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Gary Vaynerchuk

Chairman, VaynerX & CEO, VaynerMedia · 1 appearance on the record, plus 1 compilation re-air.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutiveinvestorauthorentertainer@garyvee ↗LinkedIn ↗garyvaynerchuk.com ↗Wikipedia ↗YouTube ↗Instagram ↗

Gary Vaynerchuk is the chairman of VaynerX and CEO of VaynerMedia. He gained recognition developing Wine Library TV and later co-founded VaynerMedia, Resy, and VeeFriends, alongside publishing several bestselling business books.

12statements → 5claims → 1claims resolved → 4.5/5average certainty → 1.9/5average debate potential → ≈4.5/5argument clarity, estimated → 15said about them ↓

0 supported 1 partly supported 0 contradicted 1 not yet assessed 3 not checkable as stated how the 5 claims stand · each chip opens the sources

1 prediction · 4 assertions · 3 insights · 4 disclosures · every statement was checked. The prediction and assertions are the 5 claims: statements the public record can support or contradict. 1 is resolved, 1 is not yet assessed, and 3 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Gary argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

How they sound: speaking style how? →

279 words/min while actually speaking · 5.5 um and uh per 1k words · 8 false starts per 1k · 28% of pauses land inside a clause

No argument clarity score for Gary Vaynerchuk: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews. Their coarse estimate from 24 exchanges on the produced feed is ≈4.5/5, shown at half point precision because the sample is small and produced tape scores higher.

Measured by listening to 5,283 words across 1 episode, but every recording we have of Gary Vaynerchuk is the aired feed, and an editor cleaned that audio before release. Some of the hesitation was cut before we ever heard it, so read these as floors: the true rates are at least this high. These are measurements of speaking style, not scores. How it's measured →

How the interview went all their pushback → series average →

Across 2 rated episodes:

host pushback ▾ 2.5/10
pushed back at the host ▾ 2.5/10
setup questions received 70%

Everything Gary Vaynerchuk said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Prediction Not checkable as stated
Vaynerchuk would refuse $100 billion if it meant he had to retire
“If somebody came to me and said, I will give you one hundred billion dollars in cash, but you can never work again. You must fully retire financially. Meaning, the cliche thing. Must go on a beach, in a very nice place, and actually do nothing besides drink be…”
Gary Vaynerchuk Oct 28, 2022 ▶ 17:20 20VC: Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner and more on Their Relationship To Money, How It Has Changed with Time and Wealth, How They Bring Up Their Children To Engender the Same Values of Ambition and Hard Work?
Disclosure
Gary Vee would refuse $100 billion if forced to permanently retire
“If somebody came to me and said, I will give you one hundred billion dollars in cash, but you can never work again. You must fully retire, meaning the cliche thing, must go on a beach, In a very nice place and actually do nothing besides drink beers, walk on t…”
Gary Vaynerchuk Jun 20, 2022 ▶ 28:47 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Assertion Partly supported
Gary Vee says post-iOS 14 ad pullbacks created organic arbitrage on Facebook
“I changed my mind on how big of a platform Facebook is. One of the coolest things for me right now is that I'm back into being obsessed with content on Facebook because the map of supply and demand of attention on it has flipped aggressively with iOS, 14 updat…”
Gary Vaynerchuk Jun 20, 2022 ▶ 30:39 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Disclosure
Gary Vee has never sold a single share of his Facebook stock
“I've never sold a share of Facebook since the day I invested almost 15 years ago.”
Gary Vaynerchuk Jun 20, 2022 ▶ 3:35 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Gary Vee invested his entire 20s savings into Facebook, Twitter, and Tumblr
“Saving my money in my twenties And then deciding to spend all of it in a one year period on Facebook, Twitter, and Tumblr based on at that .10 years of very hard work, diligence of saving and not wasting my money and looking for the opportunity to strike.”
Gary Vaynerchuk Jun 20, 2022 ▶ 6:42 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Gary Vee scaled his father's wine business to $60M on under $100k
“My dad had a business doing 3.8 million in revenue. And in a seven year window, I took it to sixty million. And I changed the course of my father's financial life and my mother's financial life. Yet I was never getting paid a 100,000 dollars a year and owned n…”
Gary Vaynerchuk Jun 20, 2022 ▶ 8:02 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Insight
Gary Vaynerchuk: Money and fame only expose and accelerate personal character
“All that money and fame do, Harry, is exposes who you actually are. It just accelerates your truth.”
Gary Vaynerchuk Oct 28, 2022 ▶ 16:02 20VC: Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner and more on Their Relationship To Money, How It Has Changed with Time and Wealth, How They Bring Up Their Children To Engender the Same Values of Ambition and Hard Work?
Insight
Gary Vee argues money and fame expose character rather than change it
“All that money and fame do, Harry, is exposes who you actually are. It just accelerates your truth.”
Gary Vaynerchuk Jun 20, 2022 ▶ 20:48 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Insight
Gary Vee admits his content is more therapy than traditional business advice
“My content is far more therapy than it is business HBS.”
Gary Vaynerchuk Jun 20, 2022 ▶ 21:08 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Disclosure
Gary Vee's first three angel investments were Facebook, Twitter, and Tumblr
“The first three companies I invested in, in my entire life as an investor were Facebook, Twitter, and Tumblr.”
Gary Vaynerchuk Jun 20, 2022 ▶ 3:22 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Disclosure
Gary Vee still holds the majority of his original Twitter investment
“I sold some Twitter, but still hold the majority of that holdings from then.”
Gary Vaynerchuk Jun 20, 2022 ▶ 3:41 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Gary Vee started VaynerMedia at 34 with zero cash in a boardroom
“At 34 years old, I started VaynerMedia with no money. We started the company in Buddy Media's conference room, which I'm sure you know, because you've listened to another interviews, and I'm very proud of what we've built from zero and scratch with no cash”
Gary Vaynerchuk Jun 20, 2022 ▶ 12:23 Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 · 20VC with Harry Stebbings

The other half of the tape: Gary Vaynerchuk's own voice is left out of every number here. Other people bring the name up 14 times in 7 episodes on 20VC. 1 statement on the record names them. every mention, with the transcript →

Who brings them up most Kelly Peeler 6Matt Mazzeo 2Jason Calacanis 2Nicole Quinn 1Matthieu Rouif 1Julia Enthoven 1Guillaume Moubeche 1

Statements about Gary Vaynerchuk, by other people (1)

Insight
Kris Jones advises aspiring VCs to publish startup analysis on a blog
“It's as easy as going to WordPress and starting up your own blog and, You know, you could create a blog and start to express your thoughts on, on startup companies and, you know, that space so that when you do reach out to say a Gary Vaynerchuk or a Mark Cuban…”
Kris Jones Jan 13, 2015 ▶ 19:26 20 VC 002: How to become a VC with Kris Jones

Every mention by year

tap a year for its mentions
0041822015201620172018201920202021202220232024episodesmentions
0122015201620172018201920202021202220232024episodes it came up in
0021422015201620172018201920202021202220232024episodesmentions per episode
2024 1 mention in 1 episode
2023 1 mention in 1 episode
2019 1 mention in 1 episode
2017 1 mention in 1 episode
2016 8 mentions in 2 episodes 4 per episode
2015 2 mentions in 1 episode

Appearances (2)

EpisodeDateSpeaking time
20VC: Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner and more on Their Relatio compilation Oct 28, 2022 2m
Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #89 Jun 20, 2022 24m
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