Key Takeaways
- Drake’s “Laugh Now Cry Later” video changed how brands viewed Druski and helped take his career mainstream.
- Surviving an armed robbery pushed Druski to fully commit to becoming a comedian.
- Rejection from major companies like Netflix, Amazon, and FX led Druski to invest in himself and bring his ideas to YouTube.
While we’re used to Druski being the ultimate funnyman, he showed us a more serious side of himself that we don’t see too often on “The Diary Of A CEO.” On Thursday (Sept. 24), the comedian sat down with Steven Bartlett to chat about what it took for him to become one of the most sought-after internet personalities of our time, including how he dropped out of college, was robbed at gunpoint, and turned rejection into fuel for his own ideas.
“All of the people I look up to are all like comedic legends, and I feel more connected to them than anything I’ve ever felt in my life. That is my purpose,” Druski told Bartlett of the epiphany that ultimately led him to leave school and go all-in on being a comic.
He later recalled sitting in a room with no mattress after his car was repossessed without a single fear in the world: “I fear nothing because I’m like, ‘I have nothing left.’” Even then, the Maryland native kept going despite all the odds stacked against him.
Watch “The Diary Of A CEO” interview in full below, then keep scrolling for some of our favorite moments from their conversation.
How Drake’s “Laugh Now Cry Later” video changed Druski’s career
An hour into his sit-down with Bartlett, Druski revisited the life-altering call that introduced him to the mainstream. “The thing that changed my life, at the time, was Drake calling for the ‘Laugh Now Cry Later’ music video. Everything shifted after that,” he remembered. “Brands started to take me seriously. It was no more sending free merch.”
He explained that “being seen on a higher level” alongside familiar faces like Lil Durk, Marshawn Lynch, and Kevin Durant carried a lot of weight for him. The 2026 BET Awards host added, “That shifted everything because brands started to see me in a broader light. They started to see me as an actual star.”
Druski says being robbed at gunpoint made him go all-in on comedy “or die trying”
A little earlier in the conversation, Druski opened up about the “out-of-body feeling” he had being involved in an armed robbery. He recalled, “I came home to be in this predicament where I have a gun to my head now. Now, it’s like, ‘How did I even get here?’”
“That was the last moment I said, ‘Okay, if I’m going to do anything, I’m going to become a comedian or die trying.’ That’s it. I have no other outlet,” the comedian continued. According to Druski, he and a friend found themselves in a “bad scamming situation that went left,” and evidently, surviving the incident wasn’t something he took for granted.
How rejection from Netflix and Amazon pushed Druski to invest in himself
While Druski’s success has given way to all kinds of shows like “Coulda Been House,” “Coulda Been Daddy,” and “Coulda Been Records,” to name a few, he hasn’t forgotten the rejection he faced before making it big. When asked about Netflix and Amazon turning him down, the internet personality stressed that it “wasn’t just one time.” In fact, he spent “years and years” sending proposals to companies, including FX, only to hear no after no.
Eventually, Druski reached the point where he decided to bet on himself. “If I’m getting money from these companies and they’re paying me, instead of going and buying a car or another house — maybe nice jewelry and all this stuff — I’m going to invest in myself,” he said. “I decided to just go... [with] all these show ideas that I had, I’m going to do it on YouTube and spend my own money to invest into it.”
Druski added, “Now they want to purchase these shows that we’ve made and do more in the future. So, now it’s a bidding war.”