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.

Individual contributors are rewarded for having answers and sharing their expertise. To succeed as a leader, one must fundamentally change their approach. The job becomes about empowering others by asking insightful questions and actively listening, a diametrically opposed skillset that is difficult to adopt.

The transition from a hands-on contributor to a leader is one of the hardest professional shifts. It requires consciously moving away from execution by learning to trust and delegate. This is achieved by hiring talented people and then empowering them to operate, even if it means simply getting out of their way.

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.

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.