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This explorative research paper draws evidence from a database of small to medium-size unquoted private companies (n = 240) in the UK and reports on the family business and venture capital relationship from the demand side. Following the review of literature relating to financial affairs of private companies, the main research inquiries are outlined and a set of generic hypotheses is elicited based on the pecking order theory—that is, private companies, including family-controlled ventures, have a propensity to finance their operations in a hierarchical fashion, first using internally available funds, followed by debt and, finally, external equity (Petitt & Singer, 1985). Univariate statistical analyses confirm that family companies adhere strongly to the pecking order principles of financial development. The paper explores factors governing the rationale of owner-managing directors of private and family companies for considering venture capital dealings as well as main areas of concern about the deal structures. The paper then concludes with a discussion of the policy implications from the perspective of the owner-manager, financier, and enterprise policy maker. To encourage equity development of smaller privately held companies, particularly family firms, there is room for policy initiatives that respect the financial philosophy of private companies.