The venture capital business model is exit-oriented, and trade sales are the venture capitalist’s predominant exit routes from most portfolio companies. Such transactions do sometimes entail value destruction due to the venture capitalist’s opportunistic decision to sell the firm prematurely. In other instances, however, value-destruction during the trade sale process is indeed the function of some peculiar arrangements governing the venture capitalist-entrepreneur business relationship. The resulting distinction between opportunistic and non-opportunistic trade sales paves the way to a novel policy prescription, which calls for the acknowledgment of the heterogeneity of the transactions falling under the “value-destroying trade sale” rubric, and which grounds several and significant normative and positive implications. Under scrutiny herein come, however, only those safeguards and remedies entitling shareholders external to decision-making to claim the pre-transaction value of their shares – i.e., fair value protection devices. Having argued, on the normative side, that fair value is just another default term in the corporate contract, and that contracting parties should accordingly be able to mould its protection as they deem fit or even to relinquish it altogether, the discussion shows its more tangible positive bite by looking at Italian corporate law. An analysis of the domestic corporate law regimes currently in force reveals that fair value protective devices exhibit unjustified rigidities that make them available to entrepreneurs also in the event of non-opportunistic trade sales. It accordingly explains that the regulatory status quo generates distributional problems that may contribute to the allocative inefficiency of this segment of the domestic market for entrepreneurial finance. It eventually advocates the adoption of a more plastic approach that, building on properly designed ex-post remedies, may distinguish between opportunistic and non-opportunistic value-destroying trade sales more effectively, thereby delivering a more balanced contractual enforcement and restoring the preconditions for efficient contracting.