Gary Vee runs 7 businesses doing $10M+ each
YouTube · byAExsTL4g0
Quick Read
Summary
Takeaways
- ❖Gary Vaynerchuk actively manages seven businesses, each generating over $10 million in annual revenue, including Vayner Media, Vayner Sports, ECR Group (restaurants), V Friends (NFT/brand), Wine Library, Vayner Watt (TV production), and his personal brand/NIL.
- ❖His business philosophy is 'long-term greedy,' focusing on 'rainy day human stuff' – building deep, non-transactional relationships and giving without immediate expectation of return.
- ❖He employs a 'VP of Relationships' (Nick Dio) to scale his relationship-building efforts globally, connecting people and fostering karma without direct KPIs or ROI.
- ❖Gary Vee transformed his leadership by adopting 'kind cander,' overcoming a past inability to fire or give direct feedback, which he realized was detrimental to his team and business.
- ❖His daily schedule is packed with 15-minute meetings, where he makes decisions in 70% of them, demonstrating extreme efficiency and a high capacity for context-switching.
- ❖He primarily funds his new ventures personally, often co-founding with long-term employees (7-11+ years) who are considered 'family members,' ensuring deep trust and aligned vision.
- ❖Gary Vee sees significant future potential in advanced AI (e.g., virtual people agencies focused on IP ownership) and live shopping, predicting live shopping will account for 10-15% of all commerce in 6-10 years.
- ❖His investment decisions are largely driven by 'tummy tickles' (gut instinct) and a desire to support his employees' ventures, as exemplified by his early investment in Liquid Death.
- ❖He believes the biggest companies of the future will be 'human-based organizations' led by creator-entrepreneurs who can either operate themselves or find strong operating partners.
Insights
1Scaling Relationships Through a 'VP of Relationships'
Gary Vaynerchuk employs a 'VP of Relationships,' Nick Dio, to extend his personal brand and relationship-building efforts globally. Dio hosts dinners and connects people on Gary's behalf, operating with a mandate to spread 'good karma' without specific KPIs or ROI expectations. This strategy allows Gary to scale the 'people part' of his business, which he considers his favorite aspect, by leveraging a trusted proxy.
Nick Dio is the VP of relationships. He literally goes around the world and in essence, he's been with me for 12 years... if there's something we could do something for someone for karma, right? Like no KBI, no ROI...
2The 'Long-Term Greedy' Business Philosophy
Vaynerchuk operates under a philosophy he calls 'long-term greedy,' which prioritizes building human equity and goodwill over immediate financial returns. He explains that this means investing in relationships and helping others with no expectation of direct, short-term payback, believing it creates a 'rainy day human stuff' fund that pays dividends in unpredictable, valuable ways over decades.
It's just the difference between short-term greedy and long-term greedy... And then if your law greed is about rainy day human stuff, not money in your bank, it becomes an extreme nuance of that.
3Evolution to 'Kind Cander' for CEO Effectiveness
Gary Vee admits he was an 'atrocious firer' and struggled with candor, which created fear and uncertainty among his employees. A watershed moment, triggered by negative feedback from former employees, led him to develop 'kind cander.' This approach emphasizes delivering direct, honest feedback with empathy, transforming his leadership and significantly improving business results over the last three to four years.
I was an all-time atrocious firer... I used to think of it as my ultimate strength Sam... I was unable to do cander... I rebranded it into kind cander. It became the ethos of our company...
4Operating Multiple Businesses Through Hyper-Efficiency and Trusted Co-Founders
Gary Vee manages seven active, eight-figure businesses by working an intense 8:30 AM to 8-10 PM day with no breaks, conducting 60% of his meetings in 15-minute slots, and making decisions in 70% of them. His secret weapon is a network of long-term 'family member' co-founders and A/B players who have been with him for 7-11+ years, allowing him to delegate significant operational responsibilities based on deep trust.
I have seven active businesses that are doing more than eight figures a year in revenue where I am meaning involved... 60% of the meetings are 15 minutes... The real reason is because of the 50 people from Ryan Harwood or Kalin or Claude or JT or AJ and Greg Gensky or David Rodelitz...
5Future Growth in Advanced AI and Live Shopping
Vaynerchuk identifies advanced AI, particularly in creating virtual people agencies focused on IP ownership, and live shopping as the next major growth areas. He predicts that live shopping will grow to represent 10-15% of all commerce in 6-10 years, mirroring e-commerce's impact on traditional retail. He advises betting on these areas for long-term value creation rather than short-term exits.
I'll go to places where people are betting on 5 years from now... really spending time on advanced AI... creating a entire agency of virtual people... live shopping is doing to e-commerce is what e-commerce did to real com... in six to 10 years, live shopping will actually be 10 to 15% of all commerce.
Bottom Line
The future of entrepreneurship lies in 'human-based organizations' where the individual creator is the core brand, capable of building Fortune 500-level companies by either operating themselves or partnering with strong operators.
This suggests a shift away from traditional corporate structures towards personality-driven enterprises, where personal brand equity and content creation become central to business growth and diversification.
Entrepreneurs should focus on building robust personal brands and developing strong operating partners or teams that can scale their vision across multiple ventures, leveraging AI and evolving social platforms for deeper decentralization of industries.
Investing in relationships and 'karma' without immediate financial expectation ('rainy day human stuff') is the highest ROI and lowest risk strategy in the long run.
This challenges the conventional, transactional view of business relationships, suggesting that genuine generosity and support create an invaluable, resilient network that can yield unexpected benefits over decades.
Businesses and individuals should proactively invest in non-transactional relationship building, mentorship, and community support, viewing these as strategic long-term assets rather than unquantifiable expenses.
Opportunities
Virtual People Agency (IP-focused)
Create an agency that develops and owns the intellectual property of virtual people (AI-generated or digital avatars), aiming for them to become famous and generate revenue through various channels. The focus is on IP ownership rather than just representation, anticipating a future where virtual entities hold significant cultural and commercial value.
Live Shopping E-commerce Platform/Service
Develop platforms, tools, or services that enable brands and creators to effectively leverage live shopping for direct-to-consumer sales. This capitalizes on the predicted massive growth of live shopping, which Gary Vee believes will become 10-15% of all commerce.
High-End Suburban Steakhouse Chain (Capon's Chop House Model)
Replicate the 'Ruth's Chris 2.0' model by opening high-quality steakhouses in affluent suburban neighborhoods surrounding major cities. The strategy focuses on undeniable food quality (80%) with a touch of 'sizzle' (20%) and leverages existing marketing machines (like Vayner X) to drive awareness and retention.
Key Concepts
Long-Term Greedy
A business philosophy where actions are taken for long-term, compounding benefits, often involving non-monetary 'human' investments like relationship building and goodwill, rather than short-term financial gains. This approach assumes that doing good and fostering strong connections will eventually yield significant returns, even if not immediately quantifiable.
Kind Cander
A leadership principle emphasizing direct, honest feedback delivered with empathy and care. It contrasts with 'cander' used as an excuse for harshness, aiming to improve performance and clarity within a team while maintaining respect and support for individuals. This model suggests that clear, compassionate communication is essential for effective leadership and business results.
Mimetic Rivalry
A concept where individuals or entities desire what others desire, leading to competition and often antagonism, even among successful people. This model explains why even 'winners' might engage in 'bitching' or passive aggression against other winners, driven by a desire for similar status or achievement, rather than focusing on their own progress.
Lessons
- Implement 15-minute meetings as a default to increase efficiency. Challenge the necessity of longer meetings and focus on rapid decision-making.
- Cultivate a 'long-term greedy' mindset by investing in non-transactional relationships and offering help without immediate expectation of return. Build a network of goodwill that can pay dividends over years.
- Practice 'kind cander' in your leadership: deliver direct, honest feedback with empathy and clarity. Address performance issues promptly rather than delaying, which can foster fear and resentment.
- Identify and nurture long-term 'family member' co-founders or key employees. Build deep trust over years before embarking on new ventures together, leveraging their operational capabilities to scale your vision.
- Actively explore and invest in emerging technologies like advanced AI (especially IP-focused virtual entities) and live shopping, anticipating their long-term impact on commerce and brand building.
Scaling Your Personal Brand into a Multi-Million Dollar Empire (Gary Vee's Approach)
**Build a Core 'Family' Team**: Identify and cultivate long-term relationships with trusted employees (7-10+ years) who can become co-founders or lead new ventures. These individuals should deeply understand your vision and values.
**Embrace 'Long-Term Greedy' Investing**: Prioritize 'rainy day human stuff' by investing in relationships, mentorship, and community support without expecting immediate financial returns. This builds a robust network and goodwill that compounds over time.
**Delegate Through Trusted Proxies**: Employ VPs of Relationships or similar roles to scale your personal brand's reach and relationship-building efforts, allowing you to be 'everywhere' without being physically present.
**Master 'Kind Cander' Leadership**: Develop the ability to deliver direct, honest, and empathetic feedback. Address performance issues promptly and clearly to foster a culture of transparency and growth, improving overall business results.
**Optimize for Hyper-Efficiency**: Structure your day around short, decision-oriented meetings (e.g., 15 minutes). Cultivate a high capacity for context-switching to manage diverse operational demands across multiple businesses.
**Fund New Ventures Strategically**: Leverage personal capital for new businesses, especially when co-founding with long-term, trusted partners. This maintains control and aligns incentives within your 'family business' ecosystem.
**Diversify Across Passion-Driven Sectors**: Expand into diverse industries (e.g., media, sports, restaurants, IP/NFTs, wine, TV production) that align with your interests and where your personal brand can provide a unique advantage, allowing for 'escapism' and soul-filling work within your empire.
Notable Moments
Gary Vee's admission of being an 'atrocious firer' and his journey to 'kind cander' after a negative Facebook group experience with former employees.
This highlights a significant personal and professional growth arc for a prominent CEO, offering a relatable lesson on the importance of self-awareness and direct, yet empathetic, communication in leadership.
The host's story of attending a dinner hosted by Nick Dio, Gary Vee's 'VP of Relationships,' expecting Gary to be there but instead meeting a diverse group of interesting people.
This vividly illustrates the practical application of Gary's 'scaling relationships' strategy and the concept of 'karma' building, showing how a proxy can effectively extend an individual's network and influence.
The discussion on 'mimetic rivalry' among successful people, where even 'winners' engage in 'bitching' about other winners due to envy or comparison.
This provides a psychological insight into human nature, even at the highest levels of success, and serves as a cautionary tale for entrepreneurs to focus on their own building rather than external comparisons.
Quotes
"It's just the difference between short-term greedy and long-term greedy. He goes, you know, I'm he was in the first YC batch and he goes, one of the beautiful things about Silicon Valley is you learn the virtue of long-term long-term greedy people."
"Everyone's meetings are twice as long as they need to be if they're a winner and they know it."
"I'm on a boat which has seven holes and I put my finger in the one that needs it most for every parent that knows you're only as happy as your most unhappy child."
"I might actually be a weirdly good operator at scale."
Q&A
Recent Questions
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