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In the face of unprecedented growth and high-stakes decisions, Gaston Taratuta, CEO and co-founder of Aleph Group, must navigate a critical juncture in the company's trajectory. During the pandemic, Aleph received multiple acquisition offers, including an USD800 million bid and a private equity proposal valuing the company at USD2 billion. However, these offers came with strings attached, such as requiring Taratuta to step aside as CEO-threatening the legacy and vision he had built alongside COO Ignacio Vidaguren. Guided by key advisors, Taratuta explored an alternative path: taking Aleph public. The journey to IPO required Taratuta to forge new partnerships with global companies like Snapchat, Twitter, and Mercado Libre while maintaining control and doubling down on the company's mission to democratize digital advertising in emerging markets. The case also highlights the deeply collaborative leadership between Taratuta and Vidaguren, whose partnership of over 14 years was tested but ultimately strengthened by these challenges. Their leadership propelled Aleph into strategic acquisitions in digital advertising and fintech, expanding its global reach and capabilities. Set against the backdrop of Aleph's ambitious growth, this case examines critical questions of leadership, valuation, and balancing personal values with financial opportunity. It invites students to explore the complexities of navigating bold decisions in uncertain times while safeguarding the vision of an entrepreneurial legacy.