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  • (laughing)

  • - [Chris] Yeah, so what's up?

  • - [Woman] I can leave if you're nervous.

  • (crew laughing)

  • - No, no, it's all good. - You're good?

  • - [Chris] It is all good.

  • - What do you have live?

  • - [Chris] That was performance.

  • Shit happens in the background,

  • I'm like, "Hey, we got a nice audience."

  • (Chris applauding)

  • - Anybody doing Instagram Live?

  • You are?

  • Got it, okay, good to go?

  • Hey, everybody, this is Gary Vaynerchuk,

  • episode 329 of The #AskGaryVee Show,

  • perfect timing to have this tremendous gentleman

  • who is both athlete and entrepreneur

  • as the NBA season is now upon us.

  • Chris Bosh is in the building

  • and as a die-hard Knicks fan

  • and overlooking Madison Square Garden

  • I got to start transparent in saying

  • between the Raptors and the Heat

  • not necessarily my favorite athlete of all time

  • 'cause he dropped way too many real games on our faces

  • but I've really admired Chris.

  • We haven't we had one quick dinner I think at CES

  • where we were sitting on opposite sides of the table

  • so we didn't really get a chance to chop

  • but I've been able to really watch from afar

  • as I'm always watching.

  • I think you've made a really strong transition

  • into life after basketball

  • but before before we go into that

  • actually this is a great question

  • 'cause I know a ton of my listeners

  • are gonna have a lot of awareness of you.

  • So I think the right first question is

  • what do you been up to?

  • - Man, that is such a good question.

  • - [Gary] Yeah, let me give you the floor.

  • - Yeah I've been,

  • first of all kind of had to rebound

  • in my situation.

  • - [Gary] How old are you right now?

  • I'm 35.

  • So people really don't realize

  • and I didn't realize either

  • really what happens to an athlete after you're done playing.

  • We kind of just disappear and go away

  • and maybe you'll see us on TV again

  • but that's when I think real life stars for us.

  • - [Gary] Yeah, I think that's right.

  • - Yeah, I have five children.

  • - [Gary] That's a great number.

  • - Yeah, it's an awesome number, man

  • and then getting into the swing of things

  • into being a father that's there more,

  • into being a husband that's there more.

  • - [Gary] And by the way, takes practice.

  • - [Chris] Yeah it does.

  • - People don't understand that,

  • as for me going hard and then having children

  • and even like evaluating if I'm doing too much or too little

  • or whether it's workout regimen

  • or business like that is a transition in itself.

  • - [Chris] Yeah it becomes a balancing act.

  • - It's not just so all of a sudden you're like

  • going to daycare and,

  • like it's a thing.

  • - Yeah, yeah and school and getting them prepared

  • and moving back and forth

  • and moving my family to Austin.

  • - And your situation's a little bit unique

  • in the fact that obviously

  • 'cause I follow sports enough to know like it was,

  • I don't think as many people will know this,

  • it wasn't the easiest situation

  • that led you to not playing basketball--

  • - [Chris] No, no, no, it was a very dramatic--

  • - Why don't you give them a little context?

  • - Well I mean, I got blood clots,

  • I had a pulmonary embolism back in 2014, no '15.

  • That was really bad.

  • I was in the hospital for damn near two weeks.

  • That sucked, had to have surgery--

  • - [Gary] Was it dangerous?

  • - Yeah, yeah, yeah, blood clots.

  • - [Gary] Did you know something was up?

  • - It was slowly happening.

  • I mean I know all the signs to look for now

  • but slowly, I mean, at first I thought it was cramps

  • and then a month later they come back

  • and then it became so debilitating,

  • I'm like, yo, I got to go to, there is something wrong.

  • But luckily made it through that

  • and then bounced back, got back into playing,

  • got back to my form of playing

  • the way where I was happy and everything

  • and then after that

  • my calf was sore I go to the doctor to get a scan,

  • oh I got blood clots again

  • and then it became a problem because I felt good,

  • I just everything just was just stopped

  • all of a sudden one day and

  • yeah, I wasn't a happy camper. - And you're 31 years old

  • at the time, 31, 32. - At the time I was 33,

  • 32, 33, somewhere in there yeah.

  • - [Gary] Still feeling like you had three, four, five, six?

  • - Oh man, six, seven left in me.

  • I would still be playing right now.

  • I wanted to play till I was 36

  • but I could have potentially

  • with the way things are going in the league now--

  • - [Gary] When's the first time somebody said to you,

  • hey you may want to consider not playing?

  • - Nobody ever said it.

  • A lot of people said it but--

  • - Now you're starting to sound like me,

  • nobody said it, everybody said it,

  • that's the shit I do.

  • - [Chris] I didn't listen to it.

  • - SPO, is this true, do I have this right,

  • SPO was at the game when Hank Gathers passed?

  • - [Chris] Yeah.

  • - I think that's a fact

  • that a lot of people don't know.

  • Your coach at the time, I'm 43,

  • I was outrageously affected by Hank Gathers passing.

  • I was in eighth grade,

  • super into the March Madness thing,

  • Bo Kimble, like it was a big deal,

  • no internet back then,

  • big events really took over America for a week.

  • Now Prince dies and it's a half a day on Twitter,

  • like real big stuff happens

  • and it's a half a day

  • with the way our world works now.

  • Back then, something big happens, it was a week,

  • two weeks in the news.

  • Was coach affected by that when he communicated with you?

  • I always wondered about that.

  • I know coach a little.

  • He's a great dude.

  • - I think that was kind of everybody else's thought process

  • going through that and saying

  • oh wow this is dire situation.

  • With me, you don't necessarily tell that person that right?

  • You want them to kind of exercise things,

  • yeah get there by themselves.

  • We never talked

  • about it too much. - What about doctors?

  • Were like don't play?

  • - Yeah, they were, oh, you can't play,

  • you'll be fine sir,

  • like you've had your life, bro.

  • I'm just really getting started with this stuff

  • and you're telling me that,

  • that's kind of where the disagreements came in

  • with the communication and our problem with communication

  • but we got over that

  • and it was just my stance was to continue to try and play

  • And that's what I did for about a year and a half.

  • - [Gary] And then?

  • - Then I was like, yeah, I'm not gonna do this.

  • - How did that go down?

  • Did you just wake up one morning?

  • - I tell people this story, I was watching,

  • so I was in the next year,

  • a whole year went by I said,

  • all right I know I'm gonna get picked up this year,

  • I need to get into basketball,

  • I need to watch more basketball

  • 'cause I kind of let it go last year.

  • I was still working out but didn't watch any games.

  • - [Gary] 'Cause you just needed that break?

  • - Just mentally it was messing with me.

  • It hurts 'cause--

  • - [Gary] You wanted to be out there?

  • - Yeah, I was right there

  • and I felt that we had a championship-caliber team

  • and then it just stops one day.

  • Then I saw Gordon Hayward dislocate his ankle

  • in the first five minutes.

  • - [Gary] I was at that game.

  • - You was at that game?

  • - [Gary] I was at that game.

  • Luckily, on the other side.

  • - I just turned the TV on like all right here we go

  • the season's going on, bloop bloop.

  • - [Gary] You almost threw up.

  • - Oh man I said I right right then and there

  • I knew I wasn't gonna play anymore.

  • - [Gary] Really?

  • - Yeah, I knew.

  • And I had to keep up with the Jones.

  • I told everybody I was gonna keep playing,

  • "You coming back?"

  • I'm like, "Yeah."

  • - But you knew?

  • - [Chris] But I knew right then

  • it wasn't gonna happen no more.

  • - Really?

  • - [Chris] Yeah, it's just like,

  • you know that thing,

  • I was there, we were strong

  • and then boy it took all the wind out my cell.

  • - No kidding.

  • - [Chris] Yeah, I was done after that.

  • - And so then take me through the next chapter.

  • So now yourself, you know you're done,

  • you keep up the facade a little bit

  • because it's a hard left

  • and so you want to go through that in what way yeah

  • and then what do you start thinking about next?

  • - Shh man what am I doing, you know?

  • That's not an easy question.

  • - [Gary] Do you go into like a depressed state?

  • - I think I was already there at that point already.

  • It took about two years,

  • I want to say two years after I was done playing,

  • it took me that long to kind of

  • come out the fog a little bit.

  • - [Gary] I understand.

  • - Yeah and I guess yeah that's what people call

  • a depression or something.

  • - You know it's funny,

  • my brother AJ, who's sitting right there, left Vayner,

  • we started this together, VaynerMedia

  • and then three years ago, three and a half years ago,

  • we started a sports representation business, VaynerSports.

  • We do football now

  • and we have 20 guys, 25 guys

  • and our entire thesis was off-the-field

  • dynamics that we could create

  • but a lot of it was life after football.

  • These kids are, first of all football's crazy,

  • because a lot of these guys are top of their class--

  • - [Chris] Way crazier.

  • - Yeah I mean there's real injuries in football.

  • There's real stuff going on.

  • Kids are, the first round picks

  • out of the league three years later for real for real.

  • So that's 25, that's 26.

  • - [Chris] What do they do usually?

  • What's the next step in that?

  • - Most kids really screw up.

  • They you overspend their money up front,

  • then they're done, they're 25 and they're like,

  • I mean this is why we did it,

  • we're like we think we can change it.

  • I watched, he watched from afar that agents,

  • and I don't even blame agents,

  • it's not like I razz them,

  • I don't think these are bad people,

  • they're in business.

  • Agents are there and then when you're not producing dollars

  • it's their responsibility to their company and their family

  • to go find things that do and they're done.

  • And we thought the way to hack it

  • was really be in these kids lives through and through.

  • And obviously our business acumen and all that other stuff

  • gave us a leverage that they would potentially believe us

  • and now that we're starting to do it a little bit,

  • Walter Pal, Derek Morgan,

  • we're doing real stuff for these gentlemen

  • long after football when they brought us no dollars

  • 'cause we came in late in their contracts,

  • now the reputation's working

  • which is giving us leverage

  • but going back to you, that's the thing,

  • like as a kid,

  • even right now as a 43-year-old male

  • who puts out content every day

  • that yells at people that says you're 54 and you're young,

  • I still think athletes that retire are old.

  • Like when an athlete retires, I'm like oh, they're old

  • 'cause that's the way we grew up.

  • - So garden, we're looking at the garden right there.

  • Last week the Hawks played a preseason game,

  • Vince is 43,

  • and I've been telling people this whole story,

  • it's like a running joke. - Like you grew up

  • loving Vince as a kid.

  • He's still out there.

  • - Vince Carter's so old, how old is he?

  • Like everywhere he goes and it's just,

  • and that's on TV, man.

  • You know how powerful TV is.

  • - And he's not, and he's not, and to your point.

  • Now what's great,

  • I think the best thing that's happened

  • in the culture of sports

  • is that athletes have become,

  • when I was growing up athletes only wanted to

  • maybe also or be rappers if they weren't athletes.

  • Mow they want to be entrepreneurs too.

  • And that is completely,

  • I mean I've got five star recruits when they're 16

  • hitting me up talking

  • about life after basketball and football.

  • So it is now cool, it is now legit

  • and it also feeds a little bit of their competitive spirit.

  • There's a lot of things that make me worry

  • that entrepreneurship has gotten cool

  • because I think a lot of people are getting into it

  • that aren't entrepreneurs

  • and unlike basketball and rap,

  • they can't be exposed real quick

  • and they get into like

  • their own little deep depression over time

  • because it's not meant to be.

  • But one thing I love about the rise entrepreneurship

  • is it absolutely I believe

  • something that is going to help a ton of athletes

  • in that transition.

  • - [Chris] No absolutely.

  • - So talk to me about back to the first question,

  • what are you up to now?

  • You get out of the fog and now?

  • - Now, just trying to figure things out really.

  • - [Gary] What's interesting to you?

  • - I've been in Japan,

  • I've been to Australia.

  • Media interests me.

  • I'm working on a book for a 2020 release in the fall

  • for next year.

  • That's going great.

  • I just started getting out there--

  • - [Gary] Are you working with a ghost writer?

  • - Yeah.

  • - My ghost writer actually lives in Austin.

  • Yeah, she's amazing.

  • And so how's that process been, good?

  • Are you recording, are you interviewing?

  • - Yeah, recording, a little bit of everything,

  • recording, typing, talking, interviewing.

  • It's like a whole process

  • but it's like a chemistry that you build.

  • - Let me just bounce around a little bit here.

  • When did you think you were gonna make the league?

  • - I knew I was gonna make the league when I was 17.

  • The summer going into my senior year, yeah, I knew, yeah.

  • - Prior to that there was still kind of like,

  • 'cause it's such a big,

  • actually that's great,

  • let's keep that on the shelf for a second,

  • when did you want to go into the league?

  • - Probably when I was like six or seven, pretty early, yeah,

  • very, very early

  • 'cause my dad was watching--

  • - Were you a Mavericks fan?

  • - No, the Mavericks were really bad.

  • - I'm aware.

  • - Yeah, they were really, really bad.

  • - You're like every other NBA fan bandwagon?

  • - Yeah, yeah, 'cause MJ was on TV every day.

  • So in the, at first I remember like thinking

  • like who is this guy in this same team

  • 'cause every time I go over my grandma's house in the summer

  • they're always playing.

  • And then everybody would be around the TV watching it

  • and my dad would be doing the same thing.

  • So I said, yo I want do that.

  • This is the same game that we play on the playground

  • and oh it's on TV and then after that I said,

  • all right cool that's what I want to do.

  • And it was always there but then--

  • - Was there anybody in your family that was really tall

  • or athletic or things of that nature?

  • - Me.

  • - [Gary] Really, you're an enigma?

  • My dad is like 6'3, I mean I have some couple tall uncles

  • but nothing, I don't know where I came from, yeah.

  • I'm just a little, little taller.

  • - [Gary] And when did you explode in height?

  • - From 14 to 16, thanks man.

  • - [Gary] You went from what to what?

  • - I went from like 6'3 to 6'10, 6'2 to 6'10,

  • somewhere in there.

  • So my freshman year when I got there as a freshman,

  • I was about 6'1, 6'2.

  • I left about 6'11 prospect.

  • So 14 to 16 is like oh I really want to be in the NBA

  • and I was just practicing really hard,

  • doing what I needed to do

  • and then 17, 18, the height came with it,

  • 19, I was out of there.

  • So it happened fairly quickly.

  • - Yeah, it did. - Yeah.

  • It was like oh man I'mma play in the NBA,

  • I'mma do all these cool things

  • and then they said, aight, it's time to go.

  • I wasn't sure I was ready but

  • I had to do it. - What a crazy draft class

  • you were part of.

  • - [Chris] Yeah it was crazy.

  • - Like super crazy.

  • It's actually the one time,

  • I've been telling a lot of people lately

  • that flip sneakers and entrepreneurs and hustlers

  • to get into sports cards

  • 'cause it's getting really, really, really hot

  • and I did that as a kid

  • and the one time I got back into it was your draft class

  • because there was so many of you guys, I was like--

  • - [Chris] You got some cards?

  • - I mean AJ and I were buying so,

  • we were opening up so much FLIR basketball your year,

  • there was so much

  • 'cause we were like that was just loaded.

  • I mean it's an all-time class.

  • - [Chris] Yeah for sure, it's pretty good.

  • - How did your friendship graph work with that class?

  • Like you guys were obviously traveling around together,

  • well for a couple weeks there for the draft stuff

  • but when did you first make your connections with your,

  • who were your best friends in the league?

  • - What just period overall?

  • - Yeah, yeah.

  • - Pretty much everybody,

  • the whole championship team was an amazing team.

  • Everybody got along,

  • everybody made great connections.

  • Ronny Turiaf's a great friend of mine, Jerry Jack--

  • - You want to hear something funny?

  • I have a Ronny Turiaf Jets jersey.

  • - How do you have a Ronny Turiaf Jets jersey?

  • - Because when he came to the Knicks

  • and he actually made us,

  • like when he came to the Knicks,

  • our entire friend group got pumped

  • because he was bringing back

  • a little bit of that '90s Knicks.

  • He was being like a tough guy

  • and so for birthdays we're always challenged

  • to give each other gifts that are like unique.

  • So did you give me that, AJ?

  • So AJ got me a Ronny Turiaf Jets jersey, number 14 was it?

  • Yeah, so that's how we go about that man,

  • plus, he knows about wine, so I fuck with him.

  • - Oh yeah that's my guy, yeah that's my man.

  • Jerry Jack's my guy.

  • He was my roommate at Georgia Tech

  • and we played together for a year.

  • - He had a real nice career.

  • - Yeah, he had a great career

  • and I think he's, I'm not sure if he's still trying to play.

  • I haven't talked to him in a minute.

  • - He had a really nice career, he really did.

  • - Yeah.

  • - Who was your best mentor when you came to Toronto?

  • Did anybody kind of like take you under your wing?

  • - Yeah it was a few people.

  • One was Michael Curry.

  • He was my vet coming in.

  • He was like a no-nonsense dad type, man.

  • He taught me the value of working hard

  • and getting your shots up.

  • Derrick Martin was a guy, he did a lot for me.

  • Sam Mitchell. - You had some vets

  • on that team.

  • - Yeah we had some vets.

  • That wasn't all at the same time.

  • Michael Curry was only there my rookie year.

  • Mike, Derek and Sam,

  • they pretty much took me under their wing

  • as soon as they got there.

  • I want to say the next year, second through the sixth year.

  • - So you grew up a Bulls fan.

  • - [Chris] No, I wasn't a Bulls fan.

  • - Just an MJ fan?

  • - I was a basketball fan,

  • just the Mavericks were just,

  • it was 16 and whatever that year

  • so it was tough kind of having

  • some support for the home team.

  • - Yes, I'm aware.

  • And what about now?

  • Do you literally root for the Heat and the Raptors?

  • Like were you pumped for the Raptors?

  • - Yeah, I was happy for those guys, man.

  • There was still so many people,

  • the managers and equipment guys, popcorn guys

  • and the dudes in the stands

  • that I would talk to every morning,

  • they were they were still there and I mean,

  • it's funny every time I walked in,

  • they were like, Chris can you believe it?

  • I'm like, no I can't can't,

  • I cannot at all, this is crazy.

  • And then to see 'em really get their moment was amazing.

  • But I root for those guys.

  • I root for Miami.

  • I identify with the teams I've played for.

  • - Of course.

  • What about other sports?

  • Did you grow up a Cowboys fan?

  • - Yeah, I'm a Cowboys fan, yeah.

  • - That's my only win this year for the Jets.

  • - Yeah, it's cool.

  • Everybody's always like, ah,

  • you always get that all the time.

  • Look, I'm from Dallas,

  • I grew up during the glory years

  • and it's a good franchise.

  • - Did all your homies from back home razz you

  • because of that NBA Finals?

  • That must've been

  • fucking terrible. - Which part?

  • - Losing to the Mavericks in the NBA finals.

  • - Oh, no, they didn't.

  • If they did, we haven't spoken since.

  • - [Gary] Really?

  • - Yeah, no, we didn't take it,

  • we take it very seriously. - I was thinking to myself,

  • man he loses in Dallas,

  • he loses, obviously that was very--

  • - [Chris] That really sucked, by the way.

  • - Of course, that was super disappointing

  • but you got those three or four friends

  • that are your boys boys

  • who might've actually grew up cheering for the Mavericks

  • since they were--

  • - [Chris] No.

  • - No.

  • - None of us.

  • We were all hurtin'.

  • I mean I wouldn't even call it bandwagon.

  • - It's bandwagon.

  • - [Chris] I don't have a team.

  • - Fair enough but like--

  • - [Chris] We don't have a wagon.

  • - It's a variation of a wagon.

  • It's an all-star wagon.

  • - [Chris] A wagon with no wheels.

  • - Here's my thing.

  • I got very into tech in the 2000s

  • and would go to Silicon Valley a lot in 2006, '07, '08, '09

  • and when I tell you,

  • because I'm a big sports fan,

  • and this is the time when it was all nerd land,

  • they barely cared about sports

  • but when I tell you there was not a person in San Francisco

  • that knew the Warriors played there,

  • like there wasn't a person on Earth,

  • I had never seen or anybody wear a jersey of the Warriors

  • or mention that word in the four to five year period

  • that I spent 12, 15 times in San Francisco,

  • and now every kid in Cleveland and Ohio and Dallas wears--

  • - [Chris] Steph Curry jersey, shoes, the hat.

  • - What do you think about the notion

  • of people wrapping their own lack of self esteem

  • into something else like it's like Patriot fans right,

  • like a bunch of them razzed me on Monday night

  • and I was sitting there, I was looking,

  • I'm like you did nothing.

  • Do not confuse your team's success

  • with your actual success.

  • Thoughts on that?

  • (laughing)

  • - I mean there's not much you can say.

  • Hey I get it, people want to feel good

  • I mean I remember when we got together with Miami

  • and it was more Miami fans,

  • we're like, hey that's great.

  • Then the same guy'll have a Cleveland Jersey on

  • four years later,

  • it's like okay, come on bro,

  • you got the hat and the jersey.

  • - But that's what you did?

  • - [Chris] No, I did not.

  • - Yeah you liked players.

  • - I liked players, yeah.

  • - [Gary] Yeah, well that's what that guy did.

  • He liked Clay Brian.

  • - I could not have their Jersey

  • nor could I afford their stuff or their shoes.

  • I had their posters.

  • I had the posters on the wall.

  • - The four dollar poster, for sure.

  • - That was about it.

  • - What about video games?

  • Were you good at it?

  • - Yeah, yeah, yeah, I play video games for sure.

  • - You're strong or?

  • - Now, no, no, no, I'm retired.

  • - In your prime?

  • - In my prime I was pretty good.

  • Madden was my game,

  • Madden and Call of Duty at one point in time, Black Ops Two.

  • - I love it.

  • - I actually bought part of the Minnesota franchise

  • for Call of Duty.

  • So that's my little step

  • towards ownership of the New York Jets.

  • Alright Chris, what else do you want to talk about?

  • What else is on your mind?

  • - Man, what's on your mind, bro?

  • You're the guy.

  • You got the office by the garden and everything.

  • My office is not this nice.

  • - The only reason that my office is this nice

  • is because I was smart enough to realize

  • this part in New York was gonna blow up

  • before most people did.

  • We committed to this office five years ago.

  • This was the only building in this entire area.

  • We're actually paying less rent in this building

  • than the building we left

  • that is like 80% like worse than this

  • because of the way the real estate market worked out.

  • So this was another kind of good bet.

  • What's on my mind?

  • What's on my mind is TikTok.

  • I think TikTok is the place

  • where people that are trying to make it and have no money--

  • - I've been hearing about TikTok

  • for the past couple months.

  • - I really think it's a real important place.

  • eSports, we just mentioned it,

  • is very much on my mind.

  • I'm just fascinated by the fact

  • that outside of NBA players

  • and a little bit of soccer players

  • and a couple of football players

  • like eSports athletes are more famous

  • to the 15-year-old today

  • than every single baseball player,

  • than 90% of the NFL,

  • I mean, forget about it,

  • hockey, I feel bad

  • but I'm not sure the average kid

  • can name five hockey players that are active in the NHL.

  • - What about like content creation and all that stuff?

  • - Yeah obviously.

  • So back to your point of being interested

  • in media and content creation,

  • I mean I think it's the cost of entry

  • for any relevance in our society.

  • I believe that if you're not producing daily

  • for Instagram, Facebook, Twitter, Snapchat,

  • TikTok, LinkedIn, YouTube,

  • that if you don't have a podcast,

  • if you're not thinking about a vlog,

  • that you are just leaving

  • an enormous amount of opportunity on the table.

  • - Now what made you see that?

  • 'Cause I've watched past videos and everything

  • and you kind of see,

  • you're very passionate about that.

  • - I was a super entrepreneur kid

  • selling baseball cards and all this.

  • I started working in my dad's liquor store,

  • wanted to build it up.

  • We were immigrants.

  • My mom knitted me my Jets jersey,

  • so I understand not being able to afford stuff.

  • And I just realized ironically,

  • the story goes, and it's true,

  • I was playing Madden '94 in college,

  • my friend came over, he said, "You've got to come see this."

  • It's September of '94,

  • I go into a room and a kid dials up to the internet,

  • the old cuckoo dial-up shit

  • and I was just like this is it.

  • Nothing else to say.

  • This is it, like I believe this is gonna be a big deal.

  • - [Chris] So you knew right away?

  • - Right away, I'm talking like love at first sight

  • where you just know.

  • I went all in, learned,

  • launched an e-commerce wine site in 1996

  • and the way I built my dad's business for him

  • was building a website,

  • starting the email newsletter,

  • knowing that Google was gonna be big, Google AdWords

  • My real hit change in my career

  • happened when I started a YouTube show about wine in 2006

  • when I was 31,

  • back to like, I mean I thought I was a fucking kid,

  • back to the beginning of this conversation,

  • this is why I pushed it all,

  • I'm like I think I'm a kid now.

  • - [Chris] That's interesting.

  • - Like I think Vince has 30 years of professional work

  • to be done when he retires.

  • I really understand people.

  • That's what I've come to learn.

  • I understand people,

  • I like people a lot,

  • I'm empathetic, which is why my wine brand's called Empathy.

  • I have that in me.

  • And when you have empathy

  • and you think about the other person,

  • when you have compassion, sympathy, empathy,

  • when you have those things mixing,

  • you're actually thinking about the other person.

  • As a matter of fact, if you're great salesman,

  • you're actually thinking about the other person

  • I think the reason I've been great at sales my whole life

  • is I sell things I believe in,

  • whether its wine, services, my sneakers

  • and then I try to figure out

  • why it's valuable for you

  • and if it's not I don't try to force it.

  • And so I've always been good at that.

  • Twitter came, I was right, Tumblr.

  • I mean I was right a lot.

  • I'm right a lot,

  • but I'm not guessing.

  • I already see it.

  • It's kind of like the sports card thing.

  • right now a lot of people,

  • LeBron rookies have gone up from 1,100 to 2,300

  • in the last four months since I've been talking about it.

  • It's not because of me.

  • It's just it was already happening.

  • People are like whoa you predicted.

  • I'm like I didn't predict it,

  • you could just see that people were moving.

  • I could see the people that were flipping

  • off-whites and Yeezy's were starting to post on Instagram

  • about sports cards.

  • - Yeah, oh kind of those same--

  • - Those same flip kids.

  • They're just trying to make money.

  • And you know the sneaker game's impossible.

  • You've got to wait in line,

  • you get one pair.

  • You can't get volume.

  • But like if you believe in Darren Fox

  • or if you believe right now a lot of my friends

  • in the sports card world

  • really believe in the Miami rookie, Tyler--

  • - [Chris] Tyler Hero, yeah that's my man, he's good.

  • - A lot of people are really investing in him

  • 'cause he's the 13th pick, right, I think is right,

  • and just like you can make real money.

  • I mean I told a bunch of people a year ago

  • to buy Giannis rookies

  • 'cause I thought he was super under priced,

  • and I thought he was gonna go

  • and they went from 200 to 800 for a lot of kids.

  • They're back down to 550, 700 but like--

  • - [Chris] It has this market peak.

  • - And it's liquid.

  • It's on Ebay and StockX just dropped it.

  • - [Chris] Yeah, StockX is crazy.

  • - So StockX is now flipping it.

  • So now it's cool 'cause that always matters.

  • So I think content matters.

  • I'm good at it because I understand that,

  • I understand that people are using TikTok.

  • I don't make emotional decisions and say,

  • well this is stupid teenagers

  • just doing drop songs,

  • like it's not it's not how I see it.

  • I don't think my opinion matters

  • and I think that's helped me tremendously.

  • I don't impose my opinions on my observations

  • and I think that's a core strength

  • and I think that's why I've seen a lot of things.

  • - What was your first hustle?

  • I'll tell you mine.

  • My first hustle,

  • I was burning CDs off Napster.

  • - Yeah, that was a lot of,

  • you're in that age

  • where that was a big one.

  • I love those entrepreneurs.

  • - Yeah, I was selling suckers too and it didn't work.

  • It was different though.

  • It was like, ooh, there were some big ones.

  • I haven't seen, no, those big ones though.

  • And I haven't seen 'em since then.

  • - [Gary] The Tootsie Roll ones?

  • - I don't know.

  • It was like it was made by the same company

  • but it was a different

  • sucker. - Where were you getting 'em?

  • - Some store in south Dallas.

  • Yeah and I was buying 'em wholesale

  • and going back to school and then

  • but then I learned about competition

  • 'cause one of my friends were stealing

  • from the grocery store they was working from,

  • ran me out of business.

  • - Yeah, I totally understand.

  • It's tough to beat somebody getting something for zero.

  • - Then they had a king size Snickers, 25 cents,

  • aw man he crushed it.

  • - I hate to tell you my first hustle

  • 'cause it's not something I'm proud of

  • but the first thing I did when I moved to Edison, New Jersey

  • was I would run around the neighborhood

  • and I would rip people's flowers out of their yard

  • and then ring the doorbell and sell it back to them.

  • - They didn't know those were their flowers or?

  • - I think they did but here they see

  • this remarkably cute six-year-old

  • who barely speaks English and they're like,

  • I mean first of all 98% of people said no.

  • One of the reasons I really want kids to work retail

  • or sell something

  • within the first 10 to 15 years of their life,

  • is I think that most people

  • have a terrible relationship with no.

  • They're scared of no, they're super scared of no.

  • And I think one of the things that's great

  • about working at a restaurant or working at a retail store

  • or trying to sell something

  • within those first 10, 15 years,

  • is you get real comfortable with no.

  • - Yeah, what was your first retail job?

  • - I've only worked for my dad's liquor store as a kid

  • and then have run my own stuff.

  • So I've never really worked,

  • up until 14 everything was baseball card shows

  • where I real, I mean I still believe 95% of the shit I do

  • is based on what I learned

  • in the trenches of sports card shows.

  • 100%, like I had some crazy hustles.

  • I had one all-time hustle

  • that has to do with basketball.

  • The Dollar Stores popped up in the '90s, like '91 '92.

  • At first, I know everyone here's a youngster,

  • at first, youngsters, Dollar Stores weren't

  • like they are now

  • where they have like new stuff

  • and it's made for The Dollar Store.

  • At first, it was some real shit

  • like there was warehouses.

  • The internet didn't exist yet.

  • So you couldn't get rid of stuff on Amazon or Ebay.

  • There were warehouses filled with old stuff

  • and here came The Dollar Store

  • and they're just selling stuff, like old-style,

  • I remember I bought a ton of Rambo toys

  • that were 1984 toys but I was buying them in 1992

  • 'cause they were just in a warehouse,

  • just old stuff, Zelda books,

  • like that was what I was looking up

  • but there's all sorts of stuff.

  • Anyway, one day I go to The Dollar Store

  • and they have Shaq figures.

  • Shaq made huge noise,

  • obviously when he came to the league

  • the same way he is now,

  • he was commercial from the get.

  • And there was a Shaq toy line.

  • But what was weird about this

  • was this had just come out like a year earlier

  • but they were in The Dollar Store.

  • So I looked at it,

  • so I bought all 25 that were in the store,

  • I started walking down the mall

  • and went to Kmart to look for cards and other collectibles

  • and I noticed there was Shaq figures in there

  • and they were $9.99.

  • So I was like huh,

  • so I bought something at Kmart to get the bag,

  • I went back into the food court,

  • I put the Shaq figures I bought at the Dollar Store

  • into the Kmart bag

  • and I went back to Kmart and I was like,

  • yo my grandma bought me these toys,

  • I don't really want them.

  • I don't have a receipt, can I refund 'em?

  • And they were like, yeah

  • and I'm like without a receipt

  • and cash not store credit?

  • Again, this is 1991,

  • Kmart didn't have their shit together yet.

  • So then I went,

  • so I took five of them,

  • I returned them,

  • I got 50 bucks back for what I just paid five bucks for

  • about 45 minutes earlier.

  • Then I went back to the dollar,

  • I'm still in the mall,

  • Phyllis Mall, big shout out,

  • you look like a fucking disaster now

  • but I went there last summer,

  • it was crazy,

  • there's like four stores open

  • in the whole mall, it's finished

  • but I went back to The Dollar Store and said,

  • hey do you have any more Shaq figures?

  • And the guy working there goes, yeah,

  • went in the back and brought out cases.

  • I was like I'll take them all.

  • So I bought them all,

  • then I came back two days later

  • and they had more cases.

  • Over the next month and a half, two months,

  • I bought like 400 to 500, 600 Shaq figures for a buck

  • and kept returning them to Kmart for 10 bucks,

  • made like four or five G's real quick.

  • And then went to Kmart one day,

  • then it was done and then like a month later I went to Kmart

  • just my normal run

  • looking for X-men figures or sports cards.

  • There was a whole clearance of Shaq figures for like $4.99.

  • So Gary one, Kmart zero.

  • - Yeah, my first job was Blockbuster,

  • my real first job, no I hated it.

  • I mean they don't exist anymore.

  • - I know but at the time they were hot.

  • - Yeah, it was hot.

  • - Before Netflix, like people don't understand,

  • Blockbuster was hot.

  • - They had it, man, I don't know what happened.

  • - Well what happened was they didn't buy Netflix

  • for $40 million dollars.

  • I don't remember the exact number

  • but Blockbuster passed--

  • - [Chris] They had a chance to buy 'em and--

  • - This is one of my favorite stories in business history.

  • Blockbuster passed on buying Netflix

  • for a real, real low number.

  • Now they would've bought the old Netflix

  • which was CDs in the mail.

  • Who knows if blockbuster would have innovated

  • to make it an OTT.

  • So it's not that 50, right?

  • They passed on $50 million?

  • - [Chris] Which I'm sure they had, right?

  • - They passed on 50,

  • the company's now worth 19.7 billion at this moment.

  • It might be different right now, in market,

  • but Twitter took a massive hit today, down 20%.

  • That's what's going on in news.

  • I don't know when this is airing.

  • Do we have questions?

  • I hit up Community, 212-931-5731

  • is my text community service.

  • That's another thing I'm paying attention to a ton, texting.

  • I don't know if you've seen like Diddy, Marshmello,

  • a bunch of other people,

  • like people starting to throw out their numbers,

  • it's on the back of this app called Community

  • and I'm using it, 212-931-5731.

  • On the way here, five minutes before I saw you,

  • I sent a text to 4,000 people in Miami

  • saying I got your man Chris on the show,

  • anybody got any questions.

  • And so it's really an amazing platform.

  • - And you keep saying it on this

  • and then people listening--

  • - Yeah I'm saying it on this right now

  • 'cause everybody who's listening,

  • I'm hoping more people sign up for it.

  • I'm doing a bunch of like,

  • I'm giving away access and first opportunities

  • on that platform

  • because that platform,

  • I have a direct relationship.

  • I'm not at the mercy of Instagram.

  • Instagram's algorithm has clearly taken a turn

  • over the last two, three weeks.

  • The same videos that would get a million views for me

  • are now getting 600, 700, 800.

  • The ones that used to get 500,000

  • are now getting 280, 320.

  • So it's happened and it's happening to a lot of people

  • 'cause I've been bringing up

  • for the last three or four weeks

  • and people are DM'ing me to like what do I do?

  • I'm like you should have done

  • what I've been telling you to do for two years

  • build up your fucking TikTok and your Twitter

  • and start a podcast

  • and an email service.

  • Like people get one dimensional.

  • What do you got?

  • Oh, we're doing calls, let's go.

  • What have you got?

  • You can dial it.

  • - Mobile, that's one of the things

  • I've been fascinated with

  • trying to figure out how to be multi-dimensional,

  • especially in the world today, you know what I mean?

  • What's like some things that you think are great

  • that really help you with being multi-dimensional?

  • - Self-awareness.

  • I know that I like to be helter-skelter.

  • The reason I was a bad student

  • is I like a lot of action.

  • So I don't know you well enough

  • but here would be my question,

  • being multi-dimensional first starts with self-awareness.

  • You just might be actually better

  • going super deep on one thing or it might be awesome

  • for you to do with four to five things.

  • That becomes a personality trait

  • of like do you like the chaos

  • or do you like the structure?

  • So that's first

  • Second, if you like the chaos,

  • you want to start a watch brand and have a podcast

  • and do the book and be on TNT

  • and do your own version on Instagram,

  • if you want to do all those things,

  • you have to be okay with dropping some of the balls.

  • But it's a really interesting thing I always,

  • athletes get it a lot.

  • It's kind of one of those scared money doesn't make money.

  • It's kind of like,

  • and you know this,

  • you grew up, and I don't know how you were about this,

  • but there was a lot of guys

  • that don't want to take the last shot

  • and there's a lot of people right?

  • There's just a lot of guys that don't want to

  • and there's guys that do and things that nature.

  • I think it's a self-awareness game.

  • And you have to be okay with missing things.

  • It's just like the last shot.

  • You have to be okay with missing it.

  • If you start five things with a team,

  • you need to be okay with two of them failing.

  • I'm not scared of anything failing except VaynerMedia

  • because all those other things are side dishes

  • and inevitably some of them are gonna fall

  • and I'm okay with the booing.

  • I actually use basketball a lot with this,

  • I always find it fascinating

  • that people are scared to do things

  • when their life isn't over yet

  • and I always make the analogy of,

  • if you're the home team in basketball

  • and the road team goes on an 11-0 run in the second quarter

  • and you call timeout,

  • your home team is booing you, the home crowd, right?

  • They're booing, they're upset, they're frustrated.

  • - In New York, yeah, they're booing you.

  • - They're booing in a lot of places.

  • They're booing in a lot of places.

  • So I always tell people like hey,

  • you need to you need to be okay with that

  • and wait to triple zero when it's over right?

  • That's the answer for multi-dimensional stuff for sure.

  • Who's this?

  • - [Male] This is Martin.

  • - Martin.

  • Let's see what Martin has to say.

  • (phone dialing)

  • - [Martin] Hello?

  • - Martin?

  • - [Martin] Yo, what's up?

  • - What's up?

  • It's Gary Vaynerchuk and Chris Bosh

  • and we're calling you.

  • - [Martin] Holy shit, what's up, Gary, how you doing?

  • - I'm feeling phenomenal.

  • Say what's up to Chris please?

  • - [Martin] What's up Chris?

  • - [Chris] How's it going, man?

  • - [Martin] Pretty good, pretty good.

  • - Awesome. - What's your question?

  • - [Martin] Well so my question is to Chris is

  • obviously Gary talks a lot about buying the Jets one day

  • and changing the culture,

  • potentially changing the culture

  • and I guess my question to Chris is

  • do you think that it's really possible

  • that he could come in there

  • with the same kind of mentality he does to business

  • and has made pros and the organization around it change

  • and make it like turn it into what he does

  • with everything else that he's touched so far?

  • - You talking 'bout the Jets?

  • - Yeah, his main question I think in the macro

  • for everybody's value,

  • taking me out of it a little bit,

  • is do you believe ownership has the ability

  • to make an impact on winning?

  • - Oh yeah, absolutely.

  • I mean it starts from the top.

  • In my situation in professional sports

  • if you get somewhere

  • and you're supposed to win a championship

  • and the floors aren't clean,

  • the locker room's not clean,

  • you don't know the owner at all,

  • you don't know anything about the place,

  • that takes a huge effect on the culture of things,

  • it trickles all the way down

  • and it kind of sets this precedent

  • like nobody knows what's going on.

  • So yeah it definitely can start from the top.

  • I mean that's where it starts

  • because it takes usually,

  • you've seen some gun-slinging owners coming in and saying,

  • hey it's time to win

  • and it just changes everybody's mentality.

  • - Daniel Snyder came in with that

  • It has not worked.

  • Mark Cuban did, it did work.

  • And by the way, Martin,

  • just 'cause you are gold in something

  • doesn't necessarily mean you are in the next thing,

  • like I have outrageous levels of confidence

  • that I'm gonna buy the Jets and win Super Bowls

  • but that's because I think I'm an operator.

  • Like to me a lot of times operators do well

  • in other operating situations.

  • I think if you look at owners,

  • trust fund babies do poorly

  • 'cause they've never operated anything.

  • They were just in the lineage of ownership.

  • I think Michael Jordan's done an atrocious job

  • and you see this a lot with athletes

  • when they go to coaching or ownership

  • they really struggle

  • because they did it on their back.

  • They've never managed anything,

  • they just were a superstar at their sport

  • but they don't know how to actually create a culture

  • or build something.

  • So Michael Jordan's done an atrocious job,

  • that's just fun for me to say.

  • So I think if you look at the ownership groups

  • that have done well,

  • there has been one or two,

  • there's been two ways I've seen it work.

  • One, this is an individual that has operated other things

  • and they understand how to build culture,

  • hire good people,

  • put them in a position to succeed,

  • build relationships from the popcorn guy to the superstar

  • to the GM to the fans

  • or number two, there absolutely is

  • some trust fund baby lucky sperm club ownerships

  • that I've seen, the Giants it makes me sad to say that,

  • but you see good families groom their children in a way

  • that makes them good owners

  • and you have seen that as well, not spoiled,

  • make them actually work a little,

  • that kind of stuff.

  • - [Martin] So where have you seen the best culture

  • in your professional career Chris?

  • - I mean the one I've been a part of.

  • Pat Riley, he's done a phenomenal job

  • and one of the things about setting a culture for something,

  • not everybody is going to agree,

  • it's not for everybody,

  • but the structure is there from the bottom to the top

  • of what everybody's expectations are,

  • what your job is supposed to be,

  • and just really the level

  • that everybody's supposed to meet every day.

  • So if we're here and it's,

  • we're here to win a championship,

  • that has to go into everything that we do,

  • the thought process, the things you wear,

  • the way you speak to people,

  • the way you solve problems.

  • And I definitely have to give credit to the Heat.

  • Those guys do a tremendous job

  • 'cause it has been the same and they keep going.

  • - Miami fans are a little funny

  • because it's just such a nice weather

  • like they're funny,

  • like watching you guys roll

  • and them not selling out playoff games along the way

  • that's just audacity

  • and that's just Miami,

  • they're a funny fanbase,

  • not to razz Miami,

  • it's just it's a town that is fun,

  • like the ownership for the Heat is phenomenal to me.

  • The fan base is a little funny.

  • You guys didn't sell out playoff games.

  • That's crazy.

  • - It was loud.

  • - Yeah, I know it was loud.

  • Can we talk about your rebound?

  • - [Chris] Yeah sure.

  • - Good.

  • I believe that your rebound

  • is one of the all-time most underrated plays

  • in sports history

  • because of the impact it has

  • on the enormous passion people have

  • debating the goat when it comes to basketball.

  • I mean in its basic form,

  • for the non basketball fans that are listening,

  • Chris gets a rebound in an NBA Finals,

  • kicks it out to Ray Allen,

  • that basically means just very black-and-white,

  • the series ends if he doesn't,

  • I was a little passsive with basketball,

  • LeBron I think took that shot,

  • like that means he would have missed that shot,

  • they would have lost that series,

  • that's a big fucking play.

  • - Yeah, yeah, kind of.

  • Things happen a little differently.

  • - Do people, Martin, thanks so much, brother,

  • do people sorry (laughter), no listen--

  • - [Chris] Bro, like oh my God.

  • - I'm like sports radio,

  • I want to get into a point.

  • I had to put him off.

  • I didn't need him jumping in.

  • Chris do a lot of,

  • like I'm a hardcore sports fan.

  • I've watched every play of a New York Jets game since 1982.

  • So I know every single play.

  • Obviously this is a finals game

  • it's a huge play,

  • I feel like if I was a Heat fan

  • and I came across you at an airport,

  • I would be over-the-top compelled,

  • I wouldn't want to bother you

  • but I would have to find some way to be like,

  • bro, that rebound means everything to me.

  • Like do you get a lot of love

  • or back to my point,

  • that this is one of the great

  • underrated plays in NBA history,

  • is it just that's the way life is,

  • it kind of it's a sneaky little part of it,

  • most people don't go to that extra layer of thinking

  • what actually happened.

  • - I think it kind of goes both ways.

  • People see it and they'll tell me about it

  • and then you have,

  • all I wanted to ever do is make a big play.

  • - [Gary] Is that true?

  • - Yeah, yeah, for sure.

  • I mean as a kid growing up--

  • - You probably did game seven, NBA finals,

  • two seconds--

  • - Oh my goodness, one, two, one, you missed it,

  • then say, oh, it's overtime.

  • - No, he got fouled.

  • - You play those games and stuff like that,

  • the ironic part for me

  • was that it was really an exercise for me

  • because I didn't score in that game.

  • No, game six I did.

  • It was just a struggle for me offensively

  • in that whole series.

  • - [Gary] You were just off with yourself

  • or they defended you well?

  • - Yeah, they defended well,

  • I mean it's the best team in the world

  • and the way they were defending us,

  • they pretty much, LeBron and Dwayne had to carry us.

  • They stuck to me,

  • didn't really rotate much

  • and it was working.

  • - Who was sticking to you, Tim?

  • - Yeah, me and Tim was pretty much

  • matched up the whole series

  • but the way

  • they were doing it-- - Is he a great human being?

  • He seems like a nice guy.

  • You don't know him?

  • - I'm sure he is.

  • - [Gary] He's quiet as fuck, right?

  • - Yeah, yeah, he's quiet, phenomenal basketball player.

  • - [Gary] Clearly.

  • - And great coach I'm sure

  • but at the time it was just kind of,

  • it was a very tough series

  • and everything happened so fast.

  • We were winning and we were in control of that game

  • with two minutes left.

  • We get into a situation

  • where we've got Bron on Tony Parker.

  • That was our game plan for the late game situations.

  • All right, we've executed it perfectly,

  • Tony hits that step-back three,

  • we turn it over a couple times,

  • we're down five points.

  • It just happens really quick.

  • The only thing that kept me in it was that my wife,

  • when you're about to lose a big game,

  • you look around at your family for sympathy.

  • It's just like that look when it's like ah damn

  • but I looked at her and she wasn't looking at me.

  • She just stood up and started clapping

  • and it's kind of like a shell shock

  • when you go to the bench,

  • it's kind of like holy shit, oh no,

  • and we were just kind of,

  • I was looking at everybody else and say

  • yeah, this is not a good situation.

  • I looked at my wife and she was,

  • she just stood up and start clapping

  • was like I don't know what the hell she was looking at

  • and so that snapped me back into it

  • and we were able to make the plays

  • to extend the game and extend the series.

  • That rebound just happened 'cause-

  • - [Gary] You're playing basketball.

  • - Yeah playing basketball.

  • - But it's fucking huge.

  • - Yeah well I mean,

  • I was able to watch the trajectory of the ball,

  • you know what I mean?

  • So back some time ago,

  • one of my good friends told me,

  • hey or a great player told me,

  • if you want to get a rebound,

  • you get there before the ball gets there, right?

  • So in that situation,

  • I could watch, you practice watching the ball go

  • and you just know where it goes after a while.

  • I was able to kind of watch it the whole way

  • and first person I saw was Ray.

  • - [Gary] That's a good person to see.

  • - Yeah and in my mind it happened very,

  • it's like slow-motion, like the Matrix,

  • you know what I mean?

  • In real time, it still does not--

  • - [Gary] Like a hundredth of a second.

  • - Yeah it still does not seen that way in my mind to me.

  • Like, I'll watch it, it's like, okay.

  • - I genuinely think that that play is really underrated.

  • - I don't even want,

  • I like the fact that it's kind of under there,

  • kind of hanging right there in plain sight,

  • because you just hope that you can make those type of plays

  • that people will remember.

  • I remember when Jordan hit all those shots,

  • Packson, Steve Kerr, Hakeem Olajuwon.

  • - I just think that play needs to be branded more.

  • I really really genuinely think like

  • that needs to be more known as like the rebound.

  • It is that big.

  • I really do think it's that big

  • and honestly and I, listen, I hate Michael Jordan.

  • So I've spent my entire last 15 years

  • hoping and wishing and rooting for LeBron

  • to do whatever he needs to do to climb that later.

  • It's crazy, my number one grateful thing towards you

  • is that rebound

  • because without it

  • that game would have been over

  • and the series would have been over.

  • - Yeah, they probably would've made

  • some changes with the team.

  • I mean we were fully aware,

  • we were fully aware of what we were up against.

  • But I always tell people,

  • I'll get mad when somebody say, well the game's over.

  • I get so mad

  • because it's like no, the game is never over

  • until you see like triple zeroes right there.

  • You know what I mean?

  • Like oh, we'll leave.

  • Don't leave.

  • - That was really,

  • first of all, especially in my two favorite sports,

  • basketball and football are funny like that,

  • like there's just something to,

  • actually all of 'em, actually all of 'em.

  • That's absolutely right, that's absolutely right.

  • - Yeah, just don't leave man.

  • And so any other people

  • even you have to stick with things even

  • sometimes you'll give up on yourself or something

  • like that when you're right on the cusp--

  • - What is the hottest you were in your career?

  • Like when I ask you that question,

  • what stretch of time, what period,

  • like what two weeks,

  • I was always fascinated like fuck,

  • it's funny I've been during the majority of your career

  • I was quite passive with basketball in comparison.

  • Knicks went into a coma and my career took off

  • and I was working till 11 p.m. every weekday.

  • So unlike football,

  • where Sunday I could make the commitment,

  • it was hard for me to get all in

  • but in my childhood I was super in.

  • Actually back to the Spurs,

  • I just remember David Robinson would have pockets

  • where he would just go lightning hot

  • like it was just really interesting to watch some people go,

  • like when I ask you that question,

  • do you think of like year three in Toronto

  • of just like this two weeks where you were just 30 and 20?

  • Was there ever a period that you actually remember

  • being ultra hot for like a week or two or a month?

  • - Nothing out of the ordinary.

  • Maybe it was a couple times in a month

  • I feel like I couldn't miss

  • but you forget those pretty quickly

  • 'cause it keeps coming at you.

  • Yeah, you remember,

  • I remember the big stuff.

  • After awhile, I was like, all right,

  • I was hot for a week.

  • I still didn't get the accolades.

  • So I didn't get those awards

  • that normally come with hotness.

  • So that made me kind of say aight,

  • this really doesn't mean anything.

  • - Talk to me about one of my favorite cultural moments ever,

  • that concert you guys put on

  • when you guys all signed there.

  • - That was pretty sweet, wasn't it?

  • It was pretty sweet.

  • - When's the last time you saw it

  • like on the internet or on TV by accident?

  • - I was watching it like the other week.

  • Because we've been talking about it.

  • - [Gary] It's such a fun moment, right?

  • - Yeah, we were having fun.

  • - You were real happy.

  • - I remember that part the most,

  • I'm like man he's real happy.

  • - Oh yeah, it's warm right now.

  • Usually it's starting to get chilly.

  • I like the chill and the light brisk in Toronto Falls

  • but this is something different, man.

  • - On some real shit,

  • do you view that chapter of you guys,

  • back to the four, five, six, like it really,

  • like I remember being like oh man,

  • this is gonna be boring for a long time.

  • Obviously, the Spurs had an incredible dynasty

  • going at the same time

  • and that Mavericks team got hot at the right kinda way,

  • like I mean this is a really challenging question

  • and I'm not looking to make it challenging.

  • I'm just genuinely curious.

  • I really am curious,

  • do you view that chapter as a success

  • or is there a level of disappointment

  • because you thought you could have done more?

  • - No, it's success, it's success.

  • - I can see it either way.

  • I really genuinely didn't know,

  • I was curious.

  • - Well I mean people have to,

  • so the whole story behind that was right,

  • we signed, we're there,

  • the decision is the night before,

  • we're having crazy parties as Miami.

  • I had never seen that many cameras around our hotel.

  • We were at the W.

  • I mean sea of cameras,

  • hundreds and hundreds of cameras.

  • I've never, we haven't even played a game.

  • So the next day,

  • I know basketball,

  • all right we're gonna do the press conference,

  • we're gonna go through the whole thing,

  • we hold up the jerseys,

  • boom, we gonna get out of here.

  • 12 o'clock comes noon nothing

  • to one o'clock, two o'clock, three o'clock,

  • nobody's hitting us back.

  • We're just sitting in the hotel room

  • just sitting there. - The three of you?

  • - No, no, no, me and my family.

  • I hadn't slept in 24 hours.

  • I was just up.

  • So they eventually call us,

  • aight, hey come down to the arena about five or six o'clock.

  • We pull up to the arena,

  • it's thousands and thousands of people.

  • They got jerseys printed already, posters everywhere,

  • I mean it was overwhelming.

  • So then we got in there and they said,

  • all right this is what's going on

  • and they explained everything to us

  • and I was like yo, that's so cool.

  • This is crazy.

  • And they had the build up there

  • because there was a concert there the next day,.

  • I just found this out.

  • So everybody thought we like we didn't--

  • - Honestly I wasn't even worried about that.

  • It was just that image in my head of like the three of you,

  • you guys were just like,

  • that must have just been an incredible moment.

  • - I mean come on, it was amazing.

  • It was 25,000 people there with no basketball.

  • - And you're in your 20s and optimism is attractive to me.

  • And you guys were like we're gonna win 87 fucking times.

  • - You saw what happened when Jordan and them got together,

  • what about us?

  • It was just like,

  • and you know we were just,

  • it was kind of being young and naive at that time too

  • 'cause everybody was happy.

  • We weren't worried about watching what we say.

  • We didn't know that things could get out

  • as quickly as they could.

  • - How early did you think about free agency

  • at that point of your career?

  • Like when did it start seeping into your head?

  • Like a year before it happened,

  • during that season, late?

  • - [Chris] Before 2010?

  • - Yeah like when did, as a kid, you're a human,

  • you were like, I know you were professional

  • and focused on the season at hand,

  • but you're fucking human.

  • You might have thought about,

  • I got kids that we're talking to right now

  • for next NFL Draft

  • who are worried about their second contract

  • four or five years from now

  • and I think that's smart, not stupid.

  • So I'm just actually curious for you

  • when did free agency and how that was gonna play out

  • play out in your mind?

  • - It kind of really start playing into it 2008.

  • - [Gary] Two years before.

  • - Yeah, two years before.

  • Not that I was obsessing,

  • we had signed the deal,

  • the three with the four year option.

  • So that was getting closer

  • and once that started getting closer,

  • it became this thing.

  • So people would ask you about it,

  • they force it in your head.

  • So they make you think about.

  • And people lead.

  • The people lead you and then--

  • - [Gary] You're human.

  • - Yeah well I was human

  • and I didn't put two and two together

  • as far as like having the foresight to look at the class.

  • Then you see who all's gonna be available in 2010,

  • alright yeah it's gonna be a shit show in 2010,

  • I got to get ready for it.

  • But every single day it was questions and everything

  • but I had eventually,

  • I had to get to the point where I'm back to leading my team.

  • So I couldn't really worry about that stuff.

  • Because they wanted me to leave,

  • Vince, left, you're gonna leave, aren't you?

  • I had to deal with all that stuff.

  • So that wasn't that fun.

  • - No, it wasn't.

  • It's constant story up in Toronto.

  • - I mean it kind of sucked and

  • I was just making a decision to play on the big stage.

  • I wanted to play on the big stage.

  • - Who did you think was gonna draft you?

  • This is always my favorite question.

  • - People always told me Toronto.

  • It was either Toronto or Miami, yeah.

  • And so that's why it's kind of funny going to Miami,

  • it was kind of coming full circle--

  • - Those were the two teams that you kind of,

  • your agent, the process, the interviews beforehand,

  • you felt like those were the ones zeroing in?

  • - Yeah, it was four, five for me the whole time.

  • And people were telling me

  • yeah, you're not gonna make it to five.

  • So just be ready,

  • you're going to Toronto.

  • You still don't believe 'em.

  • You still have to go through the process

  • of getting drafted and everything

  • and it worked out.

  • - What do you think about all those baggy suits?

  • - They were terrible.

  • I looked at my suit, I thought I was so cool.

  • - [Gary] Of course that was the fresh style then.

  • - Yeah, that was but man.

  • - Wait till people look back

  • at the shit they're wearing right now.

  • - Oh yeah yeah with the spikes and crystals--

  • - Beanies and tight jeans, these nerds.

  • These kids are gonna be like,

  • who the fuck was I 20 years from now?

  • - [Chris] I think what Trey Young wore shorts.

  • - I know, I know.

  • It's crazy to watch fashion evolve.

  • Chris, thanks for being on the show.

  • - [Chris] Man, I appreciate it, man.

  • - Real pleasure.

  • - [Chris] Thanks for having me, man.

  • - Yeah, real pleasure.

  • This was episode 369, was it?

  • 329, all right, we got 40 more to go to get there.

  • 212-931-5731, hit it, thank you, thanks Chris.

  • - [Chris] Thank you, man.

  • - Awesome, that was fun.

(laughing)

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