9 Business Questions with Gary Vaynerchuk

Gary Vaynerchuk answers nine audience questions on content strategy, personal engagement at scale, work-life balance, and sales. He emphasizes replying to DMs and comments as unscalable but essential, and argues that documenting your learning journey beats polished content.
So we're gonna go into Q and A. Guys, I have a question for Gary and then we have a few people ready for questions. So if you submitted your question and were selected, please come get ready for the mic. So, Gary, thanks so much for doing that. I just actually was watching as an attendee just now and I was like, YouTube shorts. I'm not doing YouTube shorts. And what's cool about YouTube, I guess, is the search right?
Huge. And not only that, YouTube Shorts is literally the most exact rip off of TikTok of all time. And what I mean by that, the reason Instagram's a problem is you can't go viral. Nobody's posting and getting 6 million views on Instagram if they don't already have a massive platform. On TikTok and YouTube shorts, you can. And for 99.999% of this audience, that's what we need. We mean more awareness and the platform's giving you that opportunity. Same thing with Facebook fan pages, big time.
So we're going through a shift. You alluded to this in your talk right now. And people are honestly like doubting themselves, you know, because the market's getting difficult. Like, I think everybody thought that they were the best player before, but it was. The market was easy, right? So now you're doubting it. Like, what's the time? We see you crush it in literally everything you do now, but like, what's the time when you were doubting yourself? And how do you get over that for this group?
I've never doubted myself in business. But to answer your question. Cause I want to bring value, because that's just the truth. I haven't. It's the one thing I'm good at. I also have never put myself in a position to need money. And that doesn't come from having it. That comes with living humbly and saving it. One of the great things about immigrant mentality is I was just as happy in my twenties when I lived in an apartment that was a shithole for a decade as. As I am right this second being fancy. I think the reason people get scared is cause they can't sustain their bills. And then what even scares me more is they can sustain their core bills. But people don't like a couple years of not having fancy. They don't want to go to a vacation that's not as nice as the one last year. Humans are bad at humility. Humans are bad at one step backwards, two steps forward. So it's a mentality game. Which is why I've never Been. But like many other things in my life I was, like, doubted myself about. And it's, you know, like, you just have to do it, right? Like when I was like, ooh, I don't know if, like, in high school, I'm like, I don't know if I can go hit on the prettiest girl in school. It was just a game of, like, you have to do it or you don't. It is what it is. And so rejection, whether boy girl dynamics, whether the market, whether your business fails and your friends and family have judgment on you, a lot of people's problems in the world are based on. They talk a lot of shit and put themselves in a corner for their failure. Like, I'm crushing it. You should have went into real estate. I told you, I'm fucking crushing it now. You're not crushing it. And all those people you were shitting on, now it's their turn. And so we need to. The world can get a lot better for everyone if they lean into humility. And that doesn't mean not having confidence and bravado. That's why I'm so weird. I'm loaded with that. But in the underbelly, it's all humility. Like, what makes me palpable in a world where I'm like, I'm fucking, is that I know I don't mean shit, that if, God forbid, I die tomorrow, I'll trend for a day on social and then you'll be moving on. Right? And so, like, I think we need more humility. Yeah, humility will help you with your fear. What, so you fail? Like, my big thing is when people shit on you for your failure, just shit on them back for theirs. Seriously, I'm always one. Like, what? So you have to get a job now? And you're not a real estate. And your aunt says, you see? And like, fuck you, aunt. What about Johnny, your son, my cousin, he's a fucking crackhead. Like, I really mean it. I really, like, you know what I mean? Like, what are you scared of? There's not a person on earth that's undefeated, so whoever shits on you, just shit on them back nicely.
Nice. Yeah. So this leads into the next question. Question. And you talk about humility. And I. This is one thing that shocks me about you, Gary. And. And people say this all the time. Why do you do things that are completely not scalable? Because, like, I'd look back at that email where you sent me an email at one in the morning on a Saturday, and you're like, I'm in for 15. I couldn't think of like the least ROI use of your time to meet with Neil in Las Vegas for 15 minutes and. But you did it. And we did the podcast because my.
North Star is to leave a kind legacy, not to maximize my time financially. It's like, you know, it's like, it's kind of interesting. Like it's really the actual answer. Like, I can't believe that I'm at a point in my career where me doing something like that means a lot to someone. It is like crazy. And like I try to do it as much as possible. Like, nothing excites me more than when I find a macro. Second, just to go into my DMs and reply to somebody who is just flabbergasted that I replied, it's flattering and I know it's nice. And I always remember 15 year old Gary, if I did that to macho man Randy Savage and he replied, I would have lost my fucking mind.
That would be dope.
And so now that I'm on the receipt on the other side of that, for a certain amount of people that have a certain interest, I just want to do nice things to the best of my ability and it makes me happy.
So I think you say yes to things that maybe people in this room would say no to.
Well, you know, this, this is where I get, you know, that's true. And that's my number one. I actually said it in the talk. A lot of you have gotten too fancy for the reality of what you've actually accomplished. I'm telling you, it's humility. I'm telling you, I love when people are like, gary, I can't reply to people. I had to hire somebody to reply. Why? You mean you don't want to. You mean you don't actually care? Gary, I want a community. Cool. Build a community instead of what you're really saying. Gary, I want customers. You know, many people here like, why is my content not working? Because every piece of content you make is self interest. Who the fuck wants to see your content of you selling them shit every fucking time? The hell are you doing for them? The only reason people raising your hand for me, the reason I'm different is I only go into my content of this needs to be valuable to them. Why in the world would they watch that? And occasionally back to jab, jab, jab, right hook. Yeah, I am gonna have a sneaker. Yeah, I am gonna have something. But. But then you ask, you don't expect when I Wrote jab, jab, jab, right hook. I made it very clear, give, give, give, and then ask. What everybody heard was, give, give, give, and then expect. The thing I love the most is when I crush two years of content without a single ask, then come out with something. And it doesn't do that well. My team goes crazy. They're so upset. They're like, no, this should have been like, what the. And I'm like, you're expecting.
Yeah.
And then even worse, people are manipulators. I love people like Gary. I'm getting walked all over. You know, nice guys finish last. I'm like, break it down for me. And what it is, is people give people things that they want something from. They give them something that person doesn't want and then are expecting something that they need. That's not giving. That's called manipulating. Nice guys.
Yeah, it's, it's a huge thing. And I, I just think like, of all the things that you do and I mean, just watching you at VCon and watching the stories and the, the YouTube videos afterwards and the amount of time you spent there with fans, talking to all these, I mean, it looked.
Like 12 hour, it was hard. 14 hour day even for my, my mom said you're the Energizer Bunny. But that was tough.
That was.
Yeah. And then it was on. Did a talk like two days later. So it's crazy. So we do have some questions from audience. Let's bring up the first question if we can, on this side. Go ahead.
Hi.
Hey, Gary. How's it going? So grateful for your time, Neil. Amazing event, Amazing people. So my name is Amber Ibarra. I've built two construction companies that I've run. I've delegated that. I've had, had them for nine years, building out the coaching business this last year. And my question to you is this building VaynerMedia and the, the multiple businesses that you have, how have you created balance in your life and what does that look like for you? And then looking back, what do you feel that you had to sacrifice to have the success you do now? Or did you at all?
I don't think I sacrificed anything. And I think that's a confusing answer. And let me explain because it has to do with the first part, which is I probably had to sacrifice a billion things. What's balance? I love when people are like, work life balance. I'm like, work life balance is every single person in here is one dimensional, one person's reality. You know, one of my great entrepreneur friends has Two autistic children. He's gonna be in a position where he can't do certain things that other people do. Everybody's got their own circumstances here, you know. So to answer your question, I probably sacrificed a ton. I definitely sacrificed my 20s of like memories and fun with my boys. Cause I never saw them. Right. I definitely did that. On the flip side, I changed my parents life. Right? That's a trade I'm willing to make. Like, would I have liked a little more balance? Of course. Who here wouldn't do shit differently if they could go back 10 years? We all would. We have the luxury of knowing what happened. That's the key. The reason I'm so happy is I make decisions knowing I don't know what would have happened if I made the other decision. Right? Like, I love when people are like, how do I make this call? And I use this analogy a lot for the people that follow me the hardest. But I want to share it. You may have a business decision that you make and you made the right one financially. Like when you go to heaven, they're like, good call. That was the right move. The problem is you might be in heaven 23 years earlier than you would have been if you made the other call because you got hit by a bus by making that decision. That butterfly effect. I didn't watch the movie, but whatever the fuck that is, that's real, right? Like, that shit's real. This is what I'm trying to get people to think about. We have to stop making happiness, have any relationship with money. We have to. Everything will change in the world. And I'm an entrepreneur. I like going garage, selling and buying stuff for two bucks and selling it for eight. But I don't see happiness and, you know, and money together. And so what that means is it reframes that whole question. I didn't build business for the money. I built it because it's the thing that makes me the happiest on earth. I do business the way people do golf. I do business the way people do cooking. I do business the way people do playing tennis or going on vacation or sailing. Like there's nothing I'd rather do than play business. Not for the money. And once you can get there. And that's why I'm always trying to challenge this conversation. So I'm sure I sacrificed everything and nothing.
Appreciate you. Thank you.
Thank you, Gary. Hi, my name is Ben Rojas. I'm with EXP Realty team Fast Shout Out. So we just got a ton of Neil love your stuff we just got a ton of scripts. We now have the list of where to post. And so in this noisy world we've got 2,000 people are gonna fucking dominate on these channels. How do we get heard? Heard? By putting out content that people want to see. And that comes through testing and learning and listening. The reason I'm so good at content is because I read my DMs. By reading my DMs, I know what's on your mind. By knowing what's on your mind, it subconsciously goes into my mind and pops up in my answers. So by listening, I watch people who want to grow their audience and they've never replied to a comment, ever. The audacity of expectation of people that produce content is staggering. 2,000 is nothing. You're competing against 8 billion, right? So the way you break through is by providing something of value. That means I'll give you a good insight that will help all of you make. When you are making content, that's for them, make it purely about them. Too many people try to mix it in, they put it about them and at the end they're like, and don't forget, I got an open house this Friday. Which then changes the energy of the whole thing. Right? You're mixing the jabs and the right hook and one piece of content. Separate them. Thank you very much. Love it. Thank you.
And that, that's crazy, Gary, because you were talking about in your comments, like, to this day I see you reply to people and more importantly, I'm like.
I. I'm nowhere at this point in my career. But from 2007 to 2011, I replied to every single tweet. I got all of them. That's how I got here. I'm not on Shark Tank. I didn't fucking like. I got here by building in these trenches. And in 2007, not a soul knew who I was on Earth. So 2007, 2011, I replied to all of them. And we just aren't grateful for what we have. You, you have 537 followers. Be grateful for the six people that reply to your stuff. Now, that's how you get to 16. But you don't do that. You're worried why somebody else has 40,000. We're in envy instead of appreciation. Right.
Go ahead.
My name is Dan Sandoval. I'm with Keller Williams, Southern Nevada here in Vegas. Pleasure. My question for you is, with lead generation being the number one priority in all of our businesses, what would be the top two or three levers you would focus on for us, content on social media. All three of them. 1, 2, and 3. I'll tell you why everything else is a commodity. Everything else you can Google right now, real estate, mortgage leads, and you'll get 100 tactics on retargeting landing page. That's the commodity. Got it. Yeah. Sales is something I adore. Do you know what sales are? I do. Bad marketing. Got it. If you don't know how to market, you have to be a good salesperson. If you know how to market, you blow away the next 10 best salespeople. Nike didn't call me and sell me this in a catalog. I bought this swoosh because it's ingrained in my soul. Branding wins every day of the week. But it's hard. Appreciate it. Got you.
And one thing really quick to add on that. You were talking about messaging comments. I noticed that even ad effectiveness, ad reach has gone down. Like we have to spend more to reach fewer people.
Now you've been on Instagram.
Yeah. And what I kind of my workaround. I don't know if I just stumbled into this was just literally sending DMs 100%. This room was filled by me sending DMs. The ads weren't really doing much, so I just sent out thousands of messages.
It's the number one thing. If I DM'd everybody here, I could get half of them, a quarter of them to buy a veefriend series two. I could. You spend six minutes, you explain why it's a good thing. Like, you could. You get to a place we all ebb and flow. Like, if you've got time. Like, if you're. And listen, this is just truth. It's not just people under 30. Other people have time for other reasons. But if you're under 30 and you're about that life and you talk that game that you're gonna dominate, like, that's the best. Like, because you just have time. Yeah. I mean, it's. Everything good is unscalable. Yep.
Go ahead. Jeff.
Gary Vee. You changed my life, man. I lost my brother to drugs, fat and all. I connected with you on Clubhouse. I think you remember me, right? My thing is I'm gonna build the biggest franchise ever called Kokomo J's. And on my brother. Don't give up America just. And I started. I documented not to create just like you did. The jets people like, where's the coffee shop, Jeff? But it's the journey of what I've learned and the content I've put out because of you. Because of you, Neil. It's amazing. That's brought me here. At what point? And now right now, you said something that just spoke to me, right? I started to get almost hire executive assistant. I'll answer everything. I'm Jeff the entrepreneur. I'm gonna come humbly before everything. That's why I'm wearing the hoodie here, man. It's not flash, right? So that's why I love the backwards hat and everything. My question is, is now companies fly me out. I look over social media. I basically take everything you do. I'm like, do this, do this. Just did it. Right now we're all doing Facebook. What point do I stop telling that old story? Okay. Because the old story to new people on Kokomo J's like, I'm gonna be. I'm not Joe Rogan. I'm the young kid who's gonna start a virtual show called Kokomo Jays here. You're gonna be on it. I'll have you pay whatever to get you at my event.
Like Neo, 63 million.
All right, dude, we got it. Write it down. You're worth it, man.
Go ahead.
No, that. So how do I stop telling the old story? People say, stop telling the old story.
New people, I think it's and not. Or I think people, like, don't tell the old story. Tell the new story. And I'm like, tell both. Got it. Everyone's so obsessed with OR when all the magic is and right. When I made the transition from wine content, that story to business content, I didn't stop doing the wine show. I just added the business content. And this is a very subtle point. This is a life advice thing that I'm really starting to try to. I'm like in the lab, cooking in my own brain. This concept of and versus or is profound. I actually think it can solve our fucking political issues. Like and over or is something that I think a lot about. And it's happening right here with your question. Just add it.
Yeah. Awesome. And I just want to say I'm going to tell you something later. I wasn't supposed to ask a question. I came out here, I saw Dutch Bros Coffee Optimist versus pessimist. I make my team watch that. One of the best videos on YouTube. Neil, you're great. All right.
Thank you. All right, we got time for one or two more. Go ahead.
Hi, how are you?
Good.
I'm a. Ello, former teachers. I'm gonna read this so I don't mess up. Gary, it is not easy balancing growing your Business and being an awesome parent spouse.
Yes.
How do you intentionally be there for your kids and family and grow your business at the same time?
By knowing that it ebbs and flows on your circumstance. I, like many people, have ebbed and flowed in my family relations, my business relations. This all comes down to judgment. The reason people struggle is they're beating themselves up even when they're trying so hard.
Yeah.
This is just about the conversation you're having with yourself. There is no perfect. Nobody's done it. Right. I have. Like, I mean, I think, again, because a lot of people follow my content. I think everyone knows how I feel about my parents. I could speak for the next year about the things my parents did wrong. Right. You know this. Right? We all know this a lot. I'm looking around the crowd. Remember when, like, we would shit. Our parents. And now our kids are starting to get a little bit older and like, fuck. Right? Like, you could be the greatest parent of all time and your kids will rattle off a hundred things. Mainly. Cause a lot of people in their youth don't want to be accountable. Right. So, like, for me, this is a game of judgment. Like people are trying out here. Yeah. Sometimes you're gonna miss a ball game or, like. And maybe you didn't want to, but, like, I didn't see my dad the first 15 years of my life. Cause he worked to build the American dream for us. And. And I love them more than anything. And yeah, I've got my things, but it's the best. And so, like, I just would tell you and every parent in here and everybody who's got a partner, like, if you have the right intent and you try, and if you feel in your soul that you're going too far and, like, you're overworking the last six months, throw the curve ball, break it up, like, bite the bullet of your business momentum and take a week off like you can. And like, you know, I just really wish that we. We loved ourselves more to respect that we're trying.
Thank you.
Hey, we're gonna fit one more in. Azeem.
Yep.
And, dude, just selfishly, I wanna ask real quick. You just brought up your dad. And I saw this piece of content where your dad was crying after what happened. Like, what touched him there.
My dad does not run his company the way I run mine. He, you know, he does not view his employees as family. Not because he's a bad dude. Because he was brought up in a country that instilled your employees steal from you. And it's been ingrained in him. And he really was like, I really felt what you were talking about. He was also seeing how my team was interacting. My dad does his thing.
It all hit him at once.
It all hit him at once. And then three weeks later, we went to France for a Vayner thing and I got my parents to go as well. And he really saw it. The problem is I was joking with him last week. He just needs to follow me around every other day because he gets really hyped. And then three days later, somebody, like, does something wrong in the store and he loses all the momentum. So we're trying to figure out a model of sustainability.
Azeem, go ahead. Last question.
Cool. Gary, I fucking love you. Thank you, bro. Your content's changed my life. I'm an actor and a new loan.
Officer on Neil's team.
My question is, if you had no money, no connections, and no experience in the mortgage real estate space, what would.
You do to dominate as fast as possible?
The last part is the problem. I loved everything about everything. That word fast is your kryptonite. Patience. It's just everything. The reason I have analyzed very heavily, the reason why winners lose is because of fast. So what I would do now, what is the most strategic thing that may give you the potential for it to happen faster? Ish. Is documenting the process of learning the mortgage industry through YouTube shorts, TikTok and Facebook fan page. Okay. The authenticity that you're learning, documenting meetings with some veterans in the game will be so endearing for the people on the other side. You will actually have people that reach out to you and say, I wanna give this kid a shot, even though I'm not so sold he even knows what the fuck he's doing. Cause they're stable enough in their own way to go through it. So documenting, titling, the whole framework of the journey to becoming the biggest thing I tell kids is don't fake it. The faking to make it thing is a problem. Cause it's all that was cool pre Internet when none of that shit was recorded. Faking to make it was awesome pre Internet. You know, just because you dress the part doesn't mean you are the part. That's super common in real estate land. Right. And so being authentic and saying the journey of becoming versus saying the young buck that knows when people can tell that you don't. Yeah. Like tricking yourself is a losing formula.
All right, guys, give it up for Gary. Thank you so much for being here, Gary. Thank you.
Thank you, guys.
Have a great session. Have a great day.
Thank you.
Have a great weekend.
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