Key Moments
Gary Vee runs 7 businesses doing $10M+ each
My First MillionKey Moments
Gary Vee runs 7+ businesses each doing $10M+ by investing heavily in relationships and people, not just spreadsheets, proving 'nice' can be the ultimate business strategy.
Key Insights
Gary Vee operates 7 businesses each generating north of $10 million annually.
VaynerX, one of Gary Vee's companies, has a revenue of $400 million.
Gary Vee believes 'doing good things for people' is the highest ROI and lowest risk business strategy.
Gary Vee's personal 'investment in his body' equivalent involves spending significantly on developing relationships through initiatives like Nick Dio's work.
Gary Vee's business philosophy prioritizes 'long-term greedy' over 'short-term greedy.',
Gary Vee attributes his ability to manage multiple ventures to a core team of 'family members' who are deeply trusted partners, not just employees.
The power of relationships and 'kind candor'
Gary Vee emphasizes that his ability to run multiple successful businesses stems from his profound investment in people and relationships. He highlights the role of individuals like Nick Dio, his 'VP of Relationships,' who networks globally to identify opportunities for karma and connection rather than direct ROI. This philosophy extends to his hiring practices, where he prioritizes building strong, long-term relationships with employees, often fostering them into key leaders and co-founders. Vee admits to struggling with firing people in the past, a trait he detailed in his book '12.5 Keys to What Matters.' He realized he was an 'atrocious firer' because he lacked 'cander,' often delaying necessary conversations and creating an environment of uncertainty. This led to a rebranding of this approach to 'kind candor,' integrating empathy and honesty to ensure clarity and respect, which he credits with improving business results and his effectiveness as a CEO.
Running seven businesses with $10M+ revenue each
Gary Vee details the surprising scope of his entrepreneurial ventures, revealing he actively manages seven distinct businesses, each exceeding $10 million in annual revenue. These include VaynerX ($400 million revenue, overall holding company), Vayner Sports (sports representation, including NIL deals for 300+ college athletes), ECR Group (restaurant group with brands like Flyfish Club, Kons, and Eto), V Friends (a brand built on NFT IP, projecting $20 million in revenue from licensing, comics, and trading cards), Wine Library (a long-standing wine business where he remains deeply involved), Vayner Watt (a TV production company with shows airing on major networks), and the Gary Vee personal brand (monetized through speaking, books, and high-value NIL deals).
Long-term greed as a business strategy
A core tenet of Gary Vee's success is his embrace of 'long-term greed,' a concept he contrasts with 'short-term greed.' He explains that while both motivations are self-interested, long-term greed focuses on sustainable growth and impact, viewing acts of generosity and relationship-building not as costs but as crucial investments. This approach fuels initiatives like hosting expensive, non-revenue-generating events or supporting employees' ventures without direct financial stakes. Vee illustrates this by sharing Alexis Ohanian's observation that Vee's spending of $250,000 annually on events, with no expectation of immediate return, is a prime example of playing a different, longer game than competitors focused on quick wins.
Automating relationships and information with OpenPhone
Vee discusses his use of tools like OpenPhone to manage the overwhelming inflow of information and relationships necessary for his multifaceted operations. He describes using it as a 'capture all for all information,' even taking photos of screens to log interactions. The system is designed to build a 'relationship graph' that can automate tasks, such as sending personalized congratulatory messages years in advance, based on understanding his network and their milestones. This allows him to scale his favorite human interactions through technology, ensuring that important connections and follow-ups are maintained despite his demanding schedule.
The '15-minute meeting' efficiency
Gary Vee attributes a significant portion of his productivity to a strict adherence to 15-minute meetings. He claims that 60% of his daily meetings adhere to this format, allowing him to achieve what others might take an hour to accomplish. This efficiency is crucial for his ability to manage multiple businesses, ensuring that every moment is highly productive. He believes that 'winners' naturally understand the need for brevity and focus in meetings, cutting to the chase without unnecessary preamble. This system, combined with having remarkable people around him, enables him to get three days' worth of work done in a single day while also maintaining family time.
Investing in people as the ultimate ROI
Vee likens his approach to investing in relationships to the 'million dollars a year' athletes spend on their bodies, framing it as a non-negotiable for peak performance. He argues that doing good for people, when done genuinely without immediate expectation of return, yields the highest ROI and lowest risk. This philosophy is exemplified by VaynerX's initiative to host emerging influencers and connect them with brand deal teams, purely as a goodwill gesture. He also highlights investing in his employees' ventures, such as his role as an early investor in Liquid Death because its founder, Mike, was a former employee and he wanted to support him, despite initial business skepticism.
Navigating adversity and context switching
A significant challenge for Vee, and one noted by his staff, is his ability to handle rapid context switching and absorb adversity. He explains that this skill, likely honed by his upbringing in retail and his mother's influence, allows him to deal with significant bad news—personal or business-related—and still show up effectively for subsequent meetings and commitments. He refers to this as an 'eat shit and firefight' emotional framework, essential for leadership when facing client losses or personal challenges, while demonstrating empathy for his employees' struggles.
Gut instinct and the 'tummy tickle' for decision-making
When deciding on new projects or investments, Gary Vee relies heavily on his 'tummy tickle' or 'gut instinct.' He admits to being very comfortable trusting his intuition, even if it means potentially 'dying on his sword.' This approach is driven by a desire to do things that feel right and align with people he wants to work with, rather than solely on quantifiable metrics. This intuitive decision-making process is a stark contrast to the data-driven approaches often taught in business schools, reflecting his belief that humanity and business operate on more nuanced principles.
Mentioned in This Episode
●Companies
●Books
●People Referenced
Common Questions
Gary Vee initially went without a laptop for four years, relying solely on his phone for emails, meetings, and social media. He has since reintegrated a computer into his workflow, using tools like OpenClaw to manage information.
Topics
Mentioned in this video
A client represented by Vayner Sports.
A client represented by Vayner Sports.
A client represented by Vayner Sports.
A client represented by Vayner Sports.
Co-founder and 1A of Resi, with Gary Vee as 1B.
Mentioned as an example of someone investing heavily in their body, prompting the question of what one's personal 'million-dollar body' equivalent investment is.
Co-founder of Reddit, who described Gary Vee's approach as 'long-term greedy' during an event Gary Vee hosted.
NVIDIA CEO quoted for his 'squeeze you so hard that greatness comes out of you' approach to management.
Founder of Barstool Sports, who stated he never fires anyone but focuses on making the employee great.
Marketing expert who advises hiring people who have already done what you need and firing them quickly if they can't.
Mentioned as an example of a creator who needs a business person to partner with.
Mentioned as someone who is a proponent of Rene Girard's mimetic theory.
Mentioned in the context of his rocket launch and passive-aggressive communication with Elon Musk regarding their competitive ventures.
Mentioned regarding his rocket launches and competitive interactions with Jeff Bezos, highlighting the concept of mimetic rivals.
Owner of the Dolphins and part of Vayner Media, who funded Gary Vee's VaynerWatt venture.
Acquired Empathy Wines for an eight-figure deal.
A company with $400 million in revenue, where Gary Vee is the day-to-day CEO, and it owns none of the other six businesses mentioned.
A sports representation company dealing with professional athletes and NIL deals for college athletes, generating tens of millions in revenue.
A restaurant group including Flyfish Club, Kons, and Eto, generating tens of millions in revenue.
An NFT restaurant that is part of ECR Group, described as 'crushing it'.
A brand Gary Vee is building through licensing, comic books, coins, and trading cards, expected to do minimally $20 million in revenue this year.
Gary Vee is still highly involved in this wine business, run by his best friend.
A TV production company with several shows sold to networks like Hulu, ABC, and Netflix.
Provided a free resource on best practices for CEOs regarding delegation, hiring, and difficult conversations.
A wine company started by Gary Vee with two former interns, sold for an eight-figure deal to Constellation Brands within 18 months.
A restaurant in Bergen County, New Jersey, part of Gary Vee's expansion plan for steakhouses in high-net-worth neighborhoods.
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