My First Million

How Gary Vee runs 7 businesses

My First Million·May 20, 2026

OVERVIEW

This episode delves into Gary Vaynerchuk's unique approach to business, relationships, and personal growth, highlighting how his long-term perspective and emphasis on "karma" drive his entrepreneurial decisions. He explains his operational efficiency across multiple ventures and his philosophy on leadership, candid feedback, and personal investment.

KEY TOPICS

  • Gary Vee's technology habits (or lack thereof)
  • The concept of "Open Claw" as a personal information capture system
  • The role of Nick Dio as a relationship builder for VaynerMedia
  • Different philosophies on hiring and firing employees
  • Gary Vee's definition of "long-term greedy" and "rainy-day human stuff"
  • The importance of "kind candor" in business and leadership
  • Gary Vee's diverse portfolio of businesses (VaynerMedia, VaynerX, VaynerSports, BCR Group, VFriends, Wine Library, VaynerWatt, GaryVee brand)
  • Gary Vee's daily routine and time management strategies
  • His secret weapon: hiring and leveraging talented people
  • The impact of "mimetic rivalry" in business and personal life
  • Personal funding and investment strategies for new ventures
  • How to navigate ethics and reputation in the public eye

MAIN TAKEAWAYS

  • Gary Vee champions a "long-term greedy" mindset, prioritizing building genuine relationships and delivering value over immediate financial gain. He believes this approach, focused on "rainy-day human stuff," is ultimately the highest ROI and lowest risk.
  • He emphasizes the power of "kind candor" in leadership, advocating for clear and honest communication delivered with empathy, rather than using candor as an excuse to be harsh. He admitted to being an "all-time atrocious" firer before embracing this philosophy, leading to improved business results.
  • His success is heavily reliant on a unique hiring philosophy: finding and empowering A and B players, building deep personal relationships with them, and trusting them to represent his brand and values globally.
  • Gary Vee operates with extreme efficiency, utilizing 15-minute meetings and a relentless work ethic, but attributes his ability to juggle multiple 8-figure businesses to the trust and talent of his core team, who operate almost as family members within his ecosystem.
  • He sees the rise of creator entrepreneurs as the next Fortune 500 companies, believing that with AI and blockchain, human-based organizations will dominate. He is personally funding and actively involved in building these ventures, often for reasons beyond immediate financial return.
  • He views current social media and entrepreneurial trends through a lens of "mimetic theory," where people often desire things because others do. He actively counters this by pursuing his own intrinsic motivations and supporting those who do the same.

NOTABLE QUOTES

"Doing good things for people is literally the highest ROI and lowest risk thing, and most people think it's the highest risk thing."
"If your greed is about rainy-day human stuff, not money in your bank, it becomes an extreme nuance of that."
"I'm the cliché girl that wants to date the bad boy because I'm gonna fix him."
"Most things that are taught in business school are short-sighted and are tactical versus how humanity actually works and business actually works."

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