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This is The Art of Charm.
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Learn everything you need to know to crush it in business, love, and life.
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The Art of Charm is where ordinary guys become extraordinary men.
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Welcome guys and gals to The Art of Charm.
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I m Jordan Harbinger.
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The Art of Charm brings together the best thought leaders, teachers, and exceptional individuals to teach you how to be a top performer in life, love, and at work.
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Imagine having a mix of experienced mentors teaching you their expertise, packing decades of research, testing, and tough lessons into a curriculum.
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We may not have all the answers, but we do have all the questions.
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Make sure to stay up to date with the Art of Charm and get some great stuff that we don t or can t share on the show by signing up for the transformation kit at theartofcharm.com.
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If you like what you hear on the show, come hang with us on the blog.
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We get really in-depth on a lot of this there, and you can engage with the AOC team there as well.
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Or, if you re new to the show and you want to find out more about what we teach here at The Art of Charm, you can go to the website and we ll email you our Fundamentals Toolkit.
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That covers topics like body language, nonverbal communication, dating, attraction, persuasion, business networking, public speaking,
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negotiation, and a whole lot more.
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We ve got our live programs running every week here in Los Angeles, California.
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In fact, we ve got guys from all over the world, which shows that no matter where you are, you can make it here if you want to learn and grow.
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We re sold out a couple months in advance, so if you re thinking about it a little bit, get in touch ASAP.
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Jordan at TheArtOfCharm.com.
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Get some info from us now so you can plan ahead.
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Looking forward to meeting you here at The Art of Charm.
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Today we re talking with the one and only Gary Vaynerchuk.
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If you ve heard a bunch of interviews with him before, stay tuned.
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We re talking about a lot of stuff that he has never spoken about or hasn t spoken about in years and we get pretty in-depth and deep dive on a lot of this stuff.
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If you haven t heard of Gary V, well, you re in for a surprise.
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He s very, very honest, got great energy, and is one sharp mofo.
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We re going to talk about why happiness is contextual and the dark side of entrepreneurship, how he sold baseball cards instead of reading Catcher in the Rye, making thousands of dollars as a kid, and why you should always be looking for a new challenge when you hit the top.
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Now, this guy turned his business from a few million into $60 million per year in sales and now runs one of the largest digital agencies anywhere.
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So enjoy this one with Gary Vaynerchuk.
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Yeah, so now I think I break, you know, I wish my wife was here because she d start laughing because whenever somebody asks me that, she thinks it s the funniest thing because I m in true entrepreneur form.
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I am doing a lot of different things.
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But the two core things that I do right now is I run VaynerMedia, which is a 600 person social digital agency.
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And I m really the CEO of that.
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And that s taking up, you know, 70, 80% of my time.
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And then I also run a fund called Vayner RSC, which is a $25 million seed fund that I started two years ago with Steve Ross, the owner of the Dolphins.
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And then I m jamming on my personal brand, right?
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So it s speaking, I m working on my new book.
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I actually just sat outside today for the last 12 and a half hours working on it.
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And there s the Ask Gary Vee show, which is in podcast and video form, and so I m pumping out a lot of content more than normal.
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And so those are kind of the three things.
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If you run a digital agency and an investment fund, I will say those are two things that probably most of the people listening don t actually understand what they are.
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In fact, I m not even sure I know what a digital agency is.
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So, basically, anybody who s watched Mad Men, that s what we do, except it s 2016 and not 1964, right?
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So, for Pepsi and GE and Toyota, Mattel, and the biggest brands in the world, we come in and say, what do you want to accomplish?
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Oh, weird, you want to sell toys?
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Oh, weird, you want to sell soda?
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Oh, weird, you want to sell cars?
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Cool, there s a lot of ways to do it.
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You can do it through television, print, radio, direct mail, Google AdWords, and there s this new thing, right?
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The current state of the internet, Facebook, Twitter,
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Instagram, Snapchat, Tumblr, and we help them lay out their strategy on those new things, and then we create the videos or pictures or animated GIFs that are tasked to achieve that goal.
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And so, we do strategy and creative production and output around businesses  objectives in a 2016 internet world.
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Right on, so it s, yes, Mad Men with Twitter.
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And the investment fund is interesting because it s VC, right, venture capital?
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That s right, so for everybody listening, early on, I built a large e-commerce wine business, and that s where I got my first start, and then I realized I was right about a lot of internet trends, so I decided after YouTube sold for $2 billion, after I was on it early and thought it was gonna be big when nobody knew what it was, that the next time that would happen, I needed to jump on it,
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and make more money than just sell a couple more bottles of wine.
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And I read in an article, there was something called angel investing, which I d never heard of before.
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I was a DNF student.
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So I wasn t super educated on financial aspects of the world.
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And I said, okay, I m an angel investor.
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And the next thing I saw six months later was called Twitter.
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And I jumped on it, I got involved, I invested in the first three things I put my money into were Facebook,
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Twitter, and Tumblr, so I came out guns a-blazing, and that started my investment career, and that s what led to the leverage that allowed me to start a fund.
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Interesting, yeah, I mean, those are three decent picks for anybody born under a rock, and the exit from Tumblr, a lot of people haven t probably heard of that, but if you have a daughter or a son,
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who s 17, ask them what Tumblr is and they re on it more than anything.
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So there s something interestingly, maybe ironic is the right word, about you having been born in the Soviet Union and now running a venture capital fund.
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It s literally the opposite in so many ways.
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Jordan, it s even more intense than that.
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I m a straight capitalist entrepreneur, meritocracist.
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Everything against the Soviet point of view, that is me.
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I m actually completely driven by gratitude.
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I m so thankful that the place that I was born was not the place that I grew up and not the place that I made my home because it was just fundamentally completely against everything that I am DNA-wise.
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I would say that is super ironic.
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How did your parents get out of Belarus?
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Because the thing that I think a lot of people don t realize is the Soviet Union is tough.
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Belarus is even more tough.
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It s almost like North Korea in that it has a dictator.
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The whole place is built around unfairness and favoritism and cronyism and poor planning and is really oppressive.
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You can t just buy a flight ticket and go, you know what?
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We re moving to New York.
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Forget this place.
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Yeah, I mean, it s the last dictatorship in Europe.
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I mean, we left in 78 when it was the Soviet Union.
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So there was no separate Belarus versus kind of Russia dynamic that you re referring to.
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But I m super impressed with your skills.
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I mean, most people never even heard of Belarus.
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Seems like you ve got a grasp on it.
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You know, so we left in 78 when Israel and the US teamed up in the late 70s and made a trade with the Soviet Union to let Jews in Russia out.
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And so basically, as weird as it sounds, I was traded for wheat.
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Yeah, you know, it s funny.
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I asked a lot of people if you came from there because you were Jewish and they said, I don t think so.
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Yeah, that s just the only way you got out of the Soviet Union in the late 70s was if you were Jewish.
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And so that s that s how we got out.
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They were they were thrilled to get rid of us, as they say.
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And so that was the opportunity and a great opportunity it was.
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Do you ever wonder how much wheat you were worth, if you could just break it down?
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Does that haunt your dreams?
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You know what s crazy?
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I don t think about that, but I swear to God, based on how many taxes I pay in this country, I do think about how awesome of a trade that was for the US.
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That s right.
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It s like this guy we traded for like a kilo or two.
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He s like a Jewish baby, literally worth, like, you know, they re trying to get rid of it, like a prisoner almost.
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And now it s like... Like literally millions of dollars a year in taxes from one dude.
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I mean, I think it was a good ARB for the US.
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Yeah, definitely.
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Really, really, really well done.
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And now you re the complete opposite.
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Coming into the country from, I don t know what it was like then, and maybe you haven t asked, I m wondering, was your father even allowed or able to run a business back then?
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No, it was, everybody who had any business DNA ended up in jail.
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It was all black market.
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You know, the Soviet Union is, the government owns everything.
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That s the game.
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So there was no business.
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My dad has business DNA.
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He was a construction worker in the USSR.
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And when we came to the US, that was his plan.
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But the market collapsed, the housing market, nobody was building.
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And so he became a stock boy in a liquor store in Clark, New Jersey.
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That started our American dream.
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But yeah, I mean, it s nasty, Jordan.
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Like, you know, one thing I talk about, you know, I
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I was excited about this interview, and thanks for having me on, and excited to get exposed to some of the listeners, because I know there s a lot of them, and I was thinking, you know, what are the things that I could talk about that I haven t in the past, and the one thing that came to mind, if we were going to go into the backstory, is I don t think the people listening right now, I talk about how much I hate complaining,
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and I hate that people complain, and I gotta tell you, I think it stems from the fact that I don t think people understand how good we have it, right?
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Like, you could talk about the shrinking middle class, which is real, I hate the separation of wealth in the US, I do think it s too disproportionate, there s plenty of racism, there s sexism, there s a lot of crap, right?
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A ton, unlimited amount, greed, there s enormous crap.
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By comparison to the rest of the world s crap, it s remarkable.
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Like literally, literally, if you re listening right now and you live in America.
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I highly recommend you just pinch yourself out of happiness because I think that people are completely flabbergasted and lost and just don t have a good context on how much opportunity there really is in the scheme of things by comparison.
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And at the end of the day, it s all by comparison, right?
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I mean, Jordan, I m sure we all have friends that people remember that said when Bush was gonna get elected or if Obama got reelected, that they would move to Canada, right?
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I had like a million friends, both on both sides over the last 10 years.
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Oh, if Bush gets reelected, I m moving to Canada.
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Cool, 48 years later, if Obama gets reelected, I m moving to Canada, right?
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Meanwhile, everybody s still in America, right?
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Nobody left.
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And so, to me, it was really bad.
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I m very grateful.
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There was so much suppression, like there is in so many other places.
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And so, the market is not perfect, but the opportunity is real.
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In the town where you came from, Babirusk, how close is that to Chernobyl or the disaster area?
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I was curious.
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I tried to look it up, couldn t find it.
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Well, I appreciate the homework you re putting into these things.
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The crazy part is pretty damn close.
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People in Belarus, I m part of a charity called Chernobyl Heart, which tries to help the kids and families that were affected, and it s really nasty.
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Chernobyl Heart, I don t want to get gruesome here, but it s a condition where your heart is, when you re born, is on the outside of your body, not the inside, all coming from that, you know, the worst atomic spill in the history of our time.
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I very much could have been affected.
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because it was close enough.
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And so, you start just being thankful.
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I m just completely driven by gratitude.
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Do you ever think about what you would have ended up doing had you stayed in Belarus?
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Like what line of work you d be in and stuff?
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I think about it all the time.
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It s something I think about more than once a month.
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It runs through my mind on a plane, after something good happens, after something bad happens, after definitely any time I m hanging out with Russian people.
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You know, and I m very in tuned to what would have happened.
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I would have been 15, 16 when Russia kind of collapsed.
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It became a complete wild west scene.
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I would have been in my young prime buck days.
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Well, there s three outcomes I ve pretty much figured out at this point.
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Number one, I d be a massive billionaire already.
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Number two, I d be in jail.
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Number three, I would be long dead.
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You know, I would have been very entrepreneurial.
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You know, sometimes my friends are like, oh, that guy s a gangster because he was aggressive in a business deal.
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I mean, you re talking about real gangstership out there where if the deal went wrong, you end up in a ditch.
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two of the outcomes are pretty negative.
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One is pretty sweet, so I ll still stick with what I ve got here, but it s something that runs through my mind all the time.
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I think even if you ended up being a billionaire over there, I think that stuff s still tough, because you hear about those cases where one guy, especially if you re Jewish, you become a billionaire, and then the state decides that you did it through crime, which is probably partially true, but they prosecute you, and then you accidentally die in jail of a heart condition, right?
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I mean, you were up to your Eastern Europe, Soviet nuances.
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I don t think people really realize what s going on over there.
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It s pretty intense stuff.
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Yeah, it s extremely tough.
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The oligarchy in it.
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I don t want to bore my audience with that stuff because I think it s interesting as heck.
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But I think it also gets into I took a class on it in law school and even I couldn t pay attention.
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So it does get really detailed and probably a little bit beyond the scope of everything.
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What values would you say that you took away besides just like work really hard?
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That s kind of almost cliche, right?
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There s more than just work really hard because lots of people work really hard, but not like immigrant from Belarus hard.
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I mean, anybody listening that does know my spiel knows that hustle is like some, I mean, you re damn right.
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I mean, guys, let s really take a step back here.
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From the ages of five to 14, talking about nine years, I literally saw my dad 11 times, 11.
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I mean, and my parents were together.
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I mean, literally, literally, he left at 7 a.m.
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and got home at like 11 p.m.
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and he had two days off a year, Christmas and New Year s Day, and he slept.
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Like, literally did not see my dad.
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Literally didn t know.
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Like, literally got raised by one parent in a house that was super happy and together.
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It s just...
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My dad worked that hard to establish the American dream for our family.
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And then I picked that up.
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I mean, I m a complete workaholic.
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I mean, I was just on a call with somebody, literally on a call with somebody just moments ago.
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And they were like, look, I m thinking about leaving my job.
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I m doing this hobby on the side 15 hours a week.
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I m trying to run the math, so if I go from 15 hours a week to the 40 hours a week that work week is, then I can do X. And I said, excuse me?
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I go, if you re going to quit your job and start your own business, you re going to work 90 hours a week.
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The hell is this 40 hours a week?
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Like all my friends that say they re hustling and working hard but have time for entire seasons of House of Cards or Game of Thrones, the level of disrespect that I have for what 99% of my contemporaries and friends call hard work is enough to make me unlikable to myself.
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That s how much discontent I have for it.
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It s so visceral, it s kind of nasty.
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That s really interesting.
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I got an email from a listener the other day who s getting an MBA, has a bunch of kids, and has a day job.
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And I said, wow, how do you balance all that?
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Because you work really hard.
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And he s like, it s funny, because I wouldn t have expected you to ask that.
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Because I have that same image as like,
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Hard worker hustler really gets everything done and we were talking about this back and forth and he said, you know It is really frustrating I think that contempt is very universal because he said I ll go to school and he s going to a great school getting his MBA and he s like these kids who have like a Part-time job as a barista will come in and go I couldn t finish my portion of the project because you know I had I had like a six-hour shift yesterday and
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And I worked on Wall Street.
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I ve seen hard work too, or at least hard office time.
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No, no, that s real hard work.
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I mean, people hustle there.
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Jay, I gotta tell you, this is a subject matter.
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I m trying to tread lightly here because I know that a big percentage of this audience that s listening right now doesn t know who I am, and this is my absolute opportunity to completely lose everybody because I m a...
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It doesn t calibrate for me.
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So at 30, I started Wine Library TV.
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YouTube blows up.
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At 31, I m on Conan O Brien, Ellen.
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There s articles being written about me.
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Now they re writing that the business grew from three to $60 million in sales.
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I m becoming this guy.
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Facebook is just coming out.
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This is 06, 07, to people that are a little bit older.
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I got so many goddamn emails from friends in high school during that period when I was showing up in all these magazines and TV shows, and every single one of them,
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I was like, hey Gary, you remember me from high school?
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It s Ricky.
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Dude, you re so lucky.
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I just saw you on this.
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I just saw you on today s show.
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Were you just on CNN?
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Oh my God, you re so lucky.
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No joke, I wrote back every single one of them and said, hey Ricky, great to connect again.
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Hope you re well, just saw a picture of your family, looks great.
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Let me just clarify one thing.
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I m not lucky.
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Remember senior year of high school when you d go to the Jersey Shore and bang chicks?
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I worked.
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I worked every goddamn weekend and every holiday since I was 14 years old.
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So you can keep that luck shit in your pocket.
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That s awesome.
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Yeah, exactly.
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And he s like, man, you know.
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Gary s really changed, the fame s gotten to him.
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But I would obviously say it in a whole, like in a soft tone and hedge it.
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That s too bad.
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I was kind of hoping you said that.
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No, no, really, I did say it to people that I was a little friendlier with.
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And then obviously people like I barely like saw the hallway.
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I kind of hedged it a little bit, but it was unbelievable to me.
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And first of all, I was pumped, right?
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Like all this good stuff was happening.
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I was flattered.
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This wasn t a negative, but it did catch my attention pretty quickly.
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I was like, my God, every single person has used the word luck.
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in describing this thing.
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And I guess that s what people really think.
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I guess they really forgot that they went to all those keg parties and I wasn t there.
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And at school on Monday, they were like, where were you?
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And I was like, you know, I was working after, you know, like I got to work at the liquor store.
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So I think hard work s a really intriguing subject matter.
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A lot of people writing, you know, work-life balance stuff now.
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There s a real shift in our world.
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I mean, look what you re up to right now.
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I mean, you re literally, you know, right now,
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You have the size of an audience of a hit radio show in our society only 20 years ago, right?
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Like all with the infrastructure of new technologies with very small infrastructure by comparison.
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The world is in such a shift.
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We re living through another industrial revolution.
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There are so many winners and losers over the next 20 years.
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It s going to be really intriguing and if somebody is confused that hard work isn t at least one of the four, if not one of the three pillars that are going to make the winners and losers.
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kind of like shape out, then they re just lost and are living in a world that is convenient for their mindset and their maybe short-term ambition.
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I like that a lot, the living in the world that s convenient for your mindset, because I see a lot of this, and we call it, it s part of backwards rationalization, where if something good happens to someone else, you can sort of build it backwards, and you might get this a lot.
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Some people might be like, well, easy for you to say, you grew a business from three to 60, how about growing from zero, or something like that.
2
SPEAKER_03
All the time.
2
SPEAKER_03
What would you say?
2
SPEAKER_03
What do you say to those people anyway?
2
SPEAKER_03
Because I actually I m curious, like, how would you defend that?
2
SPEAKER_03
Because it s an awful thing to say.
2
SPEAKER_03
And it s obviously, I mean, how do you handle something like that?
2
SPEAKER_02
It s probably been the lightning rod most that it hits my emotional center because I have so much pride in what I ve accomplished.
2
SPEAKER_02
I mean, I ll tell you something that I rarely talk about.
2
SPEAKER_02
So I was a shit student.
2
SPEAKER_02
I went to Mount Ida College, and I never went to class, and they passed me through anyway, and I d come home every weekend, but when I was 18 as a freshman in college, I d call my mom maybe six or seven times, bawling, just bawling.
2
SPEAKER_02
crying my ass off and saying, mom, I don t want to go into the liquor business because everybody s going to say that dad gave it to me.
2
SPEAKER_02
Right.
2
SPEAKER_02
That, you know, and, and, you know,
2
SPEAKER_02
When you have a $3 million business that has 12% gross profit, not net profit, gross profit, we re not talking about a large business, especially by comparison to what everybody s got today.
2
SPEAKER_02
You can build some quick businesses with bigger margin than that.
2
SPEAKER_02
But I knew that it was gonna hover.
2
SPEAKER_02
And for a long time, I thought that I really wasn t gonna go in, even though I always talk about I was always gonna be in, I was always gonna be in.
2
SPEAKER_02
There was doubts when I was 18, 19, because I didn t want that to hover.
2
SPEAKER_02
I guess at the end of the day, the truth is undefeated, right?
2
SPEAKER_02
You know, if I go on and accomplish what I feel like I m going to, when you start getting into hundreds of millions and billions, that three number starts feeling smaller and smaller and smaller.
2
SPEAKER_02
But like, if people want to use that, I mean, I ll be honest with you, and this is something I ve never said, and I ll say it here.
2
SPEAKER_02
And I don t like saying it because I don t want to hurt my dad s feelings or my mom s feelings.
2
SPEAKER_02
I think financially, I took a step back by going into my family business.
2
SPEAKER_02
Don t forget, I was making $2,000, $3,000 a weekend selling baseball cards as a 14-year-old.
2
SPEAKER_02
I m pretty sure that any hustle I would have come up with online
2
SPEAKER_02
in the mid-90s would have made me more money than what Wine Library did.
2
SPEAKER_02
Now, what Wine Library brought me was a relationship with my dad.
2
SPEAKER_02
My dad taught me a lot of great morals because I have the DNA that could have easily led me to be a bullshitter, and he, of course, corrected me.
2
SPEAKER_02
So, I ll never regret it, but as fact as what my upside was because of it,
2
SPEAKER_02
I think that I ve proven enough innovation and did enough things within that world and then later on that I feel comfortable in my skin, but it s always been a sore spot.
2
SPEAKER_02
Like if somebody wants a Razzme, they can always say, well, you had that start.
2
SPEAKER_02
I don t.
2
SPEAKER_02
And then I point to people that are way more successful than me, Zucks and Travis and a million people.
2
SPEAKER_02
you know, that have built things from zero, that are way bigger than anything I ve accomplished so far, that are easy to point to.
2
SPEAKER_02
I think people are in the excuse business.
2
SPEAKER_02
And I agree with you.
2
SPEAKER_02
I think people reverse engineer what makes them feel good.
2
SPEAKER_02
And I always just say the market s the market.
2
SPEAKER_02
I mean, listen, Bill Parcells once said, you are what your record said you were.
2
SPEAKER_02
What I say to people that kind of razz me, I said, cool, when we both die, let s see how this all nets out.
2
SPEAKER_02
And so I m gonna be who I am, and if I don t achieve the things that I think I m capable of, then I was wrong, then I had too much bravado.
2
SPEAKER_02
Because at the end of the day, you are what you are.
2
SPEAKER_03
Zucks being Mark Zuckerberg, founder of Facebook, and Travis being Travis Kalanick, founder of Uber, right?
2
SPEAKER_03
Just in case people aren t in the Silicon Valley scene.
2
SPEAKER_03
That s right, yeah.
2
SPEAKER_02
Sorry everybody, I m a little teched out, I apologize.
2
SPEAKER_01
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2
SPEAKER_03
Well, that s a it s funny because you can get really involved in a scene tech is a classic example me I live in Silicon Valley.
2
SPEAKER_03
I live in San Jose, California And so I I m surrounded by that you can go to a Chinese restaurant and hear people say, you know These names are our household here But it s funny because people hear that they ll say we don t really have an advantage just because we live around here but when you re surrounded by
2
SPEAKER_03
people talking about that, talking about ideas, talking about paradigm shifts, and then you get your family visiting you from like Michigan and things like that, and you say, yeah, just Uber on over here, and they go, Uber?
2
SPEAKER_03
Wait, do what over there?
2
SPEAKER_03
Well, yeah, Uber, do you not have it?
2
SPEAKER_03
Oh, hold on, it s an app that, no, it s like a car app, you can call a taxi.
2
SPEAKER_03
And they re going, oh, this is really cool.
2
SPEAKER_03
I wonder if you have this at home.
2
SPEAKER_03
And I m like, I don t know, because you assume the whole world has it.
2
SPEAKER_03
It s not just like, haha, you don t have Uber, but it really starts to say, wait a minute.
2
SPEAKER_03
When you surround yourself with all these people that are talking about ideas, working in companies that generate ideas,
2
SPEAKER_03
it s really easy to stay gung-ho about the future.
2
SPEAKER_03
It s a different story when you re surrounded by people that are maybe complacent or fairly placed inside the status quo and not really questioning it.
2
SPEAKER_03
And I think that might be why sometimes people from your hometown, my hometown, say things like that, because it just doesn t compute.
2
SPEAKER_03
They re not trying to be jerks about it, some of them are, but some of them, it s outside their reality of what s actually possible, given everything they know about the world.
2
SPEAKER_02
You are 100% correct, my friend.
2
SPEAKER_02
I have one of the fastest growing agencies, as I mentioned earlier, and our fourth office, while everybody was waiting for it to be in Chicago or London or Miami, after New York, San Francisco, and LA, I opened an office in Chattanooga, Tennessee.
2
SPEAKER_02
And the single reason I did was because of what you just talked about to your audience, which is in my world of advertising technology, a lot of people get what I call coast mentality.
2
SPEAKER_02
They don t realize that America isn t just New York, LA, and San Francisco.
2
SPEAKER_02
And I ve been lucky because I ve written three books and done extensive touring with it and do a lot of public speaking, that I ve been to all the corners of the U.S.
2
SPEAKER_02
Listen, I was born in a small village in the Soviet Union, where I grew up in New Jersey was actually quite rural up in Hunterdon County, New Jersey, I would say it s more Iowa than Jersey.
2
SPEAKER_02
And I have great appreciation for the fact that there s a lot of dimensions to America.
2
SPEAKER_02
And so I wanted my company to be grounded in a lot of other
2
SPEAKER_02
scenes besides just the hipster tech Hollywood, New York lifestyle.
2
SPEAKER_02
And it s been a big help to our company.
2
SPEAKER_02
It s really grounded people to understand different parts of this country.
2
SPEAKER_02
And I m going to open up more offices and you know, what many would deem as third, fourth, you know, kind of tier cities, but to me are imperative to my complete understanding of the US market.
2
SPEAKER_03
Yeah, that makes a lot of sense, right?
2
SPEAKER_03
You got to know what people are looking for in different parts of the country and the majority of the country is not hanging out in Manhattan with their friends drinking martinis at 4 p.m.
2
SPEAKER_03
on a Friday or Thursday for that matter.
2
SPEAKER_02
Yeah, I mean and especially what we do for a living so much of what we sell is being sold at Dollar General and Walmart and
2
SPEAKER_02
I feel like even though I m a high-intensity New York kind of DNA guy, I have a lot of a grounded soul in the work with different aspects of middle America, and it s important to me.
2
SPEAKER_03
Yeah, it seems like something you could easily lose touch with.
2
SPEAKER_03
It kind of reminds me of those Juicy Fruit commercials that were always about skiing, and I m like, how did that sell in Texas, where people are like, man, I don t do that, I don t know how that works.
2
SPEAKER_03
Or like water sports in the middle of America, yeah.
3
SPEAKER_01
I wonder how those ads work out.
3
SPEAKER_00
I mean, that just speaks to commercials being completely not something that people should be looking at from a marketing standpoint as much anymore.
3
SPEAKER_00
When you can run Facebook video against people in Texas and talk about things that are going on in Texas and then segment the people that live in, you know, Hawaii, because they re totally different.
3
SPEAKER_00
And so you re preaching.
3
SPEAKER_01
How do you stay hungry, or let s say back in the day, how did you stay hungry?
3
SPEAKER_01
Now it s just you re probably on a roll and have momentum like crazy.
3
SPEAKER_01
When you re looking at something and you re like, listen, this business is making three million bucks a year, I don t need to make it bigger, why should I?
3
SPEAKER_01
Or even when it was making 60 and you re like, okay, well, why should I start a venture capital fund?
3
SPEAKER_01
What is the impetus to keep leveling up?
3
SPEAKER_00
This is a really interesting question, and the truth is, this is probably what I spend a lot of my own time on.
3
SPEAKER_00
I like psychoanalyzing myself.
3
SPEAKER_00
I don t know what that says in itself.
3
SPEAKER_00
I was four foot eleven my freshman year of high school.
3
SPEAKER_00
You know, that probably helped.
3
SPEAKER_00
When I was five and just learning, maybe four years old, four and a half, five, just learning English, kids picked on me because I couldn t speak English.
3
SPEAKER_00
You know, I love underdogs.
3
SPEAKER_00
I grew up a big Yankee and New York Ranger fan.
3
SPEAKER_00
As soon as they won, I stopped caring.
3
SPEAKER_00
I m completely in love with the New York Jets and Knicks.
3
SPEAKER_00
They ve not won for me.
3
SPEAKER_00
I like the week before my vacation instead of the vacation.
3
SPEAKER_00
I love the anticipation.
3
SPEAKER_00
I love the journey, Jordan.
3
SPEAKER_00
I love the climb.
3
SPEAKER_00
I love proving people wrong.
3
SPEAKER_00
I love when people say, you know, you can t do it or you re not as good or you were bad.
3
SPEAKER_00
I mean, I loved being a bad student and all of the parents of my friends,
3
SPEAKER_00
said that I was gonna be a loser or little Ricky was going to this school, where are you going, Gary, and trying to stick it to me.
3
SPEAKER_00
I actually don t like winning.
3
SPEAKER_00
I actually think once I felt like I was at the top of the wine retail and wine game in the US, I started having kind of a roaming eye to other things.
3
SPEAKER_00
I prefer the climb, I m into the journey.
3
SPEAKER_00
I think I have a real purity when it comes to entrepreneurship, which is show me the climb, show me the challenge.
3
SPEAKER_00
I loved
3
SPEAKER_00
that everybody in Madison Avenue thought that I was, you know, the headlines were really like Twitter boy because I had a lot of Twitter followers.
3
SPEAKER_00
Twitter boy comes to Madison Avenue and starts an agency.
3
SPEAKER_00
He s going to find out it s way harder to build an agency than to amass a Twitter following.
3
SPEAKER_00
I ve really enjoyed the last four years sticking it to all of them and building the biggest and baddest and fastest and strongest business in that space.
3
SPEAKER_00
And so
3
SPEAKER_00
It comes from a bad place, that s the truth.
3
SPEAKER_00
Like I m a good guy, and I love that, and I m liked, and you know more, probably you and whoever, I mean people have back channel on me, they ve got a good sense of who I am, but when it comes to competition, I m a bad guy.
3
SPEAKER_00
I wanna stick it to people, I m motivated by others.
3
SPEAKER_00
I m motivated by myself, and that s always what people wanna say, but I don t wanna give you the PC answer, I wanna give you the truth, and the truth is, I m massively,
3
SPEAKER_00
massively motivated by others.
3
SPEAKER_00
I want to have a legacy.
3
SPEAKER_00
I want to be known as great in the entrepreneurial generation that I grew up in.
3
SPEAKER_00
And I m driven by a lot of vanity, kind of like non-noble causes.
3
SPEAKER_00
That s just the truth.
3
SPEAKER_00
I mean, I think the only good thing that I m driven by is I really want to bring my team along for the ride.
3
SPEAKER_00
I get enormous pride and excitement and really
3
SPEAKER_00
get juiced up by the thought of making millionaires out of my right hand and men and women and key lieutenants and that excites me tremendously.
3
SPEAKER_01
That s excellent and that s a really honest answer.
3
SPEAKER_01
I think a lot of people say, well, you know, I m just following my potential or I wanna help as many people as I can and create a lot of value, which is partially true, but a lot of it comes from, yeah, listen, I was short and people thought I was gonna blow it, so I wanna blow up as much as I can to make them feel stupid.
3
SPEAKER_01
There s nothing wrong with that.
3
SPEAKER_00
It s just the truth.
3
SPEAKER_00
I just really like being... I love the underdog.
3
SPEAKER_00
I mean, I hated Tiger Woods.
3
SPEAKER_00
Now that he stinks, I love him.
3
SPEAKER_00
I hated Kobe Bryant my whole life.
3
SPEAKER_00
Now that he s old and finished, I love him.
3
SPEAKER_00
Any sporting event I watch, it s always underdog.
3
SPEAKER_00
I m just a classic fan of the underdog.
3
SPEAKER_00
I hated Hulk Hogan, I was a macho man guy.
3
SPEAKER_00
It s a very consistent theme in my life and I especially love being underestimated in business context, I really do.
3
SPEAKER_00
Does that still happen to you?
3
SPEAKER_00
Yes, which is fun, meaning it changes.
3
SPEAKER_00
Now it s happening at a level that s almost so flattering, it s crazy, right?
3
SPEAKER_00
Like the people that are left underestimating me are the last kind of tier, right?
3
SPEAKER_00
You know, if you kind of break down the businessman and women game, I m probably in tier three, tier two, depending on the day.
3
SPEAKER_00
But I m still not in that billionaire girls and boys club and and kind of that 60 to 80 year old establishment and and that establishment still kind of underestimates me and I m not even in tier one of the tech space of Jack Dorsey and Mark Zuckerberg and Travis like I m in that next tier and maybe even maybe even the third tier so I think that um
3
SPEAKER_00
It still happens.
3
SPEAKER_00
I mean, I ve definitely got a lot more accolades and victories and good things under my belt.
3
SPEAKER_00
I think that I interact with people so much on social media that I m liked by the masses and so I get that value, but there ll always be more mountains to climb.
3
SPEAKER_00
I spew anywhere I can, Jordan, that I m going to buy the New York Jets.
3
SPEAKER_00
I really do believe 99% of people when they hear me say that think,
3
SPEAKER_00
don t even think twice, don t even think that s conceivable or that I m up to that level, because that s a two, three billion dollar asset.
3
SPEAKER_00
So, I think that it s going to always happen.
3
SPEAKER_01
You know, I heard you say that once, that you were going to buy the Jets, and after you had the Tumblr exit and other things like that, I was checking to see if you would actually do it.
3
SPEAKER_00
Unfortunately, I wrote smaller checks back then, because I was still, I just wasn t wealthy enough to write bigger checks, and so,
3
SPEAKER_00
I m a grinder.
3
SPEAKER_00
I m a climber, right?
3
SPEAKER_00
This is going to be a long journey.
3
SPEAKER_00
I m not going to be one of those whiz kids on the cover of, you know, Time Magazine that makes it in a four year period.
3
SPEAKER_00
That s just not in my DNA.
3
SPEAKER_00
I have a feeling that my kind of narrative plays out with me looking like Yoda, like 88 years old and like, and it just says he did it, you know, like finally, like great.
3
SPEAKER_00
Thank God he bought the jets right before he died.
3
SPEAKER_00
Like to me, it s going to be a marathon.
3
SPEAKER_01
Yeah, what s the next mountain, though, when you get the Jets and then they win the Super Bowl?
3
SPEAKER_01
You re gonna be like, ugh, I hate this team, and sell it?
3
SPEAKER_00
You know, if the Jets win a Super Bowl before I buy them, and I think I need 25 years, I m not even sure if I m gonna wanna buy them.
3
SPEAKER_00
Like, literally, the only reason I wanna buy them is I wanna control my own destiny, so the one thing that brings me pain, that is not a real thing, right?
3
SPEAKER_00
Like, I keep life pretty basic.
3
SPEAKER_00
As long as I wake up tomorrow, and none of the 11 people that matter to me the most, family and core best friends,
3
SPEAKER_00
As long as none of them had any illnesses or died or anything of that nature, I m pretty stunningly happy.
3
SPEAKER_00
The one thing that I allow myself to get emotional about that shouldn t be important is the New York Jets.
3
SPEAKER_00
And so, I don t know, it ll be interesting.
3
SPEAKER_00
But like, I always wonder in psychoanalyzing myself, and I wonder for all the listeners now, if you could take a minute and think about this.
3
SPEAKER_00
Did you create your ambition so that it was actually achievable?
3
SPEAKER_00
Or did you create your ambition so it actually drove you to go so high?
3
SPEAKER_00
I mean, you know, there s a big part of me, not that I can t believe it, but I m very grateful for what I have, both from a family standpoint and a financial and business standpoint.
3
SPEAKER_00
But it is stunningly short of what I want or what I ve put out into the universe as what I want.
3
SPEAKER_00
And then I have a lot of friends who created very small goals
3
SPEAKER_00
intimate friends, and we talk about this, and a lot of them have already achieved it, and it s just an interesting psyche.
3
SPEAKER_00
And I do think it stems a little bit from liking the underdog versus, oh, I m a Golden State Warriors fan now, right?
3
SPEAKER_00
Or I m a Patriots fan, but I live in Denver.
3
SPEAKER_00
Like, what s that?
3
SPEAKER_00
I don t understand that.
3
SPEAKER_00
That pisses me off, Jordan, by the way.
3
SPEAKER_00
I m just sneaking that into the interview.
3
SPEAKER_00
If you live in a city that has a team, and you like a different team, and they re a good team, you re a straight bandwagon, and it pisses me off.
3
SPEAKER_01
Yeah, well, you know what?
3
SPEAKER_01
Coming from Detroit, you can always buy the Lions instead of the Jets.
3
SPEAKER_01
You don t have to worry about an insurance policy against the Jets winning the Super Bowl.
3
SPEAKER_00
Yeah, Lions.
3
SPEAKER_00
You know what?
3
SPEAKER_00
That s what s so funny that you just brought that up.
3
SPEAKER_00
Like, I massively respect real Lion fans.
3
SPEAKER_01
We would go there to watch them on the big TV in the Silverdome, which is now, I don t even know if it s still there.
3
SPEAKER_01
And you d watch them on the TV and they would start, they would be like playing Buffalo and like, you know, something, we were like, oh my God, this might actually happen.
3
SPEAKER_01
And then they would eventually blow it.
3
SPEAKER_01
And I ve never seen an angrier crowd of people literally just watching TV.
3
SPEAKER_01
I mean, it was like unbelievable.
3
SPEAKER_01
We had to like, you know, my friend s dad would make us leave and we d be covering our head with a blanket because people were throwing bottles.
3
SPEAKER_01
I mean, these people were the most passionate fans of any team that has not done well that I ve ever seen in my whole life.
3
SPEAKER_01
And I ve lived in many big cities where teams blow it.
3
SPEAKER_01
But Detroit fans, I mean, it s a real deal.
3
SPEAKER_00
I ve actually been in Detroit twice in the last six to eight weeks working on some business deals.
3
SPEAKER_00
It s really cool.
3
SPEAKER_00
I m really excited about the resurgence of Detroit.
3
SPEAKER_00
It s got a grit and it s got something that I can really respect.
3
SPEAKER_00
I mean, it s far from soft.
3
SPEAKER_01
It s also a serious, serious underdog.
3
SPEAKER_00
Yes, and I love that.
3
SPEAKER_00
I mean, I feel bad for Boston fans.
3
SPEAKER_00
They had real identity with being lovable losers.
3
SPEAKER_00
Now they just win all the time.
4
SPEAKER_01
time.
4
SPEAKER_01
They ve won all these championships and like all these 25 year olds have won a championship in all four major sports.
4
SPEAKER_01
And I look at their grandfathers and grandmothers and grand, you know, parents, I respect them.
4
SPEAKER_01
They ve been through tough times, but these 23 year olds that have won six, seven, eight championships across four sports, since, you know, they re soft, Boston fans are soft.
4
SPEAKER_00
Now, bringing it back to things that people are like, Jordan s talking about sports?
4
SPEAKER_00
What happened?
4
SPEAKER_00
What the hell happened here?
4
SPEAKER_00
You were working at a brick and mortar and you kind of swung over to digital.
4
SPEAKER_00
I mean, you re 100% digital.
4
SPEAKER_00
Are there lessons that you took from brick and mortar that you took to digital and now you re taking to these Fortune 500 brands that you re doing digital for?
4
SPEAKER_01
Yeah, I mean, what I took was consumer behavior.
4
SPEAKER_01
You know, when you re 14, like my whole life, baseball cards, lemonade stands, the liquor store, I m a merchant, right?
4
SPEAKER_01
And when you re a merchant, what you re paying attention to is behavior.
4
SPEAKER_01
Like what happens when somebody walks in and sees a big display of a wine?
4
SPEAKER_01
You know, how do you get them to buy something?
4
SPEAKER_01
And so what I really learned was really, to get nerdy, what s called UI UX, like how to lay out a website, like how to make a good product.
4
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Really, I actually suck crap at 99% of things in the world.
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I just happen to be really great at one core thing, which is I just understand people s buying behaviors, right?
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I just understand what makes people tick, what makes them say, yes, I ll buy that.
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And that is something I ve learned from the real world that I ve applied to the digital world and vice versa.
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I m actually quite bullish on
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on physical retail.
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It s not going to go away so quick.
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I think that digital is a gateway drug to human interaction.
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So everybody listening who gets mad that people are on cell phones all day, I think they re connecting with people and have deeper relationships.
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It allows them to have more in-person meetings.
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The data proves it.
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So I m an optimist with all this stuff.
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And I believe in the old school and the new school.
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And so I think they both have merits.
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Now, how did you figure out some of your strengths and weaknesses?
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I mean, you said you sucked crap at 99% of things.
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How did you figure that out, and how did you figure out what you were actually good at as well, especially as you started to grow multiple companies?
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Trial and error, right?
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Like, getting Fs on your report card across the board in sixth grade is a pretty solid indicator that you suck at school.
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And then, that weekend, going to a baseball card show and having grown 30, 40, 50 year old men,
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hovering around you as a 14 year old because you re making a lot more money than them and they re asking you for tips and ideas how to generate more sales on Sunday because you just crushed it on Saturday in a hall or a mall or a fire station where everybody s flabbergasted this 14 year old that looks eight years old is just destroying it.
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It was a very weird life to live, right?
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I was getting extreme feedback from both ends, right?
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making $300 a weekend selling lemonade when five bucks was a lot as a 10-year-old, or making thousands as a 14-year-old, but then I was going to school.
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I was literally making $3,000 a weekend consistently, and then going to school and having a teacher telling me I was never gonna amount to anything, and then me, because I wasn t a bad kid and my mom really taught me right, me trying to figure out a polite way to tell Mrs. Thompson that, Mrs. Thompson, that s fine, but just to put it into math terms,
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you re making $42,000 a year and I m making prorated a buck 50 and I spend all my time at school.
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Right, yeah, I basically have a part-time job because I m here suffering with you and I made three times what you make.
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Like, sorry that I can t recall what was in Catcher in the Rye since I never read it in the first place, but I sold 87 Frank Thomas rookie cards this week because, you know, I traded and bought and anticipated and watched the market and studied how baseball cards went up for five years.
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Like, sorry.
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What did your parents, though, especially your dad, being super hard workers, think about your performance in school versus your performance on the battlefield of business?
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Because you were crushing it in business.
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Did they kind of go, all right, he s screwed up in school, but he s doing really well here?
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Or were they like, listen, proud of you for the baseball card thing, but get your shit together.
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No, they were all in on number one, which was great.
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They gave me, I mean, I m not who I am without my parents and it s not even close.
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I m, I m disproportionately affected by my parents  parenting in comparison to my contemporaries.
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They completely allowed me to bet on my strengths.
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They gave me the room to kind of attack, you know, honestly, there s been a whole lot about me in this call.
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I would love,
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love to take a few minutes to maybe say something that I hope brings you know to me bringing value in any interview or book or show is the game and so if you re listening right now and you have a student you have a child who s a student who s a poor student between third let s call it third grade and and senior year of high school please please please
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Look yourself in the mirror and ask yourself, do you want your kid to have good grades because your self-esteem is wrapped up in it?
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And you want to tell other parents that little Ricky is going to go to Harvard or Yale?
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Or you re embarrassed that they re not going to go to a community college or not even college?
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Is that you?
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Because are you not looking for the tendencies of them being an incredible singer or artist or entrepreneur?
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Are you mad that little Ricky s getting D s and F s or C s but he s selling a crap load of sneakers on Instagram right now?
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Pay attention.
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because that s what my parents did.
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They paid attention.
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And yeah, I wasn t winning there, but I was so winning in other places that they created a net net score in their mind.
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And my mom punished me for bad report cards.
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She tried to make me understand that there was consequences for underperforming, but she d also schlep my baseball cards in the snow, you know, a mile to get to the car and then drive to a show to allow me to have those experiences.
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And so I think my parents pushed me harder to work
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Like I had to work in the liquor store way more than my brother and sister, because that was going to be my outlet.
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But other than that, they supported me in an insane way.
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And as somebody who s living the happiest life of anybody you know, you can only tie me if you re super happy on the other line of this.
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Please put your kids in a position to be happy and succeed.
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Especially because never more so than now,
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if they have business tendencies, what college is selling business kids is such a farce compared to the marketplace.
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Most professors in communication schools, top communication schools, aren t even talking about podcasts yet, Jordan.
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They re barely getting around to social media.
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I mean, it s a joke.
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Yeah, the fact is those institutions are always gonna be behind, and that s okay.
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If that s not going to be your job, if it s just going to give you an ovary, you don t have to be that sharp.
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But business changes faster than pretty much anything else.
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Especially now.
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Especially now.
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So if you want to be on the top of it, business, going to school for it, not necessarily the best thing to do.
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And it s funny because I was going to ask you, we got a letter from a show fan.
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She has a student, a son, and he wants to be an entrepreneur.
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And she s an entrepreneur.
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But she s like, ah, but should he go to college first and work for a company?
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And she wrote in to ask what I thought.
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And you kind of touched on that, but let me ask you flat out.
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If you re in her shoes, and she s an entrepreneur, and her son wants to do the same thing, she s still got a little bit of a nag that he needs to go to school and get some corporate experience.
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What do you think of that?
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I think I have a lot of empathy for her because I think she, like me, like you, we re of an age where we were affected by the greatest branding of all time, which is college in America.
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And she s feeling the effects of that incredible marketing and branding.
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But I can tell you, I can emphatically with a six and a three year old in my life right now as children, if my kids don t go to college, I m super cool with that.
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That s not even, doesn t even run through my mind.
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And I would tell her from one man s point of view, that if he s truly an entrepreneur,
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not a business consultant that needs a degree to get a job at Bain or McKinsey, but if he truly is going to start his own crap or go work for somebody that, you know, a 5, 7, 12 person business, he will learn so much more in the trenches than any education.
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Look,
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I couldn t get into any of the schools that I go and speak at now.
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I mean, I m going to Harvard in the fall to speak.
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I mean, crazy stuff, stuff that makes my mom so happy.
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Cause she always, you know, she grew up with that generation where school was a value.
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And I go there and I listened to the curriculum like, Oh my God, these people are taking $200,000 in debt and being taught something that isn t real anymore.
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And so I would give her emphatic,
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emphatic advice to allow her son to do his thing and create boundaries, right?
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You don t want him to, I mean, I was an entrepreneur that wanted to work 18 hours a day.
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That s why my parents felt comfortable.
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You know, a lot of people want to throw around entrepreneur and just chill.
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So you got to make sure he s a true entrepreneur.
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Right, not somebody who wants a four-hour work week.
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I m not picking on Tim, but that s just like the cliche.
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Who wants to be able to work from the beach, but somebody who s so driven to do something else that they can t function, probably, in a corporation.
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Yeah, we are in such a rub right now between what college is teaching true entrepreneurship and what is happening in the trenches.
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And the part that really gets me crazy, Jordan, is the people that are incurring debt.
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if you re incurring debt and then it s not helping you and again
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lawyers, doctors, cliche things like that, architects, even business consultants, I get it, there s an ROI there, but if you are truly an entrepreneur, there is not a single university that s doing the right thing by you.
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Well, I hope people can underline that, and if you re just sort of listening, like, oh, wait, I tuned out for a second, looking for the exit on the highway, do that little rewind thing and listen to that part again, because I think a lot of people, well, I know a lot of people write in asking that,
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And it s a really tough answer to give because it s hard to tell if somebody s a quote unquote real entrepreneur or a entrepreneur or not really in that mode at all.
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And honestly, one final question that you re in an interesting spot to answer is a lot of people say, and you touched on this earlier,
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Well, you know, I started this business and this year s the year I m gonna quit my job and focus on my side business full time.
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When should I do that?
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How do I know when I should quit my job and focus on my side business?
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And it s actually a really tough answer.
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The one that I always give is wait until the only factor left is your time.
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You know, you can t outsource it to anybody else.
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The only thing that s driving ROI is the amount of whatever that you re able to put in
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then you quit your job, but before then it s dangerous.
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What do you think about that?
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There s a lot of people running side gigs that want to quit their job, but I think they re doing it because they just want to quit their job, not because they need to quit their job to make the business happen.
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This is tough.
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I have a lot of passion around this, but I also want to use empathy and recognize everyone s situation is different.
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I will say I m passionate about being an entrepreneur versus entrepreneurial tendencies.
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I think they re very different.
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I think if you re scared, that s, you know, lack of fear is probably the first amendment of an entrepreneur.
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And so, you know, I think you ve got to have financial stability, the people that are completely just rolling the dice, and like would be hurt by having a year of no income, if their business doesn t work out, like evicted or, or,
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get a divorce or kids wouldn t eat or welfare.
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I mean, if you re going to get hurt by one full year of taking this risk, I wouldn t do it.
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Um, because if that s your situation, you know, my, my historical view, and I ve seen it a million times is you re probably not going to pull it off.
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You know, to me, if you can t breathe anymore, that s when you do it, right?
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To me, it s about happiness.
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This isn t about money.
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This is about being happy.
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You only live life once.
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You know what s crazy?
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Is you don t need a whole lot to be happy.
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Like, and I know again, everybody s gonna be like, easy for you to say.
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Truth is, you know, I m not so much happier today than I was at 24, 25 making $38,000 a year.
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Like, happiness is contextual.
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I ve got friends that are making $15 million a year, they re miserable as crap.
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I ve got friends who make $70K a year, they re on the softball team, they have two kids, they freaking hang out, they have nothing but quality life balance, they take their couple vacations a year, like, they re good, they re pumped.
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I think it comes down, Jordan, to knowing yourself.
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Like, you clearly, this is now me asking you, just for fun, you clearly knew yourself enough to have created a scenario where you knew you needed something like this, right?
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And I think it comes down to self-awareness.
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Like, please don t jump into entrepreneurship because it s the hot thing.
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It feels like every time, there s always a hot thing, right?
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It was real estate.
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Then it was being a social media expert.
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Now just being some, any kind of entrepreneur.
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You know, it s a tough game.
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It s a lonely game.
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It s hard.
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This is really hard.
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Being an entrepreneur is a real skill.
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It s like being an NBA basketball player or a movie star.
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Like, you don t just get to be an entrepreneur because you say so.
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Yeah, that s for certain.
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That s for certain.
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In fact, up until a couple years ago, I never used the word and I still kind of hate it.
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It s just that now everyone knows what you mean when you say it, so it s become convenient, but I hated when people would be like, oh, you re an entrepreneur.
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I m like, oh, that s kind of an overstatement.
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I run a small business with some friends.
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You re generating a lot of revenue.
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It just feels a little bit pretentious to use the word, but it s crept its way up.
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nicely in the modern, trendy vernacular, and so now if you don t use it, people are confused by what you re talking about.
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Yeah, I don t get hung up on words, because everybody gets hung up on words, right?
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Everyone s massively passionate about, that word sucks now.
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Unicorns, which is a term for billion dollar companies in tech, or transparency, or authenticity, or entrepreneur.
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You re right.
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I mean, that s what happens.
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I don t know.
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I just think that it s sexy right now.
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It won t be sexy again someday.
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But right now it s sexy, sexy, sexy.
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And I recognize that it s way more dangerous than people think.
5
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We re starting to read more about entrepreneurs that are committing suicide.
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It s very lonely.
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Please just make sure you know what you re getting into.
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But on the flip side, if you re super unhappy,
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You know what, I got a great, I talk to Shpiel a lot.
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Somebody sent me an amazing email.
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They heard me talk about this similar style tone to what I m talking about right now.
5
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They emailed me that they sold their house in a upper middle class neighborhood and went to a middle class one, safe, nice, good.
5
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But that gave them the money to kind of like do their thing.
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And they haven t crushed it.
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They re actually not doing as well as they d hoped.
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but it gave him like two or three years of leeway because his expenses went down.
5
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They ve started coupon cutting and all this stuff.
5
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He did a lot of things.
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His family did a lot of things to allow him to not have to make the same level of income to really go in for the sabbat.
5
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And he goes, I m not winning.
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He s like, I m really not.
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I m probably a year or two away from having to go back into corporate America.
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He goes, but I haven t even been remotely this happy.
5
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And so I want to tell that story because if you want to be happy, you have to do drastic things.
5
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So,
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Maybe you don t have to make as much as you made in your income because maybe your expenses or the neighborhood you live in, maybe you can sell your home and move.
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Maybe you can do that.
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And so I recognize school systems, kids, what your husband or wife think.
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These are all real life dynamics, but I always say, if you want to be an anomaly, you have to act like one.
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You have to do things differently.
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And expecting to do things the same way as everybody else and having different results is just not smart.
5
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Have you heard about the Minecraft guy who invented Minecraft, sold it to Microsoft, and made like $2.5 billion, and now he s lonely, unhappy, sad, totally lost.
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Have you heard about this at all?
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SPEAKER_01
I have, I saw the headlines, I didn t read, I didn t read the article in depth, right?
5
SPEAKER_00
There s no real, I mean the article, I know it s two paragraphs, it s really short, it s just people bitching at him for being sad and talking about how he sold Minecraft, which is a video game if you haven t seen it out there,
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And it was super popular, super simple, and people loved it.
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And he said, now that I m not making things that people love, I don t know what to do.
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Because he bought a $70 million mansion.
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He made friends with a bunch of famous people.
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He has never-ending parties.
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He made a whole wall out of candy.
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He s got every toy known to man.
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And he s a Swedish guy, you know.
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So you can t blame America for this one.
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But he s really unhappy.
5
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He doesn t know what to do with himself.
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He literally tweeted something like,
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Staring at my reflection in the computer monitor waiting for friends to get home from work to see if somebody can actually Do anything hang out do anything?
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I m so bored like he s just really really depressed And I wonder kind of what you thought about that because you know you haven t hit the 2.5 billion level yet But it doesn t matter because the truth is he experienced really sudden success.
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He s not climbing anymore And that s what the looks like the problem is
5
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I have a funny feeling, and I mentioned it earlier, that I ll never have that phenomenon.
5
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But if I did, I mean, look, I passed on Uber s investment in the angel round twice.
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And that could have been a moment for me where a lot of financial windfall came in one fall swoop.
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I don t know.
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I can tell you this.
5
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I couldn t wrap my head around not climbing, right?
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To me, if I ever lost the desire to, you know, listen, a lot of times I judge myself, why don t I want to climb in curing diseases or solving world s problems?
5
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The truth is I just don t, like I don t, I can t help it.
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I m sorry.
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I m mad because it would be really noble and it d be cool and a better legacy from a noble standpoint, but.
5
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I do wonder if there ll ever be a day where I stop wanting to climb in a business environment and what will happen.
5
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Do my parents pass away from a rare disease?
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Does something tragic happen in my life?
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Something to alter the course that I m on that then shifts my passion to climb something else that isn t business oriented.
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My intuition is if I ever hit a business lull because of success or maybe
5
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flamed out or who the hell knows, that I probably would shift to something a little bit more, you know, the one thing that s always been there actually, I haven t talked about this in years, I would love to start a business school for kids K through 12.
5
SPEAKER_01
Like the school that I wish I had for me, the one that would have made me even further along in my journey.
5
SPEAKER_00
Yeah, what would you focus on in that school?
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What would you teach?
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business like real shit like let s go out and sell lemonade in kindergarten and like it s all about signage and and how much margin can you make on powdered sugar and then you know teach case studies of why new coke failed or or how twitter did it or you know what happened during the industrial revolution that s happening now or why you know why tv advertising is overpriced like just literally stuff like literally business stuff like stuff that
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that people come and watch my show for.
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Yeah, I would enroll in that even at age 35.
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So I m all about it.
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I appreciate it, brother.
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So when are you going to be a shark on Shark Tank?
6
SPEAKER_02
Every new season, I m looking for you to pop up as a shark.
6
SPEAKER_00
You know what, I really, really blew it this season.
6
SPEAKER_00
I know that Ashton and Sokka and Troy Carter, a bunch of my friends are gonna be guest sharks.
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SPEAKER_00
I m super pissed I didn t make the cut, but if you re still listening and you listened early on, you know me well enough to know that that just pumped me up even more.
6
SPEAKER_00
Now I m like, screw it, I m gonna make my own show like The Voice did to American Idol.
6
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I m gonna put them out of business if they don t think I m good enough.
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SPEAKER_00
I haven t made the cut yet.
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This will be interesting to see all my homies on it this year to see what that does.
6
SPEAKER_00
Does that open them up to more people?
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SPEAKER_00
I m just a tear underneath the people that are ahead of me in Mark Burnett s eyes, so I ve got to keep hustling.
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SPEAKER_00
I d love to see that.
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Yeah, I m all about it.
6
SPEAKER_02
Gary, this has been amazing.
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Is there anything that I haven t asked you that you want to make sure you teach the audience?
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I would say this.
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I just, I don t know how to get this across because I can say it and I can say it with passion or curse or get going, but Jordan, I put you in a weird mood or if you re in the right mindset or you ve drank a couple of good craft beers or had a nice glass of wine, which would make me happier.
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please just know this is it.
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One at that.
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And this is worldwide, this is not just US.
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The internet has created freedom, opportunities that we ve never seen before.
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It just has.
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You can be cynical all you want, and it s brought plenty of bad things, I get it, but you ve only got one life.
6
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And it s so real, it s crazy.
6
SPEAKER_00
And so, please position yourself for happiness, whether that s financial, or creative, or legacy, or whatever it is.
6
SPEAKER_00
Spend all your time and energy in trying to figure out who you are, whether you have to go see somebody for the first time, whether you have to ask people, whether you have the intestinal fortitude to switch off your brain and finally stop lying to yourself.
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The quicker you re honest with yourself for real, for real, for real, is the day you start going down a path that s going to bring you a hell of a lot of happiness.
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And the truth is,
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You may find this interesting.
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I spent a lot of time with 70, 80, 90 year olds.
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I seek them out when I travel.
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I m very passionate about that age now because they ve lived it.
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And I got to be honest with you, so many people live with regrets and they wish this and they wish that.
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And Scott Harrison from Charity Water said to me, Gary, you re a good guy.
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This is when he just started to get to know me.
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He goes, I bet you re going to wait till you get really rich and really old and then you ll start giving to charity.
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He goes, why don t you start just doing it now?
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Maybe you won t give as much, but you can do a lot more good along the way than you can in one fall swoop at the end.
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And it really hit me.
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It changed the way I thought about nonprofits and cause and giving back.
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And it s changed my behavior in that world.
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And it s also changed the way I live overall.
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As somebody who loves the climb and loves anticipation, you can t hedge for the next day.
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Since I am an entrepreneur and since we talked a lot about entrepreneurship, if you think you re an entrepreneur, if it s in there, this is the interview.
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This is the moment.
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This is the second.
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Go out and try.
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Try for a year.
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Talk to your loved ones and your family and just try for a year.
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You ll never regret it.
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Wow, that was, Jason, that was really good.
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I don t know what you thought, Jason.
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It s hard to contain him sometimes, so I m glad.
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I feel like we caught him at a chill moment, and we were in the zone on that one.
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I really enjoyed that one, Jason.
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What do you think?
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You ve heard a lot of stuff from him.
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Dude, it s incredible, and yeah, I m a Gary Vee fan.
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I ve gotten to hang out with him a couple times, and I was even at a live Wine Library TV taping once.
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And this was him at a, at a different level than I ve heard him before.
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And you, you asked me in the middle of the show, he s like, Hey, are you taking, taking notes for this?
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And I m like, Oh, geez, I forgot.
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I was so engaged with the show.
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And that s why Jason got fired during the Gary V interview, but I hope you enjoyed, I hope you all enjoyed the show.
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Show feedback and guest suggestions.
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The show s a fanarchy.
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It s run by you.
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We rely on you to help keep our finger on the pulse, so if you know someone who s a good fit for the show, let me know.
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Guests at theartofcharm.com.
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Jason and I pore through those once a month, and we ll pick out the best stuff and get them here for you on AOC.
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If you enjoy this, don t forget to thank Gary on Twitter.
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He s literally got millions of followers, but we ll have that linked in the show notes as well.
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and you can tap our album art in most mobile podcast players to see the show notes right on your phone.
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I m also on Twitter, at The Art of Charm, and I post a lot of stuff there you can t get anywhere else.
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Bootcamp details, bootcamp.theartofcharm.com.
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Remember, we re sold out months in advance.
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Get in touch now, plan ahead, and the website s got the blog, we ll engage with you there.
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Review us in iTunes, subscribe, I ll love you forever.
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Special thanks to the Jasons for their help in the production of The Art of Charm podcast.
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Go ahead and tell your friends, because the greatest compliment you can give us
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is a referral to someone else either in person or shared on the web.
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Now have a great week and leave everything and everyone better than you found them.
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Thanks for listening to The Art of Charm.
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Get more confidence, relationship skills, life hacks, and everything for the extraordinary man at theartofcharmpodcast.com.