In some ways, it was the competitiveness of law that attracted O’Reilly. In high school, he’d dedicated nearly all of his free time to basketball, and he says there was a connection between what he had learned through team sports and succeeding in law school. As he explains it, “if you work really hard and prepare better than the others, you have a great chance of winning.” So that’s what he did. He worked, and he worked really hard. Arguing in front of a courtroom didn’t come naturally to O’Reilly. Unlike his father, who he says is a gifted public speaker, O’Reilly says he struggled. “My friends had done debate in high school, and they were so far ahead of me. I felt so behind.” But just like in basketball, O’Reilly kept practicing until he finally got the hang of things. Then almost 12 years into his legal career, O’Reilly bought a hotel.
Even O’Reilly’s dad was puzzled by the move. Why would a successful lawyer, who was a founding partner at his firm, pivot into hotel management? “I’ve always been interested in this,” he says. In past interviews, O’Reilly has talked about the first time he fell in love with hotels. He was 6 years old and had tagged along with his dad to a Rotary conference in New Orleans. “It broadened my universe all of a sudden,” he says. “We stayed at the Holodome, which was just spectacular to a young kid.” It was the new people he saw and the stories he heard that captured his imagination. “I remember thinking it would be great to work in a facility like this,” he says. For years, that buzz that O’Reilly felt in that moment lay dormant. Then in the year between college and law school, O’Reilly felt it again. This time, he experienced it while he backpacked around Turkey, the Middle East and Europe. Anytime he stopped at a restaurant, he was drawn into the customer experience that was being created for him. He watched the servers and noticed when someone loved their job—or didn’t. “When you have a good server, it can change your day because it was such a great experience,” he says. “If you’re in hospitality, you enjoy serving other people. If you don’t enjoy that, it’s obvious.”