Humility is the Key to Winning in 2026

0:00Hey, this is Nicky Jam. Listen to Monday to Monday. You're gonna love it. Nicky Jam. I only like the process. It's the best thing. It's the only thing for me. Like, I'm addicted to, there's nothing else I like. I don't like stuff. I don't want stuff. I just want the legacy of the process. You know what I mean? And that's why yours is so good compared to other things. Like, when it's just like this. You don't miss the process? I'm only about the process. I always put myself in the process like that's why I jump from different businesses like once I won wine I bounced because I was like what am I going to do just milk it for the riches that's what most people do they only want to do the eat shit to get to the stuff they're willing to put in the work for the Lamborghini or the girls or the chains but once they get it they're out that's why so many people lose once they win and he's tight with brushing I know, I know.

0:59That's my guy, I love that dude. He's a good guy. Like good people. He is sharp, he's got great instincts. That's a really good way to put it. What's really interesting though is it's your time now, right, like you were born at the right time. Like you guys are taking over the world, like the whole Latin, like the Latin invasion of America is forever over. It's not going backwards, it's only, like this is just the beginning. People don't get it. like the demographics it's just math it's over it's over it's really cool it's really cool yeah hell yeah yeah and one thing we were I introduced Sid to some of your team but you didn't get a chance to meet so this is Sid right here he does international strategy for Gary one of the coolest things to me was when you were talking about how you went to Colombia and you were like going hard after YouTube to like get your numbers up and like you were really like got all your followers See the thing is when I went to Colombia, I saw there was 65 million people and my career was in a downfall so I said, if I can make this country love me and I could be the number one national, if I could make a national hit, number one national hit in this country, I'll get 65 million people to back me up and if I get 65 million people to love me, other people from other countries are like, why this guy has so many views?

2:16Yo, I gotta be straight up with you, straight up, real quick. It's my favorite thing about you, how, you understand that that's a talent that will never go away from you, right? Because whether it's Columbia or Snapchat or eSports or this famous person, it's just the math of attention. To have the understanding to get up, go, execute like that, oof. Yeah, I mean. That never will go away from you. That's, that's. It's the same game. It's all I ever do. It's just attention. Exactly, exactly. Exactly, and that's the thing, I had to study the country and make the country love me, not me not being from that country and not being active in the music in the moment, because Columbia was listening to reggaeton music, but they were listening to the guys that were active in the moment, so I had to go there and make them fall in love with me, but it was easy because they were like, yo, this guy's living in our country, he loves us, you know what I'm saying?

3:14Why isn't he living in the States? Why isn't he living in Puerto Rico? And he's coming over here, and I started doing videos, 15-second videos, and I'm like, yo, I'm over here in the streets of Medellin, walking and I'm doing this and I just bought my new Mazda 6. And normally rappers brag about Bentleys and I'm happy because I have a car again. So they fell in love with my story and it worked exactly how I wanted to. I didn't have one number one hit. I had six number one hits in Colombia, national hits, and my views were incredible and I started jumping from Colombia for the world. You know what's funny?

3:49I think about hunting and farming. now the key for you to have like a 50, 100 year career like at this new level because you've had a career you need to be very thoughtful of forever giving love to that country. Like everything you guys, right? Like the number one thing for you to be able to win in Asia, on Mars, on a new platform you need to be real thoughtful about how you continue to give love there forever. You know what you should do? you should make the day you put your first video up in Colombia like a holiday within your world and your mind and with your fan and like literally always do something special on that day.

4:30You should go back, look at the first day you posted something on YouTube in Colombia if that's what you give credit for when you first started. Look at that date and you should throw a free concert every year on that date for life. That's awesome. That's really awesome. Another thing is what he was saying about how humble he was in Colombia. What Gary loves is the lyrics and the story. And I know that you were saying in Puerto Rico it was more about beats and this and that. No, really. I don't understand beats and producers that well. I really don't. I get it. If the music, I get it. But I know that I'm not thoughtful about that.

5:08But the story, that's... That's everything. For me, it's everything. That's everything. That's for me. I think everybody has their own thing. For me, and then the story of the person, that's why usually I love people's first albums, because that's their origin story, that's their first issue of the comic book, right? That's when they're telling people, this is what happened and this is what happened. I think it takes a lot for somebody to have that second or third, it's the person that knows how to story tell of what they're going through, because the first one, that's your truth. It's kinda how my keynotes work on YouTube, my business talks.

5:41It used to be easy, because I'd just tell you I was born in Russia and lived in a studio apartment with this many family members. This is like how I grew up. But then it got harder because that was established and now you gotta come back with some hits. Yeah, he started his kino the same way you started your album. Like telling the story, like telling everything. So now what? Because it's white hot right now. You guys must all be like, okay, we need to be like. Well, you know, my mentality is first of all in my music and the general music of reggaeton it was kinda hard to work and do big things because they saw us as street singers.

6:18You know what I'm saying? So normally you'll see Ricky Martin or Luis Fonsi or any. It will be easier for them to work with brands and sponsorship and all stuff like that. So I'm breaking those boundaries. You know what I'm saying? I'm pushing it. And I'm being the first. I just signed with Hublot. I just signed with, I'm doing the Netflix thing. I got something big working with Will Smith. I'm doing the movies. I did the movie with Vin Diesel. I'm doing things for my music. and I wanna be, like you could say, the Jennifer Lopez of my music, you know what I'm saying? I want, because I'm bilingual, I'm good acting, and that's what I'm trying to do.

6:55That's what, you know. That J.Lo money is interesting money. It is. It is, it is, it is, it is. But you know what's amazing about her, and amazing about, like, as I've been really digging into you the last couple months? Work. Work. I just wish J.Lo, I get so mad at culture. when I hear J-Lo's name literally the first thing I think of is a working gangster she hustles she works and when everybody talks about her they talk about her being a celebrity or whatever she's working J-Lo's out working 99.9999 % of people Will Smith is working the reason you got something brewing with Will Smith is Will Smith is smart he realized the game he was playing for the last two decades was time was up.

7:43You can't make the same movie 15 times in a row and get paid 20 million. Exactly. This is the game. He looked around. It felt authentic. You got plenty of attention in the game. You're fucking pumped because he's a fucking icon. One plus one equals two. Right? Exactly. Yeah. Listen to me. I'm telling you right now because I can tell that you know everything so I don't have that much to give. That first day you made a piece of content, throw that free concert. Your only kryptonite right now is if you forget about Colombia. Oh yeah, no, I would never. I'm being dead serious though. I say it in the songs everywhere.

8:19You're so natural to grow. You know, like, you're like me. Like, your natural move is to grow. You're gonna win Asia. You're gonna do the same. You're gonna rep. You know you're gonna run this same racket over and over, right? Like, you're gonna win China the same way. You're gonna win some new platform the same way. This is over. Now that you've tasted it, Like, it's over. You're just gonna rinse and repeat and the only vulnerability is if it feels manipulated. It is true. No, but you know. Even the way you talk about, you know what's funny? I wouldn't even be giving you the advice. You're like me, you're transparent.

8:53There's a lot of people who did what you did that would never say, I decided to go to Columbia for that reason. 65 million, if I could make them love me. It worked exactly, like, you have to understand if you're on the other side in Columbia, humans are cynical. They're like, oh, you just can't, got it? So you need to go hard the other way. No, of course. I mean, you know, Columbia's come to the States to look for their dream. I went to Columbia to get my dream. Just need to go back. They looking for the American dream, and I was looking for the Colombian dream for the world, you know what I'm saying?

9:25And by the way, your model's right. Sid, what do I keep saying about a country in South America? What's my new thing? Where do I want to be famous? Brazil. Nope. Peru. Peru. Yes, like this. I want to be famous everywhere, but the reason I keep saying Peru, and I have no idea how many people live there. It's not a joke, it's more of a religion, which is what you did is one of the first examples of like, this works for everybody, man. Like this is the right model. Like if you're a creator right now out there for music or videos, taking a step back, especially if you're young and you can live anywhere, and if you're willing to live humbly, taking a step back and looking at different places around the world because YouTube and Facebook and these platforms work everywhere.

10:10Saudi Arabia, now with Snapchat and with this new prince, like every day I wish I was like 24 and had no responsibilities and no family, I'd pick my ass up and go to Saudi Arabia right now and fucking kill it. That's nice. That's what you did. I mean, that's what I felt when I went to Colombia. Exactly. You had even a bigger advantage because you already had an up and a down, so you had a chip. Exactly. Even better than being a young kid. You had experience and a chip. I lost my ego. No ego. Once you triple down on humility and still have ego and hunger. Exactly. As long as humility is just.1 bigger than ego, it's game over.

10:53That's what Will has. All that Will Smith has just done is he let his humility go a little bit further than his ego. That's why he was willing to vlog and be on MySpace. On MySpace. on Instagram. I'm old, guys, I'm old. Come on, Tom. I'm old. You know, the fact that he had the humility to go on there, most A-list stars don't want to go to Instagram and YouTube because they have to start at zero, and then there's other people out there like you that have more followers. They don't have the humility. Humility's the key right now for the next game. I have a question for you. Go ahead. Obviously, you told me that you get bored and you want to do new things and new things, but have you, out of all the success you already have, you never just like, I'm tired?

11:38You never feel tired? Not yet. Not yet. And I say yet, right? Who knows? You never feel bored? Never bored. Never bored. I'm too - What takes the bored away is doing something new. I'm always doing s***. I'm always doing s***. Yeah, if I get, I'm pretty disciplined, which is why I can build big companies, and they'll tell you, I'll just make up new s***. That isn't big, I'm building a Twitch studio. right outside my office, that's me being bored, right? Just need a little action, a little hint of something new, but I keep 89, 92 % got it? And it's side dishes. My steak and my chicken, it's proper, but sometimes I need some cauliflower or something new, right?

12:19Side dishes keep me going. Plus, honestly, I'm grateful. Like, to me, I'm just grateful, which never gets me down or negative or bored or just grateful. I'm just hungry. You love yourself. I love myself. I love myself. That's a really good way to put it. And for most people, that's a difficult thing to say because the world doesn't accept that super well. But that's the answer for everybody in this room and everybody behind that camera. My biggest thing, if you look at my content, I'm trying to get people to love themselves. The way you love yourself is you become 100 % accountability for your shortcomings because everybody in here is done, done.

12:59Of course. Every one of us has got shortcomings. So first you get there, but yeah man, I do love myself because my mom made me that way and no voice has been able to penetrate me to tell me the alternative. Incredible. You know, I believe in that a lot about loving yourself. I mean, and it was hard for me because I came from, my mom, she left me when I was eight years old. She was a drug addict and a prostitute. My dad was a drug addict himself. And it's kind of hard for you to love yourself when you come from that situation. It's very hard. But I was trying to blame the world when I was in drugs and I was in all this stuff and blame my parents.

13:36And when I started to love myself, everything changed for me. How'd you get there? I mean, I was tired of looking at myself and blaming people and saying my life was a piece of shit and nothing was happening for me. So one day I said, okay, first I was fat. I was like really fat. I was weighing almost 300 pounds. I was taking so much perks a day and the perks, it's not like other drugs that will make you not eat. The perks will make you eat more than a lot. So I was like the worst drug addict because I was a fat drug addict. Normally you don't imagine. You're a drug addict and you're fat. You know what I'm saying?

14:09It's like at least take the weight off me. You know what I'm saying? So I was a fat drug addict and I was tired of that and I realized that when I started losing weight, the attitude of the people when they started seeing me was different. It was a different vibe. It was like, hey, Nikki, Hey, it was good. Hey, wanna go eat something? They didn't say that when I was fat and all messed up in drugs. They wanted to take me out because they felt I looked good. So I said, okay, this is the beginning. How did that even start? What did you see? I'm always fascinated by that, the tipping point. Okay, what did I see for the weight thing?

14:47Well, first of all, I was at a Denny's actually eating and a fat girl came to me and said what happened to me. And it pissed me off. And I said, same shit happened to you. You fat. What do you mean? I was eating and I got fat. You knew her? No, she knew me because I was in the music. You know what I'm saying? And you got to understand, I was so skinny when I was famous in Puerto Rico the first time. So when I got fat, I was deformed. You could say like, this guy is not the same guy. So obviously it's okay for a fat girl to tell me. She rolled up on you and was like, what happened? What happened?

15:15You know what I'm saying? But it was like, you know, and it felt bad. It felt kind of bad, you know, and I was like, and then I said to myself, what happened? You know what I'm saying? And then I said, okay. You started shipping away. So I said, I'm gonna start with the weight thing. And then when I, and I started eating like the cleanest thing in every menu. Honestly, like, it's funny. It doesn't, you know, that was your story. My big thing is like, bald short dudes and like overweight people. Like, you've got to figure out how to like not make anything else the way you justify your, like it's gotta be an inside game.

15:51Like, listen, being healthy is just a good idea to live longer. But it's crazy to me being secure and being insecure. It comes in every shape and size. It's wild. I'm just thinking about some friends who are both overweight, underweight, rich, poor, tall, short, athletic, not. And you go through that in life. I remember somewhere in high school and then early college when I was like, wait a minute, pretty people are insecure too? Of course, they're the most. It just runs the gamut. They're the most. You just got, I'm just desperate to get people to stop judging themselves. That's what you see a lot, you know what I'm saying?

16:30And it's crazy. I see it a lot, man. And musicians are the worst. Like you could see them have, they could be number one right now on the billboard and depressed, you know? What, honestly, with the whole team here, is there anything I can help with? Is there anything we can help with? Like from anybody's perspective, your perspective, or anybody on a team that might have one? I mean, I mean there's a lot of things. Throw them, throw them, throw them. One of the things from - Listen, my natural, like just so you know me a little bit, my natural default is I love to give first because I'm perfect for giving.

16:58I don't expect shit in return. And I know it also works in the end. And if it works two out of 11, like he'll tell you, 10 years we're into this journey now. Yeah, and I was telling him a little background. You know, he's in Miami, so there's that. Yeah, I'm there a lot. Yeah. So like, I mean. No, one thing really important for me right now, like I was saying, I'm trying to be like the first for my genre of music to work with these brands. The first mogul. Work with these brands, you know what I'm saying? So, I mean, I've been working with P.A.T. already like in Latin America, but I would love to be the Latin face of P.A.T.

17:36You know what I'm saying? In the U.S. In the U.S. And sometimes, you know, it's kind of hard being a reggaeton artist, you know what I'm saying? So, you know, if you guys can help me with anything of that, it'll be awesome. The interesting thing, though, is that your music is great and your music isn't, like, offensive. It's not. It's not, it's not at all. It shouldn't be hard in that sense. But sometimes they go by the image. Honestly, honestly, yeah. It's been an image thing in the past because our branding team has always been pitching since day one. It's the background. It's because of some of the opportunities.

18:02Let me ask you, I get it, I get it. I get it. You see a lot of people with more questionable past. Oh yeah. Brother, brother, we know what it is. We all know what it is. Let's go a different route. I think you're making a mistake. Let me explain. First of all, you're making the least mistakes, but it's funny. In some places you're going real new wave and other places you're looking at a traditional. I don't think you should do because he's not gonna do anything for you except be a short term check. And I get it. I grew up with Michael Jackson and we all know where he sits. I get it. Let me throw a different one at you.

18:39I think you should be thinking about getting equity in a startup beverage like Dirty Lemon who's smart enough to know that you're exactly what they need. You get a point of the company on the back end. They market you properly, not on dumb billboards, cheesed out, vanillaed out, right? And you win twice. To me, you've pat, you know what you and I have? Guys and girls. Because their mentality is that we don't need you. You're already an organic. You know what's funny? You know what's funny? It's not even that they think that they need you or they don't need you. they don't know how valuable you are.

19:18Right? And then it's just like what? And more importantly, I think we all have to start debating how valuable they are. Yeah, makes sense. Like what's good about you? You get paid and you get national exposure. You can get national exposure now. Your fucking YouTube videos are seen by a hell of a lot more than every fucking commercial that runs this year globally combined. Let's just take a second. I want everybody here to take a second and listen to me real carefully. The video that you posted two weeks ago is consumed more. Consumed. Not aired. There's a lot of commercials being aired. Nobody's watching them.

19:55I just think you need to get yours, your value worth. I think you need to start thinking about how much leverage you have. For you to be the next J-Lo within this, you can't do the same blueprint that J-Lo did. I gotta go my route. You gotta play a 2018 to 2023 route. You need to be worried about kids that are playing on Twitch and getting your music into their channels. You need to be thinking about startup brands that are going direct to consumer, that are targeting the Latin American consumer. You need to be doing you. You need to reverse it. They need you. And their check is getting less and less interesting, thank God, right?

20:35Make it a couple dollars. And more importantly, the more you realize how much or how little you actually need, The reason I'm dangerous is I don't need to make a lot of money every year, which means I'm putting the energy into the bank, giving myself long-term leverage. So you got the number of the lemon company you've seen so I can call them? I do, I do, but we'll be happy to help. You need to look at all of it. There may be a very authentic, first of all, you start with authenticity. If you drink an orange soda, we need to look at Fanta's U.S. strategy first. you want to talk about a brand that could really get popping because of you and needs to like Fanta should team up with you and three four others they could be off to the races like Fanta is the most interesting soda brand to me because it's actually culturally relevant outside the US they want to do more business in the US but they don't have the right faces so I think you have the options I think you have the leverage now it's all so new it happened so fast the second time around you have to be thoughtful about it but I'd go backwards I would literally with the team sit down and think about everything you actually like and just know that you could actually jam with them because then it's gonna be a better relationship anyway because it's not a check, it's authentic.

21:49Exactly. And whether that's a Kleenex or a sneaker or what have you. Anything. Anything. And if it's neutral, like if you don't give a f***, then I would go to something new, not old. Like you better really, like for me, if I started from the beginning, you need to love Hublot, like love it. Love it. If not, I take a step back. I mean, listen, there's more ears on your music right now than Jay-Z's music when he dropped that song. It's just, it's real, it's hard to comprehend because it all changed. And so when you deploy humility like you're deploying, it's sometimes hard to wrap your head around.

22:25That's true. But like, you can build the next Hublot with one mention. Could. You could. Now, you can't do that for every category, you gotta be thoughtful, sometimes it's good to take the checks, sometimes it's good to have the back end, sometimes it's good to floss, I get it, but you need to be really thoughtful about your brand strategy. And it needs to be forward thinking, not what has happened. And if you own a part of a company like that, you'll be like, looked at as the business guy, you know? You'll be like, wow, he's so smart, like, Nicky Jam, the businessman, like, taking part of this company, blowing it up, that jacket, whatever, like, even that is valuable.

23:03This has been huge for me. He's here. This has been huge for me. like right K-Swiss hadn't been hot for 20 years Iced Teas a long time ago K-Swiss K-Swiss I did a collaboration you did a collaboration with K-Swiss that's a sneaker that one yeah this was the first one right and this was a limited edition thing I just did and K-Swiss that's classic always look good and that's what you need to be thinking about if I'm you I think you think you're having your second act I think you're looking at Hublot and fucking whether it's Supreme or fucking Pepsi as like the thing that's anointing you, I'd reverse it.

23:41I would think about your life over, your whole life and think about what you fuck with. Or if you're neutral, look what I did. I was neutral, but I didn't want to do Nike and this other stuff. I went to K-Swiss because I'm getting the juice for bringing it back. If you bring back Nautica, you win. Yes, you're the champion. Got it? Well, that's already been back, right? Yeah, all that stuff. But if you were the reason Champion came back, your career would be different for the rest of your life. Not just riding Supreme or Off-White, got it? You've got too much juice right now. Back to me, just throwing out some ideas, I go really look at some brand in Colombia and bring it to America.

24:27If you build a brand here in America around something in Colombia that makes jobs for everybody, now you're talking about, now you're starting to get into 100 % or like Under Armour did for the Baltimore area they haven't left they rejuvenated that area with jobs the thing is about these brands having respect for the Spanish music for some reason I'm going to give you an example and no disrespect this is what I think I was trying to work something with Adidas two minutes I was talking to my guy I don't know what I'm talking about. I'm like, I gotta go fast. And I'm good freestyling with y 'all, man.

25:10Dude, I know what you, my man, let me save you time. I know what's gonna come out of your mouth. Listen to me, you're much more valuable than they understand because they're not as hip to the streets as you think. Adidas is a corporation. They will give first a deal to Pusha T that has one million followers than me that have 22 million. Brother, we see it every day. when I told K-Swiss who we should fuck with the list they gave me in hip hop I laughed I'm like you're just thinking big companies look backwards

25:40you're asking people who don't have a pulse so it's not a language barrier it's not definitely not because they've picked other people and honestly to be very honest with you you already went through this path you stopped making excuses if I'm you you know how lucky corporate America is that I'm not a rapper This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.

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