This case details challenges Adeyemi Ajao faced in his career as a founder of three companies: Tuenti, a social media company in Spain, Identified, a data analytics company for recruiters, and Base10 Partners, a venture capital firm. At Tuenti, Ajao debates whether to accept outside funding at the early stage of his start-up. At Identified, he navigates a painful pivot. And at Base10, he deals with reluctant investors while he raises a venture fund.