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…