Gary Vee: $2 Billion Dollar Taco, Live Shopping, and Customer Service | E171

Summary

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Podcast Summary

In Search Of Excellence

Host: Randall Kaplan
Guest: Gary Vaynerchuk (“Gary Vee”)
Episode: $2 Billion Dollar Taco, Live Shopping, and Customer Service | E171
Date: August 16, 2025

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Episode Overview

In this episode, Randall Kaplan has a candid, wide-ranging conversation with serial entrepreneur, investor, and branding expert Gary Vaynerchuk (Gary Vee). They dig into Gary’s journey from the family liquor store to angel investing in transformative startups (Twitter, Facebook), why he believes live shopping is the next American retail juggernaut, lessons in customer service, investing, preparation, work ethic, and his ultimate aim to buy the New York Jets. It's a masterclass in entrepreneurial thinking and leadership, loaded with stories, actionable insights, and no-nonsense Gary Vee advice.

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Key Discussion Points and Insights

1. Early Angel Investments & the Twitter/Facebook Backstory

• Gary recounts his early video advocating for Twitter, which led to his first investment opportunity.
• Blaine Cook, Twitter’s first CTO, offered Gary, Fred Wilson, and Kevin Rose the chance to buy his Twitter shares after deciding to leave the company.
• Gary's advice to Cook:

  “I tried to talk him out of it. I said, I think you’re making a huge mistake. ...I could see he was making an emotional decision.” (00:04)

• The missed value: Cook left “$702 billion on the table.” (00:31)
• Dinner with Mark Zuckerberg after speaking at Facebook led to another pivotal moment:

  “Sister Randy called me...Would you like to buy some Facebook equity? I literally took 80% of my savings and invested in Facebook.” (00:50, 22:11)

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2. Spotting Trends & First Mover Advantage

• Gary’s superpower is identifying “where the attention is” and moving faster than legacy competitors.
• He compares the rise of email and website-based selling in wine (late 90s) to his current conviction in live social shopping:

  “If you ask me right now, out of all the optionality in the world… live shopping is at the tippy top of my list.” (02:15) “I view these trends like poker and I view live shopping...like having the nuts in poker... You go all in because you’ve won.” (03:32)

• He asserts that current American brands underestimate the tidal wave coming via platforms like TikTok Shop, Whatnot, and soon Meta.

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3. Culture & Customer Service: The Legend of the Snowstorm Wine Delivery

• A key leadership lesson: create company culture through direct actions, not just storytelling or posters.
• Story: On the busiest holiday, Gary personally delivered a case of wine to an elderly customer in a snowstorm, sacrificing thousands in sales that hour to make a lasting point about customer service.

  “Don’t make a fucking poster and put it in the hallway...do an action.” (05:08) “I might have lost $20,000 in sales that hour, but I’ve helped my dad make millions since.” (09:01)

• This became internal myth and a foundational example for his team.

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4. The Origin of VaynerMedia & Scaling Through Opportunity

• Consulting gig at ESPN after amassing a Twitter following opened his eyes to enterprise ignorance about social media:

  “I couldn’t believe the biggest companies in the world didn’t understand social media.” (12:10)

• Out of necessity and opportunity (“had no money”), he and his brother AJ set up a consultancy, later VaynerMedia.
• Early collaborative work (such as giving a quote for Buddy Media) landed him seven figures after its sale to Salesforce.
• VaynerMedia flourished, “now a $350 million a year revenue business with 2,000+ employees.” (14:16)

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5. Angel Investing Philosophy

• Gary’s progression as an investor:

  “Early on, I went for the horse. Then I went for the jockey. Now it requires both...the operator and the idea.” (23:03)

• Most pitches come via network, not cold outreach. He prefers dialog and gut feel over elaborate decks:

  “I don’t even consume decks. My team knows this... What really gets me is if somebody says something that I believe in that I can follow up with a couple of questions and they can answer it.” (24:35)

• Contrasts with Kaplan's focus on extreme preparation and impressive presentation materials. Both agree on the importance of substance over show.

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6. The Science and Art of Attention in Marketing

• Insights from Gary’s books “Jab, Jab, Jab, Right Hook” and the latest, “Day Trading Attention.”
• Believes the best social media post can outperform all but the Super Bowl in terms of impact:

  “The best social media organic post...is a more important form of advertising than any television commercial...outside of Super Bowl.” (27:34)

• Super Bowl remains the absolute king for pure attention, if creative is strong:

  “The creative is always going to be the variable of success.” (29:05)

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7. Foundations of Success: Work Ethic, Passion, and Preparation

• On choosing work ethic, talent or passion:

  “Yes. Of the three, work ethic is controllable and it’s something that I get scared that people try to downplay.” (29:22)

• Warns against using “wellness” as an excuse for inaction:

  “I am worried people are using health and wellness and mental health...as weapons to create entitlement or laziness.” (30:50)

• Preparation:

  “What baffles all my top executives...is I go into meetings cold and dominate them. They think I do no prep...It’s the only thing I do. The reason I can walk into any brand and crush a meeting is because most business is not that complicated.” (31:48) “The ultimate preparation is to actually be a practitioner.” (33:51)

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8. Goals, Money, and Personal Motivation

• Chasing the New York Jets has been a lifelong ambition, but adaptability is crucial:

  “The chase of it is the great enjoyment. It’s a lot of fun to chase that football team...but you need the ability to adjust and not be rigid.” (34:31)

• On the pursuit of money:

  “There is just no correlation in any kind of common sense way of money and happiness. It just doesn’t. It’s black and white.” (36:11)

• Only true fulfillment comes from meaning, not wealth for its own sake — a message he feels people “need to see for themselves” to learn.

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9. Relationships, Values, & Legacy

• Acknowledges the pride of his parents and how making them proud is "probably my strength and my weakness.” (37:11)
• Favorite/funniest moments include judging Miss America and first TV appearances — “I am not detached from how miraculous my life has been.” (38:38)
• Highest ambition:

  “I want everybody that I love to show up to my funeral with a very good feeling in their stomach about who I was.” (38:02)

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10. Rapid-Fire / “Filma Bling to Excellence” (Lightning Round, 37:45–43:55)

• Biggest lesson: “Losing is the thing you should always strive for because it makes winning a lot easier.” (37:47)
• Number one professional goal: “Buy the New York Jets.” (37:58)
• Biggest regret: “Not spending even more time with the people I love.” (38:15)
• Advice to kids: “Be a good human being on their terms, not how you want to define it.” (38:29)
• Key trait that defines his success: “Tenacity...I’m fucking tenacious and it matters.” (40:43)
• Who would you meet: “Vince McMahon...I want to talk to him about character development.” (41:31)
• Advice to 21-year-old self: “Don’t do a single thing different.” (43:28)

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Notable Quotes & Memorable Moments

• “I might have lost $20,000 in sales that hour, but I’ve helped my dad make millions since.” (09:01)
• “Actions carry enormous weight. Every leader should...go out of their way for the most hyperbolized executions of those things so that it becomes lore.” (09:17)
• “I literally made seven figures to give a quote.” (14:16)
• “Preparation is the only thing. The reason I do such narrow things is they’re the things I’m preparing on at all times.” (32:35)
• “There is just no correlation...of money and happiness. It’s black and white.” (36:11)
• “Tenacity...I’m fucking tenacious and it matters.” (40:43)

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Timestamps for Major Segments

• Twitter/Facebook investment stories: 00:00–01:00, 21:09–22:51
• Live Shopping as the Next Big Thing: 01:34–04:54
• The Customer Service Snowstorm Story: 05:07–09:37
• VaynerMedia and Entrepreneurial Scaling: 10:56–16:06
• Philosophy on Angel Investing: 23:03–26:18
• Content, Social Media, and Attention: 27:10–29:15
• Work Ethic, Preparation: 29:15–34:13
• Money, Success, and Motivation: 34:13–36:11
• Rapid-fire/Values and Advice: 37:45–43:55

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Conclusion

Gary Vee’s approach to life and business is defined by relentless curiosity, tenacity, and a willingness to take principled risks. His advice, war stories, and clear trend-spotting acumen offer a wealth of inspiration for entrepreneurs, business leaders, and anyone in search of excellence. The episode is packed with wisdom on making bold moves, serving customers, preparing for success, and prioritizing meaning over money — all delivered with Gary’s signature candor and unfiltered style.

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Transcript

[Gary Vaynerchuk]

One of the first videos I ever made was called Facebook. Should be worried about Twitter because Twitter just come out. I was again fascinated by it. That video went viral. Blaine Cook was the first cto. I met him for a taco at south by and he told me he was quitting and selling every share and did I want any. First, I tried to talk him out of it. I said, I think you're making a huge mistake. Second, I could see he was making an emotional decision. A couple of weeks later on emails like, do you want to buy it? I'm done. I'm like plain. He's like, I'm done. And so me, Fred Wilson and Kevin Rose bought up all his shares. That was my first investment.

[Interviewer (possibly a business or tech journalist)]

And he left $702 billion on the table.

[Gary Vaynerchuk]

That's right. Just staggering. Several months later, my video went viral. Facebook. Dave Morin asked me to speak at Facebook. Zucks was there. We had dinner that night. We hit it off. We started to get to know each other. And sister Randy called me. Mark wanted me to call. Our parents are looking to sell some shares. They're going to buy a nice home near us in California. Would you like to buy some Facebook equity? And she had literally took 80% of my savings invested in Facebook Foreign.

[Interviewer (possibly a business or tech journalist)]

You're listening to part two of my incredible interview with Gary Vee. If you haven't yet listened to part one, be sure to check that one out first. Now, without further ado, here's part two of my awesome conversation with Gary. You took a company from 3 million to $60 million in a short amount of time. You saw things that people didn't see at the time. You bought keywords, adwords, wine was 5 cents and then after nine months went to 10 cents. So what did you see that nobody else saw as really a first mover? Advantage with I think is so important sometimes in building businesses.

[Gary Vaynerchuk]

It's what I see right now with live shopping on social. I'm going to assume that I'm going to just look around the room that people here know that TikTok shop exists, that people sell things on TikTok.

[Interviewer (possibly a business or tech journalist)]

Huge.

[Gary Vaynerchuk]

I'm going to assume that people here know that. Or this might be smaller, but you might know what whatnot is. Live shopping. I'm going to assume that people in this circle know that China has been selling stuff on live social for the last seven years. At scale, I'm going to assume that people are listening and watching. Might have saw the viral video of that woman with the handbags who does a million dollars just by doing this. I know that all to be true. I also know that almost every single person in this circle right now is underestimating it. I know that 99.9% of the people who are watching this right now don't understand it the way I do. I understand it for what it is, which is it's going to be massive. Massive. That if you ask me right now, out of all the optionality in the world of how to make money in the next five years in America, that live shopping is at the tippy top of my list. That's what I saw with websites, email and Google Adwords. I don't think I was the only person that saw it. I just think what I'm very good at is I view these trends like poker and I view live shopping on whatnot and fanatics. Live and TikTok Shop and Meta will have to do it because it's going to get too big. I view it like having the nuts in poker. I feel like I've got the best. Like I know it's the best hand. And so if you know you have the best hand, educate me here. Poker players, you go all in because you've won. Sure, they may fold, but you go all in. I know that that's what I do for a living. What I'm good at is knowing what humans are going to do. And I know when it's the biggest hand, the best hand. And so the reason I was able to build my daddy's liquor store was having a website was better than having a catalog, right? I wanted to compete with Sherry Lehman's, Zakis Morels, Sam's Wine Club in Chicago, K L in California. I wanted to have the Specs in Texas. I wanted to have the best wine store in the country. What were those stores doing when I was in high school and college? They were buying full page ads in the Wall Street Journal and the New York Times Wednesday dining in section and they were sending catalogs in the mail. I outflanked them by having a website and having a new mail, an email newsletter. So my email newsletter in 1998 when 94 Dominus came out and Insignia, I would email everybody and they would buy for me. They would get the catalog from Sherry Lehman's four weeks later. Because catalogs are slow, email is fast. Catalogs are expensive to make and ship. Email was free. So even though I had no money, I outsmarted them by knowing where the attention was. Because Wall street had had moved to email. But not everybody caught up. I believe social media is now in my brain, 20% of all social media content is live shopping. It's not yet but it will be. And so I'm gonna move fast during this era on it. That's what I did with email, with having a website at all and then finally the big final atomic bomb outflanking Everybody on Google AdWords.

[Interviewer (possibly a business or tech journalist)]

You need to have great customer service to build any business. So talk to us about this crazy story about this woman who wanted a case of Behringer white Zinfandel in the two and a half hour snow.

[Gary Vaynerchuk]

This was, this is such an. So anybody who owns a business, if you're listening right now and you want to make a point a culture, do something in action. Don't make a fucking poster and put it in the hallway. Don't tell a story that happened in the past. You and I have enough war stories where we can tell the kids, do an action. So I was building this store. We're now on fire at this point. This is later. This is like 2002 or three. We built a new store. I grew up in a smaller store than we built a big store as I was growing the revenue. I am the man on the floor and this is the holidays. When I tell you from 18 to 34 years old my December and I mean all the first 24 days of December outside of when I was in college. So but even then I came home way early because I was barely going to class. I would spend from 7am to 10pm on the floor of my dad's liquor store. It was prime time, especially pre Internet. You know we are in the midst of one of the busiest days in the history of the store and now we're doing Internet business and we get a phone call in the order department. I'm running upstairs, downstairs. I'm keeping an eye on the Internet and the store and I'm fucking a maniac. And we get this call from the son of this elderly woman, wasn't even her that her case got Ms. Shipped. And this was like December 23rd or 2nd or 1st, I don't remember. But put it this way, she lived in Jersey and that's one day delivery. And I knew that if we put it back in the mail she wouldn't have gotten it for Christmas. And he made a big to do that she needed it for Christmas. I remember to stay like yesterday. I knew that there would be a day that I wasn't going to be at that store. I, I knew that I was going to have to build my own life at some Point because I knew my dad viewed it like an immigrant, which is, oh, this is your business. But it's really not. Like I can't buy a home because I have no equity. Like I couldn't, you know, like, I would inherit it when he would pass. Well, I'm fucking going to be 50 in 15 months. And my dad's still working every day. So you can imagine I was smart enough, thank God, at 22, to be like, I got to do my own thing. But I remember I needed a to do things because once I was gone, I wanted them to know how it was built. I knew then. So even though I'm on the floor and generating 10 to $20,000 an hour, just me personally on someone like you that had high net worth, that would come in and be like, I need three cases of high end wine for the holidays. I was that guy. I decide to make a huge to do about this case of Barringer White's Infidel. It's snowing, like the weather's bad. And I decide to grab a case from the basement. And I tell my inner team, just like this, in a circle, I'm like, I'm gonna go deliver this. Cause we have the best customer service in the game. And they are stunned. I never. I don't go to pee for 15 hours during the day. That's how busy it is and how committed I am. And now I'm gonna drive to Bergen County. Isn't that an hour? And that's without snow. The are you doing, Gary? And I said, this is. I just remembered that this was my moment to make a point. So I did it. I drove. I enjoyed it. I listened to sports radio on the way got back, everybody was stunned. Everybody was sweating. Brandon was like, you missed Mr. Thompson and Mr. Smith. And like, all this money was lost, but it became a story. To this day, that story is being told to employees at our store about customer service. I might have lost $20,000 in sales that hour, but I've helped my dad make millions since. And I think more companies should understand that actions carry enormous weight. And I believe that every leader that's listening right now should think about what they care about most and instilling in their company and then should go out of their way for the most hyperbolized executions of those things so that it becomes lore. I mean, look at this. I literally did that action. And here I am, 20 plus years later, having the luxury to tell that story on an important platform like this. Think about that. This is the meta of the Thesis.

[Interviewer (possibly a business or tech journalist)]

It's how you build it.

[Gary Vaynerchuk]

It's how you fucking. How do you think everything built? It's. Everything's based on stories. Why do you think religion exists?

[Interviewer (possibly a business or tech journalist)]

December 2008, and you have a meeting at ESPN. Your brother AJ is graduating BU and you walk out of there with a couple of things. What did you walk out with? And then what happened next?

[Gary Vaynerchuk (promotional segment)]

I hope you're enjoying this video so far, but before we jump back in, I want to know if you've ever thought about what you need to do to reach the next level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google, lift and Seagate. And I also co founded a company that today is worth More than 50, $15 billion. I've been incredibly blessed in my journey and at this stage of my life, I want to give back. I want to share the lessons I've learned so you can reach incredible success way faster than I did in my own journey. I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others, and I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me.

[Gary Vaynerchuk]

I'll.

[Gary Vaynerchuk (promotional segment)]

All you need to do is answer a few simple questions, and if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video.

[Gary Vaynerchuk]

Well, I first walked out with $5,000, and I couldn't comprehend how I. You got to remember, at this point, I'm still making less than $100,000 a year, even though I'm 33 years old and built this huge business. Immigrant life again, if you don't live in an immigrant business, you don't understand. But like, I built this huge business, created hundreds of millions of dollars in revenue over that course of period of time, and I'm still making very little. My dad's making super little too, but he owns the business. So I'm starting to think about my next chapter. My brother's about to graduate and we're bouncing a lot of ideas. Daily fantasy sports, which probably would have done well. Something that looked like Groupon and living social that probably would have done well. Something that looked like buzzfeed that probably would have done well. But those would have all taken time to build. And I really didn't have any money and AJ Surely didn't. And because I just invested in Facebook and Twitter, so all my liquid was gone. And so consulting, getting paid for action was a better cash flow option. And it's amazing. And I get this random email because at this point I'd masked a lot of followers on Twitter, but it's still early. And so first couple years of Twitter and ESPN asks if I could come in and consult on how to grow their social. Their Twitter specifically.

[Interviewer (possibly a business or tech journalist)]

What year was this?

[Gary Vaynerchuk]

This is 2008.

[Interviewer (possibly a business or tech journalist)]

Steve Bornstein was CEO or he had left.

[Gary Vaynerchuk]

It wasn't at that level. It was way lower down. It was three to four levels below that, maybe five if I'm thinking properly of their org at the time. It. It was marketing, but it wasn't even like. It was definitely not the cmo, let alone the CEO. And I don't even think it was the number two in marketing. It was a lower level, but the guy had the ability to write a $5,000 check, which is nothing for a corporation. So it was lower level. Anyway, I go in, I sit in a room like this. I consult for a couple hours. I enjoy it to no end. And I leave. And they literally. It's like old school. Like, you got to check back. That or. And I call my brother as soon as I'm in Midtown, because it was in Midtown or something like that. I called my brother, said, I got it. We're going to start a consultancy. I didn't even call out an agency yet. Wasn't really even an agency, but I couldn't believe that it was 2008 going into 09. And I couldn't believe the biggest companies in the world didn't understand social media, because I'd been pod committed since 06. And that's probably one of the first times I've learned about timing. I'm just talking about it right now with Live Shopping. I'll say it again. I don't think I'm a Andreessen Horowitz invested in whatnot a long time ago. I'm not a genius. I just feel like in this nanosecond that everybody's underestimating how big it's going to be. And I didn't understand that. I didn't understand that it would take that long for people to get it. And as it got bigger, it got slower. Right. I didn't know that entrepreneur lamp information and action goes faster than it does in corporate land. And so I Was like, wait, there's an opportunity. They still don't get it. And so that's why I decided to.

[Interviewer (possibly a business or tech journalist)]

Start VaynerMedia, which is also blown up.

[Gary Vaynerchuk]

Yeah, I mean, VaynerMedia started in the conference room of Buddy Media, my friend Mike Lazaro. Yes.

[Interviewer (possibly a business or tech journalist)]

And you got equity for building a website?

[Gary Vaynerchuk]

I got equity for giving a quote, not even building that website.

[Interviewer (possibly a business or tech journalist)]

And they sold the company Salesforce for a billion dollars.

[Gary Vaynerchuk]

Yep.

[Interviewer (possibly a business or tech journalist)]

That was a good outcome for a quote.

[Gary Vaynerchuk]

For me, I did extremely well. I literally made seven figures to give a quote because at that point I'd written a book called Crush It. That was the first time I'd hit the scene outside of the wine world. And very quickly after there I was starting to be viewed as an angel investor with the Super Angels, Tim Ferriss and Dave Morton and Chris Sock and Kevin Rose and Travis Kalkening. And I was definitely in the game. Calcanis. I was in the game in that era. 2006 to 2012. It was a very good era for my personal brand with books and speeches and investing, and VaynerMedia is something I'm very proud of. We literally started it in a conference room, and it's a $350 million a year revenue business now with 2,000 plus employees. And we're definitely the most progressive, contemporary agency in the world. And it's also been the foundation of my other behaviors. I started Resi inside of there with Ben Leventhal 2014. I started empathy Wines, which I sold to Consolation with Nate and John, two former interns in that company, 2019. And then Vee Friends, which I believe. And it's fun to put this on video to look back on in 20 or 30 years from now. But I'm in the midst right now of building an intellectual property. I'm very affected and inspired by Pokemon being worth $100 billion. I do not think people realize how big that company is. I also am very inspired by Jim Henson, a real creative force who really wanted to leave a deposit of good on the world. Fraggle Rock, Sesame Street, Muppets. And so, yeah, I'm building veefriends. And a lot of the talent that works inside of veefriends came from Vayner. So Vayner has been an incredible company, but it's also been an incredible incubator of talent and osmosis of, like, how I want to do things. And I'm very excited about it.

[Interviewer (possibly a business or tech journalist)]

I'll tell you, back in my life, in 1999, I'm on my honeymoon with my first wife in Hawaii at Huala Life. I don't know if you've been there or not.

[Gary Vaynerchuk]

Oh, actually, I have. I spoke to Brand Jordan there, and.

[Interviewer (possibly a business or tech journalist)]

This guy next to me is reading a magazine that no longer exists, the industry standard. And I said, hey, are you on the business? He said, yeah. I said, what's your name? I said, my name's Ron Conway. And so talk to us about Ron. And then as part of the story, tell us about how making bad decisions on emotions is a terrible strategy. And you can talk about playing cook from Twitter and how you got that deal, and then talk about Facebook. Mark Zuckerberg, your dinner. And then you got it.

[Gary Vaynerchuk]

So that whole Silicon Valley era for me started with. So now I'm right about email, I'm right about the website. I'm rounded about Google AdWords in 05. And here comes YouTube. And I see that and I'm like, fuck, I'm gonna build my dad's story with this. So I've used the tool of web, I've used the tool of search and email, and here comes video online. And I start using the tool. I start Wine Library TV on February 21, 2006, less than a year after YouTube comes out. And I want to take a moment right now and give a huge shout out to Eric Kastner. Eric Kastner was my lead developer. One of the most progressive things I've done in my life was the day I started working in my dad's store full time. May of 98. I told him from the day I started, I will take nothing in my salary, but we need to hire a computer guy. That's what I called developers back then. We need to hire a computer guy. And by 2000 or 2001, I was able to finally get to a place where I was able to hire Eric Kastner. And then later, John Casamatis was still our cto. And I, we had. We're a fucking liquor store in New Jersey, and I have literal developers full time on my staff. It was so progressive. It'd be like if I hired astronauts right now. Like, it just made no sense. Anyway, I want to give a shout out to Eric Kastner, because without Eric Caster, a lot of this does not happen. He was the one that sat closer than you and I are sitting right now at my desk and was like, read TechCrunch, read MetaFilter, read, write, web, read, know, dig. He was the one that showed me Web 2.0. And during that journey, he showed me YouTube because I asked him two years earlier if I could do videos on the site and he said no, too expensive to host. He now we found this. They were hosting it. So Now I'm doing YouTube. I explode. This is where my career really takes a turn. The wine show explodes. And then I'm now really starting to get into this tech stuff and how do I use it to build the wine store. But it's still wine store, wine store, wine store. And, and then Google buys YouTube. And one point, you, you remember this, that number. I don't think the kids can now. Everything's inflation. You remember that number?

[Interviewer (possibly a business or tech journalist)]

1.45 billion.

[Gary Vaynerchuk]

Do you remember how everyone reacted?

[Interviewer (possibly a business or tech journalist)]

It was insane.

[Gary Vaynerchuk]

I'm saying it right now cause I want you guys to hear it and be affected by it. It'd be as if you woke up tomorrow and TikTok was forced to sell and sold for a trillion. It's like you couldn't. We didn't see numbers like that. Yeah, everything was big. Numbers were hundreds of millions. I mean, Flickr sold for 40 million to Yahoo and that seemed like a trillion. Flickr was the precursor to Instagram. Anyway, I'm just like, holy shit. And now I'm a little bit older and I'm reading more business magazines, not just wine. And I read a Wall Street Journal article about the sale because I was fast. I felt different this time. I was like, fuck, man. I feel like. I know. I feel like my talents are not being maximized. I'm using these things to build my dad's business. There's got to be a way. I just felt different. I was just reading everything about it. And one article, specifically, it references Ron Conway and it says angel investor. I'd never heard the term in my life. Angel investor Ron Conway made a gadrillion dollars. I don't remember how much he put in or what he got, but it was staggering. It was like for his hundred thousand dollar investment, made $4 million or I don't know, it might even been. It was just staggering. I don't remember the details. I just remember immediately going from PR because it was, I think the Journal to computer and Googling, not Ron Cobway Googling the term angel investor, Googling it ironically. Very, very apropos. And I'm like, huh? And I literally again said to myself, I'm going to be an angel investor. I'm going to build up some savings. I had some savings at that point. And one of the first videos I ever made that wasn't a wine video was called Facebook Should Be worried about Twitter because Twitter just come out. I was again fascinated by it. And I promised myself after the Ron Conway article that the next time I felt it that I would invest and the next time I felt it was Twitter. And that video went viral. Blaine Cook was the first CTO of Twitter.

[Interviewer (possibly a business or tech journalist)]

Developer.

[Gary Vaynerchuk]

Developer. Thank you. And I met him at south by, because now I'm going to these conferences and he Twitter. I don't know if you. Were you in the mix? You remember this?

[Interviewer (possibly a business or tech journalist)]

I. I was in the mix, but not.

[Gary Vaynerchuk]

But do you remember, do you remember that Twitter would go down all the time?

[Interviewer (possibly a business or tech journalist)]

It was.

[Gary Vaynerchuk]

Yeah, down all the time. It was the hottest app in Silicon Valley, but it was down. Down did not work all the time. They did Ruby on Rails early on. It was complicated. He was getting so much heat. I met him for a taco at south by and he told me he was quitting and selling every share and did I want any first, and I'm really proud of this. Back to being a good person. First, I tried to talk him out of it. I said, I think you're making a huge mistake. Second, I could see he was making an emotional decision and he. He just went the whole way. And a couple weeks later on emails like, do you want to buy it? I'm done. I'm like playing. He's like, I'm done. And so me, Fred Wilson and Kevin Rose, if I recall properly, bought up all his shares. That was my first investment. And then a couple.

[Interviewer (possibly a business or tech journalist)]

And he left. 700 million with $2 billion on the table.

[Gary Vaynerchuk]

That's right. Just staggering. And then. And then several months later, because I become friendly with my video went viral. Facebook. Dave Morin asked me to speak at Facebook. Zucks was there. We had dinner that night. We hit it off. We started to get to know each other. And sister Randy called me one night when I was in Miami at a speaking engagement. Said, our parents. Mark wanted me to call. Our parents are looking to sell some shares. They're going to buy a nice home near us in California because they were still in Connecticut. Would you like to buy some Facebook equity? I said, absolutely. Game changer. I literally took 80% of my savings and invested in Facebook.

[Interviewer (possibly a business or tech journalist)]

Congrats.

[Gary Vaynerchuk]

Thank you. I've never sold a share. Promised myself that night that if as long as mark was the CEO, it'd never sell.

[Interviewer (possibly a business or tech journalist)]

You've invested in over 100 companies. What do you look for when making an angel investment?

[Gary Vaynerchuk]

Early on, I went for the horse. Then I went for the jockey. Now it requires both. The horse was the idea biggest mistake I made as an investor early on as a kid, a kid in my 30s, was if I liked the idea, I could see how I could run it to success. I didn't realize I was a good operator yet. Then I learned that that wasn't always working. Then it was about the kid. But even with the best operators, if you're operating a bad idea, that also won't work. So now what I look for in angel investing is the jockey and the horse, the operator and the idea.

[Interviewer (possibly a business or tech journalist)]

And so what's the best way to pitch you? I read what you're going to say and what I would give is my answer is very different. What you're going to give as your answer.

[Gary Vaynerchuk]

What's your answer?

[Interviewer (possibly a business or tech journalist)]

My answer would be to come in prepared. And if you have to get in the door and you don't know me, you can create a ridiculous PowerPoint presentation that blows you off of your chair. And I'm good on the preparation. We'll talk about that in a few minutes. But I prepared materials for people that they have to respond. Right. Because you know when you open this document, holy shit. Did this take 40 hours to prepare or more? This thing's like a Rolls Royce. It's a Ferrari on steroids. And if someone's putting that much work into it, it shows the amount of thought progress. It's brilliant. I've received a few of those. Sometimes a lot of my deals, Most of them, 99% of them come from people I know. Yeah, right. And so it's a self selecting process, of course, but every now and then I get something ridiculous in the mail. We've never invested in a cold deal like that, but we've come very, very close.

[Gary Vaynerchuk]

Interesting. Yeah. Mine's the opposite. And this goes back to self awareness. This goes back to like, you got to know yourself. Like I always say, everything works. Everything works. Like there's a version of success and happiness that comes in so many different sizes and shapes that it can work for me. I don't even consume decks. My team knows this. Like, to really prepare for me, I need to have the dialogue, I need to have the feel like for me at this point, to your point, so much comes from word of mouth, different angles. But what really gets me is if somebody says something that I believe in that I can follow up with a couple of questions and they can answer it. For example, what cliche happens to me is I make a big stink on something like this about live shopping. Now I'm going to get pitched. This is real that's what I was.

[Interviewer (possibly a business or tech journalist)]

Thinking when you were saying that.

[Gary Vaynerchuk]

I said, oh my God, I'm going to get bombarded. Yeah, I won't look at most of those emails. I won't go for the Rolls Royce deck. I will go for the person that finds me somewhere and. Or I get a meeting through a person because I want to. If somebody co signs someone, I'll take that meeting. But it's not what they say to me, it's my follow up question. I really tend to invest in things I know more and more by the way as I get older. And so I know what I'm talking about with live shopping. So to me I enjoy the back and forth because the other thing I think I do well is push. I push well in dialogue to like real places. And most people can't answer those real places. You know this. A lot of founders are very good at the surface level conversation. But when you poke and prod, they fold like cheap chairs.

[Interviewer (possibly a business or tech journalist)]

What the craziest thing is you ask someone about, they talk about run rate. Run rate doesn't apply to the cash in the bank. So I always ask what are the GAAP revenues? You know how many CEOs know what their GAAP revenues are the last three years? Less than 1%. And for me the meeting's over.

[Gary Vaynerchuk]

Right.

[Interviewer (possibly a business or tech journalist)]

I mean if you don't know your finances well.

[Gary Vaynerchuk]

And so for me you're referring to things that are a little bit further along. I do so much early stage.

[Interviewer (possibly a business or tech journalist)]

Yeah.

[Gary Vaynerchuk]

That to me it's almost the reverse of I love you for that. I wish people knew how nerdy I am with business. That just got me so fired up. But that's obviously a little bit of a later stage company in that scenario for me because I'm so intuitive of consumer behavior. I get excited about them having to answer pre revenue since I do such early stage real questions about consumer behavior and I'm so in the traffic. One of the reasons the Gary Vee brand still lives and I run the agency is I never want to be away from the dirt.

[Interviewer (possibly a business or tech journalist)]

Your Visa marketing and day trading attention. And we'll go back to jab, jab, jab. Your favorite number five. So talk, talk about that book in particular and what you want to call it. And I know you want to call it something else. So what we did is we, we actually made you a new book.

[Gary Vaynerchuk]

I'm so hyped here.

[Interviewer (possibly a business or tech journalist)]

Here's your new book. It's actually jab, jab, jab, jab, jab, jab. So congratulations on your new book.

[Gary Vaynerchuk]

Thank you. I love that. That's awesome. It was supposed to be left hook, by the way. Jab, jab, jab, jab, left. I was. I was so this book I wrote because I realized no one understood what was going on with content on the Internet. By the time I wrote this 10 years ago, 2014, there wasn't a lot of science around the art of a post. I believe as we sit here today, my friend, that the best social media organic post just post on your account is a more important form of advertising than any television commercial on television today outside of super bowl. The individual post you said the super.

[Interviewer (possibly a business or tech journalist)]

Bowl, which cost $233,000 per second is is the greatest marketing spend on it is tv.

[Gary Vaynerchuk]

It is. No, no. In America.

[Interviewer (possibly a business or tech journalist)]

In America.

[Gary Vaynerchuk]

Here's why. My newest book Day Trading Attention. I do believe that I sit at the top of the organization that is the best marketing firm in not wasting a penny on advertising and getting the most for a penny. And that requires a lot. I Gary and Vayner X the holding company cannot get 130 million Americans cannot get 130 million Americans to consume a video for 30 seconds for $8 million. But the super bowl can. No meta, no Google, no all the other things. Influencers, TikTok. There's no combination that can get there like the super bowl can. The problem is if your video is bad, you just wasted all the money. The creative is always going to be the variable of success. But buying the attention, yes, in buying the attention, the super bowl is the best.

[Interviewer (possibly a business or tech journalist)]

Let's talk about ingredients of success. What's more important? Work ethic? Talent or passion?

[Gary Vaynerchuk]

Yes. Look, you know this. I mean, look, the reason I like work ethic is it feels very controllable. It's like working out like you can get there. Working out came really not natural for me. I didn't do it at all until I was 38. Like at all. I didn't have a muscle in my fucking body. So if I who despises it to this day can get to a level of discipline that gets me there, I believe people can do the same professionally. I also believe that it's a lot easier to do that level of work ethic when you're actually passionate about it. So it's a very. The reason I answered the way I did. Yes, all three different for every one of us in here. But of the three, work ethic is controllable and it's something that I get scared that people try to downplay. Look, as someone who's unfortunately been tagged with hustle, culture and things of that nature. I have been consistent had Arianna Huffington on the AskGaryVee show a decade ago. I believe in sleep. I just think work ethic matters not to burning yourself out and being sick. That's stupid. I am worried that people are using health and wellness and mental health and all these great things that are important as weapons to create entitlement or to create laziness or to justify non action. And I think it's a mistake.

[Interviewer (possibly a business or tech journalist)]

I believe that work ethic is the most important ingredient in success of our success because as you said, you can control it. I have something called Philo first in, last out and I do a lot of coaching as I know you do as well. I tell every young professional, even mid professionals that come to me, hey, I'm not liking my job, whatever. If you're the first one and the last one out, great things are going to happen to you no matter what.

[Gary Vaynerchuk]

I think that's exactly right because even if you're in an environment that doesn't reward that, you're going to learn that it doesn't. Instead of leaning on excuses which will empower you to make the tough decision of leaving. I fully agree with you on that.

[Interviewer (possibly a business or tech journalist)]

Let's talk about my favorite topic, which is preparation. I'm writing a book called Extreme Preparation. I always want to be the most prepared person in the room. How important has preparation been in your success and are there any examples you can give about your extreme preparation leading to something successful in your career?

[Gary Vaynerchuk]

It's my entire life, so my favorite thing and Sid just stepped out, but Dustin's here so I'm going to look at him. Dustin actually probably knows this better than Sid. The thing that baffles all my top executives when they started my company is I go into meetings cold and dominate them. They think I do no prep. They make me huge decks and because the way we do our decks, they can see I didn't open it. I walk into the meeting, brand new client and they are baffled. It's one of the best compliments I get. It's. It's so flattering. They are stunned. It is by far the number one chatter conversation of VPs and above when they first joined the company, asking all the other OGs how the fuck did that just happen? It's because I only am prepared. It's the only thing I do. The reason I can walk into Nike or Smart Water or a T shirt brand or Elite or Lexus or any brand and crush a meeting is because Most businesses are not that complicated. I can promise you that. What Smart Water wants is to sell more Smart Water. And if they're meeting with me, I'm not talking about supply chain. We're not talking about other things. We're talking about demand creation. So I think preparation is the only thing. The reason I do such narrow things is they're the things that I'm preparing on at all times. The reason I have Veefriends and wine Library and winetext.com and GaryVee is I have to actively work on the craft of marketing and demand creation to feel like I have any ability to talk to anyone about it. I'm a full practitioner of the moment. I can speak about live social shopping right now with the expertise I get because I sold $130,000 worth of clothes on a live stream a week ago. So I think you're onto something very powerful. I would argue that the bad version of it is school and the good version of it is sports. I'm always prepared because I never talk about anything or act on anything or involved in anything that I don't actually do. I think some people study, but they're not about it. And that's where the vulnerability, even with prep work, comes in. Because when people start poking and prodding, you start going to 301 instead of 101 level preparation. So I think the ultimate preparation is to actually be a practitioner of. So I love entrepreneurs that are investors. They lift it.

[Interviewer (possibly a business or tech journalist)]

How important is setting goals in our success and do you believe in writing them down? 1, 3, 5 year, 7 plan. 7 year plan.

[Gary Vaynerchuk]

I think about this one a lot. So again, I play it a little looser, as you can tell, than black and white. Obviously. I've had a goal since fourth grade of buying the New York Jets. I'm sure it's had an impact on my success.

[Interviewer (possibly a business or tech journalist)]

Right. There were $7.3 billion today and it's.

[Gary Vaynerchuk]

Moving fast with private equity coming in, right? Yeah. Going to buy them one day, I think so. My intuition now is that as I get older, I'll start to put myself in a position for extreme wealth creation if I want to. But I'll be honest with you, just to be very clear, the chase of it is the great enjoyment. It's a lot of fun to chase that, that football team that's pissing me off right now anyway. You know, I think people do it different ways. I've learned that I'm not a reader and writer. I'm an audio and visual guy. And so I talk to Myself a lot about things I want to accomplish in personal life, professional life. Yeah, I think knowing where you're going is a good idea. But I would argue that the ability to adjust and not be rigid to them is equally, if not slightly more important if you're going to do this thing in five years. But clearly something's happened. Putting your goal on pedestal a when it does not contextualize the truth of your life at the moment you're in right now is a vulnerability.

[Interviewer (possibly a business or tech journalist)]

I think people look at you, they look at me, they look at all these other tech people who have done very, very well and they say, oh my God, that person is rich. They have nice things, et cetera, et cetera. And I think everyone wants to be a billionaire. Not everyone, but a lot of people. And I think that's the motivation. So what's your advice? And look straight to the camera. I mean, I talk about this till I'm blue in the face. People who are motivated by money are generally not as successful and they're generally not always happy either.

[Gary Vaynerchuk]

Either. You know, listen, I've read, I think you know this. I talk about this at. Nausea.

[Interviewer (possibly a business or tech journalist)]

Yeah.

[Gary Vaynerchuk]

I'm going to say this to the camera. I'm extremely, deeply empathetic that the response to this for most people is cool, rich guy. But I'd like to find out, like, fuck you. Easy for you to say. I. I'd like to find out we have the luxury of spending time with people that have it and we know how dark some of their lives are. There is just no correlation in any kind of common sense way of money and happiness. It just doesn't. It's black and white. So what I would say is, God willing, if that's what you want, you are able to earn, not be handed your way to a place where you have it. And I'm going to tell you right now, when you get there, you will see how right we are, period.

[Interviewer (possibly a business or tech journalist)]

Your dad at one point said, you're going to be the next Oprah and a Vcon. He wears a hat that said, I'm Gary Vee's dad.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a business or tech journalist)]

And he's so proud of you.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a business or tech journalist)]

How does it make you feel?

[Gary Vaynerchuk]

Unbelievable. Other than I wish he wasn't so one dimensional and spread some of that love to my siblings sometimes. It's unbelievable. And my dad does it very publicly and my mom does it very quietly and they both mean the same. Making my parents proud is probably my strength and my weakness. It's a big currency for me. I really like making them proud. It feels really good.

[Interviewer (possibly a business or tech journalist)]

We're at the end of the show and I always end it with a game called Filma Bling to excellence. Are you ready to play?

[Gary Vaynerchuk]

Ready to play.

[Interviewer (possibly a business or tech journalist)]

The biggest lesson I learned in my.

[Gary Vaynerchuk]

Life is losing is the thing you should always strive for because it makes winning a lot easier.

[Interviewer (possibly a business or tech journalist)]

My number one professional goal is to.

[Gary Vaynerchuk]

Buy the New York Jets.

[Interviewer (possibly a business or tech journalist)]

My number one personal goal is to.

[Gary Vaynerchuk]

Have everybody that I love show up to my funeral with a very good feeling in their stomach about who I was.

[Interviewer (possibly a business or tech journalist)]

My biggest regret is.

[Gary Vaynerchuk]

My biggest regret is already realizing that as much as I keep an eye on it, I want to spend even more time with the people I love.

[Interviewer (possibly a business or tech journalist)]

The one piece of advice that I give to my kids is be a.

[Gary Vaynerchuk]

Good human being on their terms, not how you want to define it.

[Interviewer (possibly a business or tech journalist)]

The craziest thing that's happened in my.

[Gary Vaynerchuk]

Life is fucking all of it, brother. You know, I am not detached from how miraculous my life has been. And silly things like judging the Miss America contest, when that was something I watched with my mom, to important stuff like getting an email weekly from someone who says that a piece of my content took them out of not only a dark place, but sometimes the darkest, scariest moment of their life. It was super humbling.

[Interviewer (possibly a business or tech journalist)]

You read your own email?

[Gary Vaynerchuk]

Yeah.

[Interviewer (possibly a business or tech journalist)]

The funniest thing that's happened in my.

[Gary Vaynerchuk]

Career is the funniest thing that's ever happened in my career. I mean, probably my first appearance on Conan o'. Brien. I could not explain to you how going from operating a liquor store to literally being on the hottest late night show in television in 2007, when that was a whole different game than it is today. It was. And it was funny. If you actually watch the clip, it is actually funny. So I think that's the funniest thing that's happened.

[Interviewer (possibly a business or tech journalist)]

The best piece of advice I've ever received is.

[Gary Vaynerchuk]

You know, I know you've seen that because you've done your research. Fuck, man. I'm really glad my dad tightened me again. I wasn't going to go sell like junk bonds, but I just know that I couldn't be sitting here at the level that I'm at if I didn't fear. Like, if I didn't put my reputation on a pedestal.

[Interviewer (possibly a business or tech journalist)]

Ten years from now, I'm going to.

[Gary Vaynerchuk]

Be doing exactly what I'm doing now. Waking up and working on what I want to.

[Interviewer (possibly a business or tech journalist)]

20 years same. Are you ever going to retire?

[Gary Vaynerchuk]

No. And I mean this. Not only am I never going to retire, my great preference at this point, God willing, is that I'm always operating. Retirement comes, as you know, in all shapes and sizes. People go to consulting, people go to full time investing. I defined it as operating. I prefer to be operating something for the rest of my life.

[Interviewer (possibly a business or tech journalist)]

If you could pick one trait that's led to your success, that trait would be.

[Gary Vaynerchuk]

Sorry, because I love traits. I was about to answer humility, which is not very seen in Gary Vee's content. You got to really know me. That I was about to say patience, because it has been huge, but I'm going to go with tenacity today. I'm fucking tenacious and it matters.

[Interviewer (possibly a business or tech journalist)]

The one trait that is most important to somebody else's success, who you don't know is.

[Gary Vaynerchuk]

So the one trait that I deem is most successful to someone else's, like universally a trait that is a good indicator to success.

[Interviewer (possibly a business or tech journalist)]

Yes.

[Gary Vaynerchuk]

Tenacity, hard work.

[Interviewer (possibly a business or tech journalist)]

If you could be one person in the world, who would it be?

[Gary Vaynerchuk]

If I could be someone.

[Interviewer (possibly a business or tech journalist)]

If you could meet one person in the world today who's alive, who would it be?

[Gary Vaynerchuk]

Who's alive? This is important because I've never. Because the Macho man Randy Savage is dead. If I could meet one, this is. This is a very interesting indicator of me. I am so insular. I'm very curious. It could really be a lot of people. If I could meet one person in the world that is alive, who would it be? You know who I'd like to talk to right now? Vince McMahon.

[Interviewer (possibly a business or tech journalist)]

Have you seen the Netflix.

[Gary Vaynerchuk]

Forget about, I'm sure the doc I'm only two episodes in. Let me tell you why, Vince. There's so much there and I'm sure that surprised a lot of people. And I'm very empathetic that there's plenty of there. But the angle in which I would want to talk to him and what I would want to talk to him about is strictly around character development. I believe that everything I've accomplished in my career will be dwarfed on my execution of befriends. I believe that in 30 years, when I sit here and do an interview with somebody as awesome as you, what they're going to want to talk about is veefriends. Nothing of what we talked about. Sure, they'll touch on it. I believe that Walt Disney and Vince McMahon and Jim Henson are the prominent figures of modern character development. Jim Henson and Walt Disney did it with fictional characters. Vince did it with real human beings, which I think is very fascinating. The other two are dead. So character development, how to get people, by the way, you know who my fourth one on that list is? David Stern. David Stern understood that Michael Jordan and Larry Bird and Magic Johnson needed to be superheroes, not human beings. That's what sports is. Steph Curry is a superhero for little short kids, not a basketball player. And that's what I'm going to do with my V friends. And that's why, Vince, in this moment.

[Interviewer (possibly a business or tech journalist)]

If you could go back and give your 21 year old self one piece of advice, it would be don't do.

[Gary Vaynerchuk]

A single thing different. Because at 48 and a half, almost 49, you're a very happy person.

[Interviewer (possibly a business or tech journalist)]

The one question you wish I had asked you but didn't is.

[Gary Vaynerchuk]

You know, it's so funny, I don't think in that term because when I'm sitting in this seat, I think I'm here to bring value for the audience. Thus I have no feelings towards questions. You know your audience better than I do.

[Interviewer (possibly a business or tech journalist)]

You're awesome. I want to do a shout out to Mike Hermelin.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a business or tech journalist)]

So we wouldn't be here but for him today.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a business or tech journalist)]

I just met him. He a new parent at our kids school. He just moved to la, as you know.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a business or tech journalist)]

He had been here five weeks. He shows up at back to school night and randomly we start talking to him as we're walking out and we started talking. He works at fanatics. I know someone there. And here we are. Here we are. I really appreciate it.

[Gary Vaynerchuk]

Thank you for having me. Thank you, thank you.