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Conversations with Olaitan Ojeleye

Today we’d like to introduce you to Olaitan Ojeleye.

Hi Olaitan, thanks for joining us today. We’d love for you to start by introducing yourself.
My business partner Chris White and I created our company, SidelineStories, about a year ago to give ourselves a platform to create and share content freely online. We focus mainly on sports-related content, capturing the energy and emotion that make each game unique. Over the past year, we’ve experienced more success and attention than we ever expected, gaining access to a variety of sporting events both within our region and beyond. None of this would have been possible without the dedicated team we’ve recruited; a group of passionate, hardworking individuals who share the same vision of growing our name and making SidelineStories a recognized brand in the sports media space.

We all face challenges, but looking back would you describe it as a relatively smooth road?
It hasn’t always been easy. There are times when things don’t go smoothly with the team and moments when we’re unable to gain access to certain events we scheduled to cover. When that happens, it can cause major setbacks and force us to restructure our plans on short notice. These challenges can be frustrating, but they’ve also taught me the importance of flexibility, communication, and problem-solving under pressure.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
Personally, I am a freelance photographer, but I also run web and social pages that operate as a collection of creatives covering sporting events across the nation. Photography has always been a major part of my life, but my true passion lies in photographing people. I love being able to capture raw emotion and tell stories through my images; to make viewers feel something just by looking at a moment frozen in time.

What I’m most proud of is how far I’ve come. I’ve been taking pictures ever since I was a kid, but I started doing it professionally about six years ago. If you had asked me ten years ago where I saw myself, I probably would have said I had no idea. Back then, I don’t think the younger me had the courage to chase his dreams the way I am now. Every step I’ve taken in this journey has pushed me to grow, not only as an artist but also as a person.

What sets me apart from others in my field is my artistic background and my ability to evoke genuine emotion through my imagery. I don’t just aim to take beautiful pictures. I strive to create stories that connect people, make them feel seen, and leave a lasting impression.

What were you like growing up?
I was born in Nigeria but moved to the United States when I was about seven years old. Living in the U.S. opened my eyes to a new way of life, from the education system to the social environment. I spent seven years here before moving back to Nigeria, which was hard. I felt out of place. I didn’t know where I belonged. It was difficult at first to readjust to the cultural expectations, language expressions, and overall lifestyle that I had grown somewhat distant from while in the U.S. Moving between two very different countries taught me how to adapt quickly, understand people from diverse backgrounds, and appreciate both cultures for their unique values. Even though it wasn’t always easy, those experiences shaped my perspective and made me more open-minded and resilient.

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