Amplitude's CEO describes the painful transition from founder (running to the hardest problem) to large-company executive. The latter role requires embracing hierarchy, saying "no" to most things, and managing through leverage rather than direct contribution—a skill set many founders resist and fail to learn.

The transition to managing managers requires a fundamental identity shift from individual contributor to enabler. A leader's value is no longer in their personal output. They must ask, "Is it more important that I do the work, or that the work gets done?" This question forces a necessary focus on delegation, empowerment, and system-building.

Conventional scaling crushes founders by making them hold everything. Instead, invert the model: create a supportive architecture where your frameworks hold your work, which in turn holds you. This 'nesting bowl' approach enables scaling without feeling responsible for holding everything yourself.

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.

Daniel Ek uses the analogy of parenthood to describe a founder's evolving role. In the beginning, the company is completely dependent on the founder. Over time, like a child, it develops its own personality, and the founder's job shifts from direct control to guidance and support.