
Gary Vee’s Emotional Confession About His Success & Family! | E207
Gary Vaynerchuk (guest), Steven Bartlett (host)
In this episode of The Diary of a CEO, featuring Gary Vaynerchuk and Steven Bartlett, Gary Vee’s Emotional Confession About His Success & Family! | E207 explores gary Vee Reveals Childhood Wounds, Superhero Drive, And Quiet Regrets Gary Vaynerchuk sits down with Steven Bartlett for a deeply personal conversation that moves far beyond his usual hustle and business narratives. He unpacks how his immigrant upbringing, especially his mother’s parenting and his role as an older brother, created an almost compulsive need to be a ‘superhero’ for others. Gary contrasts insecurity‑driven success with love‑driven success, explaining why his happiness is rooted in self-awareness, accountability, and serving people rather than professional accolades. The episode culminates in rare vulnerability as he discusses criticism, hidden regrets, the real cost of his ambition, and an emotional tribute to his mother’s impact on his life.
Gary Vee Reveals Childhood Wounds, Superhero Drive, And Quiet Regrets
Gary Vaynerchuk sits down with Steven Bartlett for a deeply personal conversation that moves far beyond his usual hustle and business narratives. He unpacks how his immigrant upbringing, especially his mother’s parenting and his role as an older brother, created an almost compulsive need to be a ‘superhero’ for others. Gary contrasts insecurity‑driven success with love‑driven success, explaining why his happiness is rooted in self-awareness, accountability, and serving people rather than professional accolades. The episode culminates in rare vulnerability as he discusses criticism, hidden regrets, the real cost of his ambition, and an emotional tribute to his mother’s impact on his life.
Key Takeaways
Happiness can come from serving others, but you must know *why* you’re doing it.
Gary realizes much of his drive comes from wanting to be admired and to be a ‘superhero’ for people around him—his parents, siblings, employees, trainer, and audience. ...
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Real confidence is built on truthful reinforcement plus hard external feedback, not delusion.
His mother gave him confidence by praising the *right* things (kindness, accountability, effort), not grades or status markers, and she refused his excuses (like blaming the sun for striking out). ...
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Mindset *is* a privilege, but advice still has value if offered humbly.
Gary agrees that having a naturally optimistic, low-anxiety mindset is a massive privilege, possibly the ultimate one. ...
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Self-awareness is the foundation of all meaningful self-development and career decisions.
Both Gary and Steven agree that without self-awareness, no book, tactic, or guru can help. ...
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Criticism hurts less when your self-worth isn’t tied to public perception or success metrics.
Gary describes how a Medium piece labelling him the ‘face of hustle porn’ hurt—not because it dented his ego, but because it might stop people who could benefit from his message from ever listening. ...
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Extreme competitiveness can be a ‘dark side’ that needs to be channeled, not denied.
Gary admits his only real ‘dark’ tendency arises in competition: in a rock-paper-scissors game he briefly thought about firing an employee who beat him, and he used to punch holes in dorm walls after losing at Madden. ...
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Regret is mostly about relationships and time with loved ones, not missed business moves.
Despite being known for extreme hustle, Gary’s real brewing regrets are personal: not enough one-on-one time with his best friend, maybe skipping a few high school parties or vacations. ...
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Notable Quotes
“I have this incredible need to be a superhero.”
— Gary Vaynerchuk
“When the school system was saying, ‘You’re shit,’ I didn’t believe them.”
— Gary Vaynerchuk
“The two ways to build something insane is deep, deep insecurity turned into fuel, or deep, deep levels of confidence turned into fuel.”
— Gary Vaynerchuk
“My professional success has no currency with my heart and soul.”
— Gary Vaynerchuk
“If you are shitting on others right now, it’s a complete reflection of your own unhappiness and insecurity.”
— Gary Vaynerchuk
Questions Answered in This Episode
You said your competitiveness is your ‘dark side,’ yet you also love losing because it gives you another chance to play; can you walk through a recent real-world business loss and narrate, step-by-step, how you processed it emotionally and strategically?
Gary Vaynerchuk sits down with Steven Bartlett for a deeply personal conversation that moves far beyond his usual hustle and business narratives. ...
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When that ‘hustle porn’ Medium article dropped, what specifically did you change—if anything—in the way you communicate about hard work so that your message couldn’t be as easily misinterpreted again?
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You distinguish between delusional confidence and grounded self-esteem built through market feedback; how would you practically coach a parent who already feels they’ve over-praised their child into entitlement to begin repairing that dynamic?
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You’ve said buying the Jets might actually be the first time you experience real unhappiness from achieving a goal; if you *don’t* end up buying them, what concrete alternative ‘quest’ would you design for yourself to keep that same sense of long-term purpose?
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You often say mindset is a privilege but also insist that perspective can change outcomes; for someone who grew up in constant chaos and is deeply cynical, what is the *first small, non-theoretical action* you’d prescribe to start shifting their perspective without invalidating their trauma?
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Transcript Preview
There's certain things that I'm not ready to talk about.
Why?
I just feel like... (sniffs) She made me happy. Gary Vaynerchuk. Gary V. Gary Vaynerchuk.
One of the world's leading marketing experts.
Entrepreneur, investor. A New York Times best-selling author.
And is one of the loudest voices on the internet.
I've exhausted the conversation of grinding, learning how to be an entrepreneur in the streets of New Jersey. There was a kid who wrote a Medium piece about me being the face of hustle. I was on a plane, I landed and it was just all this chaos. And there was a lot of things that weren't true. There were some things that really, like, triggered me. I didn't inherit my dad's liquor store. I built my dad's store for him. I knew at 17 that I was a fucking guy.
What's your dark side?
The only place I feel like I'm dark is when I'm competing. We did rock-paper-scissors tournament with our leadership team. I quickly thought after I lost in the first five seconds, "Should I fire him?" I was incapable of dealing with losing. What is it that makes me want to be like this? And to be very frank-
You don't have to give me the details.
I'll tell you. It's-
Five years ago when we had a conversation, I asked you what your biggest fear was, got these photos here.
In Russia.
How does that make you feel?
It's very clear to me. It's been there for a long time in my head.
Quick one. At the start of these episodes, I told you that 74% of people who watch this channel frequently haven't yet hit the subscribe button, and I told you that the bigger the channel gets, the better the guests get, and hopefully I've delivered upon that for you. So there's two things I wanted to tell you. The first is, if you've ever enjoyed this channel, could you do me a favor, and my team here a favor? Which is hit that subscribe button because it helps this channel more than you know, and as I say, the bigger the channel, the better the guests. But also, we're approaching one million subscribers and when we hit one million subscribers, we've been working for many months to do something very big in which you're all invited to. I'll reveal that when we hit a million subscribers. Enjoy this episode. With age, my perspective and my recollection of my childhood and my understanding of what was most significant, defining and important has evolved.
Mm.
You've just celebrated your 47th birthday.
Yes.
More energy than ever, shall I say.
(laughs) .
But, um, what have you... As you rel- recollect on your, your childhood from, from that vantage point now, what are the new insights that you've attained about yourself?
Probably the most recent one is, like, this incredible need to be a superhero. You know, I, I really took the being the oldest brother to heart. You know, it's funny, my sister and I have a joke that a lot of people don't know that she exists 'cause obviously me and AJ were in business together, and I talk a lot about the Jets, and that has AJ. But my relationship with my sister, who's three and a half years younger than me, may be one of the most profound relationships I have. She (laughs) undoubtedly was the first person besides my mother that kind of cheered for me. You know, she looked up to me. Uh, my mother is incredibly close to her brother, and so she spent a lot of time building that relationship. We're incredibly close. I feel much more kinship to her when I think about my childhood than AJ 'cause I was 11 years older. We didn't have the same childhood. We also moved when he was three. So, all my childhood memories have her in it. And I think as I've gotten... In l- you know, last two, three years, I'm like, "Oh, I have this, like, need to be admired, need..." You know, everything that works for me is when I feel like I'm doing it for someone besides myself. I'm doing it to make my parents proud. I'm doing it to show my sister the right way. I'm doing it for my employees. Even the way I got into better health and fitness was I hired a babysitter, but really what I hired was someone to do it for. Mike and Jordan is who I want to make proud today. My scale being 175 versus 176.8 which it was two days earlier, and Mike texting me, "Great job" on the travel day, I did it for him. And so as I'm getting older, and so much of the Gary V-ness I'm realizing is I'm happy when I'm doing things that make other people happy. Or even at a higher level, creating a framework or a blueprint that they can interpret into themselves. The thing I... You know, as I got older with my sister, a lot of the things I talked about was, "This is my DNA, your DNA is different, but, like, I just... I want you to be happy. We're... It's going to be different for..." You know, those kind of things.
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