A fierce squall struck Puerto Rico one Wednesday in late October, snarling roadways around San Juan and complicating the travel plans of Orlando Bravo, the founder and managing partner of $122 billion private equity firm Thoma Bravo. Bravo, a Puerto Rico native who spends about a quarter of his time on the island, needed to get from the capital to a meeting 20 miles away in Loíza, a small, impoverished area near the island’s coast where he has concentrated part of his philanthropic efforts. Since Bravo, 52, does very little at a slow pace, he decided to take his helicopter during a break in the downpour.
“Make sure you buckle up,” he said as we loaded into the aircraft. “This thing goes fast.”
Up we went, flying east from San Juan as rain poured down the windows. The city’s concrete skyline disappeared behind us, replaced by sodden beaches dotted with blue umbrellas and crumbling homes with missing roofs. Though this part of the island had avoided the brunt of Hurricane Fiona a few weeks earlier, it was still clearly contending with past disasters, as well as decades of government neglect.
Down below, the stretch of ruined houses soon faded away, replaced by a thick green carpet. “A mangrove forest,” Bravo said, looking up from his iPhone for a minute to narrate our journey. Reading glasses slumped on his nose, he had contentedly retreated to his phone, catching up on the voluminous text messages and emails he exchanges with his lieutenants as they hunt down software buyouts.
Intentional or not, the helicopter ride provided some very cinematic optics. With his Desi Arnaz good looks and rugged black button-down, Bravo looked every bit the later-season “Succession” character, a low-profile mogul emerging from stage left to toss a financial lifeline to a wayward Waystar heir. He certainly appeared ready to seal a deal midflight—and mid-thunderstorm—if circumstances required.
Thoma Bravo has been on an impressive run over the past year, with Bravo aggressively pursuing the biggest buyouts of his almost 25-year career in private equity. In March, Thoma Bravo made an all-cash $10.4 billion acquisition of enterprise software company Anaplan, and a month later it scooped up identity-security firm SailPoint for $6.9 billion in cash. A year earlier, it had purchased cybersecurity firm Proofpoint for around $12 billion and RealPage, a real estate data-analytics company, for $10.3 billion. Last month alone, the firm announced it had acquired ForgeRock, another identity-security company, and UserTesting, which makes customer-feedback software, and completed the acquisition of Ping Identity, yet another identity-security outfit—transactions totaling $6.4 billion.