The incredible story of Orlando Bravo’s journey from a tuna fishing village in Puerto Rico to the most successful private equity investor in the world, is one of incredibly hard work and a fierce determination to succeed.  When Orlando’s childhood dream of becoming a professional tennis player ended, he went to Brown on a tennis scholarship, was terrified he wouldn't succeed, graduated Phi Beta Kappa in the top 2% of his class, and later earned a JD / MBA from Stanford. 

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After not being offered a summer internship position at a prestigious private equity firm and graduating from Stanford without a job, Orlando made 100 cold calls to potential employers, one of whom was Carl Thoma who is considered one of the founders and pioneers of private equity.  It was here that Orlando put himself on the map.  After making a series of poor acquisitions of technology companies that survived the dot.com bust in 2010-2011, he pivoted and began investing in software companies.  His first deal was the acquisition of Prophet 21, a product distribution software provider based in San Diego where he worked for five days in the garage of the company’s founder before going forward with the deal.  The investment made a 4x return and earned Orlando a seat at the table, and by the age of 30 Orlando became a partner in the firm.  Since its founding, Thomas Bravo has completed more than 350 acquisitions worth nearly $155 billion, and presently oversees a portfolio of 50 software companies that generate $21 billion in annual revenue and employs more than 72,000 people around the world. 

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In this inspirational episode, Randall and Orlando discuss Orlando’s journey from tennis to higher education, why he focuses on investing in well-established software companies instead of startups, the importance of learning from investment mistakes and other failures, and why he believes the next generation is always better than the previous one.

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Topics Include: 

- Lessons about work ethic learned from his parents and grandfather

- How “soft landings” and limiting pressure can build environments where people thrive

- Why Orlando prefers cold calling to introductions

- How the dot-com bubble influenced his investment strategy 

- The story of the Profit 21 acquisition

- How he made a $9 billion profit in 18 months by buying and selling Ellie Mae

- How to attract and retain top talent

- The place cryptocurrency in our society

- The value of preparation

- Mentorship

- The importance of philanthropy and his incredible efforts after Hurricane Maria, and what he’s doing to help Puerto Rico and young entrepreneurs there

- And other topics…

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