Comedian and business mogul Kevin Hart credits a fierce dedication to "not quitting" and a willingness to embrace his ignorance as the foundation for an empire that took 13 hard years to build, according to his conversation on The Diary of a CEO. Hart, who views himself as a highly driven individual fueled by ideation, spent over a decade "flatlining" in the standup comedy world before achieving his moment of success. He points out that most aspiring professionals quit after two years, pursuing a quick return, thereby creating a "cycle" where they are "never completing anything".
Kevin Hart explained that his resilience was rooted in the strict lessons given by his mother, Nancy Hart, who was highly protective due to the "mistakes she saw that she made with my brother". Hart’s father was frequently in and out of jail due to drugs and crime in North Philadelphia, an environment where the "norm" was low. His mother was resolute: "You're not quitting". Hart recounted a powerful anecdote where he couldn't pay his rent, and his mother refused to help until he started reading the Bible, where he later found multiple months of rent checks hidden. This act gave him one of the "best lessons ever," solidifying the idea of not starting things that he’s not going to finish.
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For Hart, standup comedy was the thing he chose to finish, believing that if he focused and did it well, it would open the doors for everything else he wanted to do. During his early struggles, he drove daily from Philadelphia to New York, performing 25 to 28 sets a weekend. This commitment, which often left him coming home at 4:00 a.m., provided the "thickness and the depth" required for success. His patience paid off when his appearance on Shaq's All-Star Comedy Jam led directly to the success of his special Seriously Funny, which then "destroyed" due to the massive audience brought in by the Comedy Jam.
The visibility (his "likeness") generated by his entertainment career allowed Hart to pivot into ownership and entrepreneurship. Hart confessed to The Diary of a CEO that he previously viewed investing as a "scam" and was highly distrustful. Now, however, he advises others that they "can't be afraid to verbalize your ignorance". Hart is now "very secure in myself and being the dummy in the room," asking direct questions like, "How does investing really work?" or "What do you mean you make money while you are sleeping?". This practice of acquiring knowledge has led to the formation of Heartbeat Ventures and investments in companies like Function Health, 11 Labs, Moonpay, and DraftKings, allowing him to focus on business control and ownership.
Despite his monumental success, Hart admitted to The Diary of a CEO that he is "absolutely stressed out" on the daily. He manages the mental overload by defining a point in the day where he simply shuts off, asserting, "I'm not talking anymore today". He is "10,000% happy," but the stress remains a constant. Hart maintains that if his life ended today, he would be okay, believing he "did it correctly" by strengthening his family name and putting his loved ones in a better position. His future goal is not further empire building, but rather being a "grandpop," golfing, and doing sets at small, hole-in-the-wall comedy clubs, relying on the "mailbox money" generated by the autonomous businesses he has established. The entire graph of his career shows that the true exponential growth came after he leveraged his entertainment success into business ownership and control.
