Aug 2, 2021 · 1h 10m · how-i-built-this
Serial Entrepreneur: Gary Vaynerchuk
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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 How I Built This, host Guy Raz interviews serial entrepreneur Gary Vaynerchuk, tracing his journey from an immigrant family's New Jersey liquor store to becoming a digital marketing pioneer, author, and media mogul. Vaynerchuk discusses his early mastery of e-commerce, the creation of VaynerMedia, his philosophy on critics and hustle culture, and his ongoing technological ambitions.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 32.1% of the talking time here. How this is scored →
Guy as informed peer 3.9 Guest teaching 2.9 Guest disagreement 2.7 Guy pushing back 2.4
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:05:30 Forceful denial of hustle culture promotion
Gary vehemently rejects Raz's premise that he advocates toxic hustle culture, interjecting multiple times to insist critics ignore his emphasis on sleep, mental health, and modest financial happiness.
Hardest push from Guy ▶ 57:34 Raz challenges Gary's anti-audacity claimRaz directly calls out Gary's claim that he dislikes audacity by highlighting that shouting about purchasing the New York Jets for decades is the epitome of audacious behavior.
Biggest teaching moment ▶ 54:36 Distinguishing short-term NFT greed from underlying tech valueGary educates Raz and listeners on market adoption cycles, predicting an inevitable NFT crash while explaining why the underlying technology will endure just as Amazon survived the dot-com bust.
Guy holds their own ▶ 42:06 Interrogating Gary's angel investment financesRaz demonstrates sharp financial skepticism by drilling down on the math of Gary buying secondary shares in tech giants while taking home an $80,000 salary from a $60M business.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Immigrant Beginnings and the Springfield Liquor Store | 3 | 2 | 1 | 1 | Guy Raz demonstrates solid background research by correctly naming the family's Springfield store, while Gary explains the low-margin operational economics of discount retail. | |
| School Struggles and Unconventional Childhood Focus | 2 | 4 | 3 | 1 | When Raz suggests Gary simply suffered from a wandering mind in the classroom, Gary firmly reframes the dynamic as hyper-selective focus and refusal to conform to rigid school curricula. | |
| From Baseball Cards to Liquor Store Merchandising | 4 | 2 | 1 | 1 | Raz draws an insightful connection between baseball card trading and wine collecting, which Gary enthusiastically embraces to illustrate his early instincts for store merchandising. | |
| College, Early Internet Vision, and Palate Training | 4 | 2 | 2 | 2 | Raz cites wine critic Jancis Robinson and probes the viability of late-90s e-commerce, while Gary recounts his obsessive self-taught palate training regimens. | |
| Pioneering Email Marketing and the Wall Street Viral Loop | 4 | 3 | 3 | 4 | Raz openly expresses skepticism that Gary collected 10,000 email addresses purely from retail foot traffic, prompting Gary to defend his aggressive in-store capture strategy and the resulting Wall Street viral loop. | |
| Scaling Wine Library and Total Dedication in His 20s | 3 | 3 | 2 | 1 | Raz explores whether Gary's relentless grind in his twenties stemmed from insecurity or chasing financial goals, but Gary reframes his drive as paying back his parents for their sacrifices. | |
| Wine Library TV and Defying Industry Conformity | 5 | 3 | 3 | 2 | Raz references a humorous New York Times review comparing Gary to Dog the Bounty Hunter, while Gary explains how panning his own store's inventory established radical credibility in an elitist industry. | |
| Mid-Show Teaser: Transitioning from Wine to Marketing | 4 | 2 | 3 | 4 | Raz repeatedly pushes on Gary's financial narrative, challenging how someone drawing only an $80,000 salary from a family business could afford early angel investments in Twitter and Facebook. | |
| The Flip Cam Video and Launching VaynerMedia | 4 | 3 | 2 | 2 | Raz asks whether VaynerMedia was originally perceived as a one-man 'social media guru' show, allowing Gary to clarify his deliberate shift toward building an institutional agency. | |
| 'Crush It!', Book Deals, Resi, and Private Family Life | 3 | 2 | 2 | 1 | Raz explores the impact of Gary's best-selling book deals and ventures like Resy, while Gary clarifies that his public brand does not intrude upon his private family life. | |
| Mid-Show Teaser: VeeFriends and the New York Jets Ambition | 4 | 4 | 4 | 3 | Raz brings up skeptic concerns about NFT volatility, prompting Gary to lecture on market speculation versus macro technological shifts by comparing NFTs to the 2000 dot-com bubble. | |
| The Lifelong Dream of Buying the New York Jets | 5 | 3 | 4 | 6 | Raz catches Gary in an apparent contradiction when Gary claims he dislikes audacity despite publicly declaring his plan to buy the New York Jets, forcing Gary to differentiate public dreaming from premature boardroom pitch meetings. | |
| Deconstructing the Hustle Culture Narrative | 5 | 5 | 6 | 5 | Raz presses Gary on criticism that he promotes toxic hustle culture, prompting a forceful rejection from Gary, who insists his core message has always centered on passion and happiness rather than endless overwork. | |
| Maternal Influence, Redefining Luck, and Intrinsic Curiosity | 4 | 3 | 2 | 1 | Raz poses his signature skill versus luck question, which Gary reframes around his mother's parenting while Raz perceptively notes that Gary's vocal delivery prevents him from sounding arrogant. |
Statements from this episode (16)
Vaynerchuk: WineLibrary.com was one of the first wine e-commerce businesses
“In Mount Ida College, first semester, I hear the internet for the first time, and I decide, oh my god, I'm not gonna launch 800 Toys R Us of wines, which is what my plan was at that time. I'm gonna launch a website, even though I did not own a computer, even t…”
Vaynerchuk: Father invested $15,000 to launch WineLibrary.com
“The greatest thing that was ever done for me in my life professionally was my father making an enormous bet on spending the 15,000 dollars to build winelibrary.com”
Vaynerchuk: Wine Library grew from $4M to $65M in revenue
“We went to we went to ten million in 99, and 17.5 in 2028.3, you know. I mean, it was, we went from four to 65, and 60 to 65 in a blink, you know.”
Vaynerchuk never sets specific numerical business goals or targets
“I, to this day, I've never had a goal of like, we're gonna do this. I don't even think that way.”
Vaynerchuk: Reviewers who shill or compromise honesty are one moment from ruin
“If I'm shilling up here, or not telling my truth, I'm one moment away from being finished.”
Vaynerchuk: Wine Library never raised outside capital or cash infusions
“We didn't get cash infusion. We didn't raise capital for Wine Library.”
Vaynerchuk bought Twitter founder shares from original CTO Blaine Cook
“The next thing I know, I am negotiating to buy a portion of Blaine Cook, the original CTO's founder shares of Twitter, and now I'm in the game.”
Vaynerchuk capped his salary at $80,000 while building Wine Library
“I never made more than 80,000 dollars a year, even though I built this huge business cause it's a family business and we don't take salaries and I don't own the business”
Vaynerchuk's first three investments were Twitter, Facebook, and Tumblr
“I put 34,000 dollars into Twitter. Okay. Okay. The reason I had that, and then I also put money into Facebook, and then put money into Tumblr. Those were my first three investments.”
Vaynerchuk: Gillette paid VaynerMedia $60,000 for an early project
“Gillette paid us 60,000 dollars for a project, and we thought that was a trillion dollars.”
Vaynerchuk's books were his most lucrative income stream from 2009 to 2012
“Book writing was my most, Lucrative part of my life. In 2000, nine, 10, 11, 12. That's where I made most of my money. Because I was making nothing at VaynerMedia.”
Vaynerchuk: Resy Was Incubated and Funded Through Vayner/RSE
“We did through the fund that I started, VaynerRSC, and so we incubated Resi in that fund at some level.”
Vaynerchuk: 99% of current NFT projects will fail and collapse in price
“Yeah, I mean, I think 99% of the projects that are being launched right now are gold rushes, and they're gonna be projects that fail, and people are gonna buy tokens from celebrities, leagues, different things, and the price is gonna go down.”
Vaynerchuk expects to buy the New York Jets in 25 years
“I know how I'm going about doing it, which makes me feel that I'm gonna get it done in 25 to 27 years.”
Vaynerchuk: Ignoring praise is essential to withstanding online criticism
“I believe that a lot of my friends who aren't able to handle it, which is many, enjoy the accolades too much. I believe one of the reasons I can deal with this is I can't hear them cheering for me, which allows me to deal with the booing.”