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.

The most significant emotional moment for a founder selling their company is not the final closing, but the signing of the Letter of Intent (LOI). This is the point where they mentally commit to the sale and place their trust in the buyer, marking the true transfer of their "baby."

The moment proceeds from Qualtrics' multi-billion dollar sale hit, the feeling wasn't euphoria but a sense of it being "underwhelming." This highlights the common entrepreneurial experience where the journey and stories created are far more fulfilling than the financial destination.

Founders and CEOs can develop an inflated sense of their contribution by focusing only on the final executive meeting. They often overlook the months of prospecting, relationship-building, and deal choreography done by the sales rep, leading to unfair perceptions about who truly 'closed the deal.'

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.

Founders who wait until they need to sell have already failed. A successful exit requires a multi-year 'background process' of building relationships. The key is to engage with SVPs and business unit leaders at potential acquirers—the people who will champion the deal internally—not just the Corp Dev team who merely execute transactions.

The day Poppi's acquisition closed, co-founders Allison and Stephen Ellsworth had a huge fight. This highlights the often-overlooked emotional and vulnerable side of a business exit, which can be as stressful as it is exciting, reminding founders that major business milestones are also major life transitions.

The reality of selling a company is not a simple transaction. It's a grueling, months-long process that functions as a demanding second job for the founder, who must keep it secret from their team while simultaneously running the core business at full capacity.

Founder Jacqueline Johnson describes her $22M company sale as surreal and isolating. The deal closed on Zoom, and she immediately jumped into another work meeting, highlighting how major career milestones can feel disconnected from reality in a remote world.