Ray Leonard Jr is co-founder of Nobody Studios and CEO of Ovationz, the premier talent marketplace allowing SMEs, artists, speakers and athletes to monetize their time and skills effortlessly. The son of legendary boxer ‘Sugar’ Ray Leonard, and a two sport divisional collegiate athlete, Ray founded and sold his own sports agency, going on to become one of the great coaches, mentors and trainers for others looking to try and build businesses. His high energy and penchant for leadership drew him to the world of motivational speaking, where he is now one of the most in-demand speakers throughout the globe. In this episode of Unlearn, Ray and Barry O’Reilly explore the lessons he learned throughout his personal and professional journey.

Growing Up and Out

Appreciating the diversity of the world was something Ray was privileged to experience growing up. Traveling around and meeting people from different cultures, backgrounds, and socioeconomic levels transformed his life in many ways, teaching him how to be a good-hearted person, friend, and business person. One of the little moments that helped shape him as a person happened early on in his life. He remembers his grandfather’s advice to this day: always remain humble, because success can be temporary; when better, you do better; and don’t live life with your foot on the accelerator – sometimes you have to slow down and pay attention to the small things that matter. [Listen from 2:25]



Making His Way

Naivete paved the way to clearing his own path about what he wanted to achieve, Ray confesses. “I never believed I should be in anyone’s shadow.” Even with all his successes, during high school and after in his professional life, it never felt like it was enough. He knew he had so much more to give after selling and exiting his sports agency, so he went back to the drawing board. His curiosity about money led him to the financial sector. Throughout this journey he experienced soaring highs and humbling lows, and though the lessons took a little time to stick, he came out of it wiser and more experienced, ready for life’s next challenge. “I never had the thought process that I couldn’t rebuild,” Ray shares, “when something happened I thought ‘okay, I need to learn from this because I didn’t learn the first two times.” [Listen from 7:30]

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Ray’s Next Big Move

Ray’s first foray into motivational speaking came at the request of his business partner at the time. A military veteran, she had asked him to speak to the Navy base, as he had been doing some coaching for his kids and her kids. At first, he was reluctant – he wasn’t a public speaker, so why would he? Sure, he had some resonance with the kids when he spoke, but those were kids. Despite his concerns, he went down to the base and spoke. Then he was invited to speak again. After his second time, they offered to pay him. “I said ‘oh, that’s a thing,’” Ray tells Barry. This snowballed into ten years of traveling across the world speaking to militaries and corporations about his experiences. Ray got to talk to a multitude of people, including James Baldwin, who told him to never stop reading books. [Listen from 11:40]

Ray’s authenticity is off the charts, according to Barry. He’s not trying to be anybody else, he’s trying to be himself. He shows up with his calling cards of knowing better and doing better, and that resonates with people. “I think it’s admirable when people practice that as a behavior, as part of their being,” Barry says. “[You] can just find books to educate [yourself], to be curious. That doesn’t cost anything, but it can return so much.” [Listen from 15:00]

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Sometimes, You Have to Hit the Brakes

“A lot of times I would run so fast because I thought I had to be somewhere at a certain time, on my time,” Ray tells Barry. Life has a way of telling you that sometimes it moves on its own time. No matter how fast you think you have to move, you’re going to miss some things if you don’t slow down to appreciate them. “The greatest thing about being present in the moment to tell your story is knowing there’s more to write. You don’t take a book and skip the pages – you have to read every page to get the full context.” That’s where Ray is right now, he shares. [Listen from 16:05]

He talks about founding Ovationz. “[We] had a little motley group [with] everybody having successes on their own, but [we came] together saying ‘Hey, we can build something special.’” Almost a year later, it’s become a company taking on revenue. Watching the formation process from a Post-It note and a terrible name to creating unique moments through the established company is amazing, Barry says. [Listen from 17:45]

Looking Ahead

“We’re on the precipice of building something that not only connects people but builds a more prosperous world. It makes you want to get up every single morning to create and not worry about everything that distracts you,” Ray shares. [Listen from 23:35]