The single biggest business lesson from Gary Vaynerchuk is that attention is the most valuable currency in business, and the entrepreneurs who win are the ones who spot where attention is shifting before everyone else, then show up there with genuine value rather than a hard sell.
Gary Vaynerchuk is an entrepreneur, investor and media executive who built his career by recognising change before it became obvious. He grew his family liquor store into a multimillion pound business using early internet marketing, then built VaynerMedia into one of the most recognised digital agencies in the world. Along the way he has written multiple bestselling business books, built a large media platform, and invested early in companies such as Facebook, Twitter, Uber and Snapchat. His track record is worth studying because it spans decades and multiple platform shifts, not one lucky viral moment, which means the lessons underneath his career hold up regardless of which app or trend is currently fashionable.
Turning a Family Liquor Store into a National Brand
Gary Vaynerchuk joined his fathers liquor store, Shopper’s Discount Liquors in New Jersey, as a teenager and later took over day to day running of the business. At the time, the store was doing a few million pounds in annual sales. Rather than simply continuing to run it the way his father had, Gary rebranded it as Wine Library and began experimenting with direct mail, then email marketing, and eventually early e-commerce, at a point when most independent wine retailers had no serious online presence. Under his leadership the business grew from around three million pounds in revenue to around sixty million pounds within several years. He did this not by discounting harder than competitors but by treating the internet as a genuine sales channel long before most local retailers took it seriously.
How to apply this to your business: Look honestly at whether you are running your business the way it has always been run simply out of habit. Identify one channel your competitors are ignoring or underusing, whether that is email, video or a newer platform, and commit real time to testing it properly rather than dabbling half heartedly.
Spotting the Power of Early Platforms with Wine Library TV
In 2006, Gary Vaynerchuk launched Wine Library TV, a daily video series in which he tasted and reviewed wines, often in a loud, informal and unpolished style that stood in sharp contrast to the stuffy tone of traditional wine criticism. At the time, online video was not yet a mainstream marketing tool for small businesses, and platforms like YouTube were still new. He filmed himself most days for years, building a loyal audience that trusted his opinion because it was consistent, honest and free of the pretension usually associated with wine commentary. This consistent output turned Wine Library into a recognised national name and turned Gary himself into a public figure long before personal branding was a common business strategy.
How to apply this to your business: Pick one content format you can sustain regularly, even if it is imperfect, and commit to publishing it consistently over a long period rather than searching for the perfect single piece of content. Consistency and authenticity will do more for trust than production quality in the early stages.
Documenting the Journey Instead of Creating a Polished Narrative
A recurring theme throughout Gary Vaynerchuks career, especially visible in his long running DailyVee vlog series, is the idea of documenting rather than creating. Instead of scripting elaborate marketing campaigns, he simply filmed his actual working days, meetings, keynote talks and internal VaynerMedia discussions, then published the footage with minimal editing. This meant content could be produced constantly without the huge time and cost of traditional production, because the raw material already existed in his everyday work life. It also meant audiences saw a more honest version of business life, including setbacks and mundane moments, rather than a curated highlight reel.
How to apply this to your business: Instead of trying to invent content ideas from scratch, look at what you are already doing each day, such as answering customer questions, making products, or solving problems, and turn that existing activity into content. This lowers the barrier to consistent output and tends to feel more credible to an audience than heavily produced material.
Building VaynerMedia by Serving Platforms Others Overlooked
Gary Vaynerchuk founded VaynerMedia in 2009 together with his brother AJ Vaynerchuk, at a time when many established advertising agencies still viewed social media as a minor add on to traditional television and print campaigns. VaynerMedia positioned itself specifically around social platforms, helping large brands understand how to communicate on channels like Facebook and Twitter when most agency leadership teams did not fully understand them. This early specialisation allowed the agency to win business with major brands who needed genuine expertise rather than a token social media offering bolted onto a traditional campaign. Over time VaynerMedia grew into a global agency working with some of the largest consumer brands in the world, and Gary remains chairman of VaynerX, the parent company.
How to apply this to your business: Rather than trying to compete broadly against established players, find a specific area of genuine expertise that larger or older competitors are slow to take seriously, and build your reputation there first. Specialisation in an underserved niche is often more valuable early on than trying to appeal to everyone.
The Jab, Jab, Jab, Right Hook Approach to Giving Value First
In his book Jab, Jab, Jab, Right Hook, Gary Vaynerchuk lays out a framework for social media marketing built around giving genuine value to an audience multiple times before ever asking for a sale. The jabs represent useful, entertaining or informative content shared with no immediate expectation of return, while the right hook represents the eventual direct ask, such as a promotion or purchase request. The core argument of the book is that most businesses ruin their social media presence by constantly asking for sales without first earning attention and trust. He illustrated this using real case studies of brands that succeeded by adapting their tone and content format to match the native style of each individual platform, rather than posting the same message everywhere.
How to apply this to your business: Audit your own social media output and count how many of your recent posts asked for something versus how many simply gave value with no strings attached. Aim to shift that balance so the majority of your content builds goodwill, with sales asks appearing only occasionally and earning more attention as a result.
Betting Early on Emerging Platforms and Attention Shifts
Throughout his career, Gary Vaynerchuk has repeatedly identified platforms early, before they became mainstream marketing channels, including Twitter, Facebook, Instagram, and later TikTok. He has spoken often about the concept sometimes referred to as attention arbitrage, the idea that when a new platform launches, attention there is cheap and underpriced compared to its actual reach, because most businesses have not yet arrived to compete for it. As platforms mature and more brands pile in, the cost of gaining attention rises and the advantage shrinks. His early personal investments in companies such as Facebook, Twitter, Uber and Snapchat through his venture fund also reflect this same instinct, applied to investing rather than marketing.
How to apply this to your business: Regularly test new platforms and formats as they emerge, even in a small experimental way, rather than waiting until a channel is already crowded and expensive. The businesses that build an audience early on a new platform typically enjoy lower costs and stronger organic reach than those who arrive once it has matured.
Obsessing Over Customer Service
During his time running Wine Library, Gary Vaynerchuk became known for personally responding to customer emails and comments, treating individual customer interactions as seriously as major business decisions. This obsession with responsiveness extended into how Wine Library TV was run, where he would reply to viewer comments and questions directly, reinforcing the feeling that a real person, not a faceless company, was behind the brand. He has spoken repeatedly about how the businesses that win long term are the ones that treat every single customer interaction as a chance to build loyalty, arguing that word of mouth generated through excellent service is far more valuable than most paid advertising.
How to apply this to your business: Make it a standard practice for someone senior, not just junior support staff, to personally read and occasionally respond to customer feedback and complaints. Treat every response as a brand building opportunity rather than a box ticking exercise, since a single thoughtful reply can turn a frustrated customer into a vocal advocate.
Using Personal Brand to Build Business Value
Gary Vaynerchuk built his own personal brand alongside his business ventures, appearing on television, writing multiple bestselling books including Crush It!, The Thank You Economy and Crushing It!, and speaking at conferences worldwide. Rather than treating his personal visibility as separate from his companies, he used it deliberately to open doors for Wine Library and later VaynerMedia, since audiences who trusted him personally were more inclined to trust the businesses he was involved in. This approach predates the current widespread interest in founder led marketing, and it demonstrates how a well built personal reputation can act as a form of business asset, generating leads, partnerships and credibility that paid advertising alone struggles to replicate.
How to apply this to your business: If you are a founder or leader, consider building some visibility for yourself personally, through writing, speaking or video, rather than keeping all communication under a faceless company name. A trusted personal reputation can lower the cost of winning new customers and partners over time.
Patience and Playing the Long Game
A consistent message across Gary Vaynerchuks talks and writing is patience, the idea that meaningful business results, particularly brand building results, take years rather than months. He has frequently criticised the tendency among entrepreneurs to expect immediate returns from content or marketing efforts, pointing out that his own success at Wine Library and VaynerMedia came from years of unglamorous, repetitive daily effort before major breakthroughs appeared. This message runs directly against the instinct many business owners have to abandon a strategy after a few weeks of disappointing results, and it reflects the reality of his own career, where Wine Library TV ran for years before it became widely recognised as a landmark example of branded video content.
How to apply this to your business: Set realistic timeframes for new marketing or brand building efforts, measured in years rather than weeks, and judge early results against leading indicators like engagement and repeat attention rather than immediate sales. Resist abandoning a sound long term strategy simply because short term numbers look unremarkable.
Self Awareness and Hiring for Weaknesses
Gary Vaynerchuk has spoken openly about his own limitations, including admitting he is not naturally strong in certain operational or detail oriented areas of running a large company, and has structured his businesses accordingly by bringing in partners and executives, including his brother AJ Vaynerchuk, to manage areas where he is weaker. Rather than trying to personally master every discipline required to run a global agency, he has focused his own time on the areas where his judgement and energy add the most value, such as brand vision, culture and public facing communication, while delegating operational execution to others he trusts.
How to apply this to your business: Identify honestly which parts of running your business drain your energy or fall outside your natural strengths, and prioritise hiring or delegating those areas first. Spending your own time on the few things you are genuinely best at tends to produce far better results than trying to be equally competent at everything.
Taking Calculated Risks with New Ventures such as VeeFriends
In 2021, Gary Vaynerchuk launched VeeFriends, a collection of non fungible tokens built around original characters he had drawn and written, combined with utility such as access to events and business networking opportunities. This was a significant departure from his earlier work in wine retail and advertising, entering a new and unproven market, and it reflected a willingness to take a calculated risk on an emerging category rather than staying solely within familiar territory. The project drew heavily on his existing personal brand and community, and it was launched with a long term multi year vision attached, rather than positioned as a short term speculative flip, consistent with his broader message about patience.
How to apply this to your business: When considering entry into a genuinely new market or format, use your existing audience or reputation as a foundation rather than starting completely from zero. Be clear with yourself and your customers about whether a new venture is a long term commitment or a short term experiment, and communicate that honestly.
Free resource: The Discount Request Response Swipe File.
Frequently asked questions
What is Gary Vaynerchuk best known for in business?
He is best known for growing his family liquor store, Wine Library, from a few million pounds in sales to around sixty million pounds using early internet and video marketing, and for co-founding VaynerMedia, a global digital marketing agency. He is also widely recognised for his early social media commentary and his books on marketing and personal branding.
What companies has Gary Vaynerchuk founded or led?
He led Wine Library, his family business, before co-founding VaynerMedia with his brother AJ Vaynerchuk in 2009. He is chairman of VaynerX, the parent company that includes VaynerMedia, and he has also launched other ventures including the VeeFriends NFT project and various investment funds.
What is the main marketing philosophy associated with Gary Vaynerchuk?
His core marketing philosophy, laid out most clearly in his book Jab, Jab, Jab, Right Hook, is that businesses should provide genuine value to their audience repeatedly before asking for a sale, and that content should be tailored to the native style and tone of each individual platform rather than repeated identically everywhere.
Has Gary Vaynerchuk invested in any well known companies?
Yes, through his early venture investing activity he made personal investments in companies including Facebook, Twitter, Uber and Snapchat, generally entering at an early stage before these companies became widely known, reflecting the same instinct for spotting emerging attention and opportunity that runs through his marketing work.
What books has Gary Vaynerchuk written that business owners should read?
His notable books include Crush It!, The Thank You Economy, Jab, Jab, Jab, Right Hook, Crushing It! and Twelve and a Half. Each focuses on themes such as personal branding, social media marketing, customer relationships and the emotional skills needed to succeed in business over the long term.
More business lessons
- Business Lessons from Walt Disney
- Business Lessons from Karren Brady
- Business Lessons from Phil Knight
Related reading: Shadow AI: What Your Team Is Doing With ChatGPT Behind Your Back and AI Agents for Small Business: What They Are and Where to Start in 2026.
