The $2.5B acquisition of Manus exemplifies a "local maximum" exit. While VCs might push for a higher valuation later, the founders rationally chose to sell. This decision optimizes their personal, undiversified financial outcome by de-risking against future competition and market shifts.

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.

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.

When John Arrow returned as CEO of Mutual Mobile to facilitate its final sale, the experience was more fun and balanced than his first tenure. Having already achieved financial freedom, he could operate without the intense pressure of survival, approaching the role as a fulfilling final chapter.

The path to an exit is a market in itself. It's often easier to sell a $20M company you fully own than a $500M venture-backed one. The pool of buyers is larger and the process less scrutinized, making a smaller, bootstrapped exit potentially more profitable for the founder.

A founder's retrospective analysis often reveals that delayed decisions were the correct ones, and the only regret is not acting sooner. Recognizing this pattern—that you rarely regret moving too fast—can serve as a powerful heuristic to trust your gut and accelerate decision-making, as inaction is often the biggest risk.

From a buyer's perspective, founders should sell after they have demonstrated a strong growth trajectory and hit an inflection point. Pitching a 'hockey stick' forecast without historical proof is less compelling. Waiting until you have proof of the upswing optimizes both value and strategic interest.

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.