Jan 6, 2022 · 38m · startup-ideas
NFTs with Gary Vaynerchuk | Where It Happens
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of Where It Happens, hosts Sahil Bloom and Greg Isenberg interview entrepreneur Gary Vaynerchuk about his frameworks for spotting consumer trends, the macro trajectory and risks of Web3 and NFTs, and the essential mindset of intellectual humility and radical accountability.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 8.9% of the talking time here. How this is scored →
Greg as informed peer 3.4 Guest teaching 4.6 Guest disagreement 2.3 Greg pushing back 1.1
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:00 Gary rejects the failure premise and calls 99% of NFTs vulnerable
Gary firmly rejects Greg's question about whether NFTs could fail, immediately clarifying the difference between macro infrastructure and the imminent collapse of 99% of current projects.
Hardest push from Greg ▶ 7:47 Greg directly challenges Gary on potential failure modesGreg interrupts the bullish narrative by directly asking Gary to describe how the entire NFT space could fail and whether it might not pan out.
Biggest teaching moment ▶ 12:18 Gary calls hosts youngsters and lectures on tech adoption curvesGary points out the hosts' relative youth and educates them on multi-decade tech skepticism cycles, drawing direct parallels to early internet wine sales and pagers.
Greg holds their own ▶ 23:51 Sahil synthesizes Gary's core operating principlesSahil demonstrates high comprehension by distilling Gary's wide-ranging points into three structured, actionable principles, drawing explicit validation from Gary.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Gary Vee on Collectibles and Entering Web3 | 3 | 4 | 1 | 1 | The hosts open warmly, acknowledging VeeFriends and prompting Gary on his Web3 entry. Gary delivers an expansive overview of his history with physical and digital collectibles leading up to VeeFriends. | |
| Gary Vee's Research Process and Counter-Punching | 2 | 5 | 2 | 1 | Sahil inquires about Gary's intensive research methodology. Gary outlines his bottom-up process from YouTube to Discord and emphasizes actively searching for counterarguments to avoid echo chambers. | |
| Macro Web3 Inevitability vs. 99% NFT Vulnerability | 4 | 7 | 5 | 3 | Greg tests Gary by asking how NFTs could fail. Gary bluntly reframes the premise by distinguishing macro blockchain certainty from the reality that 99% of current OpenSea NFT projects are overvalued and headed for collapse. | |
| Navigating Web3 Shifts and Historical Skepticism | 3 | 6 | 4 | 1 | When Sahil suggests buying an index like Ethereum, Gary questions whether Ethereum might be the Yahoo of search and points out that NFT assets can be bridged across chains. Gary notes the hosts are younger and compares current skeptics to people who preferred pagers over cell phones. | |
| Curating Peer Signals and Web2 Veterans Entering Web3 | 2 | 5 | 2 | 1 | Sahil asks how Gary spots initial curiosity signals. Gary explains how early conversations with Web2 veterans like Kevin Rose served as a barometer for the shift into NFTs. | |
| The Strength of Changing Your Mind and High Conviction | 4 | 5 | 3 | 2 | Greg introduces Aaron Levie's swift turnaround on Web3, prompting Gary to praise the willingness to change one's mind. Gary contrasts his own policy of staying completely quiet until reaching 100% conviction with pundits who make constant predictions. | |
| Corporate Brands and Legacy IP Entering NFTs | 4 | 4 | 2 | 1 | Greg asks for Gary's projection on how corporate brands versus Web3-native IP will split the market by 2026. Gary estimates brands will capture only 10-20%, predicting that 90% of brand initiatives will fail due to short-term thinking. | |
| Humility as the Engine of Conviction and Innovation | 4 | 5 | 2 | 0 | Sahil lays out three clear takeaways from Gary's mindset, which Gary endorses before delivering an extended reflection on gratitude, humility, and radical personal accountability before signing off. | |
| Post-Interview Debrief on Accountability and Mindset | 5 | 0 | 0 | 0 | In this post-interview debrief between Greg and Sahil, the hosts break down their key takeaways, specifically discussing skin in the game, studying counterarguments, and resisting social media tribalism. |
Statements from this episode (9)
Vaynerchuk: VeeFriends originated as a planned toy brand called Workplace Warriors
“I've been working on a toy brand called workplace warriors for a long time. And that in essence was VFriends. So, it wasn't hard for me to take these characters like Patient Panda and Empathy Elephant and turn them into an NFT project instead of a collectible …”
Vaynerchuk: 99% of the top 200 OpenSea NFT projects are vulnerable
“99% of the projects on the OpenSea top rankings, top 200 right now, are incredibly vulnerable against their valuation.”
Vaynerchuk: Most NFT Projects Cannot Maintain Value Due to Supply Flood
“The far majority of projects in this gold rush cannot maintain their value because the supply of NFTs that are coming into the market is extraordinary.”
Vaynerchuk: NFTs are an easier bet than layer-1 tokens via bridging
“The reason I went into NFTs more than currency is my theory is if Ethereum loses, I can bridge over my crypto punks, right? So to me, the NFT asset class feels in a lot of ways, like an easier bet. If you feel like you really know which NFTs you want to invest…”
Vaynerchuk: The NFT wave mirrors early Web 2.0 social media adoption
“It feels like web two O's beginning when nobody understood social media and content. That's exactly what's happening with NFTs.”
Vaynerchuk: Invested in Bitcoin and Ethereum in 2015-2016
“I invested in Ethereum and Bitcoin in 1516.”
Vaynerchuk: 90% of Initial Brand NFT Drops Will Be Garbage
“I think it's gonna be just like social. 90% up front are gonna make garbage. 10%, if you remember early brands on social, Zappos had a big move on it that worked for them. There were some other brands that did a really nice job. Then you look at brands that we…”
Vaynerchuk: Brands Will Account for Only 10-20% of OpenSea Sales by 2026
“I think it'll be 10% brands, 20% brands. I think you'll see publishers, gaming companies, like IP that we, right now, VFriends, Bored Ape, Cool Cats, IP getting established, but you're gonna see Hello Kitty, you're gonna see the Flintstones, so you're gonna se…”
Sahil Bloom lost a significant amount of money trading Ether Lambos
“Like, when we, when you first got me in NFTs, the first thing I did was go and do something stupid. Like, I didn't mean to, but I put some skin in the game, and I lost a bunch of money on Ether Lambos, and that was a great learning experience for me.”