Key Moments
Why You Need to Quit Playing It Safe & Stop Letting Fear Run Your Life | Tea with GaryVee 89
GaryVeeKey Moments
A photographer is stuck at a revenue ceiling, but Gary Vee reveals that scaling a business involves consistent, high-volume outreach, not just fancy tactics.
Key Insights
To scale a business, send between 3,000 to 4,000 direct messages on LinkedIn, not just a handful.
When networking, show genuine interest by referencing personal details like a shared liking for champagne or race cars, rather than generic outreach.
Don't dismiss small podcasts as guest opportunities; they can provide long-form content and clips for social media, acting as stepping stones to larger platforms.
A garage cleanout business charging $699 per job, with 16 jobs completed in its first month, indicates significant, scalable potential, despite the owner's fear.
Fear of failure, particularly after a past business loss during COVID, can lead to "loser makeup" – presenting oneself as successful while internally being afraid to take risks.
Consuming optimistic and practical content, exercising, and changing your social circle are effective ways to combat trauma and unhappiness without expensive therapy.
The surprising profitability of garage cleanouts
The episode opens with a discussion about Paul, who is running a garage cleanout business in West Texas. He charges $699 per job and has already completed 16 jobs in his first month, even finding valuable items like $600 baseball gloves. Gary Vee expresses extreme excitement, calling it a "big business" and a "dream life," emphasizing that Paul needs to quit his marketing director job immediately. He contrasts this with how little he'd charge for such a service, highlighting the immense value Paul is providing. The core message here is that a seemingly humble service can be incredibly lucrative if priced correctly and executed with a strong marketing approach, as Paul has demonstrated through Facebook ads. The $699 price point, especially in West Texas with its oil money, is presented as a golden ticket that Paul is almost afraid to fully embrace due to fear of failure.
Fear as a deceptive force
Gary Vee repeatedly confronts the concept of fear, particularly the fear of failure that prevents individuals from taking significant risks. He illustrates this with Paul's situation: despite a highly profitable and scalable business model, Paul hesitates to quit his job due to the fear stemming from a previous business failure during COVID. Gary argues that this fear is a "loser makeup," a way of presenting as successful while being paralyzed by past setbacks. He stresses that the security Paul seeks can be found by embracing the current success and doubling down on what's working, rather than clinging to a stable but less rewarding job. The underlying principle is that fear often lies, making small risks seem catastrophic and preventing individuals from realizing their true potential.
The sheer volume of action required for growth
A recurring theme is the necessity of high-volume action, particularly in networking and outreach. Gary critiques the idea of sending a few messages and expecting big results. He advises sending between 3,000 to 4,000 direct messages on LinkedIn to top marketing executives at major brands, not just a handful. This is compared to the consistent, daily effort required for physical training, where starting with eight bad push-ups and doing them for 11 years leads to mastery. For business growth, this translates to a relentless pursuit of connections and opportunities. Gary also suggests reaching out to smaller podcasts for guest appearances, as these can generate content and build a profile that leads to larger opportunities. The takeaway is that sustained, high-volume effort, often underestimated, is the engine of significant business expansion.
Mastering the art of personalized networking
Beyond just volume, Gary emphasizes the importance of personalized and strategic networking. He advises going beyond generic messages and taking the time to research potential contacts. This involves looking at their social media profiles to identify personal interests, such as a liking for champagne or race cars, and then weaving these into the conversation. The goal is to build rapport and move towards a more significant conversation, like suggesting a coffee or meal to discuss creativity. This nuanced approach differentiates individuals from the masses sending similar requests. The advice is to be respectful of others' time and build a relationship before asking for business, thereby increasing the chances of a positive response and fostering genuine connections.
Humility as a competitive advantage
Humility is presented as a secret weapon and a critical advantage in a world obsessed with optics. Gary explains that the most successful individuals are often those willing to take the judgment of others by doing things that might seem beneath them or smaller than perceived. This includes reaching out to interns or junior staff who will eventually become decision-makers, rather than solely targeting the top dogs. He contrasts this with the insecurity displayed at exclusive events, where people rely on brand names and external validation rather than intrinsic self-worth. Humility allows one to embrace the process, learn from every interaction, and build a network from the ground up, which is far more sustainable and rewarding than chasing superficial status.
Action over optics and the 'fancy' trap
Gary strongly advocates for action over worrying about appearances or 'optics.' He notes that in fields like fashion and design, where aesthetics are paramount, it's easy to get caught up in how things look. However, he insists that very little happens in the world without action. The 'fancy' approach, or being too concerned with image, is seen as an enemy of growth. He advises getting "dirt under those pretty fingernails" – engaging in the necessary, often unglamorous, work. The people who care about 'fancy' are often other insecure, fancy people. True success comes from doing the work, being willing to be imperfect, and prioritizing progress over presentation, especially when navigating the early stages of business development.
Dealing with trauma and negativity without therapy
For those struggling with trauma or unhappiness but lacking funds for therapy, Gary offers practical, accessible solutions. He emphasizes consuming optimistic and positive content, engaging in exercise, and surrounding oneself with supportive people. He strongly advises against consuming negative news from sources like CNN or Fox News, labeling them as fear-mongers that offer the same message from different angles. The core advice is to face truth, accept that not everything is one's fault, and consciously choose to disengage from negativity. Learning to love oneself and not internalize others' negativity is crucial, as is recognizing that external validation is fleeting and often stems from insecurity.
The entrepreneurial mindset vs. a job mentality
The discussion highlights the fundamental difference between having a job and running a business. Gary critiques the mindset of prioritizing job security over entrepreneurial opportunity, particularly when a proven business model like Paul's garage cleaning service exists. He argues that even after a business failure, like Paul's agency during COVID, the ability to secure another marketing job is a strong safety net. This safety net should empower, not inhibit, risk-taking. He also touches upon the idea that sometimes a business partner's limited availability (e.g., 10 hours a week) may not align with the demands of building a successful venture, advocating for finding partners with a complementary work ethic and commitment, unless one is content with slower growth and a different lifestyle.
Mentioned in This Episode
●Software & Apps
●Companies
●Organizations
●People Referenced
Common Questions
To break through a career ceiling, you need to increase your volume of outreach and refine your approach (form). This means sending significantly more messages on platforms like LinkedIn to key decision-makers, personalizing your approach by referencing their interests, and potentially guesting on smaller podcasts to gain exposure.
Topics
Mentioned in this video
A platform used for selling items from garage cleanouts, mentioned as a current sales channel.
A luxury fashion brand mentioned in the context of a photographer's career goals.
A German automotive company mentioned as a potential target for networking outreach.
A startup that Gary Vaynerchuk is an investor and advisor for, promoted as a tool for creators and entrepreneurs.
A luxury fashion brand mentioned as a target for networking by a photographer seeking to elevate their career.
A German luxury and commercial vehicle company mentioned as a potential target for networking outreach.
A live-streaming e-commerce platform used for selling items from garage cleanouts and mentioned as a place to find Gary Vaynerchuk's content.
Gary Vaynerchuk's father's wine store, used as an example of a business that can easily generate content due to a large inventory.
A food and beverage company where a hedge fund bought significant equity, mentioned as an example of business activity.
A British luxury car manufacturer mentioned as a potential target for networking outreach.
A professional basketball player whose likeness is featured on manga stickers, related to V friends merchandise.
A legendary NFL quarterback, mentioned for his success with the Tampa Bay Buccaneers after leaving the Patriots, and in contrast to Bill Belichick's coaching.
A caller from West Texas who started a garage cleanout business and is seeking advice on scaling and overcoming fear.
A billionaire investor and philanthropist, mentioned as someone people are told to be scared of, as an example of fear-mongering in media.
The head coach of the New England Patriots, discussed regarding his coaching record and perceived reliance on Tom Brady.
A legendary boxer, mentioned in an anecdote about knocking down Muhammad Ali.
A person who runs Wine Library, mentioned in an anecdote about a card show where he unexpectedly made more money than Gary Vaynerchuk.
A legendary boxer, mentioned in an anecdote about being knocked down by Joe Frazier, illustrating that even the greatest can face setbacks.
An organization Gary Vaynerchuk suggests donating to for his birthday.
A university whose football team's performance is discussed in relation to Bill Belichick and Tom Brady.
Mentioned in relation to a discussion about Bill Belichick's coaching effectiveness.
A non-profit organization that Gary Vaynerchuk suggests donating to as a gift.
More from GaryVee
View all 47 summaries
43 minYou Might Be Making Content Completely Wrong
53 minThe Biggest Opportunity Most People Are Ignoring
23 min40 Things You Need To Hear Before You Turn 40
35 minThe Internet Changed… And Most People Missed It
Ask anything from this episode.
Save it, chat with it, and connect it to Claude or ChatGPT. Get cited answers from the actual content — and build your own knowledge base of every podcast and video you care about.
Get Started Free