The Diary Of A CEO with Steven Bartlett

Episode: Kevin Hart: They're Lying To You About How To Become A Millionaire! I Was Doing 28 Sets A Weekend!
Date: November 20, 2025

Overview

In this candid and wide-ranging episode, Steven Bartlett sits down with comedy superstar, entrepreneur, and investor Kevin Hart to discuss the realities behind his meteoric rise from a tough upbringing in North Philadelphia to global success. The conversation explores the myths around wealth, the true cost of ambition, the value of relentless focus, and the power of embracing ignorance to learn. Kevin shares never-before-told stories about his painstaking thirteen-year grind before finding fame, his philosophy for building empires, and powerful lessons on resilience, personal growth, fatherhood, mental health, and what it really means to "finish what you start."

Key Discussion Points & Insights

1. The Power of Embracing Ignorance & Being the "Dummy in the Room"

• Kevin stresses the importance of admitting what you don't know as the foundation for real growth and success.
  • "You can’t be afraid to verbalize your ignorance that’s holding you back." (01:09)
• He reflects on his initial skepticism about investing, his willingness to ask questions, and his journey from dismissing ventures as scams to understanding how real wealth is built.

2. Upbringing, Family Dynamics, and Early Lessons

• Kevin paints a gritty picture of his childhood in North Philadelphia, with a strict, ambitious mother, a frequently incarcerated father, and a brother involved in crime.
  • "My brother sold the drugs. My dad was always in jail, out of jail. And my mom wasn’t gonna let that happen with me." (01:52)
• A standout lesson from his mother: Complete what you start, no matter how tough it gets.
• Memorable story: His mother hides rent checks in his Bible, refusing to give him money until he actually opens and reads it.
  • “I open up the Bible, and like, my checks, rent, like, multiple months of rent checks have fell out. And I was like, you know what? That’s pretty amazing." (12:07)

3. The Thirteen Years Before "The Moment"

• Kevin reveals the sheer grind—doing up to 28 standup sets a weekend for years, commuting from Philly to New York, barely scraping by, driven only by passion.
  • “I was doing 25 to 28 sets a weekend. I worked that for a very, very long time... Most people opt out at year two and want to go find a [different path].” (01:52)
• He describes the "flatline" years, when success seemed distant, friends doubted him, and money was nonexistent.
• He encourages focus over trying “17 things” simultaneously.
  • “You never finish nothing. The thing you think you’re focusing on, you keep quitting to start something else... It's just a cycle.” (45:30)

4. The Breakthrough: Being Ready for Opportunity

• Kevin’s “moment” comes at Shaq’s All Star Comedy Jam, after 13 years in the game—a set that changed his trajectory overnight.
  • “That was the moment that then took me and shot me out the cannon.” (39:44)
• He likens waiting for your break to standing in line for a million-dollar shot—everyone leaves the line except the relentless.

5. From Comic to Business Mogul: How to Build an Ecosystem

• Kevin details his journey beyond comedy, leveraging his “star power” into production companies, brand partnerships, ownership stakes, and venture capital.
• The importance of creating opportunities, being the owner (not just the employee), and integrating business ventures synergistically.
  • “How do I put myself in a position to be a part of everyday movement in life? ... I embed the products or partnerships I'm now operationally attached to into the ecosystem of entertainment.” (27:25)
• On scaling up: from comedy clubs to theaters to arenas to global brands.

6. The Role of People, Networks, and Learning the Game

• Kevin attributes much of his later success to “getting behind the curtain”—being in rooms he once didn't know existed, asking questions, learning from others.
  • “You’re never going to run into a person who’s randomly gonna talk about the things you wish you had more knowledge in. Information is not free, but it’s available.” (49:47)
• Importance of finding the right people and being willing to leave behind (or grow past) those who aren't right for the journey.
• Business success relies on solving problems through others and learning to communicate and delegate, not just working harder.

7. Trust, Responsibility, and Learning from Mistakes

• Discussion of personal responsibility in business, especially in communities where financial literacy is less common.
  • “We get fucked over more than we don’t because of the lack of knowledge.” (66:51)
• The value of learning from painful contract mistakes and then building systems (“second eyes”) to avoid being victimized again.

8. The Cost of Ambition & Mental Health Struggles

• Kevin pulls back the curtain on the costs of relentless work and ambition—frequent stress, the challenge of being present, and learning to establish boundaries.
  • “I’m 1,000% happy, but I’m stressed out with the concept of I have to do.” (72:16)
• Learning to “shut off,” embrace silence, and be comfortable with others not always understanding his choices.

Notable Quotes & Memorable Moments

• On sticking it out:
  “Nobody has the confidence in the decisions that you’re making for yourself like you do... The money is never coming fast.” (33:53)
• On advice from Chris Rock:
  “Chris Rock told me... ‘Get out the country and figure out a way to make the world laugh... The world is so much bigger than your block.’” (87:52)
• On learning to ask questions:
  “I am extremely secure in saying, I don’t know what that means. Explain that.” (49:24)
• On dealing with mental overload:
  “You have to get to a point to where you actually get that and are okay with that... More today than ever, you’re seeing more people pop from mental overload, man.” (92:08)
• On fatherhood and legacy:
  “My last name and my family name is much stronger today than it was yesterday... I was an energy source of good, to bring people closer together through all things that I’ve done.” (72:37)

Timestamps for Important Segments

• Opening on admitting ignorance and asking questions: 01:09
• Kevin’s upbringing and lessons from his mom: 01:52 – 14:31
• The long “flatline” grind in comedy: 24:02 – 27:25
• Breakthrough at Shaq’s All Star Comedy Jam: 39:44
• On the myth of fast money and entrepreneurial focus: 33:29 – 46:47
• Building the business ecosystem & leveraging celebrity: 27:25 – 33:22
• Learning from being a “dummy” in investing and business: 49:24 – 55:25
• Forming the right networks and learning to delegate: 61:05 – 66:13
• Real talk on trust, responsibility, and contracts: 66:13 – 71:42
• Reflecting on the cost of success and happiness: 72:08 – 74:38
• Discussion on leadership, masculinity, and being a good man: 81:50 – 87:16
• Best advice ever received (from Chris Rock): 87:52
• Mental health and stress, learning to unplug: 90:07 – 92:08

Final Takeaways & Tone

The episode is simultaneously inspiring, brutally honest, and often hilarious—delivered in Kevin’s signature unfiltered, rapid-fire style. The key message: True success requires relentless focus, humility about what you don’t know, a willingness to endure hardship far longer than you think, and a commitment to finish what you start—even if it takes 13 years to see your moment.

Bartlett and Hart share a palpable mutual respect—the conversation is authentic, at times vulnerable, and packed with gems especially for aspiring entrepreneurs and creatives struggling through their “flatline years.”
Finish what you start. Be willing to be the dummy in the room. Ask, learn, and when your moment finally comes, be damn sure you’re ready for it.