Good Bad Billionaire Orlando Bravo: Tech dealmaker
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Apr 21, 2025 Orlando Bravo's journey from aspiring tennis pro to the first Puerto Rican billionaire is a fascinating tale of pivoting to finance. A parenting revelation about diapers reshaped his business approach, emphasizing trust and growth. The podcast delves into the profitability of software firms, revealing investment secrets during the SaaS boom. Bravo's philanthropy in Puerto Rico post-Hurricane Maria contrasts with scandals in cyber security and cryptocurrency. His story raises questions about wealth's duality and the ethical complexities of success.
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Diaper Moment Shapes Business Focus
- Orlando Bravo’s diaper crisis at a supermarket showed the importance of focusing on the immediate priority under pressure.
- This moment later influenced his business approach to focus on what truly matters at each moment.
Enterprise Software's Strategic Stickiness
- Enterprise software is essential and sticky as companies depend on it deeply for core functions.
- Changing these systems is costly and painful, creating loyal customers resistant to switching.
Hands-On Growth Strategy Anecdote
- Bravo applied the buy-and-build strategy to tech companies, growing them by acquiring competitors.
- He was hands-on, even negotiating a deal over five days in a competitor's garage.