The Jamie Kern Lima Show

Gary Vee: Your AI & Social Media Must-Knows + 7 Life-Changing Keys to Success! Pt 1 Gary Vaynerchuk

19 snips
Aug 19, 2025
Gary Vaynerchuk, known as GaryVee, is a leading entrepreneur and cultural mind, famous for his insights on branding and social media. In this conversation, he tackles pressing questions about the future influenced by AI and technology. Gary shares powerful insights on building self-worth to combat self-doubt and emphasizes the transformative power of genuine connections in content creation. He reflects on personal ambitions, the evolving job market, and the importance of storytelling to empower future generations.
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INSIGHT

Regret Trumps Fear Of Judgment

  • Regret, not judgment, should be our biggest fear because protecting against micro-judgment creates macro-regret later in life.
  • Gary Vaynerchuk urges people to jump toward their dreams now to avoid lifelong regret.
ADVICE

Do Whatever Gets You To Jump

  • Do whatever it takes (therapy, exercise, changing friendships) to get yourself to 'jump' and pursue your goals.
  • Gary Vaynerchuk lists practical ways to overcome fear and start taking action today.
ANECDOTE

From Scared Kid To Jumping In

  • Gary recounts being scared of basic childhood things like swimming, biking, and kissing but then jumping in and losing the fear.
  • He uses his own childhood to illustrate that fear is conquerable with action.
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