Transitioning from a startup to a scalable company presents significant challenges, often leading entrepreneurs to sell before reaching the billion-dollar mark. Many founders excel at building companies to a certain level but struggle with the complexities of scaling beyond 100 or 200 employees. This difficulty in navigating the transition can deter them from pursuing further growth due to the perceived risks involved. While a few, like Steve Jobs and Bill Gates, have successfully made this leap, it requires a unique skill set that not all CEOs possess. Additionally, there is a tendency to idolize tech founders, placing them on pedestals and assuming their insights on management should be universally applied, despite the fact that many traditional business leaders hold vast experience and knowledge in managing larger organizations.