Selling a business often triggers a period of depression. A founder's self-worth is deeply intertwined with the daily grind and pressures of their company. When that is removed, they experience a significant loss and must redefine their identity outside of their work.

Achieving time and financial freedom doesn't automatically lead to fulfillment. Instead, it often creates an existential vacuum, leading to anxiety and depression. The key is to proactively fill this void with learning and service, rather than assuming leisure alone is the goal.

Despite selling their company for nine figures, founder Cass Lazaro reveals she suffered from PTSD after the sale. The intense pressure of growing to $50M ARR in three years, marked by 14-hour days and neglecting personal health, left her nervous system 'fried.' This highlights the hidden, long-term mental and physical toll of startup hypergrowth.

Many founders treat their startup as a temporary vehicle to an exit, which can lead to an identity crisis after they "win." A healthier approach is to build a company as a "way of life"—a system of activities you want to engage in for the long term, regardless of specific outcomes.

Contrary to the dream of retiring after an exit, data shows 92% of founders start another project, even those with nine-figure exits. The drive to build is a core part of their identity that a large financial windfall does not eliminate.

Unlike professionals who move to similar roles, entrepreneurs enter a vulnerable "in-between time" after their company ends. Their personal narrative was tied to their last venture, leaving them in a "weird wasteland" while figuring out what's next, a period that is often overlooked.

Achieving external markers of success, like a multi-million dollar exit, often fails to provide a sense of accomplishment. Instead, it can lead to feelings of emptiness, anxiety, and imposter syndrome because internal self-worth was tied to the struggle, not the outcome.

To ensure a smooth leadership handover, John Zimmer transitioned from an operating role to a board seat before fully departing Lyft. This deliberate, two-year process provided stability and support for the company's new leadership team during its next chapter.

After selling his company, the founder experienced six months of bliss followed by a period of feeling useless and lacking purpose. This 'valley of shadows' is a common but rarely discussed phenomenon where accomplished founders struggle with a loss of identity and intensity, ultimately driving them to build again.