Boxing to Billions

Leo Holland ’26 has a vision for his future. He’s going to be the next Floyd Mayweather, Jr., if Mayweather had invented Nike in addition to his boxing success. He’s going to be a professional boxer by 18 (ok, it might take him until he’s 19), fight at MGMGrand in Las Vegas, and be on pay-per-view. He plans to make his family’s first billion…yes, BILLION…through a combination of boxing success and business acumen. Pretty big plans for a 15-year old.

It all started (as many good boxing stories do) with Rocky. At age nine, Leo watched Rocky and Creed, and with the confidence only a child can possess, thought to himself, “I can do that.” He asked his mother if he could start boxing and he got a resolute “no” as a response. Next he tried his father, who was more receptive, and within the week he was in a gym. He chuckles as he recounts this part, saying that his mom didn’t find out until a few weeks later. Nine-year-old Leo lost his first two fights. Since then he’s hit his stride and partnered up with the right trainer, earning multiple belts and the respect of the local boxing community. He’s running three miles a day, Monday through Friday, and training at Bishop’s Training and Fitness Gym five days a week. His coach is James Perella (aka “The Slim Reaper” in the ring), and the two have a rapport that’s working for Leo. Last summer, he won his first international competition at USA Boxing’s Boston vs. Ireland event. “Boston won, obviously,” says Leo.

“I like the hustle of boxing,” says Leo. “I have really big goals, so it’s something for me to work toward. The feeling is great after a fight, after you win, after you knock someone out — it’s a huge achievement. But even just after a practice, I feel like, ‘I know I did something good today.’” “Plus,” he adds, “it keeps you in shape and keeps you healthy.”

In October, Leo secured the title of 2023 USA Boxing New England Champion in the 138 lb. junior novice category for the second time, but he’s not stopping there. His sights continue to be on bigger things, like following in the footsteps of Mayweather. “He’ll fight people who are faster or stronger, but he’s the smarter fighter. I’ve always wanted to be like that.” 

Leo’s determination might at first seem like the foolhardy optimism of youth — his dreams too big, his goals too high. But when you dig into why he wants to be like Mayweather and why he wants to be a billionaire, it becomes clear that success for Leo is about something more than himself; it’s about his future family. His ultimate goal is to build generational wealth so that he can give his own children something that he doesn’t have. And, he says, he will make sure they don’t take it for granted. “Generational wealth is me making sure my future family will be fine. Anything can happen, but that would guarantee that my kids will be good, and their kids will be good.”

Here at Xaverian, Leo has found support for his dreams from students and faculty alike. “I think Xaverian’s unique—you can’t find support like that everywhere. And it’s all about where you are and the kind of people you have around you. If you’re in a bad environment, you’re not going to have good outcomes. But if you’re in a good environment like Xaverian, you will find that support.” Keep on dreaming and fighting, Leo. Xaverian will continue to be in your corner.