A violent storm hit Puerto Rico on Wednesday in late October, complicating roads around San Juan and complicating travel plans for Orlando Bravo, founder and managing partner of the $122 billion private equity firm Thoma Bravo. Bravo, a Puerto Rican native who spends about a quarter of his time on the island, needed to commute from the capital to a meeting 20 miles away in Loiza, a poor little area near the island’s coast where he focused part of his philanthropic efforts. Since Bravo, 52, doesn’t do much at a slow pace, he decided to take his helicopter out during a break in a downpour.
“Make sure you fasten your seatbelt,” he said as we were being loaded onto the plane. “This thing is going fast.”
Up, we flew east from San Juan while the rain was pouring down the windows. The concrete city skyline disappeared behind us, replaced by damp beaches dotted with blue awnings and crumbling homes with missing roofs. Although this part of the island had avoided the brunt of Hurricane Fiona a few weeks earlier, it was still clearly dealing with past disasters, as well as decades of government neglect.
Below, the expanse of ruined homes quickly gave way, replaced by a thick green carpet. “Mangrove forest,” Bravo said, looking down from his iPhone for a minute to recount our trip. Reading glasses slipped on his nose, and he retreated contentedly to his phone, catching up on the voluminous text messages and emails he exchanges with his assistants as they chase software purchases.
Whether intended or not, the helicopter provided some very cinematic visuals. With his Desi Arnaz good looks and rugged black button-up, Bravo looked every part of his “Succession” persona later in the season, a high-profile mogul who walked off stage left to throw a financial lifeline to wayward Waystar heir. He certainly seemed ready to close a deal mid-flight—and in the middle of a thunderstorm—if circumstances required it.
Thoma Bravo has been on an impressive run over the past year, with Bravo aggressively seeking the largest purchases of its nearly 25-year career in private equity. In March, Thoma Bravo acquired enterprise software company Anaplan for $10.4 billion, and a month later it acquired identity security company SailPoint for $6.9 billion in cash. A year ago, it bought cybersecurity company Proofpoint for about $12 billion and RealPage, a real estate data analytics company, for $10.3 billion. In the past month alone, the company announced that it has acquired ForgeRock, another identity security company, UserTesting, which makes customer feedback software, and completed the acquisition of Ping Identity, another identity security hardware — transactions totaling $6.4 billion.