Podcast Summary: Uncensored CMO – Gary Vee on the Most Undervalued and Overvalued Media

Host: Jon Evans
Guest: Gary Vaynerchuk (Gary Vee)
Date: November 12, 2025

Overview

This episode features an in-depth, energetic conversation between Jon Evans and marketing icon Gary Vaynerchuk (Gary Vee), recorded fittingly in the Wine Library, the retail store where much of Gary’s career began. The discussion covers Gary’s formative years, his philosophy of customer obsession, and—centrally—the shifting values of different media in modern marketing. The pair debate where brands should spend their money, the undervalued gems and overhyped channels, and Gary’s prescription for authentic, audience-driven content in an AI-powered era.

Key Discussion Points

1. Origins and Early Business Lessons

• Homecoming at the Wine Library [01:01]: Gary describes the emotional connection to the Wine Library, the family store that shaped his work ethic and marketing mindset.

  • “This is a very, very cozy home for me. This retail store, this is where I think I refined the skills I picked up on business and marketing as a kid...” [01:05–01:35]

• Customer Obsession & Work Ethic [02:44]:

  • Gary attributes his edge to relentless customer focus: “I’ve been blindly obsessed with delivering value to the customer. Not because I’m a good dude… but I don’t understand why you wouldn’t want to give the customer the disproportionate most value.” [02:44–03:33]
  • He highlights the discipline and hard labor: carrying boxes, long hours, manual jobs from age 14–28. “Sacrifice, discipline, work ethic, commitment, lack of complaining, lack of entitlement—I learned everything here.” [05:53–06:38]

2. The Myth of Luck and Defining Success

• Both host and guest reflect on the role of luck and response to adversity. Gary: “The word luck is the weapon of choice of the hurt and the lazy. I really don’t think anyone is lucky...” [06:58]

• Quote: “Everybody on earth is gonna get punched in the face. Everybody on earth is gonna win a scratch-off ticket. Life is life.” [08:04]

3. Purpose-Driven Content Creation & Brand Generosity

• The Secret to Scale [10:21]: Gary attributes his large, loyal audience to genuine intent and selflessness: “The ultimate way to be selfish is to be selfless.” [10:40]

• He critiques creators who are focused on their personal gain, status, or envy, instead of true audience value.

  • “I think life is about confidence and insecurity ... I want that for [my audience] too. In a lot of ways... I’m mothering the universe through my content.” [11:53–13:13]

• Generosity Fuels Brand [13:15]: Jon shares his discovery that giving more value freely increases reach and opportunity, to which Gary replies: “It’s called brand… Brand beats sales every day of the week.” [13:43]

4. Relationships Over Ruthless Negotiation

• Negotiation Philosophy [14:30]: Gary contrasts his approach (leaving some value on the table, building long-term relationships) with his father’s aggressive deals.
  • “Every time I leave a penny or a nickel on a deal and the other person feels it, it allows me to make another deal the next time and the next time and the next time.” [15:08]
  • He emphasizes the power of reputation: “Somebody’s way of communicating about me matters.” [16:30]

5. Spotting Trends (and Missing Them)

• Early Adoption Success—and Regret [18:05]:

  • Gary candidly discusses missed investment opportunities (notably Uber): “My most famous passing is on Uber... I made a humongous financial mistake by passing on Uber.” [18:13]
  • He shifted from backing great people (the 'jockey') to just ideas, which led to losses.

• Customer-Centric Trendspotting [19:17]:

  • “When you are obsessed with the consumer, you win… I don’t care about Wall Street or Madison Avenue… they are not consumer-centric.” [19:36–20:11]

6. Debate: Undervalued & Overvalued Media

Over-Indexed Corporate Focus [21:19]

• Gary criticizes the Fortune 500’s (and agencies’) emphasis on internal politics rather than the consumer, calling out “Cannes Lion-centric, Ad Age-centric, industry insecurity-centric” mindsets.

The Current Winners in Media [21:49]

• “The brands that are doing it well are living on social media. … Nobody gives a fuck about billboards. … A television commercial … is wildly overpriced. Digital banner ads are complete and utter rubbish. … Google AdWords are declining in our face because of AI chatbots. …The foundational ecosystem of our society is the mid-funnel known as organic social media.” [21:49–22:52]

TV vs. Social: The Great Debate [24:09–28:27]

• Jon points to studies claiming TV still delivers more attention per second, to which Gary emphatically disagrees:
  • “I do not believe in 2026 that people are giving any seconds to a television spot. 0.0. Not to mention, have you looked at the creative that is the modern commercial? They’re all dog shit.” [27:41]
  • Super Bowl ads remain the exception: “The best deal in marketing is a television commercial. It just happens to be a cultural phenomenon in America called the Super Bowl.” [29:16]

7. Quickfire: Overrated vs. Underrated Channels [28:27–41:09]

Gary's verdicts, with rationale and context:

• Podcasts: “Wildly undervalued.” [29:28]
  Deep engagement and long attention span, especially when integrated authentically, not as vanilla readouts.
• LinkedIn: “Wildly underpriced... should be your number one spend [for B2B].” [31:39]
  Underutilized by both B2B and B2C (fitness, sneakers, etc.).
• Email: “Underrated.” [32:27]
  Only if used for value, not spam; admits even he misused it for sales over brand.
• SMS: “The most underrated of the four that we've already mentioned. … That's how much SMS has mattered.” [33:32]
• YouTube: “Underpriced, but nuanced… most people are wasting a ton of money on YouTube... treating it like television. … Media support should only go behind creative that’s been validated organically.” [34:11–35:13]
• Search/AdWords: “Overpriced… AdWords, the companies that are reliant on it, many of them will be heavily damaged over the next 36 years if they don’t quickly diversify.” [37:48–38:16]
  • Wishes it was called “search sales,” not “search marketing.”
    “Google has effectively made people pay for their own brand equity, which is wild.” [36:08]
• TikTok: “Might be the most underpriced aspect … you are literally one 49-second clip away from the next day being in a different place. ... TikTok has the biggest upside in this generation.” [38:43–40:11]
• Twitter/X (as an ad product): “Very much is underwhelming… dramatically less effective than Meta and TikTok. … Organically, more upside than in the past.” [40:22–41:08]

8. On Truth, Sports, and AI’s Coming Disruption

• Sports & Business vs. Politics & Academia [43:37]:
  • “You can’t hide in sports. … business makes money or doesn’t. … There is no debate.”
• AI’s Challenge to Authenticity [45:17]:
  • “AI is gonna do so much. We're gonna have more time to be human… but we’re about to go into an era where no one will believe any video.” [45:17–46:32]
  • Gary believes the blockchain will play a key role in guaranteeing media authenticity as deepfakes become ubiquitous.

9. Actionable Advice for Marketers [49:14]

• Gary’s unmissable prescription:
  • “Document and create the content on social media. … The mid funnel, which is organic social, has AI algorithms across seven platforms that have the far majority of attention of society.” [49:14–51:35]
  • He urges everyone, especially new brands and creators, to start documenting and sharing their journey—letting real-world content performance drive scaled investment, not the old campaign model that cascades “matching luggage” from a single idea.

Notable Quotes & Memorable Moments

• “I’ve been blindly obsessed with delivering value to the customer. … I don’t understand why you wouldn’t want to give the customer the disproportionate most value.” —Gary Vee [02:44]
• “The ultimate way to be selfish is to be selfless.” —Gary Vee [10:40]
• “Every time I leave a penny or a nickel on a deal and the other person feels it, it allows me to make another deal the next time … and the next time.” —Gary Vee [15:08]
• “Nobody gives a fuck about billboards.” —Gary Vee [22:00]
• “I do not believe in 2026 that people are giving any seconds to a television spot. 0.0. Not to mention, have you looked at the creative that is the modern commercial? They’re all dog shit.” —Gary Vee [27:41]
• “Brand beats sales every day of the week.” —Gary Vee [13:43]
• “The mid funnel ... has now become the most important funnel.” —Gary Vee [50:43]
• “The number one underrated brand in the history of the world is the human being.” —Gary Vee [47:59]

Key Timestamps for Important Segments

• Wine Library reflections / Customer obsession: [01:01–06:38]
• Luck & success: [06:40–09:28]
• Brand vs. Sales / Content motives: [13:15–16:30]
• Trendspotting discussion: [17:51–21:19]
• Media value, Social & TV debate: [21:49–28:27]
• Overrated/Underrated Media—Quickfire: [28:27–41:09]
• AI and the future of authenticity: [45:17–47:59]
• Advice to new marketers: [49:14–52:13]

Tone and Takeaways

Gary Vee is as energetic, direct, and pragmatic as ever, challenging industry orthodoxy and repeating a central mantra: deep consumer focus, transparency, and relentless value delivery always win—especially when the rules of media are shifting faster than established players admit. His advice is bold, actionable, and, as always, steeped in earned confidence—not just theory.

This episode is a must-listen for any marketer rethinking their media mix, building a personal brand, or confronting AI’s impact on authenticity.