Jul 9, 2025 · 1h 18m · bigdeal
The Biggest Bets I Made — And How They Paid Off: Gary Vee
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Entrepreneur and investor Gary Vaynerchuk joins Codie Sanchez on The Big Deal to share actionable operational frameworks, talent evaluation strategies, organic content playbooks, and forward-looking predictions on artificial intelligence.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Codie holds 19.2% of the talking time here. How this is scored →
Codie as informed peer 3.5 Guest teaching 3.0 Guest disagreement 2.0 Codie pushing back 0.9
speaking balance: gold is Codie, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:40 Gary Vee explodes on ideological polarity
Vaynerchuk emphatically attacks binary political and cultural mindsets, shouting that life is purple and calling dogmatic thinkers idiots.
Hardest push from Codie ▶ 1:04:43 Sanchez champions Beehiiv over SubstackSanchez interrupts Vaynerchuk's Substack endorsement to advocate for Beehiiv, defending the founder's execution speed and market dynamics.
Biggest teaching moment ▶ 1:01:11 Gary Vee educates on live social commerce in ChinaVaynerchuk drops macroeconomic figures revealing that live social shopping accounts for 30 percent and half a trillion dollars of Chinese e-commerce, catching Sanchez off guard.
Codie holds their own ▶ 37:03 Sanchez provides exact wealth distribution oddsSanchez asserts authority by citing exact statistical probabilities for reaching 1 million, 10 million, and 20 million dollar income tiers in the US.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Codie as informed peer | Guest teaching | Guest disagreement | Codie pushing back | Why |
|---|---|---|---|---|---|---|
| Gary's Early Investments: Evaluating the Jockey and the Horse | 4 | 3 | 1 | 0 | Sanchez opens by cataloging Vaynerchuk's top early investments and correctly identifies Tinder founder Sean Rad. Vaynerchuk breaks down his shift from idea-based investing back to evaluating the founder ('jockey and the horse'). | |
| The Interview Playbook: Emotional Intelligence and Player Grading | 2 | 3 | 1 | 1 | Sanchez prompts Vaynerchuk on his hiring and founder evaluation techniques. Vaynerchuk explains his reliance on emotional intelligence and why he welcomes C players who can be upgraded to B players. | |
| Executive Weaknesses, Radical Candor, and Difficult Firings | 3 | 2 | 2 | 2 | Sanchez pushes Vaynerchuk on cultural toxicity versus performance. Vaynerchuk clarifies personality versus skill and openly discusses his personal executive vulnerability with candor and firing people. | |
| Guidance Counselor Energy: The Highs and Lows of Helping People | 2 | 1 | 1 | 1 | Sanchez highlights how intimidating Vaynerchuk's public stature can make feedback feel. Vaynerchuk reflects on operating with guidance counselor and therapist energy. | |
| The 'Purple' Reality: Insecurity, Modern Excuses, and Tough Love | 2 | 3 | 6 | 1 | Vaynerchuk launches into an impassioned critique of modern excuses, calling out parents who subsidize adult kids and reframing imposter syndrome as plain insecurity. Sanchez mostly serves as an active listener and validator. | |
| Childhood Hustle: Skipping School and Finding Validation in Business | 3 | 2 | 1 | 1 | Sanchez shares an anecdote of a teacher telling her she had no future in finance to match Vaynerchuk's story of academic struggle. Vaynerchuk recounts finding early validation through adolescent baseball card dealing. | |
| The Science of Merchandising: From Card Racks to E-Commerce | 5 | 4 | 1 | 1 | Sanchez engages deeply on retail merchandising, citing the Harry Potter flagship store and Sam Walton's greeters. Vaynerchuk details early e-commerce cart abandonment hacks and visual product positioning. | |
| Scaling the Unscalable and the 10-80-10 Leadership Framework | 4 | 4 | 1 | 0 | Sanchez provides personal evidence of Vaynerchuk scaling unscalable touchpoints when he texted her directly at an event. Vaynerchuk outlines his 10-80-10 executive involvement framework. | |
| The Trap of External Validation vs. Loving the Work | 2 | 3 | 2 | 0 | Sanchez asks what young founders overlook. Vaynerchuk diagnoses the modern addiction to superficial status symbols and highlights genuine passion as the only sustainable engine. | |
| Building Real Empires: Inside the Vayner Portfolio | 4 | 3 | 2 | 1 | Sanchez demonstrates thorough research into Vaynerchuk's holding companies (VaynerX, VaynerSports, VeeFriends). Vaynerchuk highlights the brutal reality of actual profitability and operational grit. | |
| The True Difficulty of Wealth and Systems of Merit | 5 | 3 | 2 | 1 | Sanchez introduces statistical distribution data on top income tiers to ground the discussion. Vaynerchuk contrasts meritocratic systems like sports with bureaucratic structures. | |
| The Pitfalls of Flashy Content and the Value of Selfless Posting | 4 | 2 | 1 | 1 | Sanchez calls luxury flex posts an immediate red flag. Vaynerchuk agrees, framing flashiness as selfish content creation aimed at extraction rather than audience value. | |
| Starting from Scratch: Building a Local Empire via Content | 3 | 4 | 1 | 0 | Sanchez challenges Vaynerchuk to create a growth playbook starting from a single local laundromat. Vaynerchuk maps out combining personal storytelling with geo-targeted 10-mile radius ad campaigns. | |
| The 'Store Studio': Why Low Production Content Wins | 4 | 2 | 2 | 0 | Sanchez shares performance metrics from her portfolio showing that low-fi authentic ads outperform high-budget productions. Vaynerchuk reinforces the 'store studio' concept. | |
| Responding to Haters with Compassion and Preserving Drive | 4 | 3 | 4 | 1 | Sanchez brings in philosophical concepts of nihilism to discuss personal drive. Vaynerchuk details managing online hate with 90% compassion and 10% competitive ruthlessness. | |
| Mastering Social Media Literacy to Identify Top Talent | 3 | 4 | 3 | 1 | Sanchez inquires about hiring social media operators for portfolio companies. Vaynerchuk insists executives must attain social media literacy themselves before delegating to junior staff. | |
| Live Social Shopping: The Next Wave of Underpriced Attention | 5 | 4 | 2 | 3 | Vaynerchuk presents data on China's massive live shopping industry. Sanchez counters on newsletter platforms by pushing Beehiiv and defending multi-platform market expansion. | |
| AI Predictions: Ubiquitous Intelligence and Future Human Relationships | 4 | 4 | 3 | 2 | Sanchez queries Vaynerchuk on AI predictions and highlights voice dictation tech. Vaynerchuk predicts AI companionship and ubiquitous infrastructure integration. | |
| Embracing Inevitable Tech Shifts and Podcast Conclusion | 4 | 3 | 3 | 1 | Sanchez shares an ethical thought experiment posed by her in-house AI specialist regarding cyborgs and human boundaries. Vaynerchuk concludes with the historical inevitability of tech shifts. |
Statements from this episode (25)
Gary Vee's first three angel investments were Facebook, Twitter, and Tumblr
“Facebook, Twitter, and Tumblr were my first three investments of my life.”
Gary Vaynerchuk made payroll for 27 straight years without outside funding
“For 27 straight years, every day of my life, I have had to be responsible to make payroll. With no funding.”
Gary Vaynerchuk welcomes hiring C-players to develop them into B-players
“C players, for my businesses when I hire, I love a good C because I think we have a system to get people to Bs, and I think Bs are great.”
Gary Vaynerchuk: A C-tier personality is fatal to an organization
“Give me an A plus personality and a C player, because C personality is death on arrival.”
Gary Vaynerchuk: My biggest executive flaw was struggling to give critical feedback
“When I realized, you know, five to seven years ago, that lack of candor, which is crazy, because Gary Vee's candor's off the charts, but Gary Vaynerchuk, the executive, when I realized lack of candor, I struggled giving critical feedback.
Yeah, and then the fi…”
Gary Vee: Financially supporting adult children signals they are losers
“Because parents don't realize if you're paying for your kid when they're a grown adult, you're telling your kid you don't believe in them. Through your actions, not your words. They know they're a loser. Yeah. That shit hurts. You know?”
Gary Vaynerchuk: Imposter syndrome is just a euphemistic label for insecurity
“Do you know what imposter syndrome is? It's called insecurity. We've just given it makeup. Nobody's like, yo, I'm insecure. Nobody says that code, but so many people are like, man, I have imposter syndrome. Makeup. Got it? The definition, literally the definit…”
Gary Vee: Wine Library started abandoned cart email recovery in 2000
“I remember going to my developer in 2000 being like, can we see who didn't check out? Like, I like, it was like, you gotta understand this is an early internet... He's like, yeah, we started emailing people that had abandoned carts and fucking crushed.”
Gary Vee: Early-stage creators must reply to every comment and DM
“If you're just kind of getting into your early stages, and you have like, 10,000 followers, and you're posting, and you're getting 14 comments, you're getting 13 DMs a day, reply to all of them. Scale the unscalable.”
Gary Vee: Leaders should only touch the first and last 10%
“When we're doing important shit, I tell the team, I have to be involved in the first 10%, because I'm molding it. Then I disappear. And then you need to come back to me to close it. I open and close. The middle's the problem. And winners, and people aspiring t…”
Gary Vaynerchuk: Most achieve success from insecurity rather than confidence
“I continue to believe that most people get successful because of insecurity, and there's a rare breed That gets there through confidence, and I'm so grateful that I'm in that small group, and I see it in others.”
Gary Vee: VaynerMedia generates $350M annually with 2,000 employees
“Now it's 2000 plus people, three hundred fifty million a year revenue. Not valuation.”
Gary Vee predicts he will be known primarily for VeeFriends
“VFriends is the other biggest business I run. That's my Marvel Pokemon. It's an intellectual property. That's, I do actually believe in my eighties, that's what I will be known for more than anything else I've done.”
Gary Vaynerchuk: Restaurants and sports agencies are bad businesses
“Restaurants and sports agencies, bad businesses.”
Gary Vee: Influencers who flex luxury struggle and are less happy
“People that have over-indexed on that move, I have found over the last 20 years, tend to struggle to stay on top, Tend to be less happy.”
Gary Vee: A personal brand is the only asset AI cannot commoditize
“Building your personal brand, I do believe is a moat. I've always believed that it was the moat. I've talked about it for 15 years that it's the moat. It is the one true asset that doesn't get commoditized even in the AI world. You still have your IP. It's you…”
Gary Vee: 10-mile radius Facebook ads drive local business growth
“Disproportionately, the biggest opportunity to grow your business, traffic to your business, average receipt size, is to run, if you're a local business that people come to, is to run 10 mile radius Facebook ads.”
Gary Vee: Obsessing over video production value frequently disguises creator insecurity
“Production often, often again is Disguising insecurity. A lot of people talk about production, if you listen carefully, it's just an excuse to not do.”
Gary Vee: Eliminating competitiveness causes nihilism and severe depression
“Winning and losing is incredibly imperative to the human race. Nothing is good out of balance. Of course, people are like, Gary, winning and losing, like, is it ok to, like, hurt people to win? No, no, it's not ok. But is it okay to completely eliminate merit …”
Gary Vee predicts Meta, Google, and X will enter live shopping
“I expect Meta, Google, Twitter, everybody to get into this game. Live social shopping is the underpriced attention.”
Gary Vaynerchuk identifies Snapchat Spotlight as heavily under-saturated
“Nobody's posting on there. So I, I'm very hot on Snapchat Spotlight”
Gary Vaynerchuk predicts some people's grandchildren will marry AI robots
“Well, I've gone pretty viral lately because I, my craziest prediction is that most people's grandchildren will marry an AI robot. Some of them will, not everyone's going to”
Gary Vaynerchuk: All consumer shopping will eventually be done by AI
“I think all of shopping will be done by agents for you based on your behaviors. Like, it will know better that you wanted that outfit than you knew.”
Gary Vee avoids AI startups because rapid iteration causes obsolescence
“Also, real quick, because I know a lot of smart investors listening here, be very careful in investing in AI. The reason I haven't yet is every week, you think you just invested in the best X, and a week later, somebody crushes that.”
Gary Vee: Real-time translation earbuds will eliminate learning foreign languages
“What about the fact that nobody has to learn a language anymore? Everyone's going to have ear pods that like, you're going to talk to somebody, they're going to be speaking Spanish and you'll hear it as English and you're going to speak English and they'll hea…”