Gary Vaynerchuk: Entrepreneur, investor, marketing expert and New York Times best-selling author who built Wine Library and founded VaynerMedia.
What this episode covers
In this emotional conversation, Gary Vaynerchuk reflects with host Steve Bartlett on how his immigrant childhood and his mother Tamara shaped his happiness, confidence and accountability. He distinguishes between confidence built on love versus insecurity, and argues that delusional positive reinforcement and 'eighth place trophies' harm kids. Gary discusses how public criticism (like a viral Medium hit piece) hurts but never lasts, his belief that material status is 'makeup for insecurity,' and his deeply competitive 'dark side.' He reveals that none of his professional accolades give him self-worth, only being known for how he treats people. He closes by tearing up over his mother and stating he wants his tombstone to read 'he gave more than he took.'
The guest's own work
Crush It!
Gary Vaynerchuk
“go read crush it which is my coming out moment it doesn't talk about making money and buying a yacht when it talks about working hard at night”— Gary Vaynerchuk
Twelve and a Half
Gary Vaynerchuk
“recently last couple years I've talked more about Candor when I wrote 12 and a half I'm like this is My Kryptonite”— Gary Vaynerchuk
Also referenced (named, not recommended)
Madden '94
EA Sports
“anytime I lost in Madden 94 in a dorm room I would punch a hole in the wall knowing I would have to pay a fine”— Gary Vaynerchuk
Big reveals from this episode
- Gary refutes the viral claim he inherited his dad's liquor store, saying he built the business and left with nothing to start VaynerMedia.
- Gary admits he never reads books, saying the only thing he reads is his feelings.
- After losing a Rock Paper Scissors tournament to a leadership team member, he briefly thought about firing the guy.
- In college he punched holes in dorm walls and paid fines because he was incapable of dealing with losing at Madden '94.
- Gary says his entire self-worth is predicated on people knowing the truth of how he interacts with them, not any professional accolade.
- Gary believes his 50s will be his peak, calling everything he is now 'minor leagues' compared to what's coming.
- He shares the lifelong dream of buying the New York Jets, told to friends since age 12.
- Gary confesses a resentment toward how humans love dogs with all their heart but won't do the same for each other.
Worth remembering
- Gary's family left the Soviet Union in a narrow 1970s window after a 1970 hijacking attempt triggered global pressure on Russia to release Jews.
- His mother refused to let him blame the sun for striking out in baseball, instilling deep accountability.
- Gary credits years of door-knocking, lemonade stands and snow shoveling rejections ('99.9% of cars drive by') with building his resilience.
- His Wine Library TV first episode aired February 21st, 2006, when he was about 30.
- In 1971 America, astronauts and pilots were more famous than nearly all athletes; Joe Namath helped shift celebrity toward sports.
- When Gary hit Twitter in 2007 the consensus was he was the one person who 'won't be here in a decade' for being too hot too fast.
- He stopped following the Rangers and Yankees the day after they won championships, suggesting his addiction is the game not the trophy.
- Gary says he shares an estimated 83% DNA-level similarity with his mother Tamara, his most accurate judge.
- V Friends, Gary's NFT/character project, includes characters like 'Self-Aware Hair Tortoise' meant to teach kids self-awareness.