Don't wait until you're completely exhausted to sell your company, as buyers will sense your desperation and gain the advantage. The ideal time to exit is when your passion for the market wanes or growth slows, allowing you to negotiate from a position of strength before burnout sets in.

Investors spend hours on due diligence before buying but rarely pre-define their selling criteria. This leads to emotional decisions, typically selling after a period of underperformance, which undermines the initial long-term thesis. A pre-defined sell plan is crucial for success.

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 making emotional decisions, establish "kill criteria" for each investment: a specific KPI (a state) that must be met by a certain time (a date). If the company fails to meet the predefined metric, you sell. This provides a disciplined, objective framework for portfolio management.

Reflecting on his major exit from Mutual Mobile, John Arrow shares a powerful heuristic: he's never met anyone who regretted selling their company. However, he has met many who regretted turning down an opportunity to sell, highlighting the importance of seizing favorable market conditions.

Investors fixate on selecting the right companies, but the real money is made or lost in the decision of when to sell or hold a winning position. The timing of an exit can create a 100x difference in outcomes. Having a disciplined approach to portfolio management and liquidity is more critical to fund performance than the initial investment choice.

Wilson advised against trying to perfectly time the peak of a successful company's dominance. Competition will eventually emerge, but anticipating its impact is futile and often leads to premature selling. He believed you can make a fortune by riding a winner for years before the problems become acute.

Pzena’s firm maintains strict selling discipline by automatically exiting a position once it reaches its calculated "fair value." This rule applies even if there isn't an immediate new stock to buy, forcing them into cash temporarily to avoid emotional attachment to winners.

A perfect exit window never materializes. The initial trigger is the fund's need to return capital. If that need exists, the signal to sell is when at least two of these three conditions are met: the company is trading well, there is strong buyer appetite (including an open IPO window), or market valuations are favorable.