Kevin Hart: They're Lying To You About How To Become A Millionaire! I Was Doing 28 Sets A Weekend!
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this candid episode of The Diary of a CEO, world-renowned comedian and entrepreneur Kevin Hart opens up about his extraordinary journey from a struggling kid in North Philadelphia to building a billion-dollar entertainment empire. (03:01) Hart shares intimate details about growing up without his father, his mother's strict parenting that shaped his work ethic, and the thirteen grueling years of rejection and failure that ultimately led to his breakthrough moment. (38:14) The conversation explores how Hart transformed from someone who "fucked off" opportunities in his youth to becoming a disciplined business mogul who now operates across comedy, film, production, venture capital, and brand partnerships through his company Heartbeat.
- Main themes: The episode focuses on persistence through failure, the importance of finishing what you start, building business acumen from ignorance, and redefining modern masculinity while maintaining traditional leadership values.
Speakers
Kevin Hart
Kevin Hart is a world-renowned comedian, actor, producer, and founder of Heartbeat, a global multi-platform entertainment company. He has built a billion-dollar career spanning stand-up comedy, blockbuster films, and successful business ventures. Hart is also the author of bestselling books including "It Will All Work Out: The Freedom of Letting Go" and features in the upcoming Netflix comedy special "KEVIN HART: ACTING MY AGE."
Steven Bartlett
Steven Bartlett is the host of The Diary of a CEO podcast and a successful entrepreneur and investor. He built his marketing expertise over fifteen years before launching his media business and expanding into various other ventures including the stock market.
Key Takeaways
Embrace Failure as Your Greatest Teacher
Hart emphasizes that "there is no success without failure" and that both go hand in hand. (05:05) He explains how failure provides amazing lessons and adjustments that make you sharper, teaching you how to approach situations you didn't know how to handle before. Rather than avoiding failure, Hart learned to embrace it as much as success because it's an essential part of growth. This mindset allowed him to persist through thirteen years of struggle in comedy, viewing each setback not as a reason to quit but as education for future success.
Commit Completely to One Thing Before Moving to Others
One of Hart's most powerful lessons came from his mother's insistence that he finish what he starts. (13:12) He made the deliberate choice that stand-up comedy was what he was going to finish, believing that if he focused and did it well, it would open doors to everything else he wanted to do. Hart criticizes the modern tendency to cycle through multiple ventures without completing any, noting that most people "opt out at year two" looking for quick returns instead of seeing something through to completion. This focused approach became the foundation for his entire business empire.
Don't Be Afraid to Be the Dummy in the Room
Hart credits much of his business success to being "extremely secure in saying I don't know what that means." (49:30) He shares examples of initially rejecting investment opportunities because he thought they were scams, but then asking genuine questions about how investing really works. This vulnerability and willingness to verbalize ignorance opened doors to conversations and opportunities that pretending to know would have closed. Hart argues that information isn't free but it's available - the only barrier is being too insecure to admit what you don't know.
Build Your Empire Through Strategic Partnerships and Ownership
Hart's transition from entertainer to mogul came through understanding how to leverage his star power to gain entry into business rooms where he could add value. (29:38) He realized that his entertainment success was like being a "car" that others wanted to attach themselves to, which led him to pursue brand partnerships, start his own production company, launch a VC firm, and create multiple revenue streams. The key was not just being a spokesperson but becoming an owner and partner who could genuinely elevate other businesses while building long-term wealth.
Set Boundaries to Protect Your Mental Energy
Despite his drive and ambition, Hart has learned the critical importance of saying "I don't really give a fuck" when it comes to others' expectations versus his own well-being. (92:52) He describes how he used to put everyone's needs before his own, leading to constant mental overload. Now he's comfortable shutting down earlier in the day, refusing additional calls, and not feeling guilty about prioritizing his mental health. Hart emphasizes that without these boundaries, "people just keep dumping more shit on your plate" until you can't function.
Statistics & Facts
- Hart performed 25 to 28 comedy sets per weekend during his early struggling years, driving from Philadelphia to New York daily and not coming home until 4 AM. (22:26) This relentless work ethic during his formative years built the foundation for his later success.
- It took Hart exactly thirteen years from his first stand-up performance to his breakthrough moment at Shaq's All Star Comedy Jam. (40:00) This timeline demonstrates the extraordinary persistence required for overnight success.
- Hart's movie "Think Like a Man" grossed over $90 million at the box office, while "Ride Along" made $140 million, launching his successful film career. (28:08) These numbers illustrate how his entertainment success provided the platform for his business ventures.
