorphosis is realizing the market only rewards a great business model, measured by revenue and margins, not technical elegance. Appreciating go-to-market is essential.

Early versions of Figma failed to gain traction because designers, its target users, fundamentally didn't trust the tool's own subpar visual design. This meta-problem highlights that for a tool to be credible to its expert users, its own execution must embody the principles it espouses. A redesign was the key to unlocking user trust and adoption.

All founders make high-impact mistakes. The critical failure point is when those mistakes erode their confidence, leading to hesitation. This indecisiveness creates a power vacuum, causing senior employees to get nervous and jockey for position, which spirals the organization into a dysfunctional, political state.

Block's CTO argues that engineers mistakenly equate code quality with product success. He uses the example of early YouTube, which had a famously poor architecture but became wildly successful, while the technically superior Google Video failed. The focus should be on solving a user problem, not on perfect code.

Dogfooding isn't enough. Founders should use every feature of their product weekly to develop a subjective feel for quality. Combine this with objective metrics like the percentage of unhappy customers and the engineering velocity for adding new features.

In a fast-moving category like AI coding, platform features are fleeting. The more durable factor is the founding team's vision and ability to execute. Users should follow the founders of these companies, as choosing a tool is ultimately a long-term bet on a person's leadership and trajectory.

The number one reason founders fail is not a lack of competence but a crisis of confidence that leads to hesitation. They see what needs to be done but delay, bogged down by excuses. In a fast-moving environment, a smart decision made too late is no longer a smart decision.