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When asked when founders should sell, Glenn Fogel pushes back on a universal rule. He advises founders to look inward: Is your goal simply to make money, or to build something that matters? The answer depends on what you want to do with your limited time and what gives you meaning.
Founders who focus only on the exit as their goal often feel empty after achieving it. The journey is like hiking: you must enjoy the process, not just the brief moment at the peak. Real fulfillment comes from improving at the craft of entrepreneurship—managing people, process, and vision.
When a potential acquirer asked for his exit strategy, Kevin Mandia laughed. For him, Mandiant was his life's work and what he did for a living, not a project designed for a financial exit. This mindset separates founders focused on building a craft from those optimizing for a sale.
Founders who sell their single best idea often struggle through decades of working on lesser second and third acts. The observation is that one cannot recapture that original magic, suggesting founders should never get out of the game on their primary creation.
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.
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.
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.
Ask a founder what they'd do on a Monday morning after they've made a billion dollars and fulfilled all their fantasies. This thought experiment strips away financial incentives and reveals their core drive. An inability to answer suggests they haven't thought beyond the exit.
Despite his immense wealth, Matt Paulsen has no plans to sell his company. He equates the business to one of his own children, driven by a deep love for operating it rather than a financial exit strategy. This challenges the common "build-to-sell" mentality prevalent in entrepreneurship.
Melissa Wood Tepperberg challenges the common entrepreneurial goal of building a company to sell it. After experiencing investor-led growth, she realized her true desire was to continue doing the work she loved, not to cash out. Founders should define their own "North Star" beyond a lucrative exit.
Weiss advises founders to invest time in non-business pursuits that provide value, like non-profits or coaching, while still running their company. He argues that if your entire identity is tied to the business, any exit—no matter how lucrative—will ultimately feel hollow and leave you feeling lost.