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The Diary Of A CEO with Steven Bartlett

Kevin Hart: They're Lying To You About How To Become A Millionaire! I Was Doing 28 Sets A Weekend!

with Kevin Hart

Published November 20, 2025
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About This Episode

The host interviews Kevin about his journey from an unfocused teenager in North Philadelphia to a globally successful stand-up comic, actor, and entrepreneur. Kevin describes how his strict mother, his father's failures, and his own 'dummy moments' taught him to finish what he starts, persist through a 13-year grind before his big break, and later learn the worlds of business and investing by admitting ignorance and asking questions. They also explore the costs of relentless ambition, his approach to fatherhood and masculinity, setting boundaries to manage stress, and his evolving perspective as reflected in his stand-up special "Acting My Age."

Topics Covered

Personal narrative Entrepreneurship Stand-up comedy Investing Persistence Fatherhood Relationships Masculinity Mental health Personal development

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Kevin believes you must be willing to openly admit what you don't know in order to enter the right rooms, learn, and access real opportunities.
  • His strict mother drilled into him the importance of finishing what you start, which later became the foundation of his 13-year grind in comedy before his breakout moment.
  • Kevin's career graph was flat for years as he worked countless unpaid or low-paid sets, then gradually rose through clubs, theaters, arenas, and film before expanding into production and investing.
  • He argues that constantly quitting and jumping to new ideas prevents people from ever completing anything, whereas committing deeply to one craft opens doors to everything else.
  • Kevin only began to understand business and investing after dropping his defensiveness, asking basic questions, and allowing himself to be the "dummy" in the room.
  • He stresses that in business you often have to detach emotion, bring in better talent, and step back from trying to control everything in order to grow.
  • Kevin sees time as the main cost of his ambition; he's happy but stressed and has had to learn to set hard daily boundaries on work and calls.
  • His model of being a "good man" centers on leadership, responsibility, and accountability, shaped largely by his father's shortcomings and late-life remorse.
  • Chris Rock's advice to make the whole world laugh, not just his neighborhood, pushed Kevin to broaden his material and think globally about his craft.
  • Looking ahead, Kevin's ideal future is a simpler life of small comedy clubs, golf, and family time, supported by "mailbox money" from businesses he has built.

Podcast Notes

Opening mindset: admitting ignorance and entering the right rooms

Being willing to be the 'dummy' to access opportunities

Kevin says you can't be afraid to verbalize your ignorance[0:58]
• He notes many people stay silent about what they don't know, which keeps them out of important conversations and opportunities.
Example: his initial skepticism about investing[1:03]
• Kevin recalls thinking investment pitches promising "20x, 30x" returns were scams and refusing to participate.
• He comes from an environment where "everything is a scam," so his default was deep distrust.
How asking questions changed his trajectory[1:01]
• By asking basic questions like "How does investing really work?" he could enter better conversations and new opportunities.
• He frames his current success as a direct result of once being willing to be the ignorant person in the room.

Early life in North Philadelphia and family background

Growing up in a tough environment

North Philadelphia upbringing and family dynamics[1:48]
• Kevin grew up in North Philadelphia with an older brother who sold drugs and a father frequently in and out of jail.
• His mother was determined not to let Kevin follow his brother's path and became very strict with him.
His mother's strictness vs. brother's leniency[5:59]
• He says his brother had more leniency-later curfews and freedom-but also got into crime and drugs.
• Kevin "got the short end of the stick" with curfews and restrictions, which made him crave hanging out even more and rebel in areas like school and activities.

His mother Nancy Hart's influence and lessons

Bible and rent checks story[12:04]
• Struggling to pay rent, Kevin asked his mom for help; she refused until he started reading the Bible.
• He lied that he was reading it, and she kept insisting.
• In desperation he finally opened the Bible and multiple rent checks fell out-she had hidden them there as both help and a lesson.
Lesson of finishing what you start[12:30]
• As a child he often wanted to quit activities; his mother forced him to finish them even if he did them with a bad attitude.
• As he matured, he realized starting things he didn't intend to finish was pointless and that he was too comfortable quitting when things got rough.
• He adopted a rule: if he starts something, he must see it all the way through, so he can be proud he put a "period on that sentence."

Relationship with his father Henry Witherspoon

Father's troubled life and absence[6:55]
• Kevin describes his dad as a "fuck-up" in most people's eyes due to gang activity, crime, jail, and drugs.
• His dad lived with them only when Kevin was very young (around ages five to seven or eight); afterward he became a weekend or occasional dad and then disappeared more when on drugs or in jail.
Normalizing father absence in his neighborhood[9:12]
• He says in his environment almost nobody had a consistently present father, so his dad's absence felt normal rather than traumatic.
• He contrasts his own cramped home (sleeping in a hallway with bunk beds and no yard) with a friend's house that had a bedroom and backyard, which felt astonishing to him.

Realizing the consequences of not applying himself

High school 'dummy moment' and lack of planning

Senior ditch day and college shock[14:34]
• He skipped school with friends to go to a theme park for "senior day" and discovered all his friends had already applied to college, taken SATs, and received acceptances.
• He had no idea any of that was happening, realizing his friends had quietly left him to be "the dummy" who hadn't planned his future.
Lesson: nobody cares more about you than you[15:28]
• That experience taught him that nobody will give you the roadmap to success; you must seek information and care about your own path.
• His lack of desire to do things and failure to apply himself put him in a "fucked up position" early on.

Early jobs and first sense of direction

Working as a lifeguard and in a sneaker store[16:41]
• After community college he worked as a lifeguard and then at City Sports, a sneaker store.
• He became excited about sneaker sales, imagining a career path from manager to corporate roles despite lacking a formal degree.
Discovering stand-up via a coworker[17:41]
• A colleague named Alice at his workplace told him he should try stand-up because he was funny.
• He had never seriously considered pursuing comedy before; he knew he was funny and liked attention and stages, but hadn't connected that to a career.
• He tried an amateur night and instantly fell in love with stand-up.

Falling in love with laughter and the role of the comedian

Why the stage and laughter hooked him

The power of the laugh[18:44]
• Kevin describes there being "nothing better than the laugh"-hearing an audience laugh felt energizing and different.
• He felt that making people feel better and brightening their day was a "service of good," making him feel like a shepherd responsible for others' happiness.
Seeing comedy as a global service[19:24]
• He imagined bringing people to a shared destination of laughter that all connected back to him, and saw potential for this to scale globally.

Early stand-up grind and first industry recognition

Caroline's set and getting his first tape

Importance of the Caroline's tape[20:24]
• He recalls a set at Caroline's comedy club in the early 2000s as his best early-career set.
• The club handed him a videotape afterward; he saw this tape as "gold" because he could copy it and send it to clubs and casting directors as proof of his talent.
• He was about 18-19 years old at the time and started getting auditions and club spots based on that tape.

Agreement with his mother about pursuing comedy

Time-limited deal to make comedy work[22:19]
• Kevin's mom agreed to give him a certain amount of time to make comedy make sense and support himself.
• If he failed, he had to follow her plan: pursue education and get a job while studying.
Burning the boats on college[22:39]
• Kevin decided his plan did not involve college at all; he left community college and committed fully to comedy.
• Winning amateur nights convinced him it wouldn't be hard because he had no other option and put all his "eggs" in the comedy basket.

Career 'graph': years of flatlining before sharp rise

Describing his success vs. age trajectory

Early flatline: performing for food and small fees[24:22]
• He knew what he wanted to do around 18, but money and true career success flatlined for several years.
• At first he was paid in food or very small amounts; later he learned he could earn $20-25 per spot on weekends.
• He pushed himself to do 25-28 sets per weekend, eventually making $400-500 per week by about age 22.
Comedy festival and holding deal[25:11]
• Getting into a comedy festival exposed him to industry people who noticed his energy and potential.
• He landed a holding deal (he thinks with ABC) for about $250,000, but nothing ultimately came from it, leading to more "flatlining" while he waited for the phone to ring.
Creating his own opportunities and moving to LA[26:05]
• He realized he shouldn't just wait; he could create shows himself, get them picked up, and repeat that process.
• He moved to Los Angeles with no plan, experienced more stagnation, then decided to hit the road as a headliner doing both colleges and clubs.
Scaling from clubs to theaters to arenas[26:56]
• Over time he began selling out comedy clubs, prompting his team to suggest moving up to theaters.
• Theaters sold out quickly, leading to arenas as the next stage of success.

Breakthrough films and building a business ecosystem

Film hits: 'Think Like a Man' and 'Ride Along'[27:29]
• Producer Will Packer approached him to star in "Think Like a Man," which did around 90+ million dollars at the box office.
• They followed with "Ride Along" with Ice Cube, which did about 140 million, and then more films like "Get Hard" and "Central Intelligence" came in rapid succession.
Starting a production company and ventures[28:12]
• Even as the films were working, he wanted to create his own source of opportunity via a production company and later Heartbeat Ventures (a VC).
• He noticed his "likeness" opened doors, so he sought brand partnerships and ownership positions in various companies, mirroring a NASCAR car covered in sponsors.
Leveraging visibility into long-term revenue[28:35]
• He integrates his brand partners into his entertainment work-e.g., wearing partner products in films or including them in health and wellness activations-to bring them value.
• He wants partners like studios and streamers to feel secure that he never quits and always gives 100%, echoing his mother's lesson on finishing what you start.

Enduring a long stagnant period and why he didn't quit

Lack of belief from others early on

Friends doubting he could be a star[33:06]
• He recalls friends saying he was funny but not "comedian funny," and doubting he could ever be like Eddie Murphy or truly become a star.
You can't wait for other people's confidence[33:51]
• He argues nobody will have as much confidence in your decisions as you do, especially at the beginning, and their lack of belief shouldn't stop you.

13-year grind before his 'moment'

Staying for the love of the craft[35:09]
• Kevin says he didn't quit during years of low pay and doubt because he had finally found the thing he truly wanted to do.
• He believed there was "sun at the end of this dark tunnel" and was willing to figure out how to get there, including moving to LA and taking acting classes.
Learning from Cat Williams' BET Comedy Awards moment[36:24]
• Opening for Cat Williams, Kevin watched Cat destroy on stage at the BET Comedy Awards in a leopard suit and saw the audience's roar and standing ovation.
• He recognized that as Cat's "moment" and noted how ready Cat was-his material and performance fully met the opportunity.
• Kevin resolved to stay with his craft so that when his moment came, he would be prepared to knock it out of the park.
Kevin's own breakout: Shaq's All-Star Comedy Jam[39:01]
• He headlined Shaq's All-Star Comedy Jam alongside talents like Tommy Davidson, D-Ray, and Cedric the Entertainer hosting.
• He had one of his best sets ever; the crowd gave a standing ovation and the special's edit included a dramatic slow-motion walk-off he hadn't anticipated.
• Cat Williams was in the audience during this show, which Kevin notes as a curious alignment given Cat had been his earlier example of a "moment."
• This special led directly into taping his stand-up special "Seriously Funny" two weeks later, which benefitted from the attention and then "destroyed," propelling him to arenas.

Scooter Braun's fastball analogy about persistence

Most people drop out of the line[42:23]
• Scooter told him if a million-dollar prize was offered for hitting a fastball from the best pitcher, the first day's line would be huge.
• Most people would strike out once and leave; very few would get back in line repeatedly to try again.
• Kevin sees himself as someone who keeps getting back in line, while the line thins as others drop out rather than endure years of hard struggle.
Cycle of quitting and starting new things[44:44]
• He observes many people quit around years 2-6 of a pursuit, then chase quick money via new ideas, never completing anything.
• He insists that money becomes easier to understand and generate once you've built education, understanding, and a persistent mindset by sticking with one thing.
• He chose stand-up comedy as the thing he would finish, confident that being a strong headliner would open doors to all his later ventures.

Becoming T-shaped: deep expertise as leverage

Deep craft as the entry screw into other industries

Using stand-up as his foundational value[45:41]
• Kevin sees the value of self-his honed stand-up craft and star power-as the core asset that allows him into other rooms and businesses.
• Once in those rooms, people know him from entertainment and are open to talking about what he does and exploring partnerships.
Translating fame into partnerships[46:26]
• He mentions opportunities across domains like mental health, wellness, and education, where his voice can amplify existing platforms or help form new partnerships.
• He describes an ecosystem where his entertainment visibility is mirrored by a business of growth, and he integrates partner brands into his content and appearances as a way to elevate them.

Learning business and investing by asking naive questions

From seeing everything as a scam to understanding multiples

Dropping the fear of looking ignorant[48:06]
• Kevin emphasizes he's very secure being the "dummy in the room" and saying "I don't know what that means" or "explain that."
• He contrasts this with many people's insecurity, which leads them to stay quiet and hope someone randomly teaches them-something he says never happens.
Abundance of information for those who ask[50:57]
• He notes that while information isn't free, it's widely available via how-to content, motivational teachers, and domain experts online.
• He gives golf as an example: millions are made teaching others to improve their swing because people silently struggle instead of just asking for help.
Behind the curtain: how wealthy people invest together[54:04]
• Kevin agrees with an analogy about discovering that rich people are "behind curtains" doing deals he didn't even know existed.
• He describes how big investors rarely go alone; they prefer to invest together, bringing in others like "Gary," "Michelle," or "Melissa" to share in the opportunity.
• Successful investors use their resources to scale companies, create more jobs, and promote people from the bottom to leadership roles in new ventures.
His early suspicion of investment pitches[57:53]
• Initially, when told his money could "20x" or "30x" via a venture, he assumed someone was trying to steal from him and demanded slow explanations.
• He comes from a world where deals feel like scams, so he insisted on slowing people down to truly understand terms.
• Over time he understood the game of multiples and realized his participation and voice could materially increase a venture's prospects and value.
Using new knowledge to inspire others[59:02]
• Kevin now uses his acquired investment knowledge to have organic conversations like this one, which may encourage others who are already building things.
• He lists several tech and startup investments he's been involved in as examples of ventures people might not expect him to be part of.

People, trust, and building a team-driven empire

Running through wrong people before finding right ones

Growing with people vs. replacing them[1:00:23]
• Kevin says you encounter wrong people before the right ones; you can either discard them or try to grow together.
• He prefers the idea of growth-starting together and ending in a different, better place-even though some won't make it because they don't want the same for themselves.
Emotions as a liability in business[1:01:26]
• He argues that emotions attached to business decisions are rarely beneficial to the business.
• He had to detach his emotions from "want" and instead focus on what would best position the business and the people who helped build it.

Learning to delegate and become solution-driven

Letting go of control[1:02:31]
• Kevin had to learn to stop trying to control everything and instead hire the right people, then actually let them do their jobs.
• He believes strongly in rewarding high-level talent and bringing in better personnel when his organization hits a ceiling.
Leadership as a constant problem-solving role[1:03:04]
• He describes himself as more of a hard drive for other people's issues than a person, constantly hearing problems and needing to provide solutions.
• He insists that if you're not solution-oriented in your communication, you shouldn't be in the chair of control.
• Effective leadership requires repeated clear communication so that everyone can trust and follow your direction.

Trust, exploitation, and ownership, especially in the Black community

Why certain communities get taken advantage of

Ignorance vs. laziness in bad deals[1:04:55]
• Kevin says the Black community often gets taken advantage of due to lack of knowledge, not laziness.
• Young talent may trust lawyers, managers, or others who say contracts are fine without knowing to get a second opinion or read the fine print.
Standardizing checks and removing offense[1:06:17]
• He now tells people he'll have someone else review documents not because he distrusts them, but because it's his standard practice.
• He encourages others not to take offense when asked to be background-checked or verified; it's simply good business.

Artists learning the business and going independent

Bad contracts as early lessons[1:08:52]
• Kevin notes many artists signed bad deals, later realized how they were taken, and then chose to create their own labels or companies.
• He likes seeing artists become independent, control their own labels or studios, and replicate major conglomerates' models on a smaller scale.
• He describes partnering with big companies in ways that allow him to own his own machine while leveraging their distribution and brand power.

Cost of ambition, stress, and future vision

Time and stress as the main costs

Insatiable ambition and daily stress[1:11:13]
• When asked if his ambition is insatiable, Kevin answers yes and says he is "stressed the fuck out" daily but functions within that stress.
• He nonetheless considers himself 1000% happy, but burdened by the constant feeling of "I have to do."
If life ended today, would he have regrets?[1:11:53]
• Kevin says if life ended now he could sit comfortably, feeling he did it correctly, applied himself, and improved life for those he loves.
• He views his last name and family name as much stronger now, and values having traveled, met many people, and served as an energy source of good.
Fear of his star dimming[1:13:44]
• He acknowledges a realistic fear that his current visibility won't last forever; nothing does.
• He wants to maximize this period of good health and strong mind, using his bright star to get into rooms he might not access later.

Example of reinvention: Jay-Z ('Hov') and Michael Rubin

Jay-Z's recreation across music and business[1:14:32]
• He highlights how Jay-Z had albums of varying perceived quality, then built Roc-A-Fella, helped launch artists like Kanye and Rihanna, and created major brands in spirits and clubs.
• He admires how Jay-Z keeps finding energy in new ventures, using earlier successes as backdrops and amplifiers for later ones.

10-year vision of a simpler life

Retiring into small rooms and family time[1:33:47]
• In 10 years, Kevin imagines himself performing in small, 30-seat comedy clubs twice a week, golfing, and spending time with his children and, hopefully, grandchildren.
• He wants "mailbox money" from businesses he built to fund this simpler life, with those ventures operating independently.

Acting My Age: embracing adulthood and changing priorities

What 'Acting My Age' means to Kevin

Letting go of a younger lifestyle[1:19:35]
• He says growing up means sacrificing the things the younger version of you with fewer responsibilities thrived on.
• He decided to let go of a certain version of life and embrace his age with all the fun that still comes with it.

Masculinity, being a good man, and fatherhood

Complex modern challenges for men

Foggy definition of a 'good man'[1:21:06]
• Kevin finds today's definition of a good man "so foggy" and believes change over time is natural, but the concept of manhood feels stuck.

His father's late accountability and its impact

Father's apology and focus on being a grandparent[1:22:17]
• In later years, his father acknowledged his failures, saying he was aware of what he didn't do and wanted to be the best grandfather he could.
• Kevin told him he couldn't change the past, but focusing on being a great grandparent would be a win.
Learning leadership by inversion[1:23:23]
• His father's lack of leadership put Kevin in a position to decide he wanted to do the opposite as a man and father.

Kevin's model of manhood and parenting

Leadership, responsibility, and accountability[1:23:23]
• He wants his two sons to see him as a leader who takes responsibility and is accountable.
• He tells his kids their father deals with struggles they'll never know because it's his job to carry that burden and make life easier for them.
Balancing emotions and awareness of 'sharks'[1:24:20]
• Kevin isn't against emotions but warns that in a world of prey and sharks, overt weakness can be taken advantage of.
• He emphasizes being smart and aware about when and where to be vulnerable, while still sharing openly with his children.
Respecting differing approaches to manhood[1:25:22]
• He stresses that his model of manhood doesn't have to fit anyone else's and vice versa.
• He criticizes a societal tendency to fight and label others as dumb if they don't see things the same way.

Key advice from Chris Rock: think globally

Broadening his comedic perspective

Don't just make your block laugh[1:27:17]
• Chris Rock told Kevin early in his career that he shouldn't just make people in his neighborhood laugh; the world is much bigger.
• He advised Kevin to get out of the country and figure out how to make the world laugh so his comedy could be much better.
From hyper-local to universal material[1:27:54]
• At the time, Kevin's material was very specific to his block and experiences (e.g., neighborhood drugstores), which not everyone could relate to.
• Chris encouraged him to broaden his material so he could perform anywhere in the world without needing to change who he was.

Stress management, boundaries, and mental overload

Stress vs. mental health struggle

Kevin's self-assessment on mental health[1:29:28]
• He says he hasn't struggled with his mental health in the sense of anxiety or other conditions; his issue is more stress and doing too much.

Learning to shut down each day

Setting a daily cut-off[1:29:54]
• He now intentionally shuts off at a certain time each day-stopping calls and work-even if people want to keep going.
• That shut-off time has been moving earlier as he realizes late-night work is unhealthy.
Needing silence[1:30:37]
• He values silence, such as riding in a car with no music, as a counterbalance to constant mental racing.

Letting go of others' expectations

From over-giving to preserving himself[1:32:00]
• He used to care deeply about others' feelings and would keep doing things to avoid disappointing them, putting everyone before himself.
• Now he is comfortable saying he doesn't care if people understand when he sets boundaries like "I'm done for today."
Analogy of the overflowing plate[1:32:30]
• He compares constant demands to people endlessly piling food on your plate; eventually, you can't breathe and "bust."
• He extends this to mental overload, saying people "pop" from too much, and their snapping isn't craziness but a breaking point.

Closing reflections and impact

Host's personal appreciation of Kevin's work

Comedy as escapism and connection[1:34:47]
• The host shares that he first watched Kevin's specials during a lonely, difficult time as a teenager and found them to be moments of escapism and joy.
• He describes Kevin as a source of joy and connectivity for millions, including bringing his own family and girlfriend to Kevin's shows.
Kevin's view of his role[1:34:35]
• Kevin reiterates he aims to be an energy source of good, bringing people together through his work.

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Admitting what you don't know and being willing to look like the 'dummy in the room' is a powerful strategy for accessing the knowledge, rooms, and opportunities that transform your trajectory.

Reflection Questions:

  • • Where in my life am I pretending to understand something instead of openly admitting I don't know and asking for clarification?
  • • How might my career change if I deliberately sought out rooms where I'm the least knowledgeable person and asked basic questions?
  • • What is one area this week where I will explicitly say "I don't understand this, can you explain it to me?" to someone more experienced?
2

Finishing what you start-sticking with one core craft or path long enough to get good-creates leverage and opens doors that constant quitting and idea-hopping never will.

Reflection Questions:

  • • Which important project or path in my life have I been closest to abandoning before truly seeing it through?
  • • How would my options expand over the next 5-10 years if I committed deeply to mastering just one core skill or domain?
  • • What is one initiative I'm currently involved in that I will commit to finishing before I allow myself to start something new?
3

Struggle and long periods of apparent stagnation are often the training ground that prepares you for your eventual 'moment'-the key is to stay ready so you can fully capitalize when that moment arrives.

Reflection Questions:

  • • When have I experienced a long 'flatline' period that, in hindsight, actually prepared me for a later opportunity?
  • • In what ways can I use my current frustrations or lack of visible progress as practice and preparation rather than as signals to quit?
  • • What specific skills, systems, or habits should I be sharpening now so that if a major opportunity appeared tomorrow, I'd be ready to execute at a high level?
4

In business and leadership, you must learn to separate emotion from decision-making, delegate to capable people, and focus your communication on solutions rather than complaints.

Reflection Questions:

  • • Where am I letting emotional attachment to people, habits, or old structures stop me from making the best decision for the mission?
  • • How could delegating more and trusting qualified people to do their jobs free up my time and mental energy for higher-leverage work?
  • • What current issue could I re-approach this week by asking, "What is the clearest, most constructive solution here?" rather than dwelling on blame or frustration?
5

Healthy ambition requires boundaries: if you don't intentionally shut down, protect silence, and say no, other people's demands will consume your capacity and eventually lead to overload.

Reflection Questions:

  • • How do I currently recognize that I'm approaching my physical or mental limits during the day, and what do I typically do in response?
  • • What would it look like to set a firm daily 'cut-off' time for work and communication, and how might that improve my presence with myself and others?
  • • Which recurring commitment, call, or interaction could I pause or reschedule this week to create a small pocket of true silence and recovery?
6

Your upbringing-even the failures and absences of those before you-can serve as a blueprint for the kind of leader, parent, or partner you choose to become through conscious inversion and accountability.

Reflection Questions:

  • • What patterns from my family or early environment do I most want to repeat, and which do I most want to invert?
  • • How might openly acknowledging my own past mistakes, like Kevin's father did, strengthen my relationships and my sense of integrity?
  • • What is one concrete behavior I can adopt or change this week to better align with the type of leader or role model I want to be for the next generation?

Episode Summary - Notes by Dakota

Kevin Hart: They're Lying To You About How To Become A Millionaire! I Was Doing 28 Sets A Weekend!
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