Gary Vaynerchuk — better known as Gary Vee — brought his signature energy to Diary of a CEO for one of the most intense and revealing conversations in the show's history. The serial entrepreneur, CEO of VaynerMedia, and social media pioneer sat down with Steven Bartlett for over 1.5 hours to discuss what it really takes to build an empire, why most entrepreneurs are miserable, and the one thing he values above money, fame, and business success.
This episode shattered preconceptions. If you think Gary Vee is just about "hustle harder," you haven't been listening. This conversation reveals a deeply thoughtful businessman whose core philosophy is far more nuanced than his Instagram clips suggest. For more entrepreneurship-focused episodes, see our best Diary of a CEO episodes for entrepreneurs.
Gary opens the conversation by going deeper into his backstory than he typically does on social media. Born in Belarus (then part of the Soviet Union), his family immigrated to the United States when he was three years old. They arrived with almost nothing — his family of eight lived in a small studio apartment in Queens, New York.
He describes the moment that fundamentally shaped his relationship with money and success. As a child, he watched his father work 18-hour days in a liquor store, never complaining, never taking a day off. But what struck young Gary wasn't the work ethic — it was the gratitude. His father was genuinely grateful for the opportunity to work that hard, because in the Soviet Union, the opportunity itself didn't exist.
"My dad didn't hustle because he was chasing money. He hustled because he was grateful. There's a massive difference between grinding out of desperation and grinding out of gratitude. One destroys you. The other fuels you."
— Gary Vaynerchuk, CEO of VaynerMedia & Serial Entrepreneur, on Diary of a CEO
This distinction — gratitude-driven work versus fear-driven work — becomes a recurring theme throughout the episode and fundamentally reframes how most people understand Gary's "hustle" message.
Steven Bartlett pushes Gary on the criticism that his message promotes toxic hustle culture. Gary's response is surprisingly measured. He explains that his message has never been "work 18 hours a day." His message has always been "work on things you actually care about, and stop spending time on things that drain you."
He points out that people who hate their jobs work 40 hours a week and feel exhausted. Meanwhile, people who love what they do can work 60 hours and feel energised. The difference isn't the hours — it's the alignment between the work and the person.
"I don't think everybody should work 15 hours a day. I think everybody should figure out what they actually enjoy, and then go all in on that. If you love painting, paint for 15 hours. If you love your 9-to-5 and your weekends, that's beautiful too. Stop letting other people's scorecards define your success."
— Gary Vaynerchuk, CEO of VaynerMedia, on Diary of a CEO
He adds a layer that rarely makes it into the social media clips: he genuinely believes that most people should work less, not more. The problem isn't laziness — it's that people spend enormous amounts of time on activities they think they "should" be doing (scrolling social media, attending pointless meetings, maintaining relationships that drain them) instead of activities that actually matter to them.
When the conversation turns to social media strategy, Gary shifts into pure practitioner mode. He breaks down exactly what's working across platforms and why most businesses are getting it wrong.
His core insight: attention is the most underpriced asset in the world. Every generation has an attention arbitrage opportunity — in the 1950s it was TV, in the 2000s it was Google AdWords, today it's short-form video content on TikTok and Instagram Reels. The businesses that recognise where attention is cheap and produce content for those platforms will dominate.
"Every business in the world is a media company that happens to sell a product. If you're not producing content, you're invisible. It doesn't matter how good your product is — if nobody knows about it, it doesn't exist."
— Gary Vaynerchuk, Social Media Pioneer & CEO, on Diary of a CEO
He gives specific tactical advice that makes this episode incredibly valuable for anyone building a brand or business. Post at least 6-8 pieces of content per day across platforms. Don't worry about quality initially — volume creates data, data reveals what works, and then you double down on the winners. He argues that most people never post enough to even understand what their audience wants.
One of the most compelling stories Gary shares is about selling his father's wine business. He took Wine Library from $3 million to $60 million in revenue through one of the internet's first viral video series — Wine Library TV. He could have sold and cashed out. Instead, he walked away to start VaynerMedia with zero revenue and zero clients.
Why? Because he was playing a longer game. He saw that the next 30 years of business would be defined by social media and digital attention. Building VaynerMedia was a bet on that future. Today, VaynerMedia does over $300 million in annual revenue and serves some of the world's largest brands.
"Patience is not passive. Patience is doing the work every single day while being at peace with the fact that the results haven't shown up yet. Most people quit three feet from gold because they expected the timeline to be shorter."
— Gary Vaynerchuk, CEO of VaynerMedia, on Diary of a CEO
He emphasises that the biggest advantage any entrepreneur can have is a long time horizon. When you're not in a rush, you make better decisions. You don't take bad deals out of desperation. You don't compromise your values for short-term gains. Time becomes your greatest ally.
The conversation takes an unexpected turn when Bartlett asks Gary what he optimises for. The answer isn't revenue, followers, or empire-building. It's happiness. And not some abstract future happiness — present-tense, everyday happiness.
Gary explains that he's met too many billionaires who are miserable. He's met too many successful entrepreneurs whose marriages have fallen apart, whose children barely know them, whose health is deteriorating. They "won" by society's scorecard but lost by any meaningful measure of human fulfilment.
"I know guys worth a billion dollars who are the most miserable humans on earth. And I know a teacher making £40,000 a year who wakes up excited every morning. Who actually won? We've got the scoreboard completely backwards."
— Gary Vaynerchuk, Entrepreneur & Author, on Diary of a CEO
This segment resonates powerfully with the Diary of a CEO audience. Steven Bartlett, who has been open about his own struggles with mental health despite massive business success, connects deeply with Gary's point. They agree that the entrepreneurship world glorifies sacrifice and suffering as necessary ingredients of success, when in reality, the best businesses are built by people who are genuinely happy and present.
Perhaps the most emotional moment of the episode comes when Gary discusses his relationship with mortality — specifically, the inevitability of his parents' death. He explains that he thinks about this regularly, not out of morbidity, but as a way to maintain perspective and gratitude.
He argues that most people waste their time on trivial anxieties — worrying about what people think of them, stressing about losing followers, obsessing over competitors — because they haven't truly internalised the reality that life is finite and that the people they love will not be here forever.
"When you truly accept that your parents are going to die — not intellectually, but emotionally — everything else becomes background noise. The opinion of a stranger on the internet? Irrelevant. A bad quarter? Doesn't matter. You get one shot at this life. Act like it."
— Gary Vaynerchuk, CEO & Speaker, on Diary of a CEO
Steven Bartlett is visibly moved by this segment. He shares his own complicated relationship with his parents and how success has both connected and distanced him from his family. It's raw, unscripted, and exactly the kind of moment that makes Diary of a CEO stand apart from typical business podcasts.
In the final stretch of the episode, Gary delivers specific, actionable advice for aspiring entrepreneurs. His recommendations are refreshingly practical and counter to most "guru" advice:
For more practical business wisdom from the show, explore our Diary of a CEO business advice for entrepreneurs and Steven Bartlett's key podcast lessons.
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