Many founders who successfully exit their companies feel depressed and unfulfilled, realizing their best idea is behind them. The alternative is to reject the exit-focused mindset and commit to building a durable, lifelong business, finding satisfaction in the infinite game.
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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.
Every successful founder journey includes a point where quitting is the most rational decision. Spencer Skates argues the only way to persevere is to anchor to a deeply held intrinsic motivation or a "mission that's greater than yourself." External motivators like money or recognition are insufficient to overcome this existential pain.
The primary error founders make is confusing external achievements (revenue, exit) with internal fulfillment. Financial success should be viewed as a tool that enables a life aligned with your personal values, rather than being the source of fulfillment itself.
Instead of optimizing for a quick win, founders should be "greedy" and select a problem so compelling they can envision working on it for 10-20 years. This long-term alignment is critical for avoiding the burnout and cynicism that comes from building a business you're not passionate about. The problem itself must be the primary source of motivation.
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.
Founders who try to perfectly time an exit with market conditions are twice as likely to have second thoughts and report less satisfaction. The most fulfilled founders are those who sell when they are personally ready, regardless of market timing.
Instead of chasing trends or pivoting every few weeks, founders should focus on a singular mission that stems from their unique expertise and conviction. This approach builds durable, meaningful companies rather than simply chasing valuations.
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 often believe success will bring ease and happiness, but building meaningful things is a constant, hard grind. The goal shouldn't be happiness, which is fleeting, but contentment—the deep satisfaction derived from tackling important problems. The hardness itself is a privilege to be embraced.
