#80 The Biggest Bets I Made — And How They Paid Off: Gary Vee - BigDeal Recap

Podcast: BigDeal

Published: 2025-07-09

Duration: 1 hr 21 min

Summary

Gary Vaynerchuk shares his journey in entrepreneurship and investment, emphasizing the importance of intuition in identifying winning founders and businesses. He also makes bold predictions about the future of AI and the evolving landscape of attention in marketing.

What Happened

In this episode of BigDeal, host Cody Sanchez sits down with Gary Vaynerchuk, known for his impressive track record of predicting social media trends and building successful businesses. Gary emphasizes that to scale a business effectively, one must possess 'outlier behavior' and a relentless drive. He reflects on his early career, noting how he relied on intuition to gauge the potential of startups like Facebook, Twitter, and Tumblr. Gary describes a pivotal moment when he realized the importance of understanding not just the business idea but also the founder's character, comparing it to selecting a good jockey for a horse race.

As the conversation progresses, Gary discusses the principles that guide his investment decisions today. He stresses the need to assess both the entrepreneur ('the jockey') and the business ('the horse'). Gary recalls his experiences with various investments and highlights the significance of emotional intelligence in identifying potential. He reveals that while he can quickly recognize average performers, discerning true talent takes more time and context. This insight leads him to discuss the balance of hiring B and C players in organizations, arguing that they are crucial for scaling a business effectively, as A players are often on the lookout for new opportunities.

Key Insights

• Intuition is key in identifying successful founders and businesses.
• Emotional intelligence plays a significant role in investment decisions.
• The balance of hiring B and C players is essential for business scalability.
• Predictions about AI's future include the potential for human-AI relationships.

Key Questions Answered

What characteristics define a great founder according to Gary Vaynerchuk?

Gary Vaynerchuk emphasizes the importance of both the entrepreneur and the business in his investment strategy. He refers to this as the need to like 'the jockey and the horse.' He states that he relies heavily on intuition about the human behind the business, which has evolved over his career. He learned that understanding the founder's character is just as crucial as the business idea itself.

What does Gary Vee say about hiring B and C players?

Gary believes that most companies need a mix of B and C players for scalability. He argues that A players are often looking for new opportunities, and that a balanced team can contribute significantly to retention and overall success. He highlights that not every employee needs to be an A player in terms of intelligence; work ethic and character also play critical roles in a team's effectiveness.

How does Gary Vee assess investment opportunities?

Gary's approach to assessing investments has evolved from relying solely on the idea to a deeper analysis of the founder's character. His process begins with an open-ended question, 'Tell me everything,' which allows him to gather context about both the person and the business. He listens carefully and tailors his follow-up questions based on his initial impressions, which helps him gauge the potential for success.

What predictions does Gary Vee make about the future of AI?

Gary makes a bold prediction that in the future, most people's grandchildren will marry AI robots. This statement reflects his belief in the profound impact that AI will have on society and human relationships. He discusses how these developments will reshape various industries and personal interactions, highlighting the importance of adapting to these changes.

What has Gary Vee learned from his investment successes and failures?

Gary reflects on his journey and acknowledges that early in his career, he was 'unstoppable' due to his intuition about startups. However, he also shares lessons learned from failures, such as investing in a company without fully understanding the founder's capabilities. Over time, he has come to appreciate the importance of thorough analysis and emotional intelligence in making successful investment decisions.