“There were a lot of hedge fund blogs out there saying software is going to get destroyed...And guess what happened? Our recurring revenue stream was really nearly untouched in a pandemic. Corporate customers paid their subscription software revenue, but they didn't pay rent. It was more stable than real estate.”

To this day, Orlando Bravo would rather have played Wimbledon than become the first Puerto Rican-born billionaire. As a teen, he was a top-40 junior player; as an adult, Bravo eventually co-founded Thoma Bravo, a private equity firm specializing exclusively on software deals. Forbes recently called him “Wall Street’s best dealmaker.” He may also be one of its most generous: In the aftermath of Hurricane Maria, Bravo chartered planes to Puerto Rico carrying $10,000,000 in essential goods and committed an additional $100,000,000 to foster entrepreneurship and economic development on the island.

As he tells Mike, “After the hurricane in Puerto Rico...that was my personal moment in philanthropy where I understood for the first time that if I didn't do anything about it, nobody else was going to.”