Airway Therapeutics' CEO sold his first company, a CRO, when he realized he couldn't personally guarantee his core promise of quality engagement on every project. This highlights a critical decision point for founders: sell when growth threatens the very value proposition that made the company successful.

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.

A successful exit is a highly choreographed dance, not an abrupt decision. Founders should spend years building relationships with line-of-business leaders—not just Corp Dev—at potential acquiring companies. The goal is to 'incept' the idea of an acquisition long before it's needed.

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.

The default that all businesses must scale forever is flawed. Society needs a "death doula for companies"—a framework to help businesses that have fulfilled their mission or become zombies to wind down gracefully. This allows talent and capital to be reallocated to new ventures.

A key, yet sensitive, reason for a sale is when the current management team lacks the skills for the company's next growth phase. For example, a manager skilled at early-stage growth may not be suited for a larger enterprise requiring extensive M&A. A sale brings in a new owner with the capital and team for that next level.

Even a skilled entrepreneur with strong marketing abilities will struggle in a shrinking industry. The constant headwind makes growth an expensive, uphill battle. It's more strategic to simply not fight against a declining market trend than it is to find the fastest-growing one.

Despite bootstrapping a profitable, growing business, the founders sold it because it wasn't on track to fulfill their grander vision. They recognized they were becoming the bottleneck and that new owners could scale it better, freeing them up to pursue a bigger opportunity.

When considering an exit, the primary risk isn't financial; it's the founder's time locked in a stagnating company. Spending productive years on a venture that's not working—even if well-funded—prevents a talented founder from pursuing the next big thing during a period of rapid technological change.