The founder received harsh 360 feedback, with colleagues labeling him 'Hurricane Ben' for his disruptive behavior. Instead of being defensive, he recognized the feedback as a critical inflection point, forcing him to fundamentally change his leadership style to effectively scale with the company.

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.

When presented with a new strategy, high performers are drawn to it because they are mentally disciplined to be comfortable with risk. In contrast, middle and low performers often resist change because it feels like a personal judgment on their past methods, triggering fear and shame.

When a founder advises a successor to 'make decisions that energize you,' it's a strategic directive, not a wellness tip. It serves as a guardrail against the 'death by a thousand cuts' that comes from compromising core beliefs just to make others comfortable, thereby preserving the vision.

To prepare her son, Green provided a list of specific negative commandments (“Don't cheat,” “Don't kick a man when he's down”) and negotiation heuristics (“Sleep on it overnight”). This focus on real-world ethics and decision-making proved more valuable for succession than any theoretical business education.

When an experimental campaign failed, Edelman's CEO Richard Edelman protected the mid-level employee responsible. He framed the mistake as a necessary cost of innovation in a new field, explicitly telling the team to "keep pushing boundaries." This response fosters a culture where calculated risks are encouraged rather than punished.

The founder hired an experienced CEO and then rotated through leadership roles in different departments (brand, product, tech). This created a self-designed, high-stakes apprenticeship, allowing him to learn every facet of the business from experts before confidently retaking the CEO role.

Success at the leadership level requires a developed tolerance for pressure and uncertainty—a skill the CEO calls a 'stomach' for it. This resilience is a distinct capability, and its absence can cause even the most intelligent and talented individuals to fail under pressure, making it a crucial trait for high-stakes roles.

When transitioning leadership, you must allow your successors to make mistakes. True learning comes from fixing failures, not just replicating successes. As the founder, your instinct is to prevent errors, but you must permit 'fuck ups' for the next generation to truly develop their own capabilities and own the business.