A great founding engineer may not be the right person to be CTO of a larger team. Recognizing this misfit can lead to a mutual, amicable departure where the exiting co-founder retains their fully vested equity, preserving the relationship and acknowledging their early contribution.

Entrepreneurs often prefer being the indispensable "most valuable player" because it feels good and gives them control. However, this ego-driven desire makes the business less valuable and prevents it from scaling. To truly grow, a founder must transition from the court to the owner's box.

Blippar's co-founder realized her skills were perfect for the startup-to-scale-up phase but that she became a bottleneck at scale. Her inability to delegate meant others were better suited to lead the scaled team. This self-awareness is crucial for founders to prevent stalling growth and empower their organization.

Founder Alex Marechniak stepped down as CEO not from a lack of skill, but because personal crises and burnout depleted his capacity. He recognized that leadership requires being "fully in the game," and transparently told his board he wasn't, prioritizing the company's health over his ego.

Tariq Farid shares his grandfather's wisdom: "brawn to brain." In a company's early days, a founder's physical work ("brawn") is crucial. As it matures, their value shifts to wisdom, strategy, and system-building ("brain") to enable scale and prevent burnout.

The CEO role is not a joyful or fun job; it's a high-pressure, problem-solving position. Founders who love their craft, like software engineering, often take the CEO title out of necessity to solve a larger problem and bring a vision to life, not because they desire the job itself.

The distinction between a 'big company' and 'small company' person is irrelevant. A founder's mindset—hustling to bring new ideas to life and driving outcomes—is equally applicable and valuable in a large corporation as it is in a startup.

Despite success, founder Kevin Wagstaff felt like an "imposter" as the company scaled beyond $10M ARR. He recognized his strengths were in the early, scrappy "bias to action" phase, not managing a larger organization. He proactively brought in a seasoned CEO better suited for the next stage of growth.

A founder's role is constantly changing—from individual contributor to manager to culture builder. Success requires being self-aware enough to recognize you're always in a new, unfamiliar role you're not yet good at. Sticking to the old job you mastered is a primary cause of failure to scale.