Gary Vaynerchuk's Insights on Success, Family & The Future of Business

7 Oct 2023 · 51 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Podcast Summary: The School of Greatness - Episode with Gary Vaynerchuk

Episode Overview In this episode of "The School of Greatness," host Lewis Howes interviews entrepreneur and motivational speaker Gary Vaynerchuk. They discuss insights on success, the challenges of entrepreneurship, and the importance of family. The conversation is rich with inspiration and practical advice, making it a must-listen for entrepreneurs and anyone seeking personal growth.

Key Themes and Insights

  1. The Reality of Entrepreneurship
  2. Dedication is Key: Entrepreneurship requires relentless dedication and hard work.
  3. Balance is Essential: Successful entrepreneurs must balance career, relationships, and health.
  4. Not for Everyone: Acknowledge that not everyone is suited for the entrepreneurial path.
  1. Hard Work and Humility
  2. Hard Work Revolution: Vaynerchuk emphasizes that hard work is increasingly being recognized as crucial to success.
  3. Art Over Work: He describes his work as more of an art form, suggesting that passion can drive success.
  4. Humility in Success: Acknowledging one's strengths while remaining humble is vital for long-term success.
  1. Overcoming Self-Doubt
  2. External Opinions: Self-doubt often stems from the opinions of others. Learning to ignore these can liberate individuals from fear.
  3. Confidence vs. Humility: Vaynerchuk balances self-confidence with humility, which allows him to stay grounded.
  1. Entrepreneurial Trends and Opportunities
  2. Post-Pandemic Opportunities: Vaynerchuk predicts growth in certain sectors, such as direct-to-consumer brands and home office renovations.
  3. Innovative Thinking: He encourages entrepreneurs to think creatively about business models and services that cater to changing consumer needs.
  1. Family and Personal Growth
  2. Being a Parent: Vaynerchuk shares insights into the joy of parenting and how it influences his life and work.
  3. Lessons from Parents: He reflects on the work ethic instilled by his parents and the importance of kindness.
  1. Challenges and Resilience
  2. Business Challenges: Vaynerchuk discusses the challenges posed by market downturns, emphasizing the need for resilience and adaptability.
  3. Anticipating Crisis: He stresses the importance of preparing for economic fluctuations and maintaining a financial buffer.
  1. The Future of Business
  2. Innovation in Business: Vaynerchuk believes that the future will see continued innovation driven by changing consumer behaviors and needs.
  3. Long-term Vision: He discusses the goal of building a "Death Star" business model that can withstand economic challenges and thrive.

Key Takeaways

  • Gratitude and Humility: Embracing these qualities can serve as a springboard for success.
  • Continuous Learning: Entrepreneurs must constantly adapt and learn from experiences, both good and bad.
  • Balance is Personal: Everyone's idea of balance in life is different; it's essential to find what works for you.
  • Community and Giving Back: Supporting others and contributing to causes can enhance personal fulfillment and success.

Additional Resources

  • [Wine Text](https://winetext.com): A platform for buying wine via text message, exemplifying innovative business models.
  • [All In Challenge](https://allinchallenge.com): A charitable initiative showcasing celebrities offering unique experiences for fundraising.

Conclusion This episode with Gary Vaynerchuk is filled with actionable insights for anyone interested in entrepreneurship, personal development, and achieving greatness. The emphasis on hard work, humility, and innovative thinking serves as a powerful reminder of what it takes to succeed in business and life.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00There's never a bad time to start a great business. The reality is you and I have audiences that will listen to this and watch this that are really great entrepreneurs that are destined to build$500 ,000 a year businesses. Welcome to the School of Greatness. My name is Lewis Howes, a former pro athlete turned lifestyle entrepreneur. And each week we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin.

0:36Welcome to today's special episode. Over the last 1 ,300 plus episodes, there have been so many impactful interviews that I've been lucky enough to have, and I always like to reflect on some of the most powerful. And this episode was one that resonated with most of you guys in the past, and I'm excited for the value it's going to bring you today as well. So I hope you enjoy today's episode. welcome back everyone to school greatest podcast i've got my man gary b in the house gary good to see you brother good to see you man you're looking good you know the thing that i appreciate it you're looking you're looking lean yourself the thing i appreciate about you the most that most people don't know about is i've known you since 2009 and what people don't know is that i am the all-time thumb wrestling champion of the world and there's there's proof somewhere someone has a video clip of me holding it for three seconds you know it was a two and a half count everybody that is is watching or listening to this knows you're an incredible physical specimen you know like it is just the truth you're a you're a god amongst men my friend but the thing i appreciate and love about you the most gary uh is i've known you for 11 years i believe 2009 maybe it's 2008 but i think it was 2009 january i believe it was an affiliate summit when I first met you.

1:53I think it was January 2009 in New York City. And I've gotten to see you behind the scenes over the years at different events. And, you know, I've driven you in a car from one of your book events early on in like a beat up car. You know, we just had moments here and there at different settings. The thing I appreciate about you is how giving you are of your time, your energy, your resources, your wisdom, your money. You know, you've been donating to Pencil of Promise for years. I see you at the gala all the time. You're giving your time and energy and money. I think it's the thing that a lot of people don't see about you enough is how giving you are and you're especially involved in the uh the all-in challenge right now I think you guys have raised like 40 or 50 million dollars already yep and I know how much time behind the scenes it's taken for you to coordinate work with Ruben and just like put this together and call in favors like there's so much giving you do so I just want to say thanks for all I appreciate that look I think you know I think it's really funny right because I'm very much you know willing to self-promote myself I'm willing to promote my businesses but you know this about me because we have been friends for a long time like I'm a little bit more quiet about of the best version of me right and and I I'm okay with that because I think you know we're all affected by things I think I was affected as I was coming up the game of realizing wait people use charity or other things for their own self interests like they're positioning themselves and you know and by the way i i definitely don't uh begrudge people promoting their philanthropic kind of ventures either i think we're all wired differently but i that's very nice for you to say and and i appreciate it of course and i think there's like i've tried to learn like how do you balance like self-promotion versus like promoting something that's a good cause that people need to be aware about and for them to promote uh to donate also it's like a balance of the balance what to talk about what not to talk about so i think you've done an amazing job of that and uh people need to know more about that can you share quickly about all in for people that can get involved yes what it is if those haven't seen it from every celebrity yet yeah so michael rubin the founder of fanatics came up with this idea the all in challenge all in challenge.com uh he was sitting around like everybody else wanted to give back called uh his buddy alan tish called me we started hacking at it and the idea evolved into the greatest experiences from people in culture music film you know television sport of course um it's gotten into some experiences we've got some and it's basically auctions and sweepstakes for people you know tom brady's flying somebody out to tampa for the first game and and they're sitting you know 50 yard line they're getting on the field beforehand and then he's going to dinner with them and giving them the first jersey he wears in the cleats from his first tampa game that's great you know that that auctioned off i think that went for almost a million bucks then there's raffle tickets for ten dollars somebody is going to be somebody actually won for ten dollars the ability to have a speaking role in leonardo dicaprio marcus Scorsese film.

4:57So there's just all sorts of crazy stuff. If you go to allinchallenge.com, unlimited$10 raffle tickets for Bieber to come and sing at your house, like just crazy, crazy stuff. And it's completely popped off for the last month, over$40 million raised at this point. We're super proud of it. You're right. It has been 15 hour days while still trying to navigate VaynerMedia and VaynerX while also losing all my income from speaking, which is really kind of what allows me to invest. That's your money. Yeah. Yeah. That's the place where I make revenue that allows me to kind of invest in top line growth for Vayner, not worry about profit as much or make investments or try new ventures.

5:36So like a hundred thousand be nice and do nice things. Like, you know, um, so it's definitely been a very intriguing eight weeks. Uh, I asked a bunch of people about an hour ago on my Instagram live. I said, what's a question because you're doing, you know, Tea with Gary Vee every day. You're giving so much content right now, which is amazing and helping so many people. And I said, what's a question that you haven't seen Gary talk about? And you've seen a million posts a day from Gary share a lot of incredible stuff. Is there a question that he hasn't answered yet? And I wanted to ask my audience this.

6:11So I want to get to that in a second. Before I do, I posted, I saw a stat out there about a bunch of different companies that launched from 2008 to 2010, Right around the time I met you, when I was on my sister's couch and I had no money and I was like, what's happening? It's kind of a similar feeling of the economy. And some of the startups that founded back then, Uber, Airbnb, Slack, Pinterest, WhatsApp, Square, Venmo, which you're an investor in. And they have blown up in the last decade. I'm curious, what are the ideas or businesses that should be created today, moving forward, that in 10 years, we'll be looking back at the next, you know, crisis and say, this is the companies that were started in 2020.

6:53What are those industries? What are those topics? What do you think? Practical direct to consumer brands, you know, ones that are like DTC for brands is an incredible business over funding and trying to go public or sell to somebody is why a lot of them are going to go out of business. I think that you're going to see some really fascinating innovations. I've been thinking a ton about co-working. Obviously we had WeWork and obviously they have their challenges for over valuations and over, but, but I do think business as usual, I mean, geez, talk about like, I've been thinking about things like for just small entrepreneurs, like create a business about renovating home offices to be epic because the amount of people that are going to work one to two times a week from home is going to be, So just like, think about if you're a carpenter, right?

7:41Like you just put up all the, you know, billion dollar things. And honestly, those, there's never a bad time to start a great business. And the Travis's and the, all the other people that you, the companies you just mentioned, those were individuals that had that talent. The reality is that's the 1 % of the 1 % of the 1 % of the 1%. The reality is you and I have audiences that will listen to this and watch this that are really great entrepreneurs that are destined to build$500 ,000 a year businesses if you're a general contractor or a handyman or woman positioning yourself as a home office specialist right now I couldn't even imagine you probably could go from being a 35 to 50 thousand dollar a year person with one or two projects to like a million dollar person because that is clearly coming so that's on my mind um you know little things like I saw AJ bought for our entire family some sort of like keychain ring that helps you you know ring doorbells and put keys into like like like i i do think you know like people are about to be germaphoed out in perpetuity similar to similar to 9-11 i you know which sucks for me because i'm a very other way like like hug kiss like you know slumber on someone's face like yeah i'm very like you know like don't wipe down anything when i get on the plane like let's share drinks and eat hot No, honestly, eat off people's food.

9:06I'm a little bit worried that I'm about to be shunned from society. But I think cleanse, clean, safe, those are going to be great. I mean, somebody should create a high-end hand sanitizer business. That's true. So I think there'll be some trends. And then back to the point I made, a good business is always a good business. um i for example opening a restaurant immediately after this sounds insane except if you're opening up a great restaurant yeah you know it's interesting and i'm in la near beverly hills and i'll drive down this side street with uh sprinkles cupcakes i don't know if you've heard of course no it's amazing well all these restaurants are shut down or they're like doing their own version of delivery or whatever it may be sprinkles cupcakes had an atm machine four years ago, five years ago, before it's time, where you can go at any time of the day and get a cupcake out of the ATM machine fresh made that day.

10:02I tell you, I kid you not, there's a line down the street in Little Santa Monica of people who had sprinkles all day long just getting out of this ATM machine. And people are in there all night working because they can't supply the demand fast enough. So something innovative like that. Listen, my dad a year ago said, hey, you're helping all these companies. What about helping old dad out? and I launched Wine Text, which I've been promoting very heavily. And it's an innovation. You get a text, you reply with a number. Anybody who's listening that's into wine, if you really buy wine on the internet, you have to go check out winetext.com.

10:37You sign up, you put your credit card in, it takes two minutes. And then you get a text every day and you reply with four, five, two, one, 12. And it's like Brandon hired nine people today for Wine Library because obviously alcohol sales are exploding. but but on top of that this is above and beyond because the innovation is so strong what is the direct direct result from you guys implementing that for this new kind of business for wine library how is that it is i'll tell you exactly i don't have the exact math i actually have a p &l meeting tomorrow roughly it's it's going to grow the business by 30 to 40 percent percent from last year just one initiative one initiative wow and that's a do you guys use community for that um You know what?

11:20We don't because the way we structured it, community wasn't far enough along. Obviously I'm an advisor and use community for my personal brand. We built a middleware between our platform and broadband.com. And it's like, it was custom built with our dev team at Wine Library, but it's just working and innovation. And by the way, let's call a spade a spade. Bainer Wine Library, excuse me, has been declining for a decade because I'm not there. And then one idea is going to close. Yeah, it's going down five, 10 % a year or whatever. and now, boom, let's get back to where I was 10 years ago. I think there's a chance next year, if this keeps going the way it's going, we'll be at heights we've never been.

11:57One idea, one execution. And what is it? It was my observation 18 months ago that people are willing to get marketed to on text more in America than they were five years ago. It's brilliant. Now, you've been teaching this for years about shifting your perspective, shifting your mindset, having self-awareness. You've been teaching this for years. and people don't listen when times are good they stay stuck in their mindset or their fears i'm afraid to launch this put this out there how do people shift their mindset even in a horrible time for most people when they can't even do it during a great time easy i'm my stuff does better during bad times crush it have to right you and i hung out during the crush it book signing that's when you drove me crush it hit a nerve because people needed it 2009 right right and that's when hustle was good and then hustle during good times becomes manipulated into burnout but i promise you right now i don't use hustle anymore because i understand how the word got mutated into leading to anxiety and so i don't want that so i i changed it even in crushing i talk about nine to five making 40 thousand a year being happy but but i promise you hard work is about to be put on a pedestal again huge pedestal i'm always at 20 30 million people unemployed like people are gonna be grateful just to have an opportunity job that's it i don't think people i think people are still in a little bit of a shock slash fake environment if we get back to normal in september i'm just gonna be and i know we won't be back to normal let's just talk about january if god willing we're back to real kind of normal in January I think by February by Valentine's Day people can walk around be like oh wait a minute there's some real lasting ramifications big time big time I can't get a raise I can't get a job I mean I'm just hearing people who are are in key positions are getting 20-30 % cuts even if they are the key player and they're irreplaceable it's kind of like this I said Gary's like somebody said to Gary that's not fair I'm like let me give you an analogy you are you are in a forest a tree falls on you and it's on your leg and you sleep there for a day and you're in big trouble and a ranger comes along and tries to help you and she says to you listen you're gonna have to cut off your leg to to live you're cutting off your leg we don't business owners and you know funds and banks they don't want to and companies they don't want to lay these people off they're their legs they love them if everything was okay they wouldn't have they don't want to ask all their executives to take a 30 percent decrease but that's cutting off your leg otherwise you die yeah people are just so funny with this kind of like ideology like okay or the business goes out of business yeah we have no money yeah yeah what's been your biggest fear in all of this or do you feel like you're pretty fear-proof at this moment with everything i'm fear-proof because i'm willing to go to zero yeah you can live on a small apartment and you know live at your parents house i really can man yeah i don't want us to say like this has proven it to me even more you know any 0.0001 percent of me that thought well i've been saying this for the last two years am i full has completely gone away yeah like i just i don't fear because i don't value things and money i my biggest fear is my parents getting sick like my biggest fear is like somebody getting sick and dying nothing else like business i can always like i'm too capable right like you know back to back to the thing you brought up back to why you were an olympian back to like why you beat me everything anything when we were on summit at sea basketball whatever basketball you aren't worried when when it comes to sport you know So your mind just goes into, this is going to be a good situation for me.

15:50Yeah. I feel comfortable. Yeah. And for me, that's business. Like I know for fact that if I became a 100 % full-time garage sale, thrift store, Amazon flipper, that I'd make a million dollars a year. I know that for fact. So what the hell am I? And that doesn't take into account that I built a brand. And sure, my brand would take a hit if all my businesses went to zero. but the reality is America's funny, man. Like there's people following and helping OJ Simpson. There's, you know, Wolf of wall street. Like, like this is a country that gives second, third, fourth chances regardless. And so like I'm already at a place right now where between brand and capability and humility, I'm bulletproof.

16:34I believe that. This is a question from one of my audience members that asked me his name. Chris Turcotte. Chris. Oh, I know Chris. Chris Turcotte. I think his last name is. he said uh he doesn't hear you talk about this much favorite thing about being a father that all the good things that i'm doing for the world with my advice and my wisdom i get to actually do for a human that's going to get the purest execution of it deepest execution of it and i get to watch it from coast to coast and so and just like that and just like pure love, right? Like my daughter got a 53 out of a 50 on a Spanish test.

17:18So we went to get the, you know, check in on the school stuff. Like I'm bringing it up right now. The pride was like, and remember me, right? Like school, like that's her game and it works for her. And I just sat there and I was like, you know, like every parent that's listening that right now knows they're blown away by the pride that comes along with a child. And then just really knowing that I also have my own self-esteem so one of my favorite parts is knowing that I'm not going to f**k it up from making them do things like if my kids are if they start non-profits and give away all of the family's money I'm going to be proud of them as long as they're happy I don't need them to be an entrepreneur I almost I almost don't want my kids to be entrepreneurs because I don't want them to have to live in the shadow or try to climb the mountain I'm creating now the pressure the pressure of like living up to dad yeah i mean louis you know we're not we're young like you know my little guy is turning eight in august like in 10 years he's 18 you and i hang out with 18 year olds in business how old are you right now 37 you're gonna be 47 slightly older than i am right now and you're gonna know xander for real right i'm gonna be like working with him exactly and And then if the way the chemicals played out, if he's not of my entrepreneurial cloth, that's gonna run through your mind, just like it does with me.

18:38I mean, I've met a lot of famous people, accomplished people's kids. And I don't even like judgment and don't even think about it. But I'd be lying if I didn't say after you have a meeting with somebody, you're like, oh, okay, that's how they're different than their mom or their dad, right? It's so cliche. And so like, I want them to be happy. And if, by the way, if they do what I do, which is I looked at my dad, And by the way, coming from zero and looking what my dad built, you know, in our little Russian community, that was like a big deal. And I wanted to climb that mountain. And if my kids look at my bigger mountain and say, I'm going to climb that mountain, I'm going to cheer them on.

19:10Slash not big the outcome. They're not getting a$50 million check. They're not getting a$5 million check from me. They're going to get the relationship graph, which already gives them a huge upload because Uncle Lewis is going to give them$100 ,000 for their. but you know i listen there's no way to completely create fake environments unless they want to do the john travolta you know nicholas cage face rip thing and change the name so but i i definitely think that the best part is just building it just like a business building that relationship but building it with hands off instead of building it with hands on i think parents build too much with hands on would you want your kids to repeat your same insane amount of work ethic if that makes them as happy as it makes me.

19:51Yeah. And I want them. You wouldn't want to expect it from them though. No, I don't expect it from anybody to be frank. I think I'm, I'm really in rarefied air of like deep obsession with my process and enjoyment and lack of anxiety from it and lack of burnout from it. I think I hit my crescendo. I think I'm more of an artist. I don't think people realize that business women and men are actually, there's a certain version of us that are artists that genuinely like this more than anything like like we like singing like beyonce's a workaholic yeah you know like kobe was a workaholic obsessing over their craft their art form their expression so for me like like we demonize it in entrepreneurship and corporate life but we don't in art we we put artists we put oh he's in the studio all the time wow you know painting all the time wow cooking and traveling the world to buy food wow business oh he's gonna burn out he's gonna suicidal why is that is that just because of the old way of thinking like getting burnt out in the corporate world of doing a job you hate yeah money money you know i don't think people like mark texierra made 213 million dollars playing baseball but if some entrepreneur makes 30 million they get demonized it's just culture it's just culture and it's okay like i don't i don't think that's wrong, right, or indifferent.

21:07It's just the obvious observation, right? We demonize the startup founder or the businesswoman much, much more than the entertainer that makes way more money. What was the greatest lesson that you talk about your parents a lot, which I think is amazing that you constantly speak about them as your mentors and heroes, even now? It's not like you said it for a few years, you say it every day or week or month. Because it's true. What is the greatest lessons that they taught you about you being who you are now which i already know the answer but i want everyone else to hear and what is the thing you wish they would have taught you that you teach to your kids a little bit differently very i do think my parents for me and they parented all three kids a little bit differently but like but they're like we really they were such workaholics both my mom my mom was a stay-at-home mom but like did everything like you know like like you know and i think people very much underestimate stay-at-home moms as workaholics like she just worked her face off no help no breaks no breaks we were all spoiled kids from the fact of laundry and doing our bed and she cooked everything and like and then my dad came home late because and cooked right like she worked her face off so they could have created a little more balance we only took two family vacations so they taught me work ethic kindness everything everything i am is them but i do think the thing that we have more is balance with, you know, leisure and offsetting 24-7 work.

22:33But that makes sense. It's generational. They came here with nothing and it was 24-7 work. And I have so much of that in me, but I've had the luxury of my talents leading to a success that's allowed me to post, you know, listen, that's how my first 10 years professionally looked too, but now being able to take a little bit of time. And so maybe a little balance because I think they regret that. And so you try to take your parents' regrets and not have the same. And so I look at that. That's cool. But kindness, kindness, my mom instilled kindness, like, you know, some of the stuff you started this show with, and they both instilled work ethic and my dad, my dad, you know, just genuinely, like, just willed his way into success.

23:14And I think I have a lot of that as well. Yeah. Now, over the years, people have seen you daily vlog for years and just post about your entire life. And I think we did an episode three or four years ago together. I think you've been on a few times now. And we talked about the idea of balance from like business to family. And I remember people being in awe of the responses you had around this at that season of your life. I'm curious now, how do you find the balance between being a great husband, between being a great father, having great health and building a great empire and what do you feel like you could improve more at this season of life you know i think i think you know back to extremism right like extreme which i use i you know all of it can be better and all of it is just great i i think you know here's a good place to go with this let's really bring value so you can go back you know four years ago and listen to like how i think about extremism going hard and then vacationing hard and it's all there i think what this has evolved into is something a little bit deeper and more important that I hope really brings somebody value right now, which is stop beating yourself up and stop judging yourself.

24:22We all go through chapters, right? Like sometimes you're super in love with your partner and like, that's all you can obsess about. You know, it feels like that's, you've been through that chapter recently. Like other, other times you're, you know, super into your profession because you got a new initiative and you got to go hard. It's another baby. Sometimes it's an actual baby. And, and, And by the way, for some people, the first two years are actually super boring because the baby does nothing. And it's okay to not be like blown away and spending every second. On the flip side, if you just can't believe this little miracle and you need to like cut workout, like I think this comes down to judgment.

24:57Stop beating yourself up. There is not even a close framework for what's right. Everyone's balance is massively individual. And more importantly, balance ebbs and flows forever. For example, my kids are starting to get into, I'm like, uh-oh, they're gonna be teenagers one day. Like if they double their age, you know, all of a sudden they're 20 and 16. And I'm like, what? Like, you know, like, and, and, and immediately I go to things like, oh, they can go on business trips with me. Wait a minute. They're going to just take an Uber and I'm going to sit courtside with my little guy and my daughter, cause she's really into basketball as well.

25:30Like often, like I'm going to see them two nights a week. Oh, that means my Nick courtsides are going to convert from business to 50 % personal, which is going to mean those, you know, now all of a sudden it's Tuesday and Wednesday, you know, like technology, like FaceTime culture, I've exploded by FaceTime interaction with them. And so like those kinds of things. Yeah. How does Gary eliminate self-doubt and self-sabotage when it seems like there's so many wins that you hit, but also people don't see all the big losses that you have as well and the risks and the... Yeah. I've loved myself the whole time.

26:09thank god most don't uh but i haven't allowed me to get high on my own supply my humility is my great offset to my confidence and i think that manifests and i think one of the things you were saying when you were saying it i knew what you were saying which is you have the luxury of seeing really behind the scenes truly yeah and i think what you know is forget about like giving to a non-profit it's just the genuine kindness of replying to somebody's request or doing something for somebody with no ask, no expectation, and nobody knows. And you know this because you run in entrepreneurial circles like I do.

26:41And you know, when you stumble on somebody who knows me as well, they're going to bring up something that I did that was nice and nobody knows about it. And that is only one thing that is called humility. That is not reading your press clippings. That is not thinking you're somebody. And I think I have deep love for myself, which leads to huge confidence. But I but I'm practical. So I don't try to overextend myself, which should keep me away from being losses. But there is no doubt, like I think things through. And if I lose, I lost. But I'm never doing anything for any other reason than I think it's right.

27:15And that leads me to a place where I'm not very vulnerable. Because when you start doing things to impress the girl, or to or to keep up with the Joneses, or you're jealous of somebody else's success, and you want to close the gap on their net worth on their Google search or all the dumb shit that people are like thinking about you become vulnerable i mean so many people over i mean listen there's some big personalities that are going to get smoked out over the next 12 months that like have played the part on instagram they're going to lose they just are yeah i also think if you're focused on like chasing the money game of competing against someone financially and you make the wrong decisions then you start to take things personally get defensive get angry at people that aren't making money or whatever it's just everything becomes an attack so if you lost a if you let's hypothetically say if you lost a million dollar bet on a business or investment or whatever and i've got i've got one that's going to happen soon so go ahead and it went to zero it's going to how do you tell yourself i still love myself this doesn't you know affect my self-confidence because i knew the vulnerability was other people i did the most i can i was stretched in more than i wanted to be which didn't allow me to really fix it along the way i just didn't have you have too many plates in the air and i focused my energy on things that are so fruitful that are going to offset that million loss it's an l i don't want it but it's real wow i think also do you go into the mindset of knowing like this could be 100 million or it could be zero and you're okay if it's zero or do you still i go into everything thinking it's going to be zero really yeah it really makes it why do you think notice doesn't make sense now all of a sudden i go in with no hope no expectation no expectation i don't do it for my kicks and giggles i think i think it's gonna work yeah if i'm running it it's gonna work because that's what i'm good at but almost everything i don't run i don't run i don't run pure well 137 hardwood does i don't run vayner sports aj does i don't run vayner speakers zach nadler does i'm impacting the living shit out of those businesses.

29:14You're influencing them, yeah. Oh, in a real way. Yeah. But, you know, push comes to shove, I don't make those decisions. And so, and I support my partners in crime. And so that's kind of how it is. Yeah. I think you start, when did you start VaynerMedia? Was it 2010, 2011? 2009. So I was in the office, I think it was Soho, when there was like six people in there and a ping pong table. Yeah, sunshine, sunshine, sunshine, sweets. And I remember at one point, it must have been 2011 or 12, when you said somewhere in an interview, maybe it was with me or somewhere, a speech, you said, you know what?

29:50We were okay as an agency the first couple of years. We actually were not that good. I think you even said, we were okay, we weren't great, but now we're really great. After three, four, five years of in the business, what would you feel like is the thing that you regret the most over the last decade or one of the hardest challenges within the agency that you had to face? Maybe that's two questions there. There's several things there. One, the biggest challenge I had to face was about year six, seven, six. I was creating entitlement because I was putting too much on my own shoulders. What do you mean by entitlement?

30:27I was making it too easy for everybody and people got entitled. Within the company? Yep. So you were saying, I'll take this on, I'll take this on? In the macro. I was creating so much top line revenue and everybody was getting raises like crazy. And I was creating such a great culture that I made us soft, which is wild. Because you were doing the sales and the pitching and everything yourself? I was impacting so much that 300, 400, 500 people had it too easy. And we had to do like a 35 person layoff because I just kind of cut the fat. because I just, I, and I didn't need to do it financially. I needed to do it to just culturally get everybody to understand like these people that were just like, Oh, weren't good at their job.

31:09They were nice people. But if we keep carrying this, this will die. They weren't great at their job. They were not even close. They weren't even close. Like I was, it was nice people over everything. And that, and that was it. If you weren't nice, you were getting fired. But if you were nice like it was and it was it that was tough and it was tough for me to realize wow on tea with gary b on keynotes and interviews on the stage i have great candor and accountability but in my own shop i wasn't candorous enough and i created entitlement because i love happiness and la la and all that and everyone loving you and yeah but i but i went too far with it so that was tough that was a moment because i never got to that level with wine library because it was still happening there but it was a small enough business and a family business and it was real family cousins and best friends that it had a different dynamic so i didn't see it coming so that was that was interesting uh aj leaving was tough i was gonna say that was that's what i thought you'd say there yeah that was a big blow i didn't see it coming you guys built this together this was 50 50 this was yep we're gonna grow this as a empire with a family yep yep and like being with my bro and all that and and so that was rough he left for anybody doesn't know because he has Crohn's disease and he just wasn't feeling great to be frank he just didn't like the business enough clients or client service business suck um and he just said I'm out I don't feel well and so that was rough and that whole process was rough like buying him out and like you know we were 50 50 but I you know what I love about my brother is I'm sure if he sat here he would say that wasn't how it played out we didn't know how it was going to play out so those are dynamics of like you know like that was rough that's just real talk you know but like we're obviously in an incredible place thank god because we genuinely love each other more than money but it's still you know you have your your true it's not even egos you have your own merit you know radars that kind of feel like what is the situation so unwinding that is always tricky i'm so grateful that we're in such a great place with each other and we by the way for the record we were never in a tough spot me and my dad were in tough spots all the time because of the two cooks in the kitchen me and aj like really figured it out and we really leaned into each other so that was good but that was challenging um this this two months has been really challenging because you know i structured for economy break but not one that was the whole world had liquidation issues and speaking went to zero you know like just a lot of things that you know production which is a big part of us went to zero you know and clients aren't paying like you know so it was like you know I was super prepared for 2008 I was not prepared for something that looked like this we got lucky and I hate using that word but this is the truth.

34:00If Hilton and JetBlue and Morton Steakhouse were my biggest clients, we would be in real trouble. Like luckily for us, food and like the serendipity of like financial services, food, beverage, being our biggest clients is going to let us get through this in a good way when it's all said and done. But we could have gotten, like, honestly, I sit here and say, my God, if Marriott, Hilton, if American Airlines, if, yeah, I'm trying to think of other people, clothing, if Neiman Marcus, you know, retail, like if our product, if our client mix was different, this would have been maybe it. Really? Really.

34:35I mean, if you go, if all your clients go to zero and you're in client services, you're not selling wine, you're not selling, you know, subscription business. You know, if you, there are agencies that have gone out of business because of this, because, because, you know, yes. I mean, you know, nobody could ever think of zero, zero, But by the way, I've always thought about war. This is the closest thing to war. I've always thought about like, what if World War III happens? But what my mind would always go is like, well, you don't care about business, then you're actually genuinely scared of a bomb or dying or whatever it is.

35:04So this is like war without war, real life. Now, what's really cool about that is that happened. Let's say Hilton and American Airlines and Chuck E. Cheese. I'm trying to think of a million different things. And sports, what about that? The Jets and the NBA. all these the serendipity that's like we just got the perfect wrong hand three seven offsuit i would have been super i'd be doing this video and be like that's what happened and and i couldn't see it coming and i deserve to lose like literally that would be like my reaction to it yeah and you'd almost be excited to start from oh you always talk about i wish something happened so i could build it back up again how how much has your business been affected have you lost you know we've lost yeah maybe uh or we're definitely 12 down in like top line revenue expectations we've had we have like i still don't think this is over i think there's gonna be a you know relapse and that will trigger things we pay liquidity more than revenue people are stretching terms they don't have the money like there's you know that what are you doing and I'm paying my employees.

36:09Yeah. And I'm paying rent. Exactly. That's tricky, man. You got to get a Higgins to give you a little break on that rental. Yeah. The problem is him and even Ross, like he has partners and banks and it's crazy work that way. And so, and by the way, my business is too big for the little bailouts and too small for the big bailouts. So I'm in that perfect middle, like us 50 to$300 million businesses are the ones that are going to go out of business. what are you doing personally to supplement the speaking fees the nothing nothing are you innovating anything to launch or create or no i'm massively tripling down on you know empathy is doing really well so you know empathy wines are doing well so my wine business and my my dad gets all the income for the family business so that's i'm doing wine techs because i love them and it's fun, but that's not hitting my pocket.

37:00And I'm focused on VaynerMedia. I got to make sure VaynerMedia gets through this properly because when it does, it'll be two times bigger because we're built for this kind of world. So this is why savings matter. It's so important why savings matter. It's something I remember in 2008 when I was on my sister's couch, I remember saying to myself, never again do I want to feel broke. Like I need to go back to my sister's couch. Like hopefully there's enough time where I can be smart enough to not buy. I wear the same$20 shirt probably like you every day i'm not out buying stuff like i like to feel good but i don't need to buy fancy things i'd rather have money or investments or something that i could use for a time like this yeah but a lot of you know most of my most of my net worth is tied up in non-liquid investments right it's true so you know investments is fine but like the one thing that made me feel good from day one is i have a certain amount of money in the bank that like that is just to me like do not touch and like i feel i can live on and again if everything went to zero that's not the case and that's why i'm focused on this but if everything went to zero i would start looking at that and like literally sell homes and like rent a little apartment and use that capital to start my flipping empire because that's what i would do on the record if that ever happens i'm gonna buy and sell because that's my core basic skill set that is liquid on the transaction i mean i mean you know this like i've been yelling for a year and a half about sports cards they've gone through the roof i know i feel that i didn't get any mj cards after this uh you told me a year ago you're like get the bra give jordan get all this and now it's going up because of this stuff i'm curious jordan rookie cards went from 20 to 100 000 that's crazy man like everyone's like getting into startups i was like i put my you know like lebron rookies i bought for 1100 or 7 000 oh man And when you buy 55 of them, that's money.

38:47That's money. I'm curious. We talked about how you overcome self-doubt. How would you inspire other people or educate them on how to eliminate self-doubt in their life? It's completely predicated on valuing other people's opinions. If you actually make pretend nobody else lives on earth, nothing is scary. Why is the opinions of others such a heavy thing for people to overcome? I think it's humanly. like this is where I think like this is truly my my great gift I'm so grateful for it I think people got caught I think they just get caught that everybody's in this framework of other people's opinions like just it's how we're raised like how do we train ourselves to get out of it if it's something for 10 20 30 years 50 years we've been living that way the same way I trained at 38 and a half that I have no way taking care of my health I don't like eating habits I don't like exercising and just pounding, pounding, pounding, pounding.

39:41Every day, everybody should, this is why I put out so much content. Maybe today's the day that I say it a different way that makes people realize their mom and their girlfriend and their boyfriend and their uncle and definitely anonymous people on social media and Lewis and Gary's opinions actually don't matter. Wow, the liberation to then actually do shit. And now you're doing shit full throttle because is that whether you win or lose, it doesn't matter. You can't hear the cheering. This is why I'm trying to get people out of hearing the cheering. It's my newest thing in the last year or two.

40:11I'm like, wait a minute, right? Because everybody says you're so hot on Instagram that when they say you're not, you start doing plastic surgery, right? When everybody says, like, you're such a great business person, you start keeping up that facade instead of, like, it just makes so much sense. So to me, the biggest thing is the humility was such a factor. I didn't realize how big of a deal that was, how much that worked for me. is like, I don't believe I'm as great as I know I am. Like my logical side knows that I'm up to something, but I just don't internalize it. I won't let it penetrate my soul.

Read the full transcript

40:42I think I have the ability to be the biggest deal, but I will never believe it. That's powerful. Yeah, I think, you know, even I've never said it that way. Like, I'm like, thank you. I was like, literally when you, I got to clip that for Instagram. Like, you know, like, that's what it is, man. I really genuinely think, and you know this about me. Like, I think I can be the guy. Like, I think Bezos and Zucks and Elon will make so much wealth during this time. But I think the way I'm going about it, I think I can be that entrepreneur's entrepreneur when it's all said and done in the end. And I think, even if you look at what's happened with me, you've been along for a ride.

41:18Like, over the last two or three years, I can feel, I know, because I'm a branding guy, like, the brand is in a different place. It is. I've separated a little bit. You know what I mean? Yeah, you have. And I'm like, okay, well, I'm 44. and i'm like you know what i mean i love the stories of like colonel sanders at 50 launching kfc it's like you're a way they take off at 50 it's like you're just getting started sydney frank started gray goose in his 80s you haven't even got started yet this is i really believe that this is the preseason by the way i think i said something similar to you on a personal note not too long ago because i remember thinking like watching you from afar like the ebbs and flows like you know a lot of times i was on an interview the other day and i somebody said Gary Vee you did a really really good job you know you were super early on podcast you know saying all this stuff I said oh stop on podcasting because my homie Lewis and uh you know and some of these other characters Jordan and you know all these art of charm right and Pat Flynn and others Dumas right like others I'm like they were a little earlier Ferris like they were earlier I'm like I did I've done a fine job and and so I think about you because we're friends and I'm like okay he really wanted like podcasting was that thing that took you to the next place you know and obviously i made the the uh nice reference earlier like i love seeing you being in your relationship life you're putting that out there a little bit and now i'm like okay you know you know you know just fun to think like i wonder what if what if what is it gonna be or is he like where is he in his life like is he gonna have another chapter and that's what's fun about this right like when i think back to like early you know twitter like chris brogan right right he was Guy Kawasaki and Twitter.

42:53Right, right. And both of them are still doing their thing. Everybody does different things though, right? Like some people come, those two haven't, others completely disappeared. And the reason I'm not bringing them up is because they disappeared because they weren't good in their soul or their capabilities. And I remember thinking in 09, 10, 11, when I was popping for the first time, I'm such a loud mouth. I'm so much, I have so much energy. I cursed. I remember knowing, and this was absolutely true. A lot of people thought that I was going to be kind of like this phoenix of like and then disappear because it just didn't seem yeah yeah and i remember thinking man i remember then thinking wait till they see in 10 years where i sit and it's happened and i think and i think man wait till people see where i'm going to be in 10 years from today you're just getting stuck i feel like i'm i feel like okay i spent the last 10 years of foundation work researching like trying stuff making mistakes something's working well like figuring it out reinventing really trying to find my true lane yeah and okay now i can get started yeah you know it's like all right now let's do something cool and let's build off of what we've done with the personal brand and leverage it look look what i did in 11 i went all in on vayner media everybody thought i was stupid why didn't i raise a fund why didn't i start a startup it seems super left field but a lot of those homies in silicon valley their startups failed and are gone now right they're too big about valuation and now stock and now and now i have a marketing foundation that's a supernova you can launch anything anything you've got the engine to launch a product empathy wines is a meaningfully successful direct-to-consumer wine brand that that john and nate run crazy into software and a couple of interns yeah but they were interns now they're 10 years under my watch now they're executives wow ballin what is the um you mentioned earlier you know client work is and agency work it is why put your life's attention into business model essentially because because i'm building the death star i'm sure the death star was to build for you know for darth vader and the emperor and all that but when it was done it could press a button and blow up a planet it wasn't fun for me to eat in the prime of my career except here I am at 44, empathy being the first one, the rest of my life are gonna be the next ones, including Lewis for governor in California, including let's cure Crohn's disease because AJ has it, including many other things.

45:20So I'm building a Death Star. I'm building a Vayner, and it's VaynerX now, right? It's got the publishing side. It's got a speaking bureau. It's got, you know, tracer.tech. People should check out. It's a data analytics SaaS business. It's got, you know, the Sasha Group for small businesses. I'm building literal mass machine that's the scalable version of who I am as a human. It's amazing. Like if Vayner Publishing would be a top book publisher if I decide. Vayner Real Estate, I would be a major broker. You know, Vayner anything in perpetuity now that I've eaten dog for a decade. if you could predict uh what was your prediction 10 years ago when you launched vayner media was it to be where you're at with whatever six seven eight hundred employees and kind of it was i did think by now i would have one brand owned and because i thought the economy would collapse earlier like a shoe deal because you were to buy like a some type of shoe it's why it's why i did it's why i did the k-swiss thing right it gave me a chance to test it when i realized i wasn't going to be doing that just yet and it came in front of me and i did it and it really worked and they sold that cut look at resi resi had a big exit right resi is my biggest exit i never talk about it i co-founded it wasn't that a 200 million or what was it yes plus so like i'm winning out here like resi is kind of like the like i remember resi and being like it came out hot and then it kind of like you didn't hear about it for four years and then oh it just exited it was the winner it beat reserve and reserve had all the uber guys and gals behind it we won we but we just built a business it wasn't like i'm not out here worried about making sure it's in the headlines every minute like vader why not talk about that though why not talk about like the thing that you launched and it was a big hit it's just not on my mind plus ben leventhal and mike montero the cto deserve a lot more credit to me i came up with the idea jointly with ben we i found mike montero who was a big time cto that built the incredible product i personally wrote a big check when the company was in trouble at one time i did a lot of great things but i'm a fan of the operator they executed day in and day uh-huh so i don't like to go out there because i think that's faking the funk a little bit but i feel like my dna is really in it and i feel like in comparison to a lot of other people that have a lot of wins that they claim i have plenty of my dna in resi but that has been most most first and foremost that's ben's win so okay so you didn't reach that level of what you thought would happen within this decade but it's 2020 now imagine 2030 what do I thought I was going to build like a, I thought I was going to build the millennial Falcon and buy, you know, K Swiss.

47:58What ended up happening is building the death star. And so when I buy Puma and then flip it 12 years later, I buy Puma at 54, 10 years from now, I flip it at 64 and I buy the jets and win six Superbowls. Like this has been written Lewis. Give me the year and the date and the time that you're going to sign. Okay. Okay. For the jets. What is the exact time? date uh november 11th 9 a.m november 11th 20 uh what do you mean 2020 2048 wow i'm marking it down november 11th 9 a.m 2048 what is it that day and time does that have any meaning with you not necessarily just yeah amazing man what is the uh the final word you'd like to share with people about let's sorry i got excited go ahead let's come out of this leaning into humility and gratitude and that will be the springboard to everything you want.

48:53If you can, like, just be grateful. Yes, you lost your job or your business not as good, but your grandfather didn't die from Corona. You know, just be grateful. Like grateful for the time you're spending with family now, grateful for the innovation time, the thinking time. I'm sleeping more than ever. I put on a couple pounds, so I gotta be a little bit more careful, but I'm gaining real muscle. I'm starting to really do it out here. You're strong, man. Let's play some ball soon. But no, I'm gonna dodge you on that. You're too good. But gratitude and humility. people can follow you anywhere online they can find all in all in challenge if they want to wine text wine text that that's the thing i'm most proud of here's why wine text.com here's why it's literally the best way to buy wine right now in the world i genuinely believe that we sold a 125 cabernet for 39 we sold a 42 red meritage for 19 bucks we have a 40 dollar rosé premium rosé coming for nine dollars next month like it's it's really cool and here's the other reason for this audience seeing how text commerce is coming in the future really matters but don't sign up if you're not into wine because it costs money to send a text so i don't need the pity or the kindness this is if you buy wine at all then sign up and if you don't don't i hope today's episode inspired you on your journey towards greatness make sure to check out the show notes in the description for a rundown of today's show with all the important links.

50:14And if you want weekly exclusive bonus episodes with me, as well as ad-free listening experience, make sure to subscribe to our Greatness Plus channel on Apple Podcast. If you enjoyed this, please share it with a friend over on social media or text a friend, leave us a review over on Apple Podcast, and let me know what you learned over on our social media channels at Lewis Howes. I really love hearing the feedback from you, and it helps us continue to make the show better. And if you want more inspiration from our world-class guests and content to learn how to improve the quality of your life, then make sure to sign up for the Greatness newsletter and get it delivered right to your inbox over at greatness.com slash newsletter.

50:52And if no one has told you today, I want to remind you that you are loved, you are worthy, and you matter. And now it's time to go out there and do something great.

From the publisher

In this episode, we're revisiting a conversation that's packed with inspiration, wisdom, and actionable insights. So, whether you're a long-time listener or new to The School of Greatness, grab your notepad because this episode promises to inspire you and empower you to live your best life today.

Let’s face it: Not everyone is cut out to be an entrepreneur. It takes an insane amount of dedication and work to make your vision become something tangible and real. Starting your own business is a process and one that is always changing. 

Being an “all-out” entrepreneur not only requires a massive amount of dedication, but it also requires being able to balance different areas of life. Things like family, physical health, and mental health are also extremely important, and when you’re an entrepreneur, you’ll have to learn how to balance career, relationships, and health simultaneously.

Becoming an entrepreneur is a difficult journey, but an enriching one and one that is worth taking. Today on The School of Greatness, I have Gary Vaynerchuk here to share his secrets about entrepreneurship, family, and self-confidence to help you on your business journey.

In this episode you will learn,

  • How hard work is revolutionizing things right now
  • How Gary’s work is more art than work
  • How humility plays into being a success
  • How Gary being too soft made things hard for business
  • How self-doubt is predicated on other people’s opinions

For more information go to www.lewishowes.com/1511

For more Greatness text PODCAST to +1 (614) 350-3960

More episodes on entrepreneurial greatness:

Jaspreet Singh - https://link.chtbl.com/1257-pod

Ray Dalio - https://link.chtbl.com/1266-pod

Rachel Rodgers - https://link.chtbl.com/1183-pod

Get more from Lewis! 

Get my New York Times Bestselling book, Make Money Easy!

Get The Greatness Mindset audiobook on Spotify

Text Lewis AI

YouTube

Instagram

Website

Tiktok

Facebook

X


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

More from The School of Greatness

All 567 episodes
Gary Vaynerchuk's Insights on Success, Family & The Future of BusinessThe School of Greatness · 51 min
Listen in VO