[2] After the group won NBC's The Sing-Off in 2011, they released eleven albums, which have sold over 2 million records,[3] and have amassed more than two billion views on their YouTube channel.

At that time, his father had just come from medical school in Nigeria and an internship in Trinidad and Tobago to Loma Linda University, where he met his wife while she was doing her MPH.

Olusola started his education at Greater Philadelphia Junior Academy, but his family eventually moved to Owensboro, Kentucky, where he was raised.

He started as an academic music major, but decided to switch to East Asian Studies after being introduced to China through a 10-day Chinese government sponsored trip for 100 Yale students.

When Olusola was 12 years old, he was selected as the principal saxophonist of the United States Collegiate Wind Band and toured Europe during the summer for three weeks.

Olusola says that, during that spring break, his pre-med mentor C. Brandon Ogbunu (who was an MD/PhD student at Yale at the time) helped him to make the decision to finally go into music, saying medicine would always be there.

After a summer of neurobiology research at Yale, Olusola moved to Beijing for his academic year of Chinese study and continuously honed his celloboxing skills.

He started uploading celloboxing covers to his YouTube channel and performed for Ambassador Jon Huntsman, Jr. at his residence, and on Beijing Television with Li Yu Gang and Chong’er (Chinese beatboxer).

[citation needed] At the time the video was going viral, Olusola was contacted by Scott Hoying who was impressed by his musicality and beatboxing skills.

Hoying was forming a group with Kirstin Maldonado, Mitch Grassi, and Avi Kaplan to compete in season three of NBC’s The Sing-Off and he wanted Olusola to join.

After the taping of the show, Olusola did a brief stint as the cellist for Gungor on the David Crowder Band "7" Tour before returning with Pentatonix for the season finale.

The group won the Sing-Off title on November 28, 2011, which landed them a recording contract with Sony Music Entertainment and a $200K cash prize.

[21] On February 15, 2016, Pentatonix won their second Grammy in the same category for their rendition of "Dance of the Sugar Plum Fairy", which was featured on their holiday album, That's Christmas to Me.

[26] On September 16, 2019, Olusola married college admissions consultant Leigh Weissman in traditional Nigerian and American ceremonies.