Jeff Staple: Let’s get into it.
Levi Maestro: Cool, man.
Jeff Staple: So I got a little checklist for us, a pre-recording checklist, so silence your phones, do not disturb.
Levi Maestro: Got it, it’s already away.
Jeff Staple: Speak into this, you probably know what that is. Feel free to speak freely and we can slice stuff out if we need to.
Levi Maestro: Okay.
Jeff Staple: I am checking my levels, my clock is moving.
Jeff Staple: From Hypeb east Radio, I’m Jeff Staple and this is the Business of Hype. A show about creative entrepreneurs, brand builders, innovators and the realities behind the dreams they’ve built.
Jeff Staple: Okay, do me a favor, do this. Take a camera, hold it in your hand, extend your arm outward and slightly up at a forty degree angle. Now turn the camera back towards your own face and film yourself. What you’re doing is obviously a selfie. Now according to the Oxford English dictionary, the word selfie was first used back in 2013, a little over 5 years ago. But back on March 24, 2009, which is over 9 years ago, a man named Levi Maestro donned a pair of unreleased Nike Air Yeezy’s and attempted to slam dunk a basketball using the same exact camera technique. The sensationalism of wearing those shoes to do that went viral. Kanye West himself posted the video on his own Kanye University Blog. It put Levi and his signature shooting style on the map. From there Levi would go on to make some of the most influential videos documenting this culture and he’d be an inspirational voice for young creators everywhere.
Jeff Staple: Alright. So let’s start, you know, I think like, on these shows I like to sort of just bypass a lot of the biography stuff that people can just look up online and in other interviews and I kind of want to dive deeper, but just for the people who really don’t know, just introduce yourself, who you are and what you do.
Levi Maestro: I’m Levi Maestro or Levi if we’re in Europe, we’re talking to Europeans and I make ideas. I just decided that last week actually. I’ve been making videos for many years, you know, the consulting kind of thing here and there, a little bit of product development. I’m always very careful not to call myself an artist or a director because I hold those terms in such high regard. But I was thinking, yeah, I make ideas.
Jeff Staple: Okay, that’s a good one.
Levi Maestro: And I am living in Los Angeles.
Jeff Staple: I think the biggest revelation so far is that you can pronounce your name Levi, that’s kind of cool.
Levi Maestro: Yeah, right.
Jeff Staple: Do you like Levi?
Levi Maestro: Yeah, totally, I mean it’s-
Jeff Staple: It’s kind of exotic, Levi.
Levi Maestro: Yeah, it’s makes you laugh, you know?
Jeff Staple: Right.
Levi Maestro: But it’s very true, it’s funny when you begin to hang out in different places and with different people, the things you pick up on. A lot of people, almost everyone new that I meet ask me “where is your accent from?” and I tell them I don’t have one and they for sure insist that I do and I say “Oh well if I do it’s from hanging around too many foreign people.” Because you know you pick up on things without knowing that their inflection, their tone, the way they say a word and then you mimic it because you like it and you don’t even notice. So I always notice that the Europeans and Hispanics/Latins will-
Jeff Staple: Levi.
Levi Maestro: Levi, but then everyone comes with the thing right after with Levi’s, “Oh, like the pants?”, you know it’s like no.
Jeff Staple: Right. I think a lot of people who are listening might know you for your videography work, right. Do you still consider yourself, is that your preferred craft?
Levi Maestro: Yes. Absolutely, very much so.
Jeff Staple: So when you say, maker of ideas, it’s currently through the guise of video.
Levi Maestro: Yeah, totally. There is a few… Yes, yeah.
Jeff Staple: Cool, I don’t -
Levi Maestro: Well because each day there’s so many thoughts running through my head and I suppose a greater percentage of them are ideas and so then you try to finesse those things into something or some things. It’s a danger zone as well, right, because too many ideas is not a good thing. Ideas are very easy. I’ve never been impressed with anyone with ideas nor I don’t think anyone should be. It’s about the quality of them obviously, and how you can execute and bring them to life. So much so that I actually gave up or turned away or molded everything in my life into just making videos now.
Levi Maestro: Because this was where I began and it’s that age-old classic idea that you should do one thing and do it well, at least before you try to go do other things because a lot of times, especially today everything’s right in front of us. You get an opportunity to do something else that’s super attractive and you go and before you know it you’re several hundred yards away from where you’re supposed to be, you know? So you can barely make it out, right?
Jeff Staple: Right.
Levi Maestro: If you’re several hundred yards away you definitely can’t hear anything, and you can barely see it.
Jeff Staple: Right, and it’s like you’re so far away maybe from what you’re meant to be doing, you know?
Levi Maestro: Right, yeah. So I’m super excited actually and feel this awesome simplicity of just paying attention to, okay, I’m going to make videos each day now. Not to say that I can actually make them every single day, but that’s where my priorities are.
Jeff Staple: Word. So you have ideas now, and you try to now redirect them through the lens, no pun intended, of like a video?
Levi Maestro: Totally.
Jeff Staple: Versus before, you were dabbling in many different mediums.
Levi Maestro: Yeah, several years ago for sure.
Jeff Staple: Are you pretty good at now, knowing… to me, the real power is across this line, is going to be a regretful action, but you haven’t crossed that line yet.
Levi Maestro: Self control.
Jeff Staple: Self control. Are you good at now, say like that’s a regretful area, that I shouldn’t step in? And maybe then you could cautiously still do it, because you’ve sort of weighed out the pros and the cons or are you still learning, oh shit I did it again?
Levi Maestro: You know, for me, the more proper decision making, I’ve always been pretty good at. It’s the stuff that when you don’t realize you’re making a decision that I’m not. So for instance, just a common day, the type of things that can be distractors. Social media, going out to eat, simple things that you don’t realize are decisions.
Jeff Staple: Mm-hmm (affirmative), totally.
Levi Maestro: This, I’m not so good at.
Jeff Staple: Yeah. That’s good that you… but the first step is recognizing.
Levi Maestro: Totally, totally.
Jeff Staple: Right. You’re so… and it can even be like what you choose to eat. Like, I’m going to go healthy and then the whole day’s productive but then you start the day with like “I’m going to get some french fries and a burger” and it just kibosh’s your whole day.
Levi Maestro: Yeah, what is this kibosh? I’ve never heard of it.
Jeff Staple: Kibosh? I don’t know, it’s an expression for like, destroy.
Levi Maestro: Oh, okay.
Jeff Staple: I should check that etymology of that one.
Levi Maestro: I will definitely google that one shortly here.
Jeff Staple: You’ve never heard of that term?
Levi Maestro: Kibosh? Absolutely not.
Jeff Staple: Nice. Alright, so going back to creating content and video. You were probably… just going back in the early days, I think, you were known for one of the earliest people to utilize video in a whole new manner, right? I mean this goes back to for sure pre-Instagram, pre-Twitter, maybe we’re talking just blogging, blogging was maybe around; and then you started to do this new video format which at the time in my opinion and to the peers that were sort of in the industry were really innovative and different and I would say that, that was probably validated by the number of major corporations that wanted to fuck with you, immediately.
Levi Maestro: Yeah.
Jeff Staple: Right? You were onto something for sure. So, take us back to that time. How did you get the video camera in your hand and starting to create? And you can go back as far as you want.
Levi Maestro: Yeah, yeah. Well actually I do want to bring up this cool memory that just clicked. You and I met in 2009, the Summer of 2009, at Bread and Butter in Berlin. Our friend Phil, Phil G, introduced us and there’s one of the people that call me Levi right there. And I was six months into making my show, Maestro knows, and it was the very beginning of things really starting to crack off for client work and me building a career out of things. And I met you because we went to dinner but we didn’t really connect, and then I put out the video and you had saw it and I remember you tweeted something, I believe comparing me to the guy who photographed Obama.
Levi Maestro: You were saying, “I am to street culture what that guy is to Obama”, and I thought that was so unique. And so I remember that being kind of our first interaction and I think that’s when I realized as well that’s sort of where I see you also in this culture. You’re this person, who sort of takes notice on a little deeper level of what anyone is doing that you think is unique. So I think that’s super cool.
Jeff Staple: Thank you.
Levi Maestro: And as far as those special days of the early internet and video, I put out my first episode of Maestro knows, which is a show about what I say is my life and friends. Because I wanted to highlight creative people that I thought were badass and I do most of the heavy lifting. So I would play the personality and kind of storyline it so to speak which really always happened as we were doing it, but with good intent, because the idea was that we’ll pick a location or we’ll pick an activity but as far as what we’re talking about, we know what to talk about. This is us.
Levi Maestro: In March 2009, you were right this was pre-Instagram, I believe, maybe they were in beta or something and no one knew. Twitter was there, I had actually joined twitter the day I put up my first video, March 24th, because it was a big day on the internet for me. Kanye West had posted the very first episode on his website, I think Virgil, I think got it from Hypebeast and Virgil was posting on Kanye University at the time, which was also a very special thing in the internet days.
Jeff Staple: It was.
Levi Maestro: For an artist or a celebrity of this caliber to be doing any form of blogging or to have even a frequently updated website was one of a kind and for it to be that guy, was just a really special time. I remember when I was having the idea at the end of 2008 I went on a tour with this guy, Anthony Hamilton, who’s an awesome R&B singer, and I think we went to 26 cities and I made a short 1 to 3 minute video for every city that we went to, just cut it up each night on the bus. And it was such a fun, cool thing, and at the time no one was really even doing that so I wasn’t even in those videos, I was just making them about him. But it felt very obvious and very necessary to me that artists should be doing that. You know 2008, I think YouTube launched in ‘06, maybe ‘05. The first time I ever uploaded something onto YouTube was not even for me it was for someone else. I leaked a video back in the day, was in 2007.
Jeff Staple: A music video you leaked?
Levi Maestro: Mm-hmm (affirmative), yeah, with permission from the director, because some artists label thing they couldn’t… so anyway, that was 2007. So YouTube I think is ‘06 or something, which is just insane to think, my God, only 10 years man. Only 10 years ago this happened. The only other player I knew before then was Daily Motion which I think is from France and this is all talking about video being hosted online. I never touched YouTube because I felt that I did not want to be associated with its content which was primarily videos of cats, bum’s fighting, random stuff.
Jeff Staple: It was like the junk food of video content, like just crap.
Levi Maestro: Yeah, yeah. There weren’t even real videos, let alone someone trying to make a show.
Jeff Staple: Right.
Levi Maestro: Right, That I had seen. But there was Vimeo and Vimeo felt like this sort of better looking player in the option. Again, no one was making their own show on it. But I just guessed that this is where media was going to go. The idea of online series, and people just figuring it all out and putting everything there. So, the way that I started making my videos, which was in what is now called selfie style or vlogging style. Again, March ‘09, that was pre-both of those words, another insane thing to think about, because I feel like the world selfie has been around my entire life, and it’s only 8 years old.
Jeff Staple: Yeah. But when you were doing this style that you call selfie style, I still think of it as Levi style.
Levi Maestro: Cool.
Jeff Staple: Because I had never seen someone walking around with an extended straight arm camera facing themselves.
Levi Maestro: Giant camera, man. For real.
Jeff Staple: A giant, heavy ass camera, yeah.
Levi Maestro: For real. And so, here’s the most beautiful piece of the puzzle to me, Maestro Knows, the title, was not what it seems to be. It’s not here’s the things Maestro knows, or here’s the people Maestro knows. It’s about when I moved to LA, I wanted to be this guy, Dave Meyers, he’s one of the greatest music video directors of all time and I interned for him. If I could’ve written my future, it would have been to be just like him. And even today, I think, hey that’s still pretty… that would have been a great reality, you know. But, I didn’t feel that it was going there and I didn’t feel that was my route and the style of video that I knew how to make was skateboarding videos. That’s how I ever first picked up a video camera.
Levi Maestro: And there’s this thing in skateboarding where you film people and your friend will land a trick, a lot of times, the filmer would take the camera, turn it on them, and either put their hand over the camera or say something, like kind of claim it as a homie would. You know, whatever it might have been.
Jeff Staple: Like to show their excitement of what they just saw.
Levi Maestro: Yeah, exactly. I just had that natural urge to know that I could turn the camera on myself and with a wide angle lens, you can see a lot still. So that was the title, I’m Maestro, and this is the style of video that I know how to make.
Jeff Staple: I see.
Levi Maestro: And that’s how I decided this could work. I can film it, I can edit it, I can be the personality slash host and I’m just going to tell stories.
Jeff Staple: Okay, that’s so dope.
Levi Maestro: Thanks, man.
Jeff Staple: What Levi does here that I love is that he took something from his roots of skateboarding and making skate videos and applied them to the new format he was working on. Instinctively, he wanted to turn the camera on himself to sort of sign the piece. But he didn’t check himself and say “Oh this isn’t a skate video so I shouldn’t be doing this.” It’s actually the remixing of different techniques from different mediums that made his new style totally unique. Do you remember the first interview you did in that style?
Levi Maestro: Mm-hmm (affirmative), absolutely. The first one I did was on Anthony Hamilton because it was right after we came off the tour. And it’s a great… it’s one of my favorites, I think the guy’s phenomenal. However, when I was getting ready to launch it, so this a story I don’t think I’ve ever told. I had the first Air Yeezy’s 3 weeks before they came out and they came out I believe in the top of April of ‘09, because when the video come out it was still ahead of the shoes, that’s why a lot of people were freaking out, my first ever episode was on the Nike Air Yeezy. It was actually the second one I shot. The reason why it moved up to the first one, is because one day an unmarked box showed up outside of my apartment and I opened it and it was the gray Air Yeezy Nike, right. And, at the time, the only social media I had was Facebook so I took a photo of it, I posted it on my Facebook.
Levi Maestro: It was some other people in LA that had them and people were blogging them and this and that. People were freaking out when they saw the picture on Facebook. At this time, I’m no one. I’m just a local kid who a couple of people know. I got no following, no nothing. So this is just some friends bugging out that someone they knew had the shoes. Mind you, I don’t believe there was even product shots of the shoe at the time. Don C, I know had a cell phone image that had leaked onto Kanye’s site, but this was pretty crazy to see the shoe, let alone someone holding it on video.
Levi Maestro: So I got the shoe 3 weeks early and I thought man, what could I do with this that would be exceptional. Posting it on Facebook, who cares, right? So I thought, oh man I should go try and dunk in these shoes because I’ve always wanted to dunk and it would be quite hilarious that people would see them on a basketball court. So I did that, I went and shot the video, I cut it up, and I made that my very first episode. I also contacted Hypebeast and asked them, “Hey, I really like this blog page that you guys are doing”, you had one already at the time.
Jeff Staple: On Hypebeast?
Levi Maestro: Yeah, remember when they had their page of blog, it was about 40 different people, mostly people like you, who owned brands or were part of the industry for a pretty serious cause. And I said, but, you know, “you don’t have anyone blogging who’s young”, at that time, I’m thinking I’m 20 years old, right? Everyone is like a real adult, “and you don’t have anyone from the West Coast”, I think the only person they had was maybe Huff and maybe Eddie Cruz had one at that time, maybe he didn’t, and I was able to convince them, Kevin Ma, ended up allowing me to have a blog on there. So that’s how the very first day, it went up. Well, a week previous, I put out a trailer.
Jeff Staple: There of the Yeezy [crosstalk 00:20:42].
Levi Maestro: No, of what the Maestro Knows show would be. This is still on Vimeo, it’s the very first video I uploaded, it’s like a minute and a half, yeah. So they posted that and then the next week they posted this Yeezy video and it started it all, man.
Jeff Staple: Oh wow. So I didn’t realize that there was a link already between Hypebeast and Maestro Knows from the beginning.
Levi Maestro: Yeah, they were straight up like where it sprouted from. Because I wrote them this email and I’d have to look back at it. I hope it didn’t sound cocky, but I remember writing it with confidence like I had explained, “You don’t have anyone young and from the West Coast and I’m going to be making this show each week that will have relevant people and content to your website. So it would behoove you to post these”, right, “because you post content anyway and I’m going to post something to where you’re not producing it or making it, but you’re basically sourcing it”, you know? So it was kind of like a very loose partnership in a way.
Jeff Staple: So, I want to go back to Anthony Hamilton because he’s a pretty big, respected artist. How did you get involved with him?
Levi Maestro: Ah, man. This is two things, right, speaking things into existence and also everything happens for a reason, so. I really loved his music, he was one of my favorite, I love R&B and soul music and when I moved out to Los Angeles, I worked at a restaurant on Sunset Boulevard called Katana, which it’s still there and at the time was definitely one of the hot spots in L.A. Jordan brand actually throw Anthony a dinner, some honorary dinner for an award he was nominated for and he came into the restaurant and he was on his way to the bathroom and I said, “Hey man, I want to-”
Jeff Staple: You were a waiter?
Levi Maestro: I was running food.
Jeff Staple: Okay, you’re a food runner.
Levi Maestro: So, I’m bringing food to everyone’s table, right. I saw him and I stopped him and I said “Hey, I just want to tell you I’m a huge fan, I actually just moved to L.A. and I saw your show two months ago”, you know. And he said “Aw, thanks”, he said “what’s your name?” ,and I told him, he said “what’s your last name?”, I told him and I thought, Ah, that’s very sincere. And he spoke to me for like two minutes, I’m going to come to know in the future that’s just how this guy is, he’s amazing. So, fast forward, I think two years roughly, Hancock Park, I’m moving into this apartment building, I’m breaking my lease from where I’m moving, I only had lived there four months and it was too loud, I couldn’t sleep.
Levi Maestro: I found this other building. I’m going to sign my papers for an apartment and I show up and the woman’s not there, the landlady. So, I’m ringing, I’m ringing, I’m ringing, I wait ten minutes, fifteen minutes, finally I see her come out to the lobby, she has this group of people with her, it looked like she had just shown them an apartment. She opens the door, I walk in and it’s Anthony Hamilton, his manager, their wives, and I said, “Wow, hey man I don’t know if you remember me but I used to work at Katana and I…”, and he said “Oh, yeah, yeah” and “how you been?”, this and that, “Oh so what are you doing?”, I said “Oh, well I’m signing an apartment to here today”, he said, “Ah, me too”, wow, you’re kidding me right?
Jeff Staple: How are you affording an apartment that also this Grammy Award-winning artist are.
Levi Maestro: It was a old hotel, really cool, they flipped into apartments and it had some units that were just so tiny that God knows what kind of rooms they were before.
Jeff Staple: Okay, so you got the tiny room.
Levi Maestro: Like a laundry room or something that turned into my apartment and then he has like a nice property-
Jeff Staple: [crosstalk 00:24:26].
Levi Maestro: Yeah, exactly. So then-
Jeff Staple: Do you think he actually remembered you?
Levi Maestro: I think he did, face wise, right. Like a lot of people remember faces, I don’t he know my name, I don’t think even know what I do, whatever, because he asked me, I tell him I’m making videos. So a month later after that, he pops out the elevator while I’m walking through the lobby, so we catch up and he tells me, “Oh, I’m shooting a music video this weekend, come by if you want”, I said “Great, I’ll shoot a behind the scenes for you, so you can see what I do.” And we went, we did it and I showed it to him next time I saw him at the building, I mean it was hilarious, like these are how things happening back in the day right.
Jeff Staple: Wait, you made the behind the scene video but you had no way to show him? You had to run into him literally again-
Levi Maestro: No, I’m sure I had a contact, I probably had his email or a number or something but I just saw him and I said “hey” and then he comes into my apartment, I play it for him on the DVD player, right, it’s so good man, like stories don’t happen this way anymore, it’s crazy. So, he really liked it, even wrote me a personal check, it was… was it the first check I ever got for making, no, I had done some other brand work locally, filming some parties and this and that. But it was the first thing creatively for something I definitely would have wanted to be doing. And he had slipped this check under my door one day, Jeff, I can’t tell you how badly I wanted to never cash that check.
Jeff Staple: Right, because you lose the check, yeah.
Levi Maestro: To just save it, right, because back in the day you lost the check, today you can photocopy it and send it and no one ever touch it but you. But it meant a lot and so I think several weeks later he calls me up and he said, “Hey, I’m going on a promo tour for six weeks and I’d like you to come on the road with me and let’s film some stuff.”
Jeff Staple: Yeah, crazy.
Levi Maestro: I said “Man, cool I’m there.”
Jeff Staple: So, I want to go back a little bit because I think a lot of people comment on today’s generation as having this feeling of entitlement-
Levi Maestro: Okay, yeah.
Jeff Staple: That like whoever big star comes up to struggling creative and says “Hey, why don’t you come to the shoot”, and you know you were offered to the BTS, you know behind the scenes, I think a lot people be like, “Well here’s my rate”, like right off the bat, just be like, “How much you got? What’s your budget?” And you just went into it and just fucking shot it knowing, thinking that you wouldn’t get paid, correct?
Levi Maestro: Oh yeah, of course.
Jeff Staple: Yeah. But the dope thing is you did get paid.
Levi Maestro: Yeah. I think it’s a mix of both, there’s a lot of people out there that still have super respect and I think there’s some others that just aren’t hip to it, yeah, like you say. And who knows what’s the right way to go about it.
Jeff Staple: Do you remember how much that check was from [crosstalk 00:27:28]?
Levi Maestro: Yeah, yeah I do.
Jeff Staple: How much?
Levi Maestro: I don’t want to say.
Jeff Staple: Come on.
Levi Maestro: It was nothing-
Jeff Staple: Yeah.
Levi Maestro: Exceptional, it’s just the point was it was the gesture right?
Jeff Staple: Totally, totally, okay.
Levi Maestro: Yeah, yeah.
Jeff Staple: And then, switching back to that Yeezy story, how do you get the Yeezy’s three weeks early? Like, that’s what the kids want to know, right, like wait did they just show up at the doorstep? No, do you got to know somebody-
Levi Maestro: Doesn’t that make such a more fun story? A random unmarked box came to my door. I was shooting a few events locally for Nike West, so this woman, Lena Batista, she was having me do these event coverages and she was sending them back to Nike internal, so, a funny with the whole video thing happening early as well. At this time, I mean something equivalent to that today, they might actually put it somewhere, right?
Jeff Staple: Yeah.
Levi Maestro: But Nike has no Twitter at this time-
Jeff Staple: Uh-huh (affirmative), no Instagram.
Levi Maestro: They don’t have a video on their website, if they just “Hey, what are you guys doing with our money out there”, right and they’re sending it back to Portland, ah, here’s this event we did.
Jeff Staple: Right, it’s like internal use only, yeah.
Levi Maestro: Yeah, so I did a couple things like that and I was sort of… also this was thanks to Arson from Hall of Fame because he referred me to them as kind of, “Oh this is a local kid, whose cool or whatever”, right?
Jeff Staple: Mm-hmm (affirmative).
Levi Maestro: It was how they were seating stuff back in the day and yeah Nike, gave me a couple pairs of shoes previous to that and then I had got a text message one day that says “Hey, do you like the Air Yeezy’s?”, and I just thought nothing of it because if you were to ask me, I would have told you one thousand percent, that shoe will never come out. I just didn’t believe it. It seemed too, yeah right, you know. Oh cool, they made a sample, who cares. It’s Kanye West, he’s a music artist, they’re not giving a music artist a shoe, Nike doesn’t do that. “Sport, we’re so sport”, that’s how they always want to… well now they’re changing things but, typically they’re very scared to stray away from sport too much. So I was thinking, the shoes never coming out, let alone it’s going to show up at my door, right?
Jeff Staple: Right. So Arson from Hall of Fame, did he hook you up with the jobs too at Nike?
Levi Maestro: No, that just sort of materialized, because-
Jeff Staple: How?
Levi Maestro: Probably the same way that if I were a DJ, they would have gotten me to DJ they’re event, you know what I mean? It was, “Oh, you’re a cool kid, we’re going to put product on you to be…”, I mean this was influencer, before influencer was a thing to the world, it was just a thing in the neighborhood or a thing in the community.
Jeff Staple: Yeah, but were you making money from those?
Levi Maestro: No, no, no, no.
Jeff Staple: Oh, okay, so this was just to get some gear-
Levi Maestro: [crosstalk 00:30:33] from the events that I shot, videos of, yes?
Jeff Staple: Yes, okay.
Levi Maestro: Yeah.
Jeff Staple: So you were making a little bit of money from that?
Levi Maestro: Yeah.
Jeff Staple: Okay, and did you have a full time job at this time?
Levi Maestro: It was right there on the brink of having several jobs, yeah.
Jeff Staple: Mm-hmm (affirmative), like what?
Levi Maestro: There was a summer that I worked 60 days in a row, I remember. I think 62 days in a row, I had four jobs at that time. I was working at a clothing store, I was doing bar back at a bar in Santa Monica, which is like stocking the bar, keeping the bar stocked. I was working at a restaurant and… what was the other one? I think it was two restaurants.
Jeff Staple: Okay.
Levi Maestro: It’s the two Japanese restaurants, a bar back and a clothing store, my god. I was working some two jobs a day but I remember that man, I worked 60 something days in a row. I was probably 21 and I was just, yeah you can’t tell me nothing, I’m in L.A., you know.
Jeff Staple: And you were sprinkling in this event coverage and-
Levi Maestro: Yeah, yeah, trying to turn it really to making videos for a living, and there was another guy, Kenny Mac, who is from New York and he used to work for Belvedere Vodka, and he really helped spark those, I guess jobs as well, because he would do the same. He was throwing events and he would have me shoot them and then he would send them back to LVMH. It’s so crazy how it’s the same type of companies, you know. So Louis Vuitton with Hennessy is a group that you’re obviously well aware of, they own a bazillion super, influential brands; and it’s the same one today, Nike, New Era-
Jeff Staple: Yeah.
Levi Maestro: You know. Yeah, it’s so funny man, gosh.
Jeff Staple: Yeah. So you do the Yeezy video of you dunking.
Levi Maestro: Yeah.
Jeff Staple: Did you make the dunk?
Levi Maestro: No, no I didn’t, not even really close either.
Jeff Staple: But that’s what made the video dope, probably.
Levi Maestro: I think… sure it made it amusing and it probably made it relatable to a lot of kids-
Jeff Staple: Yeah, right, right. But the… explain in metrics if you recall, how that blew up.
Levi Maestro: Nothing. In comparison to what people are doing in viewership today, I would not even say that it went viral, I think it went culturally viral. Viral is millions.
Jeff Staple: Yeah, today.
Levi Maestro: Today. And even back in the day, what were those videos Chocolate Rain and stuff like this, you know what I mean. Culturally, it went-
Jeff Staple: Mm-hmm (affirmative) [crosstalk 00:33:25] everyone, who mattered though.
Levi Maestro: There was no one in street culture, street wear, sneaker culture, I don’t believe who did not know of what I was doing. And still to this day, it resonates in a way that’s super impressive. Because I’ll go to different countries, you know, Amsterdam and major cities, of course, people who follow it, but still, people will recognize me in the street and I think it’s insane, it’s been seven, eight years. And it’s people who don’t even follow me anymore and they’ll tell me a story about how they started DJing after, or they went to this class for college or they moved to Japan because they saw the Japan video.
Jeff Staple: Mm-hmm (affirmative), that’s dope.
Levi Maestro: And that’s always why I think it was such a special time, because for what was out there back then, it meant more. There’s a lot of people doing stuff today. I could easily open up my telephone, find good content, find sexy girls, find all these things that I would be interested in, you just couldn’t do that eight years ago man.
Jeff Staple: Yeah, absolutely.
Jeff Staple: Levi’s willingness to build his dream is admirable here. He understands that going viral with millions of views and tons of money wasn’t as important at that time as going culturally viral. The value of each viewer had so much more impact. People changed their jobs and people moved to the other side of the planet after watching a Maestro Knows video. Some people find their place in this culture without making it all about the money. They value opportunities as currency, and they not only try, they know that’s their way to make an impact.
Jeff Staple: So after that went culturally viral, did the work start flowing in after that, like did you get a lot of requests?
Levi Maestro: Six months later.
Jeff Staple: Really?
Levi Maestro: Yeah because I probably did two or three jobs in those first six months of people who were hip to what I was already doing. So, I remember Lena and Nike messed with me again, they let me do Nike campus, which was absolutely insane. I mean that’s like another piece of history that you’ll never get again.
Jeff Staple: Going to be [crosstalk 00:35:54].
Levi Maestro: Still, to this day, I’ve never seen a video show Nike campus. Maybe there’s stuff online, I’m sure here and there, but I made a video showing the entire Nike headquarters. And somehow too, I don’t even know, this was really just Lena and me. She got whatever some approval over there, but they stuck me with one guy and me and him rode the whole place, the whole day and I don’t know if anyone knew what we were doing or what. And I edited that video and I put that thing up. I mean it just would not work like that today.
Jeff Staple: No, there’d be so many layers of approval, disapproval, yeah.
Levi Maestro: They’re the ultimate red tape company man that’s who they are like Nike quote on quote the red tape company, right? Like this would be super appropriate for them, so she got me more stuff.
Jeff Staple: What other projects [crosstalk 00:36:52]?
Levi Maestro: Jen Yu who as New Era at the time-
Jeff Staple: Yeah, Jen Yu.
Levi Maestro: I did some stuff for her. Erin Lovant who created agenda was doing Seventh Letter, him and Keland Rowland, they let me do some stuff for Agenda and Seventh Letter, so, it was people who were already familiar and then they saw what I was doing and then it was really Phil, who brought me out to Bread and Butter. This was my first time to Europe and then he brought me out again and when I went the second time I went all around Europe for a month. But that summer too, it was… you know six months [inaudible 00:37:31] one year and then it was really on.
Jeff Staple: Yeah?
Levi Maestro: Yeah, then I was getting stuff. Then all of a sudden I had six figures and I would say “Wow, this is really… this is real”, you know. And it’s not even real yet, because still, okay, let’s say one year later, Summer 2010, content still wasn’t doing nothing. Brands still didn’t have social media accounts, and they for sure weren’t putting video content on it if they did. If they were it was their proper T.V. commercial or something. And the jobs started rolling and it was getting… you got to remember too, let’s say, I’m getting 40, 50 thousand for some job doing a couple of videos or something. This is peanuts to these people.
Levi Maestro: I mean they’re spending parties, throwing way more money than this. You might as well spend it on something that’s actually beneficial, it’s going to get some advertising, do some marketing for you. You’re going to go throw an event on the corner in one major city and you wouldn’t put some photos up online, who cares? You’re not telling any story. And you got to remember too, what they’re shooting and actual paying production companies. You should see in commercial, it’s a million plus dollars. Then you’re going to run it on television, how much pay you got to put behind that for people to see it.
Jeff Staple: Right, yup. So it’s a bargain to actually pay you $50,000 to make a quick video?
Levi Maestro: Still, to this day, it’s a bargain.
Jeff Staple: Yeah, right, [crosstalk 00:38:55]-
Levi Maestro: And that’s why companies love new media. What! People think it’s so crazy that so and so got $10,000 to make a Instagram post because they got 300,000 followers or whatever it is. I guess, sure it is crazy in a certain sense but not to the company.
Jeff Staple: No, it’s a joke to the company.
Levi Maestro: If you saw the money that these companies were printing, my goodness, man, this is how they make money. They spend $10,000 to make 20, 30, 50. They’re not stupid, that’s why they have billions of dollars.
Jeff Staple: Yeah. This whole time in that first six to 12 months, did you still have those jobs? When did you stop the bar back, the food running, when did you stop all that?
Levi Maestro: No, no. No I stopped those from the very first video that I put out of Maestro Knows, I did not have a job. Even maybe six months before that. When I went on tour at the end of 2008 with Anthony, I didn’t, and I was barely getting by. I mean I have stories man. I had to move out of an apartment, use my last months rent as the final payment because I didn’t have any money, so like “Here, give me 30 more days, take my money and then I’ll be out” and [crosstalk 00:40:10]
Jeff Staple: Uh-huh Did you leave that apartment?
Levi Maestro: Yeah.
Jeff Staple: Wow.
Levi Maestro: Jeff, how about I went to Japan twice. Two times in a row, my first two times to Japan. I came back both times, to turn on my phone when the airplane landed and didn’t have service because I hadn’t paid my bill. I just came back from Tokyo, either for free or getting paid, and I don’t even have money to pay my phone bill. I mean it was so close, it’s just memories don’t even understand how that happened. I went to Europe for my first time traveling around Europe for one month. I went to five countries, when I left, I had $360 in my bank account. When I went to go on a trip for a month! When I came back I had 40 bucks.
Jeff Staple: Would you call that recklessness?
Levi Maestro: I guess I call it living man. Because what were the choices? Go or don’t got. What I’m going to do run out of money? Somebody I’m going to find a way back. Somebody’s going to help me get back or I’m going to pay… somebody’s going to hire me for a job there and I come back some way.
Jeff Staple: Well someone more conservative, might say, “I have $360 in my bank, maybe I shouldn’t go to Europe for a month.”
Levi Maestro: True, but how many conservative 21 year olds are there in this world? Plus, the trip was taken care of, so I knew I had a flight there and back. Worst case scenario where am I going to eat and where am I going to stay. And most of the things-
Jeff Staple: Those are pretty worse case scenarios.
Levi Maestro: Those are however, I knew a lot of them were already handled. Because at this time too, I’m a real cool guy now, right? I’m the cool guy making videos. People really wanted to hang with me. So they were hosting me here and there and I pretty much knew that I wasn’t going to need money. But I had no job on the table-
Jeff Staple: When you came back, yeah.
Levi Maestro: No one was giving me a check when I got there.
Jeff Staple: Right.
Levi Maestro: $360, one month in Europe. That’s a story I can tell for the rest of my life.
Jeff Staple: Yeah, that’s true.
Levi Maestro: And it just trips me out because, yes today, no I’m not doing that. I’m not going today for a month and $300.
Jeff Staple: Right.
Levi Maestro: Not going to happen.
Jeff Staple: That’s dope. Man, it’s crazy right?
Levi Maestro: Life’s wild.
Jeff Staple: The age old question, how bad do you want it? How far onto the ledge are you willing to walk? I don’t want to say I necessarily condone Levi’s behavior. Some would say it’s actually insane, but like Levi said, he has a story for the rest of his life now. Would I have done it, at any point in my life? I don’t think so to be honest. It’s not in my nature. I’m a lot more calculated and risk averse. I also like knowing when my next meal will occur. But the moral of the story here is when you see an opportunity, you must assess for yourself what the pros are and what the cons are, then make a decision and live with it 100%.
Jeff Staple: I would say you sort of like, in my opinion, you always walk your own path, and you don’t do the obvious thing. You had this momentum going with the videos and if someone had to be like predict what Levi is going to do in three years, oh he’s going to have boutique agency and he’s going to have 30 different clients or a team of a dozen and he’s going to be cranking out these videos. But it’s like, then at that point you stop seeing the videos and now… then there was a time where you dabbled into other things like pop up retail stores, a clothing line, I still to this day use a coffee mug that you designed-
Levi Maestro: Yes! Epic.
Jeff Staple: Like we have a beach towel that has your name on it, random fucking shit, right. And then I don’t know if it’s because of, and maybe you can expound on this but I don’t know if it’s because of the platforms have changed, for how people consume video, but you stepped away from doing the videos that you were known for. And now you’re doing it in a different way where it’s more like self expression storytelling. So to me, if there’s one consistent thread throughout all of that, is that when you do something and it starts to check, you then exit and do something else.
Levi Maestro: Oh no.
Jeff Staple: That’s my outside observation.
Levi Maestro: I got to change my ways.
Jeff Staple: No, maybe not. Maybe that’s your calling. What do you think, do you agree or disagree?
Levi Maestro: I definitely agree. So from 2009 to ‘11 I was rocking. I think I made a lot of the right choices and I really had something special built out.
Jeff Staple: And financially too?
Levi Maestro: Yeah.
Jeff Staple: Like you said you were making six plus figures a year, you’re cranking.
Levi Maestro: Yeah.
Jeff Staple: Okay.
Levi Maestro: I think a few things got in my way. The biggest one was distraction, it’s very hard to continue to produce whatever you produce. So, I made videos. It was very hard for me to continually make videos because editing is a pain in the ass, especially the way I cut stuff together. I mean, I’m making stories that have no script. It’s miserable storytelling dude. I mean you basically go out and you shoot a ton of stuff and then you go sit in front the computer for 20 to 40 hours and try to make sense of it. And it’s just not ideal. I love it, sure, but I also hate it. And I don’t know, I’ve definitely made over a hundred videos. In the scheme of things, I suppose that sounds pretty measly, but I look back on that, it’s a heck of a body of work.
Jeff Staple: For one man.
Levi Maestro: For one person. And you mix in a little things with that. You mix in some money, a nice place to live, a cool car, girls, food, all this stuff that’s just really lovely in life, and I didn’t just go sit around and get fat or something, right, but I really began to allow myself to spend time on things that were not entirely beneficial to my progression. This is a mistake. It’s still something I fight to this day. I notice it’s just a difficult thing. I was terrible in school growing up. I probably still would be if I went to school right now. It’s difficult for me to focus. I don’t know if I have ADD, I don’t really know that I believe in it anyway, so I’ve never checked. But I think I might be a little more disabled than your regular person. And at that same time, I also was shooting for some other things. My goal when I began my show was to have a television show.
Levi Maestro: I wanted to recreate… I wanted to redefine reality television, because what I make is real and those are the stories that I’m passionate about.
Jeff Staple: Verus what you see on reality television, is not-
Levi Maestro: Reality television has 90 some odd percent of… which is just made up and scripted in shock value and so on and so forth, and unfortunately, I feel, really influenced so much of what is online content today. Because people saw, oh shock value really infatuates people so let me go make my videos real shocking and stupid and over the top because it’s just going to make people either talk about it or say how dumb it is and da-da-da-
Jeff Staple: But they’re tuning in regardless.
Levi Maestro: Regardless. So I wanted to make a show just as I did but in 22 minute format and I wanted it on MTV. I didn’t think it had to be on MTV but of course I think that’s where it should have been. And I got all the way to the point where I was on the 23rd floor in the corner office with the Executive Producer and had to deal with my name on paper. And we negotiated deal points for three months and I had to make a choice to risk my livelihood on the show’s success or continue to try to build outside of it, and I chose to try that. Because, if my show went for several episodes and got canceled, MTV would have owned a lot of my, not my life, but they would have owned a lot of my financial life. And what I had created previously.
Jeff Staple: Right. All of it belongs to them.
Levi Maestro: Not all of it but a heck of a lot of it. And at this point, we’re in 2011, I think it was getting a bit risky. Rob Dyrdeck was owning the network, I mean his stuff was doing super great, but he was also kind of on a tail end a little bit. I mean what he had already done was super cracking, and he’s maintaining now. But, I focus so much on pushing it to that and then once that sort of was there I also had this other thing come up with the infinity piece, which I then formed into this company Bicone, with your help and this was maybe the best idea of my entire life as far as the product. I really believe that the thing could be so enormous that it may have been more significant than anything else I would have ever made. But then there was the tear of being in a relationship with two people. And which one do you love more?
Jeff Staple: Who were the two people?
Levi Maestro: The two people was videos and Bicone.
Jeff Staple: Yeah.
Levi Maestro: Yeah. And one of them treat me super well because they come in, “Hey, we’re this brand over here, we have money make a video”, “Okay, great”. I got to pay my living for my nice rent and all this stuff, yeah right. But then the other thing I was making money as well, and it even started doing good and I understood the potential of having a backup plan in life and being able to creative direct, and come up with more unique ideas and there was such purpose and meaning behind it. I mean the product was created for someone that I loved. And in turn, people were buying it for people that they loved.
Jeff Staple: It’s beautiful.
Levi Maestro: How powerful, right?
Jeff Staple: Yeah.
Levi Maestro: So then the worst thing happened. Both things that I loved, began to suffer and they suffered more and suffered more and suffered more and I didn’t know how to fix them. And, it came down to it that I end up choosing one and I chose videos because I think it was the wiser decision all around. And that took four years, [crosstalk 00:51:56]-
Jeff Staple: Mm-hmm (affirmative), to figure that puzzle out.
Levi Maestro: That was a four year process from the day that it launched. Really it was kind of a five and half year process. This whole time, right, four years of doing things insufficiently or less than my best.
Jeff Staple: Because you’re stretched thin.
Levi Maestro: Yeah. I mean did I make some great videos and partnerships in four years? Yes. Did Bicone touch peoples’ lives and make some moments? Yes. But neither of them reached nearly their potential. And I think that’s really what life is about as an individual is reaching your full potential.
Jeff Staple: With the MTV conversation that you spoke about, do you think there was a miss where you became obsessed with one definitive finish line goal? Verus just making videos you felt were right, making content you felt was right. Did you start thinking, I’m going to make stuff so MTV gets this deal done with me?
Levi Maestro: No, I don’t think so. I really wanted the television thing. I met with plenty other networks too. I got close with other ones as well. I ended up being on a show on MTV as well for a little bit of time.
Jeff Staple: And you ended up getting a show on Fox Sports.
Levi Maestro: Yeah, they ended up doing the good thing that I wanted it just became difficult because it’s with athletes and I think athletes are even harder to get time with than celebrities because they’re training and they’re availability and then the amount of money they make for doing media… I mean I’m talking people who are even my friends who was hard to get time with. And people I text message every week, it was still difficult to find time to shoot the episode with them. But Fox was really smart because it was a guy who saw the videos with athletes and said “Will you do this, just how you want, just the way you did it, but for us?”
Jeff Staple: That’s dope.
Levi Maestro: And I said, “Wow, absolutely”, you know. “Okay, tell us what you need”, told them what I need they gave it to me and they ordered five of them and I made five of them.
Jeff Staple: Was it lucrative for you?
Levi Maestro: Yeah, I mean it was… it’s not the golden days of, “Oh, dude you’re on that network”, you know, [inaudible 00:54:11] no, it’s not like that. It was more the point of the entire situation was just a really solid great one. That those are the types of things that would be great to do always.
Jeff Staple: Okay, so go back now. You said, you’ve made the decision where you’re spreading yourself too thin. Bicone stops, you’ve made the decision to stop Bicone and focus on video. Does that bring us the current day or-
Levi Maestro: Pretty much. It takes us to about one year ago.
Jeff Staple: Okay. And now if you look at your feed today, your videos have taken a different angle where it’s much more like, you don’t interview people now, you interview yourself essentially.
Levi Maestro: At the moment, yeah.
Jeff Staple: Tell us the evolution to what we see today from Maestro Knows.
Levi Maestro: So at the moment if you look at the page, yes, you see a bunch of videos of me talking. And I guess it’s sort of a reincarnation period. Because I feel my… me at my strongest, me at my best is I’m a communicator. I tell stories, so in telling stories visually, yes, but I actually tell them audibly. So, that was the strongest link in Maestro Knows. As you see it’s plenty of people vlogging today and even though I don’t want to affiliate myself with that because I think the entire definition of what that is, is something so separate; aesthetically it is quite similar, however I always had this sort of sentimental, motivational you can do it to feel. That’s why people watched. That’s why they related, that’s all I’ve ever heard from feedback, you know what I mean?
Jeff Staple: Mm-hmm (affirmative).
Levi Maestro: Cool, the shoe looks cool. Nike campus looks great. It’s really about, “Hey, what are you doing? because you should be doing what you want to be doing. Look at my friend and what he’s doing”, you know?
Jeff Staple: Mm-hmm (affirmative).
Levi Maestro: And that’s my superpower, if I had one. And I’m so hyped to have found that because a lot of people don’t find theirs, or until very later in life and I’ve known that for almost 10 years now. So I’m figuring out the ways to adapt to this current landscape that is society. Society’s in tune with right now, which is so much online and social media, because I understand that at my highest frequency I was putting on video a week, that’s nothing anymore. That’s not impressive.
Jeff Staple: I know.
Levi Maestro: You know? There’s people putting them out every day. Now how do I fall somewhere in between? Because I’m not going to make a video every day. Not until I have several people working with me, then I’d be down to do it. But it’s just too much work. You can drive yourself insane. One of my friends does it. He puts a video on YouTube every single day, he seems miserable. He really does. And I understand, he’s on a mission but he really complains about it a lot. Even though he’s doing good and he’s growing and everything. And the videos are just about absolutely nothing and it’s a person I really love. He’s… anyway, I admire what he’s doing but it’s almost suicide, it’s insane so-
Jeff Staple: It really robs the love out of the thing that you love to do, right?
Levi Maestro: Man, what? So, the videos that I’ve been making recently are one minute long so that they can go across all the different social medias. If you’re listening, yes there is more social media then just Instagram, there is one called Twitter and Facebook. And I’m talking about the things I’m going through in life. It must be the most fun thing I’ve done that I can remember. It’s therapeutic, it’s memorable, it’s emotional, it’s everything that I am. I mean one time I’m going to tell you about how I think I’m done eating meat and the next time I’m going to tell you about how I have to take a shower every day before I go to sleep, you know? It’s really things. And then I’m connecting them to why they’re making sense in my life or what they’re making me learn.
Levi Maestro: So I supposed I used to want to reinvent reality television, now I want to reinvent what a motivational speaker is. Because I think that the ones that I see are out there are ridiculous. To me, I would just never buy into it and I understand there’s lots of people that identify with different voices but the last thing that I’m going to let someone do is militantly speak to me, telling me the things that I should with my life. I’m not buying it. I don’t care if you are a trillionaire. I love Bill Gates man, I wouldn’t even let Bill Gates talk to me like that. So what I am doing is allowing people to relate.
Jeff Staple: Mm-hmm (affirmative). Yeah they’re pretty raw, some of them too.
Levi Maestro: It’s unadultered communication, there is nothing in between us but these words. And in a day like today, I think that’s super special so each time I go out and I have a location in mind and I kind have a thought in mind, I start saying it in my head until I feel like I have about one minutes worth.
Jeff Staple: Oh you’re not scripted-
Levi Maestro: I don’t write it down.
Jeff Staple: Really?
Levi Maestro: Nope.
Jeff Staple: Get out of here.
Levi Maestro: I can’t because if I do then I’m going to be so super uber television host, because I got that in me. I can really be that on camera guy right?
Jeff Staple: Uh-huh (affirmative).
Levi Maestro: The funny thing that a lot of people don’t know if they’ve never been on screen before is you sort of have to be overzealous because the way that you come off on the screen, if you’re sitting there and you’re super boring-
Jeff Staple: It’s like dead boring.
Levi Maestro: Yeah.
Jeff Staple: Yeah, it’s weird. The camera sort of removes 40 percent of your hype right, like in a way.
Levi Maestro: So again, I’m trying to find that balance.
Jeff Staple: Word.
Levi Maestro: Where can I speak straight from the heart, but not be sitting there pausing and talking about “Um” and “you know what I’m saying” and “uh, like this and like that.” Every word that I’m choosing is carefully chosen. Because what I’m actually doing with this, the whole reason why I’m doing this series, I’m writing a book. I wanted to write a book for six years and I’ve never began it, until I started making the videos.
Jeff Staple: This is the content for your book?
Levi Maestro: This is the content for the book because once I do it I can finish and I can say, “Hey, do you know how I wrote this book? I wrote this book so many different days in my life, going out, making a video.” And the entire book would also be available as a visual if you want to watch it. I think that’s extremely unique.
Jeff Staple: That’s dope.
Levi Maestro: But, nonetheless, the reason why I am doing it, is because this is how I’m allowed to do it. It’s my work around. If I’m going to sit down and try to write a book, I’m running into a wall. How do I get around the wall? I go the only way I know how, it’s by filming myself. And the only last to add to that is just today I finished a episode of Maestro Knows. So I will make this until the end of time. And really I want to make several different series about all the things I’m interested in life. The one I was just talking about is my thoughts. But I love food, I love music, I love people. So I would like to have this space which may be my YouTube page now, maybe every social media, I’m putting them on everywhere; where I show everything that I love.
Jeff Staple: Oh, so Maestro Knows is still like a separate show?
Levi Maestro: Still, alive. I think I have six of them shot right now. I need to edit them and I want to shoot more. You and I still have one that we’ve never made. So I don’t think those ever end, I just don’t know if it ever becomes some weekly series like it once was, you know?
Jeff Staple: Yeah.
Jeff Staple: Levi and I get really deep in the last few minutes here. He speaks extensively about a mistake he feels he might’ve made that took over four years for it to work itself out. It takes a lot of courage to speak about something like that. Losing businesses, losing direction, losing loves, these are topics that could touch a sensitive nerve with almost everyone. Even as Levi was saying it to me, I began wondering, “Well what if I didn’t have a clothing line and a design agency and a retail store. Maybe if I just concentrated on clothing, Staple would be the size of Ralph Lauren today. Maybe I should have never opened Reed Space, was that a 15 year long mistake?” Being unafraid to listen to your regrets and reinvent yourself is a key to life success. Change is hard but we either step forward into growth, or step backward into safety.
Jeff Staple: When we ran into each other, most recently in Dubai, at Sole DXB, you had just come off a month long, right? Month or three months? Four month-
Levi Maestro: Three, yeah.
Jeff Staple: Three month sabbatical basically, through Europe-
Levi Maestro: Sabbatical, yeah.
Jeff Staple: And I think one of the reasons why I thought you’d be really interesting to speak to now is because you have gone from zero, right. Like growing up, hustling, working like four jobs, to then getting to a point where you are by all means of a definition, a success. Doing what you love, making six figures plus out of it, owning your own companies, and then when I met you last month it was like, “I just went through Europe for four months and I didn’t know you”, you were telling me that you didn’t know where you were going or coming from or where you were sleeping or staying, right?
Levi Maestro: Yeah.
Jeff Staple: And it’s like, that to me is, I think a lot of people might say, “Wow, how did you fuck up? What happened?”, but to me, because I’m sort of living in the Matrix, to me it’s like you unplugged from the Matrix which takes a lot of balls, you know. So I wanted to speak to you more about how did it feel to unplug yourself out of the game in a sense. And now maybe with a clearer head you can decide, this is how I want to re-enter. Maybe I want to try something else but just exiting yourself out of the race is a very ballsy thing to do.
Levi Maestro: Yeah.
Jeff Staple: Comments?
Levi Maestro: I went through a pretty struggle-som two years of life. Or maybe one and one and some change and I got to a point where I realized I didn’t have a place to live and I didn’t have any obligation really then to myself. And as stripped and sad as it was, it was also a super luxury. Because I think a lot of people make commitments in their lives that they then have to grasp screener effect and would like to change but it’s too late or too deep. It’s never too late in a way-
Jeff Staple: Right, but they think it is. They create these-
Levi Maestro: Well once you got other people and other things involved it can be pretty deep and pretty messed up if you just are entirely selfish. With my thing, my life was kind of handed right back to me and… what do you want to do Maestro? That was my POV. And I had said a lot of things that I would have wanted to do before I thought I was committed to all sort of different stuff. And I had just gone to Europe for the month of April, so yes I did spend four months there this year, one month and then three months separately. And I ran a half marathon in April for a job, my friend Joey with the Berlin Braves. And I went to three cities, well, Berlin, Amsterdam, Paris, I had the time of my life.
Levi Maestro: Me and Europe man is just, that’s a place for me. I love the short visits you can make everywhere. It’s just I never mature as quickly as when I go there. So I said “Man, I want to come back. Maybe I can get a job, maybe I can do something. I want to spend the summer here.” I was a little late, I didn’t get back until the end of July, but I was able to stay until October. I went to eight or nine countries, 15 cities, and the reason I went was because that’s what I wanted. If I can live the rest of my life right, I will live it by what I want.
Jeff Staple: Some people would say that’s called selfishness.
Levi Maestro: Yeah, absolutely.
Jeff Staple: But do you think it’s okay?
Levi Maestro: Depends what you’re choosing as your destiny. Again, if you’re involving other people and you have responsibility and obligation, then you need to honor that and be good to it. But I suppose if you’re living your life for you and it’s pretty much up to you what you want to do.
Jeff Staple: Word.
Levi Maestro: Now there’s certain people in my life that if they called me, if they asked me, I’m going to be there, no matter where I am. So it’s not like I’m entirely detached to something, but it’s extremely liberating to ask yourself what do you want to do right now? Or where do you want to be? And be able to grant that to yourself. And I can’t even… I mean right now I’d love to be in Tahiti, I’m not there and I can’t go right now, but this summer I could go to Europe indefinitely and I went, and it was for sure one of the most amazing trips and times in my life, I learned so much stuff. I was a super sponge. I absorbed, I went and spoke to everybody that I was wanting to speak to, just totally living in the free world. As much as you can in 2017, 2018, you know. Because we’re really in the hole right now man in all sort of ways. But there’s still so much beauty around you wherever you are.
Jeff Staple: Yeah. Is the career path a concern of yours right now? Or is it-
Levi Maestro: Yeah, totally.
Jeff Staple: So it’s not just living for Levi, it’s like-
Levi Maestro: No. I still want to make a lot of million dollars, a lot of them. And the reason why is because I’ve seen what money does.
Jeff Staple: Mm-hmm (affirmative), you’ve seen it first hand.
Levi Maestro: Man, money can make some cool things happen. And, I just recently calculate it by old emails… I hope it doesn’t come off whack but really I don’t care man; I donate money and I’ve donated more money than maybe I make in a couple years of my life. And I kind of didn’t even know that, because I just give when it’s there and I try to give as much as I give, because the people I give to are doing the most amazing things in life. They are saving people’s lives. This is the stuff that matters. I mean, it’s people in our world that don’t have food and we’re not feeding them. A lot of us can feed them, with next to nothing. So the way I see my life unfolding is the more that I go earn, influence, financially, knowledge wise, I can give. The more that I earn the more I can give.
Levi Maestro: And I’m not saying I’m holier than thou, I’m not trying to go give everything that I earn, but it’s a huge motivation in my life, because man. When you have fed someone, when you have given someone a medical operation, oh man, you really understand why we’re here. It’s compassion, it’s got to be the most special part of life. To be able to show compassion to others is next to nothing man. And I want to do so much more of that and it’s a lot of people doing really cool things, that are in high places. It’s slightly unfortunate that maybe the world is built out like that but it’s also a huge motivator to get further. Somebody was talking to me, at the interview in Dubai they asked me some question and I had that realization for the first time. I said, “You know, everybody is trying to get further.” It was so simple when I said it out loud, I don’t even remember to what. But I just thought, “Oh, everyone’s trying to get further than where they are.” That makes life just seem so simple, you know?
Jeff Staple: Yeah.
Levi Maestro: Day by day, some people mesmerize themselves trying to do too much at once. They don’t even begin because they haven’t thought of an entire blueprint yet; when you’re not going to ever really get anywhere if you try to solve the whole equation first, you know?
Jeff Staple: Right.
Levi Maestro: Do some multiple choice. Phone your friend. Get a little closer and then you’ll realize the next step, right?
Jeff Staple: Right. So you’re not a believer in figuring it all out before you make your first move?
Levi Maestro: It’s impossible. I don’t think anything’s impossible but that.
Jeff Staple: Could be.
Levi Maestro: Yeah. That was another huge thing I’ve learned in the last year or two of my life, I know nothing. The only thing I know is that we’re having a conversation right now, really. The only stuff I know is in the past man. Anything I’m trying to go do, that whole cool idea, how I told you I’m writing my book with what I’m making my videos, I don’t know that’s going to work, but I’m going to get there and find out. And I believe it will. You know the more I believe the closer I know to it? And I’m going to tell you that I know, but I don’t actually. It’s fact in belief.
Jeff Staple: Yeah.
Levi Maestro: Yeah. If you believe something you know, but it’s not fact.
Jeff Staple: It’s factual in the end.
Levi Maestro: Yeah, 100%.
Jeff Staple: Let’s talk a little bit about balancing your brand, your business life, what you’re trying to accomplish on a professional level versus personal life. Like the difficulties or not difficulties, what have you learned in the past few years about trying to make it all work out right?
Levi Maestro: One thing fun I guess to say, because I definitely learned something, well I don’t know that I learned something from you, but I observed it. You’re super good at making decisions without taking it personal or without connecting yourself to it. Because as a creative person you’re passionate, right? A good creative is a passionate person. See here I am, like hitting the table as you told me not to. And it’s really hard for me when I’m making something I care about, I’m making decisions based off of emotions. And I’ll see you say things sometimes and you were able to look at it in such a further perspective, well this is how it actually looks. It may look gray to you right now because you been up for 24 hours thinking about it but trust me I just came off a night sleep and this thing’s yellow, that’s super helpful. Probably to be able to balance that business and maybe that’s why I’ve never been a good businessman. I’m so passionate.
Jeff Staple: And it’s personal. This thing you created, if someone doesn’t support it, or buy it, or sign on to it, you’re sort of saying, “You’re making a character judgment on me, because I made this.”
Levi Maestro: You know what? I’m not that connected.
Jeff Staple: Not a character judgment but it is a personal judgment.
Levi Maestro: I always want to go the way I believe. I’ve always said the realest, the greatest artist make what they want. They don’t make for anyone else. You cannot own a brand or a company and do that. Unless you are an artist selling artwork, right?
Jeff Staple: Yeah, but even then, they have the same-
Levi Maestro: Even that way it’s smarter to maybe cater to your audience.
Jeff Staple: Yeah, exactly.
Levi Maestro: I can’t cater to the audience man, I don’t want to do that, because I know that it’s possible, I know. I know that it’s possible to do it the way that I want and for it to still be a success. So that, I think has hindered me a lot of times, because a lot of people don’t mind making the decision. “Oh, people like red shirts right now, cool. Aye, this season we’re making red shirts.”
Jeff Staple: Yeah because if you go back to what you just said about you want to make to then give back, isn’t it then advantageous for you to make red shirts for everyone? Because then you can give back faster.
Levi Maestro: True. Great point. Another one of the difficult decisions to make in this thin long plank that is success.
Jeff Staple: Yeah.
Levi Maestro: Yeah.
Jeff Staple: And you know, even if you look at it from like, musicians as an analogy, because I’m a fan of music and you are too, and you see how some artists just play the formulas, right?
Levi Maestro: Oh yeah.
Jeff Staple: They just know what hits and they make what hits. And in doing that, they spread fast. So everyone knows about them, but maybe we don’t respect them. And then you got the other artist which is like the ones that we respect, that put out one album every ten years and you’re salivating for a single, right. But it’s like, “Man you just put out some more.”
Levi Maestro: Okay so, perfect example of what this would have meant in my life, “Levi Maestro join YouTube and daily vlog.” You know how many people over the years have told me to do that? And who knows, I don’t know what… it’s hypotheticals, right?
Jeff Staple: Yeah.
Levi Maestro: Sure, maybe I would have a million subscribers, maybe I’m looking exactly the same. I don’t think it would have worked for me, because I don’t have that type of personality. I’m not going to be in the camera all loud, super stupid, throwing stuff at people, like whatever they do, that’s not me, I just simply cannot do it. However, if you look at the formula of what works, that’s where you should stick me.
Jeff Staple: Yeah. Right. But you chose self happiness over that. And self respect really.
Levi Maestro: I think, and also I thought it’s possible to build a brand and more of a production company by being away from there. Because so many of these people on social media do not realize that if you do not have an obvious talent or service, you will be out of here soon. As soon as that social media that you’re popping on has turned over or whatever it may be-
Jeff Staple: Or changes an algorithm, like literally like-
Levi Maestro: Changes an algorithm.
Jeff Staple: Dude, when Instagram changed the algorithm, people lost their mortgage.
Levi Maestro: So for me, it’s never been about followers, it’s been about, I provide a service and a talent. My service is video production, my talent is storytelling. Now, there’s plenty of people that do both of those and with more numbers than me; and that’s great they’re probably doing better than me. But what I am not is a YouTube vlogger, and I won’t be. I think I have a pretty good idea of where content is headed in the next two to three years. I just saw Facebook put up a billion dollars and Apple put up a billion dollars for production for 2018. That gives me a pretty good idea of who’s going to be running media in two to three years from now. And I think that those people are going to get behind and invest money in people that know what they are doing and that have a story to tell.
Levi Maestro: So I’m building now for what I am forecasting is going to be the landscape in 2020, which is the first time I’ve done something like this. I’ve never thought ahead like that, but because of what happened to me since 2009, I’m now able to look back and say, “Wow you really on to something back then and now maybe you should blend this new thing to sort of be in the proper space for those people to get behind.” Because, you can do creative and you can do business in two ways; one you go direct to consumer or the other you get people to pay for everything. And the smartest successful people will tell you, “Never spend your own money.” Not saying you have to spend your money to start a business, I mean some people, be even you probably, I think you started with pretty much nothing. You were able to build it to be crazy successful, but you’re dependent now upon the people who support your brand which really may be the better way.
Levi Maestro: It’s such a 50, 50. Which one’s better, having the support from the people or having the support from the higher ups with lots of money. It’s a tough call, it’s the freelance employee, just in between right. So, for me, I think people are very fickle these days and again on both sides, but if I’m sitting on social media and I think I personally follow 400 people or something like this, I follow a lot of those people that I just clicked on them because it looks cool. I’m not invested, at all. I can unfollow them tomorrow and never even think about them again. Unfortunately, this is where we are now of days. Whereas before, I wasn’t buying some guy’s album for 9.99, that I didn’t know I really wanted. You had to make a wiser choice because you were investing.
Jeff Staple: Yeah, you had to really consider it [crosstalk 01:23:02].
Levi Maestro: There’s no more investing needed today. Everything is free. I mean goodness, even Apple music cost me 9 or $15 or something and I’m getting everybody. Give me more. Greed, greed, greed, you know?
Jeff Staple: Yeah.
Levi Maestro: I mean how much money have I paid Drake over the years? I have no clue, because I’ve never had to buy his album. I listen to it a lot. Dude, I would love to see that percentage, I would love to see have I paid Drake $47? I don’t know.
Jeff Staple: Probably not.
Levi Maestro: Probably not. And that blows my mind, because I’ve even been to the concert I think and even that was free. And so, it’s just such a big question mark. So the only thing you got left is either to try to earn money right now today or to forecast and set yourself up like a business plan that hopefully pans out well in the future.
Jeff Staple: So in your best case scenario, in that five years, where do you see yourself now?
Levi Maestro: I will be traveling the world, speaking to people in real life, in exchange for money.
Jeff Staple: That’s very specific, that’s good.
Levi Maestro: Because it is something that already exists and I’ve gotten paid for it before. I’ve gotten paid thousands of dollars to speak for one hour to people, like years ago. Already, I’ve done it numerous times. So, if that already existed in my own life, I for sure know it’s possible. Because I’m not talking hypotheticals, right?
Jeff Staple: Yeah. You’re talking-
Levi Maestro: Not talking Tony Robbins, I have no clue how much that guy gets paid but I know it’s pretty good, right?
Jeff Staple: Mm-hmm (affirmative).
Levi Maestro: This will never go away. Live interaction, they might figure out how to make it feel distant as possible with VR and all this stuff, but there will always be a demand. And maybe the more distance they place in between it, the more demand will come.
Jeff Staple: Yeah.
Levi Maestro: But-
Jeff Staple: The more value on in real life experience.
Levi Maestro: [inaudible 01:25:00] all these artist making money on the road. And these celebrities and influencer blah, blah, blah, they’re getting paid to post and they’re getting paid to show up at events and, yeah. So there is money to be made in being able to reach out and touch something. And the idea I guess is if the people want the product. And I want to bring it back around to, let’s be here in this space and interact. Let’s be here with each other, because there’s no substitute for that. We will try and we will try and we will get very close to succeeding but there simply will never be a substitute for it. We’ve got hologram, we’ve got VR, we’ve got some machine that you can touch and smell and feel, you know what I mean, but it will never be like the real thing.So my plan is to continue making videos, to communicate to people until the point that I get to communicate with them in real life and in exchange for that I plan on being able to charge money.
Jeff Staple: I love it. Alright, anything else you want to add?
Levi Maestro: I think this went really well.
Jeff Staple: It did. No I’m glad that you sat down with us and shared your deepest roller coaster ride of life learnings.
Levi Maestro: It’s just like this, you’re here doing this today because you also understand the value in it and if it were up to us we probably would have done this in front of an audience right now, right?
Jeff Staple: Yeah.
Levi Maestro: We’ve kind of even done it before. But, yeah, that compassion realization is something I’m always trying to remembering it closer to, because I’m such an opinionated person man, I’m really trying to draw myself back from that. I totally judge a book by its cover, even though I know not to. So on my better days I don’t, but on a lot of my days I do.
Jeff Staple: I do too.
Levi Maestro: I think we all do and it’s trying to figure out those moments…it’s so weird, sometimes I have a memory about the oddest things. I remember that other thing on Twitter and I remember this other now too that I once tweeted that, you know the moment in life when you experience something and it clicks? I’m trying to make that moment my entire life because I’m aware and awake and however I worded that, I remember that you retweeted it. I don’t know how I remember that I just remember it. So it’s such a fun moment to reflect on because it’s something that makes sense to the both of us and that’s why conversation and words are so amazing. Everything in life can be fixed by communicating and so little can be fixed without communicating.
Jeff Staple: Right, exactly, it’s crazy.
Levi Maestro: This is when me and Jeff dap now, we dap it up.
Jeff Staple: If you were here in real life you’d see that.
Jeff Staple: Thanks for listening to the episode. You should definitely follow Levi and his positive messages on Instagram at Levi Maestro. You can find out more about the show or listen to other episodes at Hypebeast.com/radio. Subscribe to us wherever you listen, I use Overcast and you can reach out to me on Twitter at Jeff Staple. Check us out on the web at businessofhype.com and you can email questions you might have in questions at businessofhype.com. The Business of Hype is directed by Daniel Noveta, it’s edited and produced by Bryght Young Things, you should check them out at BYT.NYC. Engineering was done by Patrick Morris, our intern is Caroline Khao. This was recorded at Sibling Rivalry Studio in New York and on location in Playa Vista, California. I’m Jeff Staple and you’ve been listening to the Business of Hype on Hypebeast Radio.
