This episode explores the life and career of Orlando Bravo, the first Puerto Rican-born billionaire, and analyzes his journey from a privileged background to becoming a major player in the private equity world. Against the backdrop of his early success in tennis and subsequent education at Brown and Stanford Universities, Bravo's career in investment banking and private equity is detailed. More significantly, the podcast delves into his unique investment strategy, focusing on established technology firms in niche markets and employing a "buy and build" approach. For instance, his acquisition and turnaround of Profit21 showcases his hands-on management style and focus on leveraging existing teams. However, the discussion also highlights controversies surrounding his investments in SolarWinds and FTX, raising questions about his business practices and risk assessment. Ultimately, the episode concludes by evaluating Bravo's wealth, philanthropic efforts, and political leanings, ultimately classifying him as "just another billionaire" despite his unique origin story and significant financial success.