The Real Reason Why You're Not Winning on Social Media

Gary Vee opens by saying he will keep the formal talk brief and leave substantial time for questions, because detailed Q&A may provide the most value. He frames “overcoming impossible” as both simple and difficult: the business tactics are often obvious, but people do not act on them. During his wine-business years and especially from 2009 through 2012, he gave away highly tactical advice about WordPress, Twitter, Google AdWords, Facebook, and YouTube. By 2014–2016, he had shifted toward talking about self-esteem, accountability, and fear because he realized people were not failing for lack of instructions; they were afraid to execute. To illustrate, Gary asks everyone selling physical products to stand. He tells them that becoming “psychotic” about TikTok Shop, TikTok affiliates, TikTok content, and TikTok Live—using organic content rather than ads—could dramatically grow their businesses. But he expects only a small number of those people to follow through. His first assignment is therefore not another tactic: after leaving the conference, they should ask themselves, in his words, “what the fuck you’re scared of.” He compares this to health and fitness, where people generally know that exercise, cleaner eating, and more protein would help; the obstacle is not confusion about the solution but the inability or unwillingness to do it.

Gary argues that this is one of the greatest periods ever for building a business because social media gives entrepreneurs free access to consumer attention. Older audience members confirm that television ads, newspaper and magazine pages, and direct mail used to require substantial spending. He rejects complaints about being “shadow banned,” saying that many people simply make weak content. In his view, social platforms have been offering an unprecedented free route to fame, customers, and cultural influence, but that opportunity will eventually diminish when glasses or another device replaces the phone as society’s primary screen. He urges businesses and personalities to post every day at a volume that feels uncomfortable, using AI to make the process more affordable and efficient. He says people should spend roughly 100 hours over several weeks learning how algorithms, content, and AI work; the information is freely available through AI chatbots. The real unanswered question is whose judgment they fear. Gary describes complaining as a major waste of energy and says people commonly blame governments, billionaires, politicians, or other groups instead of accepting responsibility. Complaints are usually heard either by an enabler who loves the complainer or by a “ping-ponger” waiting to complain in return. Business, he says, is merit-based: if someone is not winning, they need to acknowledge that their current approach is not good enough and work out how to improve it.

Gary describes success as “shockingly easy and impossibly hard.” The easy part is that social media is free and the necessary information can be learned; the hard part is answering why someone has not posted or put in the work. He says there has never before been a free, gatekeeperless way to reach society’s attention at this scale. Even if platforms had charged two cents per post from the beginning, he says he would gladly have spent $10 million a year because the access would still be so valuable. He acknowledges that social media exposes insecurity and that two months of posting without visible results can be mentally difficult. His answer is to become a practitioner. He compares entrepreneurship to football: attending a class about football does not teach someone to play; they must play, watch the film, adjust, and play again. He says the market is the film and the trenches are where businesspeople learn. Gary especially values marketing because he sees it as the offense of business: products such as T-shirts and bottled water can be commoditized, and even an excellent product can be copied within 30 seconds, but communication can make people know about and want it. For people insecure about appearing on camera, he recommends written platforms such as Substack, Twitter, and LinkedIn, or audio if they dislike writing. He even suggests wearing a mask. His point is that a business can communicate in whatever format makes consistent practice possible.

Gary says that the current social-media opportunity will eventually be remembered as a lost 20-year window if people fail to act. He distinguishes between lacking craft and refusing to learn it: someone may not yet know how to choose a thumbnail, shape the first three seconds, or edit differently for LinkedIn, YouTube, and Twitter, but those skills can be learned in about six months. He cites Alex Cooper/Earle, Logan Paul, MrBeast, Donald Trump, Zohran Mamdani, and multiple brands as examples of cultural growth made possible by social media rather than traditional gatekeepers. He argues that most people are “stuck in high school,” worrying about an insulting comment from someone like “Johnny Pant 16” calling them ugly. Gary says humility is what brings people to the top: he knows he is bad at many things and not everyone’s preferred personality, and listeners must accept that they also have weaknesses. People who enter a business only because they think money is waiting on the other side will not sustain the required hours; this explains, in his framing, why some people keep moving through their seventeenth industry or business. He says the only way to do impossible things is to live for oneself rather than factoring everyone else’s judgment into every decision. He presents that emotional independence—not another motivational speech—as the condition that lets people finally begin doing the work.

During the Q&A, Gary returns to the TikTok Live opportunity and asks a young seller how much revenue the business is doing. The participant says the operation, which has been running for roughly a year and a half, is doing about $1 million. Gary says TikTok Live and Whatnot together are expected to generate $50 billion in gross merchandise value in America that year. He calls live shopping “the QVC of social media” and a land grab, comparing its current stage to social media in 2008–2010: there is substantial attention but relatively few skilled participants. The seller explains that he is still in elementary school. Gary tells him he should quit, provoking a discussion with the boy’s father, whom Gary calls “Pops.” Gary argues that the boy is already driving the business and could reach $20 million if he focuses on it, while also saying that conventional advice to stay in school may come from people who have not achieved comparable results. He claims his own company has 4,000 employees and that even with $72 trillion he could not identify the colleges attended by five of them, using this to argue that credentials are often less important than demonstrated ability. The business also sells broken merchandise that would otherwise be discarded. By putting it on live broadcasts, they may generate roughly $1 million in sales because artists, refurbishers, and international resellers see value in it. Gary’s conclusion is that live commerce rewards experimentation and reveals demand that conventional assumptions would miss.

When an audience member asks how to attract investors or strategic partners, Gary asks about posting frequency. The person says they post about once every other day. Gary contrasts that with his own roughly 900 pieces of content per day across ten platforms and about 100 handles, and says he is aiming for 100,000 pieces a day. His recommendation is not to jump immediately to 900, but to distribute every piece across TikTok, YouTube Shorts, Instagram, Facebook, Twitter, and other platforms such as Threads. For regulated financial professionals, he says they should use LinkedIn to discuss legally permissible subjects such as interest rates, market observations, and the effects of a new tax plan. One useful article, he says, could attract people with millions in savings more effectively than cold-calling or attending a golf event. For people in their twenties, Gary recommends trying many things during a period of discovery rather than immediately following the older formula of getting a job and going to sleep. He says young people can live cheaply while figuring themselves out, but should not rely on their parents’ money. Asked how to know whether a decision was right, he says the best part of life is that no one knows the answer. He recounts passing twice on investing $25,000 in Uber, a decision that would have produced about $586 million at the IPO. Rather than dwelling on the missed money, he imagines that investing might have led to his death in a hypothetical accident and chooses optimism. His rule is to follow his gut, accept consequences, and neither celebrate excessively when right nor cry when wrong.

Gary gives an audience member who charges $150 per hour a concrete plan. He says the person should raise the rate by $50 or more, preserving an hour of time while earning the same amount. That recovered hour should be used to launch TikTok Live, Whatnot, and eBay Live selling. The person should continue for 24 months, clip the livestreams into additional content, and gradually move from one piece every two days toward dozens of pieces per day or week. Gary says a live-shopping session is valuable even when it produces no sales because it doubles as a production session: one hour can yield roughly 13 clips, and sales spikes can reveal which phrases make viewers buy and should therefore be reused in evergreen content. Another participant describes trying for nine years to sell a Russian-Egyptian street dessert, working restaurant-management hours while attempting to create demand in Brighton Beach. Gary says the product may not have obvious existing demand and cannot scale through personal effort alone. His proposed breakthrough is a video that is half English and half Russian: if the right post reaches 14,000 people in the Brighton Beach area and nine visit the store, that can start the business. He again emphasizes that one post can change a company, but the creator must increase the posting volume. For a founder seeking $1–10 million, Gary recommends emailing 5,000 venture capitalists on LinkedIn or directly messaging 5,000 wealthy people on Instagram. He warns that perhaps only three may respond, so sending 113 messages and declaring failure does not count as following the advice. Contextual, non-salesy messages are more likely to work, but the required scale is still thousands of attempts.

In response to a question about people who follow his advice without immediate success, Gary says they may simply be doing it poorly. He acknowledges being exceptionally lucky, including having a mother who parented him in a way that helped him succeed, and says serendipity is real. He also uses the roughly 400-trillion-to-one odds of being born human to illustrate that everyone has benefited from luck. But he rejects luck as an excuse for not winning: anyone who invokes luck to justify inaction is, in his words, a loser. Gary compares business to his own basketball practice. He works at basketball but is not going to the professional league; the appropriate response is to recognize that he is not good enough at that activity, not invent a reason. He says it is fine to be bad at something, while it is damaging to make excuses for being bad. In business, unlike some other areas, the results do not lie: if a company is not making money, its current business performance is not good enough. Claims of shadow banning, algorithmic unfairness, lack of luck, or stolen ideas distract from finding the actual problem. His final formula is knowledge, disciplined practice, and accountability. People should identify what they are genuinely good at, become practitioners of the knowledge they acquire, and accept that discipline is the core of the game. The episode closes with Gary thanking the audience and directing listeners to earlier podcast episodes before the final Vanta advertisement.