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Milestone Chapter 3 Deep dives

How investors receive liquidity: the concept of a structured path to liquidity

In conventional ownership models, investor liquidity is often tied to exits – typically through IPOs or acquisitions – which also marks the moment when returns are realized. This can work well when investors and entrepreneurs are fully aligned and heading in the same direction. But when financial expectations and long-term mission diverge, pressure can mount: companies may be driven to grow at a pace or in a direction shaped more by investor timelines than by their own purpose. Because (equity) capital usually comes with voting rights, companies are eventually left to their schicksal, as investors can steer the business toward the outcome they aspire. The result is a misalignment: capital dictates the pace and direction, while the company's deeper purpose can be sidelined.

In steward-ownership, control stays with the company – not with capital. Guided by the principle of self-determination, decision-making remains in the hands of those closest to the mission. Investors still play an important role, but they don’t get to steer the company based on individual liquidity needs. Instead, steward-ownership relies on something else: structured exits.

Structured exits are exits that provide a clear, agreed-upon path to liquidity – one that protects the integrity of the company while honoring investor needs. One welcomed side effect of focusing on these kinds of liquidity options – especially those that don't involve an IPO or sale – is that companies tend to stay more closely aligned with their mission, their long-term vision, and the next meaningful steps in their journey. Rather than chasing rapid increases in valuation, these businesses prioritize corporate health and purpose. And in the long run, this orientation pays off: steward-owned companies show significantly higher survival rates compared to those with conventional ownership structures.

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