On Feb. 6, Sidwell welcomed back Modi Oyewole ’05 as a Meeting for Learning speaker to commemorate Black History Month. He told the high school students the story of how Sidwell cultivated his passion for music, and how this passion ultimately became his full-time career. 

Oyewole is an entrepreneur with experience in the music and entertainment industries, from co-founding his radio show and blog with fellow alumnus Quinn Coleman ’07 to producing concerts and eventually creating the award-winning Trillectro music festival with over 20,000 annual attendees. Additionally, he has worked with companies and artists such as Netflix, Giveon, Def Jam, Dickies, Red Bull, Spotify, Kid Cudi, Epic Records and, most recently, Nike. 

Oyewole shared that he is a “product of his own lived environment,” and that a CD burner and Napster in middle school changed his life. He would go around the school in search of students who wanted the latest hits, selling them mixes he created on CDs. His CD business not only showed him a small-scale version of entrepreneurship but also gave him the courage to pursue a career in the music industry. It proved that his interest was somewhere he could find success despite not typically being considered a “prestigious” field of work.

Growing up, Oyewole’s two Nigerian-born parents supported his passions. Despite the inconsistency of the music industry, he made a successful career for himself. His parents are very proud of him for his success in doing what he loves. Oyewole not only had a supportive household but also found support from the Sidwell community. 

Oyewole has accumulated a substantial social media presence over the past few years, with 17,600 followers on Instagram alone. In a recent post, he reflected on his presentation at Sidwell, saying he was impressed by the amount of participation and interest the upper schoolers showed in what he had to say. He wrote that many students reached out to him through Instagram to express gratitude or ask questions. 

He posted an anonymous conversation of a text that a Sidwell student had sent him highlighting the similarities they saw between themselves and Oyewole when he was younger: “I usually sit back and fall asleep but everything you said connected with me in a way a lot of things in my life can’t do … I’ve wanted to be an artist since I was a kid, but I stopped writing and focused on school and other aspects of my life because of the pressure put on me to go to a good college. I just want to thank you again for helping me think of my dreams. You are the best speaker the school has ever had.”

In his presentation, Oyewole also noted that one of the inspirations he had in choosing his career path was Upper School English Teacher Ashish Patwardhan: “My English teacher, Mr. Patwardhan, changed my life by showing me what passion is, and how I eventually found mine, followed it, and never looked back, about investigating the pressures of attending a competitive, prestigious high school,” Oyewole wrote in an interview. He was happy to find Patwardhan still teaching English at the place where it all started, and Oyewole even included a picture of the two of them together in his Instagram post.

Many Sidwell students can feel pressured to gravitate toward certain subjects due to the school’s reputation and distinguished alumni. However, Oyewole is an example of how individuals can find their passions and formulate their chosen career path around them.

Freshman Nadia Lall touched on the positive impact Oyewole had on her: “His presentation inspired me to follow my passions. It’s hard to not think about how decisions that you make right now will affect you in the future. However, I think how he worked hard at what he was passionate about without questioning what may come of it resonates with me,” she said.

Freshman Jake Snow agreed, saying, “Modi’s presentation was really interesting to me because it made me think about my future in ways I had not before. I admired the fact that he took his passion and made it his career. He proves that careers are not limited and you can make money doing anything you love.” 

Additionally, freshman Ava Tavakkoli shared how she is interested in how one’s childhood informs their future life decisions and career paths: “Modi Oyewole attended Sidwell just like I am right now. He was able to formulate such a successful career path for himself while following his own passions that he discovered at an early age, even at this school, and I feel very inspired by that,” she remarked.

Oyewole’s presentation left a lasting impression on the Sidwell community, as he inspired young students to reframe losses as lessons and take the leap of faith to follow their dreams.