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Over the last few decades the interest of scholars in habitual entrepreneurship has grown progressively. In-depth studies of the phenomenon have brought to light the widespread presence, in several industries, of entrepreneurs developing and managing, either simultaneously or in succession, more than one business during their working lifetime. Likewise, within the context of business managed by members belonging to the same family, scholars usually find members creating subsequent or parallel businesses.

Therefore, in the family business context there is a frequent presence of members, acting as habitual entrepreneurs, who create new businesses by leveraging values, resources, and experiences accumulated in the existing business and belonging to the family.

The investigation presented in this chapter, carried out with habitual entrepreneurs who owned, or had owned, at least two family firms, yields initial promising results regarding the widespread presence of habitual entrepreneurs in the context of family business.

The chapter simultaneously contributes to the literature on habitual entrepreneurship and family business by highlighting the connections between entrepreneurs who found new firms, simultaneously or sequentially, by involving family members.

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