Before the fame, the vibes, and the viral content, Joseph Onaolapo, popularly known as Jay On-Air was just another Lagos hustler trying to find his voice in a loud city.
In a candid interview on the WithChude podcast, the 31-year-old content creator and on-air personality took fans down memory lane, sharing a raw and emotional account of his pre-fame struggles. From unpaid jobs, street survival, and a secondhand clothing business.
Jay’s Lagos journey began with big dreams and bold moves. “I want to roll with the big boys and big girls,” he said, recalling his arrival in the city. But reality hit hard.
Despite flooding radio stations with his CV, nothing clicked. Eventually, he landed a gig with an online radio station, but it didn’t go as expected. That’s when he switched lanes into the corporate world, taking on roles like executive assistant and communication executive.
But even that came with its share of heartache. “I was owed salaries a lot. I was treated like I was not worth anything,” Jay recalled. The constant feeling of being undervalued eventually broke him, and he walked away into the unpredictable world of entrepreneurship. He revealed:
“I was selling Okrika by the way. And it was becoming a thriving business. I was becoming the shorts guy. People would come to me to buy shorts. I tried.
This one was actually starting to work. It was starting to work. I remember, I am a big fan of Waje. And I remember she was having a concert at the time. And I could afford it.
“Right. To use this money. So it was such a big deal to me. And it just hit me because of N10,000.”

But just when the business was catching fire, the COVID-19 pandemic shut things down. He shared:
“I didn’t have a job. Nothing was working for me. And then people were on TikTok… and I was just like, what is happening here?”
“I wake up in the morning. I have my bath. I would be on TikTok… How many sounds can I create in one hour?”
It was in those moments of sadness and uncertainty that Jay rediscovered himself. TikTok became therapy. Content became healing. And eventually, the hustle paid off.