For comedian Druski, the ball is in his court now.
Druski has always loved making everyone around him laugh, from his family to his classmates. Thanks to the internet and his sketches, he now makes millions more people laugh. But he has turned that attention into a business of his own, headlining his own shows. He credits Drake’s “Laugh Now Cry Later” music video with helping shift the trajectory of his career.
“Everything shifted after that because brands started to take me seriously. It wasn’t no more ‘send in free merch’ and ‘oh you get this’ or we’ll bring you out to this event and we just want your appearance and you can get in free.’ Now it’s transactional with everything,” Druski said in an interview on “The Diary Of A CEO” with host Steven Bartlett.
Forbes listed Druski on its top creator list in 2026 with an estimated $20 million in earnings. Brands he has worked with include Nike, Beats by Dre, Raising Cane’s, Mountain Dew, T-Mobile, and Dunkin’ Donuts.
He has put his earnings to good use, self-producing and investing in shows such as “Coulda Been Love,” “Coulda Been House,” and “Coulda Been Records” on YouTube, as well as activations such as the “Coulda, Woulda, Shoulda Tour” and Coulda Fest.
Going full throttle also coincided with rejections from various streaming giants, including Netflix, Amazon, and FX.
“I eventually said, if I’m getting money from these companies and they’re paying me, instead of going and buying a car or another house or maybe nice jewelry and all this stuff, I’m going to invest in myself,” Druski said on the podcast.
“You’ve seen in the Druski universe of taking it to another level with all the sketches and the production I’ve done and the millions of dollars I’ve spent and all these things,” he added. “I started to just believe in myself and not turn around and try to ‘Oh I’m going to come back and try to do the same proposal again in a better way.’ It’s like I’m gonna just bet on myself.”
