Gary Vaynerchuk

Use an AI 'capture-all' to build and act on your relationship graph

Gary uses OpenClaw as a capture-all for relationship/CRM prep—snapping photos and texting them in—then layers logic and agents on top of his relationship graph to automatically prompt him (e.g. auto-sending a congrats email at a milestone).

“I'm using it as a capture-all for all information. What's been really fascinating, even with 3 admins and chief of staff and all this, I'm still like— I never got there like some of my friends where they're chief of staff is with them in every meeting. So there'd be like so much context lost, right?”

Steal thisPipe every meeting note and photo into one AI tool, then build agents on top to surface relationship follow-ups automatically.

Hire a full-time 'VP of Relationships' to scale your goodwill

Gary Vaynerchuk employs Nick Dio, a 12-year employee who started as an intern, as 'VP of relationships' to travel the world representing Gary, hosting dinners and spotting ways to help people with no KPI or ROI attached.

“Nick Dio is the VP of relationships. He literally goes around the world and in essence, he's been with me for 12 years, started as an intern, grew up in VaynerMedia. I trust him to represent me to some degree. Because I can't be everywhere. And about 2, 3 years ago, I realized my favorite thing about business is people.”

Steal thisHire a long-tenured, high-trust person to be your proxy at events and relationship-building when you can't be everywhere.

Doing good for people is the highest-ROI, lowest-risk move

Gary argues that genuinely doing good things for others is the highest ROI and lowest risk investment, and that most people mistakenly treat it as the highest risk because their 'good' acts are actually calculated with an expectation of return.

“Doing good things for people is literally the highest ROI and lowest risk thing. And most people think it's the highest risk thing. Because when they're doing something good, they're not doing something good. They're doing something calculated with the expectation, or at least minimally the hope, that something comes back to them.”

Kind Candor: deliver hard truths early and with love

Gary admits he was an 'all-time atrocious firer' who held criticism in until it exploded into surprise firings. He rebranded blunt honesty as 'kind candor'—the discipline of delivering hard feedback continuously and lovingly—and made it his company's ethos, crediting it for being a far better CEO.

“As long as you're delivering things with candor, all of it becomes dramatically more palpable. I was not. I was holding it all in. That became the vulnerability. And I'm really glad as I've gotten to 50, I'm now in that place where I could be a lot better. And it's showed up in the business results. I've been a dramatically better CEO the last 3, 4 years where I've cleaned up my candor. I rebranded it into kind candor.”

Steal thisGive people candid feedback continuously and kindly so nothing is a surprise; never sit on it for a year.

VaynerX does $400M in revenue with Gary as day-to-day CEO

Gary names VaynerMedia/VaynerX, where he is the day-to-day CEO, as a $400 million revenue business—the largest of his seven active 8-figure-plus companies.

“VaynerMedia, VaynerX, which is $400 million in revenue. I am the day-to-day CEO.”

VeeFriends to do $20M+ in revenue from comics, coins and cards

Gary says VeeFriends—the IP brand born from his NFT era—will do at least $20 million in revenue this year across licensing, comic books, coins and trading cards, and he predicts it becomes a Marvel/Pokemon-scale property.

“VeeFriends is going to do minimally $20 million in revenue this year in licensing and selling comic books and coins and trading cards. I'm building a true brand like that. By the way, that is a dark horse chance to be really one of my greatest roses because all the ashes of the NFT era that I'm going to get to the other side and be Marvel and Pokémon is going to fuck with everyone so heavy in 15 years.”

Creator entrepreneurs become the next Fortune 500

Gary's forthcoming book 'The Individual Empire' argues that with AI, blockchain, evolving social and the decentralization of Hollywood/Madison Avenue/Wall Street, the biggest companies in the world will be human-based organizations led by a creator entrepreneur paired with an operator (or one person who is both).

“the rise of the creator entrepreneur and the entrepreneur creator as the next Fortune 500 companies. And my belief with AI, blockchain, evolving social, you know, decentralization of Hollywood and Madison Avenue and Wall Street, that the biggest companies in the world are human-based organizations where the human either has a partner that can operate or they're a me where they can be both.”

Empathy Wines: built with two interns, sold to Constellation in 18 months

Gary started Empathy Wines with two former interns who had worked for him 11 years and sold it to Constellation Brands in 18 months for a 'hefty 8-figure' deal—an example of his pattern of building with long-tenured insiders rather than hired strangers.

“And I had Empathy Wines, two former interns of mine who worked for me for 11 years, and we started Empathy Wines, and in 18 months sold it for almost 9-figure, hefty 8-figure deal to Constellation Brands in 18 months.”

Empathy Wines: built with two interns, sold to Constellation in 18 months

Gary started Empathy Wines with two former interns who had worked for him 11 years and sold it to Constellation Brands in 18 months for a 'hefty 8-figure' deal—an example of his pattern of building with long-tenured insiders rather than hired strangers.

“And I had Empathy Wines, two former interns of mine who worked for me for 11 years, and we started Empathy Wines, and in 18 months sold it for almost 9-figure, hefty 8-figure deal to Constellation Brands in 18 months.”

The 15-minute meeting: every meeting is twice as long as it needs to be

Gary's secret weapon for running seven businesses is the 15-minute meeting—60% of his meetings are 15 minutes. His claim: every winner's meetings are twice as long as they need to be, and they know it.

“Everyone's meetings are twice as long as they need to be if they're a winner and they know it.”

Steal thisDefault your meetings to 15 minutes and force the point to surface fast.

Live shopping hits 10-15% of all commerce in 6-10 years

Gary predicts that what live shopping is doing to e-commerce mirrors what e-commerce did to physical retail: with e-com at roughly 25-30% of the market today, live shopping will be 10-15% of all commerce within 6 to 10 years.

“like in 6 to 10 years, you know, I think e-com now is what, 25, 30% of the market? Like in 6 to 10 years, live shopping will actually be 10 to 15% of all commerce. And that is scary big.”

How to tell if Gary is actually invested: he posts about it early

Gary reveals a tell for his own portfolio: whenever he invests in something he'll have to talk about a lot, he makes content disclosing he's an investor upfront. So if he hypes something heavily early on, he's an investor; constant praise without that early disclosure (like Whatnot) means he isn't.

“Anytime I've invested in something that I end up having to talk about a lot, I make a lot of content upfront that I'm an investor. So the way you know if I'm an investor in something is I'm saying it a lot early on.”

Gary's Liquid Death miss-turned-win: invested only to back an ex-employee

Mike Cessario emailed Gary the day he left VaynerMedia to launch Liquid Death and offered him an investment. Gary—'a cliche businessman that thinks creatives aren't business people'—almost passed, but invested purely to support an employee's venture, and got the first check into what became a huge winner.

“I just wanted to invest because I want to support my employees on their own ventures. So I literally did it for that reason only. And, you know, that's going to be a fucking money. It was first check-in.”

Gary's Liquid Death miss-turned-win: invested only to back an ex-employee

Mike Cessario emailed Gary the day he left VaynerMedia to launch Liquid Death and offered him an investment. Gary—'a cliche businessman that thinks creatives aren't business people'—almost passed, but invested purely to support an employee's venture, and got the first check into what became a huge winner.

“I just wanted to invest because I want to support my employees on their own ventures. So I literally did it for that reason only. And, you know, that's going to be a fucking money. It was first check-in.”

Winners who waste hours shitting on other winners out of envy

Gary marvels that many people who have clearly won—money, status, everything—still spend most of their time tearing down other winners out of envy, and his advice is blunt: stop acting like '14-year-old bitches' and go build something instead.

“will actually still fucking spend most of their time shitting on other winners out of envy, or I don't even know what. And I'm like, this energy Like, I'm like, what do you— like, I had to say this to a couple buddies not too long. I'm like, you guys are a bunch of fucking 14-year-old bitches.”

Ruth's Chris 2.0: roll out 50 steakhouses in wealthy suburbs

Gary's restaurant model with Cape Hones Chop House: build the best New York-style steakhouse but place it in high-net-worth suburbs outside the city (Bergen County, Westchester), going 20% less on nightlife sizzle and 20% more on an undeniable food program to win retention and LTV. He plans 50 locations.

“those places have their cool, right? There's that nightlife element. We're going 20% less on that and 20% more on food. We think the secret to retention, LTV, is just execute a food program that is so undeniable and a little bit of that sizzle, but your steak's got to be right, right, right.”

Steal thisTake a proven city restaurant concept and open it in affluent suburbs that lack a great version of it.

Gary Vee failed German for two years, did zero homework all of high school

Gary Vaynerchuk recounts failing language freshman and sophomore year, taking Spanish 1 as a junior alongside 9th graders to graduate, and never opening a book or doing a single homework assignment in four years of high school. He frames school grades as 'dirty data' and a poor indicator of future success.

“I literally in 4 years of high school did zero homework. Zero. Like, I— something happened where I just knew that, you know, at that point, high school, I was already working in my dad's liquor store and selling a lot of baseball cards at shows and just kind of— and it was, look, this is pre-internet.”

Don't guess if something will work — execute and deal with the upside

Gary Vaynerchuk says he never tries to guess whether a tactic will work; he executes on anything that might work and then handles the ramifications of the upside. Shaan reframes it: why guess when testing is cheaper than guessing.

“Like, what I know is that I'm— I never have an interest in guessing if something's going to work. I have an interest in executing on anything that might work and then dealing with the ramifications of the upside.”

Steal thisStop debating whether an idea will work — run the cheap test and let the results decide.

Attention is the universal currency: win it before you say anything

Gary Vaynerchuk's mental model: attention is the only universal asset class because everyone — from a PTA fundraiser to a presidential candidate to a parent — needs others to consume their message. Nothing you sell or say matters until you first capture attention.

“it doesn't matter what you're selling and it doesn't even matter what you're saying until you first get their attention. And then everything is about what you're saying.”

Steal thisTreat attention as the first thing you must win in any pitch, sale, or message; only then optimize what you say.

PAC: judge every play on platforms + culture, overpriced vs underpriced

Gary Vaynerchuk's internal VaynerX framework is PAC — platforms and culture. He tracks the top ~25 attention platforms (their algorithms, features) and cultural trends (slang, people of interest), then asks which execution is overpriced or underpriced. Example: the Super Bowl ad slot is underpriced media, but creative is the variable of success.

“the acronym I use internally at VaynerX, VaynerMedia, is, uh, PAC, platforms and culture. Right. And so Break the Web plays in culture, right? Like there's two different currencies that I think about constantly, or two different frameworks. One is platforms. What is, what are the top 25 platforms that have people's attention doing?”

Steal thisMap your marketing decisions onto two axes — what the top platforms are rewarding and what culture cares about — then bet where execution is underpriced.

PAC: judge every play on platforms + culture, overpriced vs underpriced

Gary Vaynerchuk's internal VaynerX framework is PAC — platforms and culture. He tracks the top ~25 attention platforms (their algorithms, features) and cultural trends (slang, people of interest), then asks which execution is overpriced or underpriced. Example: the Super Bowl ad slot is underpriced media, but creative is the variable of success.

“the acronym I use internally at VaynerX, VaynerMedia, is, uh, PAC, platforms and culture. Right. And so Break the Web plays in culture, right? Like there's two different currencies that I think about constantly, or two different frameworks. One is platforms. What is, what are the top 25 platforms that have people's attention doing?”

Steal thisMap your marketing decisions onto two axes — what the top platforms are rewarding and what culture cares about — then bet where execution is underpriced.

Build toward the future, buy the present

Gary Vaynerchuk explains why VaynerMedia never did search: he bet on mastering social in 2009 and figured that if he built a big company he could always acquire an established search capability via M&A. The rule — build toward what's next, since you can always buy what already exists.

“Remember that you can always buy the current. And that's how I thought about search. I was going to master social in '09, and I felt like social was going to eat up search anyway.”

Steal thisSpend your build energy on the emerging frontier; assume you can acquire the established, current capability later.

Build toward the future, buy the present

Gary Vaynerchuk explains why VaynerMedia never did search: he bet on mastering social in 2009 and figured that if he built a big company he could always acquire an established search capability via M&A. The rule — build toward what's next, since you can always buy what already exists.

“Remember that you can always buy the current. And that's how I thought about search. I was going to master social in '09, and I felt like social was going to eat up search anyway.”

Steal thisSpend your build energy on the emerging frontier; assume you can acquire the established, current capability later.

Gary's 'zero' is $1M liquid — everything else is in play

Gary Vaynerchuk keeps a $1 million safety net (his personal 'zero') untouched and puts literally everything else into play. Sam runs the same structure: a forever-safe Vanguard/bonds account, then bets anything above that line.

“My, I'm very fortunate. So my zero is $1 million, but that's it. That's it.”

Steal thisDefine your personal 'zero' — a safety-net number you never touch — and aggressively bet everything above it.

Gary put $200K of his $236K savings into Facebook in 2007

Gary Vaynerchuk describes betting $200,000 of his $236,000 in savings into Facebook in 2007 because it gave him the same gut feeling he had about the internet in 1995 and about Friendster/MySpace. He hunts for those rare 'the world is changing' moments to bet large.

“I haven't bet everything on everything, but if I ever feel the way I felt about Facebook in 2007, when I put— I had $236,000 in savings and put $200,000 into Facebook, right? If that ever happens again, like I'm willing to bet very large because that feeling, similar to the feeling I felt about the internet when I saw it in '95”

Facebook was Gary's best bet — he's never sold a single share

Asked which of his pre-IPO bets paid off most (Twitter, Slack, Facebook), Gary Vaynerchuk says Facebook, and that he has never sold one share. His rule: he won't sell until Mark Zuckerberg is gone, a 'jockey over horse' commitment.

“Facebook. I haven't sold one share yet.”

Jockey over horse — but A+ person AND A+ idea or it's a pass

Gary Vaynerchuk's investing rule: he tries to be obsessed with both the person and the idea, and if either one isn't an A+, he passes. Pushed by Shaan, he clarifies that when forced to choose, he backs the person (jockey) over the idea (horse).

“what I've learned is when I only invested in the person, when I've hit this new state where I'm really trying to be obsessed with the person and the idea, and if either one isn't an A+, then I'm like, eh, right?”

Steal thisOnly invest when both founder and idea are A+; if forced to pick, back the jockey over the horse.

Zuck is uncomfortably underrated — he understood attention is the only asset

Gary Vaynerchuk calls Mark Zuckerberg 'uncomfortably underrated,' arguing he uniquely understood that attention was the only asset — he tried to buy Twitter and Snap, and bought Instagram and WhatsApp. Gary frames him as a nerdy, well-intentioned operator who put in the coding hours as a kid.

“I think he's uncomfortably underrated. Like, he's the only person that I've met back in '07 Like in this era now, I think it's getting more obvious, but he understood attention. He literally tried to buy Twitter. He bought Instagram. He bought WhatsApp. He tried to buy Snap. He just understood attention was the only asset.”

One bad year strips your leverage in an M&A negotiation

Gary Vaynerchuk, drawing on CPG M&A experience, argues Prime's owners won't hold out for a $20B exit because one bad year takes massive leverage off the table — and their product sells on 'cool,' which (like Z Cavaricci jeans) only lasts so long once distribution saturates.

“And don't forget one bad year. You guys know this, how businesses work. One bad year takes a lot of leverage off the table in a negotiation.”

Gary's dad ran Wine Library with no line of credit

Gary describes how his father's immigrant 'pay with what you have' philosophy meant Wine Library scaled with no line of credit, which trained Gary to always play within his cash position even as VaynerMedia exploded.

“It was, my dad ran his fucking business with no line of credit, which I love, right? It's old school immigrant, you know, pay with what you have. But it trained me because that business even crazier. That business went from $4 million to fucking $25 in like 30 months, like so fast. And inventory and payroll, like, but I got so trained in playing within myself.”

Steal thisGrow only on cash you've actually collected, not on credit you hope to cover later.

Gary's dad ran Wine Library with no line of credit

Gary describes how his father's immigrant 'pay with what you have' philosophy meant Wine Library scaled with no line of credit, which trained Gary to always play within his cash position even as VaynerMedia exploded.

“It was, my dad ran his fucking business with no line of credit, which I love, right? It's old school immigrant, you know, pay with what you have. But it trained me because that business even crazier. That business went from $4 million to fucking $25 in like 30 months, like so fast. And inventory and payroll, like, but I got so trained in playing within myself.”

Steal thisGrow only on cash you've actually collected, not on credit you hope to cover later.

Selling hides everything

Gary's answer to how he managed cash flow while hiring fast: when you sell at a level beyond normal expectations, top-line revenue 'hides everything' and you outpace the vulnerabilities a slower company would feel.

“When you are selling at a level that people are not accustomed to, like when you're outpacing normality, it just fucking— selling hides everything. You know, when I'm landing fucking client week after week, like, you know, you start getting into a place where you're just outpacing vulnerability.”

Steal thisIf cash flow scares you, fix the top of the funnel first — aggressive sales papers over a lot of operational weakness.

Gary turned $270 of Magna into $6,400 on eBay

Demonstrating his 'digital garage sale' content series, Gary recounts buying a batch of Magna at a garage sale for $270 and reselling it for about $6,400 on eBay after fees.

“So for $270, I bought what ends up being about $6,400 in eBay post-fees sales, right? It's crazy because it's like the thrill of the hunt.”

NFT a unique home with a 1% royalty on every future sale

Gary pitches NFT-ing a wildly unique high-value property and embedding a smart contract that pays the original owner 1% of every future transaction in perpetuity — buyers won't mind because the holding periods are so long.

“If you own a home that is wildly unique and is a $25 million home on a beach or something wild, right? You NFT that fucking home right now, put into the smart contract that you get 1% of every transaction of this home in perpetuity. And the first person that's going to buy it from you is going to be fine with that.”

Steal thisEmbed a perpetual royalty in the smart contract of a unique asset you sell — you keep upside on every future flip.

NFT a unique home with a 1% royalty on every future sale

Gary pitches NFT-ing a wildly unique high-value property and embedding a smart contract that pays the original owner 1% of every future transaction in perpetuity — buyers won't mind because the holding periods are so long.

“If you own a home that is wildly unique and is a $25 million home on a beach or something wild, right? You NFT that fucking home right now, put into the smart contract that you get 1% of every transaction of this home in perpetuity. And the first person that's going to buy it from you is going to be fine with that.”

Steal thisEmbed a perpetual royalty in the smart contract of a unique asset you sell — you keep upside on every future flip.

The St. Louis ABA brothers who took an NBA royalty forever

Gary tells the legend of the St. Louis Spirits owners who, blocked from joining the NBA in the ABA merger, negotiated a perpetual cut of the league's economics instead of a buyout — and rode it as the NBA exploded.

“And in perpetuity, we get the economic split for that. So we're out of the league, but economy, we get it." And so as the league exploded—”

Your crypto wallet becomes the new social profile

Gary predicts that a public wallet — the tokens, tickets, and collections you hold — becomes a more honest social identity than filtered social media, because it's verifiable black-and-white data of what you actually bought.

“Like, how about this? You know how everyone's like, social media is full of shit. Like, everyone takes photos and fakes it. You know what's going to be a much better social identity? What tokens do you have in your wallet publicly?”

VeeFriends' 3-year conference lock-in to stop flipping

Gary structured VeeFriends Series 1 to include conference tickets to VCon 2022, 2023, and 2024 — deliberately 'tricking' his hardcore supporters into holding for three years so they'd grow attached and never sell.

“so the answer is it's a 3-year contract. VFriends Series 1 says you get a conference ticket to VCon 2022, 2023, 2024. I'll figure shit out after the fact, but I knew that that would have such inherent value that people would lock in for that.”

Steal thisBundle multi-year utility into a token so early believers are incentivized to hold rather than flip.

Gary nearly bought the dead Animal Crackers brand for ~$48

Gary reveals he had a signed deal to buy the Animal Crackers brand from Mondelez for about $48 (million implied), planning to turn the lion into an animated IP character before the seller pulled out.

“$48, I think the deal was at the time.”

Why Gary passed on Uber twice: 'defense always loses'

Gary explains he passed on investing in Uber twice because it looked like Garrett and Travis's side hustle rather than their main focus — a lesson that he had played too conservatively until 35 and that 'defense always loses.'

“What I learned there was defense always loses. I bought my first apartment in Manhattan. I played so conservative up until 35.”

Invest only on the jockey: 'Is this person one of us?'

After missing Uber by judging the idea rather than the founders, Gary flipped to investing almost purely on the person — he'd have to hate the idea to pass on a founder he sees as 'one of us,' because great operators will their way to success even after pivoting.

“I am now completely infatuated with investing only based on the person. I have to hate, that would be the word I use, and I don't like that word. I would have to hate the person's idea to not go if I think that the jockey is a gangster, and it's worked out for me.”

Steal thisBet on the operator, not the idea — the right founder will pivot their way to a winner.

VaynerMedia's $10K office tour was a ~$20M/year business

Sam describes VaynerMedia's 'Four Ds' (Daily Digital Deep Dive): aspiring agency owners pay ~$10K to tour the office, learn how an agency runs, and meet Gary Vaynerchuk for ~20 minutes — reportedly a ~$20M/year line.

“VaynerMedia did that where— and you could— well, I don't know about COVID anymore, but prior, I think it was like a $20 million a year business. It would cost $10,000 per person or per like couple.”

Build the agency as an access point, not a service business

Reed and Shaan invoke GaryVee's logic that VaynerMedia is a near-breakeven service grind whose real value is the access it creates. Reed says he never built the agency to be the business; it's the access point to investments, app launches, and high-leverage partnerships.

“He's like, the reason I built Vayner is like the access to everything else and the access to these brands and being able to do different things with personalities and who we work with. That's the same thing that I'm doing is it's an access point. I wouldn't want to do it any other way because I get access to everything”

Steal thisTreat a low-margin service business as a deal-flow and access engine, then monetize through what it lets you into.

Solopreneurs are under-monetized: stack funds, courses, and real estate

Shaan argues the old guard (Tim Ferriss, Gary Vee, Seth Godin) massively under-monetized their audiences with just books and ads, while newer creators like Pomp stack rolling funds, paid newsletters, and courses to convert audience trust into value.

“He chose books and ads from a podcast as his two models, and he's so popular that he still made a killing doing those two. But that killing is like— there's people with an audience a fraction of his size that are making as much money, if not more, than he's making off his podcast and books.”

Steal thisDon't rely on books and ads alone; stack a fund, a course, a paid newsletter, and products to monetize the same audience.

Marketing is day-trading attention

Mike credits Gary Vaynerchuk for the frame that marketing is really day-trading attention: attention has a different price depending on where you buy it. A billboard overpays per eyeball, while a stunt like an LA yoga studio can generate more attention at far lower cost. Always hunt the most cost-efficient source of attention.

“marketing is really just about day trading attention. Like it's marketing's all about attention and attention has different cost to it and different price to it depending where you go. The price for a billboard, you're paying so much per eyeball that sees it.”

Steal thisTreat attention like an asset class: compare cost-per-eyeball across channels and buy where it's underpriced.

Sell paid corporate tours: $10K to spend a day learning how your company runs

Sam describes VaynerMedia charging $10,000 for agency owners to spend a day at the office learning how the business operates—time with Gary Vaynerchuk and each department head—and notes Tucker is considering the same play.

“VaynerMedia does this thing called 3Ds, or I don't know what it's called, something like that, and it's $10,000, and you go to their office for a day, and you learn how their business operates”

Steal thisPackage a paid day-in-the-office tour where outsiders learn how your company actually runs.