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.

In today's founder-centric climate, many VCs avoid confrontation to protect their reputation (NPS) within the founder network. This fear of being blacklisted leads them to abdicate their fiduciary duty to shareholders, failing to intervene even when a company's performance is dire and hard decisions are needed.

The demands of the CEO role—focusing on external stakeholders and high-level strategy—inevitably distance them from operational realities. This counterintuitive insight argues against the "Imperial CEO" model and highlights the constant risk of losing touch with the business.

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.

A CEO who stays too long creates an organization optimized to respond only to them, causing other skills and response mechanisms to weaken. Leadership changes are healthy because they force a company to develop a more balanced and resilient set of capabilities, breaking the imperial CEO model.

The sign of a high-performing, intensely driven CEO is when they create enough productive tension that their board members occasionally worry if the team is being pushed too hard. This "occasional gear grind" indicates the company's engine is running at maximum capacity, which is necessary for breakout success.

Even with full board support, a successor CEO may lack the intrinsic 'moral authority' to make drastic 'burn the boats' decisions. This courage is harder to summon without the deep-seated capital a founder naturally possesses, making company-altering transformation more challenging for an outsider.

Investment research suggests the significant performance signal in governance isn't achieving a perfect score, but rather avoiding companies in the worst decile. The key is to steer clear of clear red flags—like misaligned boards or poor capital allocation—as this is where underperformance is most clearly correlated.

A key indicator of a healthy company culture and CEO leadership is the absence of back-channel complaints from the management team to the board. This loyalty stems from the CEO operating with transparency and directness, which prevents the build-up of resentment that leads to mutiny.