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The Big Boss Talks: Daddy Yankee Is Teaching Reggaetón’s Stars How to Own Their Careers

Daddy Yankee took reggaetón from San Juan to a global stage — and taught its stars a new way to do business. As he prepares his 10th album, he's showing why he's still The Big Boss.

Daddy Yankee sat in the tiny apartment he shared with his wife and three children in Villa Kennedy, a housing project in San Juan, Puerto Rico, listening to the sounds of the streets.

Cómo le gusta la gasolina!,” shouted the voices beneath his window, taunting the pretty girls who got rides from guys with flashy cars.



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A mi me gusta la gasolina, dame más gasolina,” Yankee chanted to himself — a refrain he couldn’t get out of his head.

It was 2004, and Yankee (born Raymond Ayala), then 28, was the leader of a burgeoning underground musical movement known as reggaetón. He knew the music was too big to be confined to the streets where he lived — and that it would need a megahit to bust out beyond his island home.

He took the chorus and flow to his friend Luny, of production duo Lunytunes, then the leading producers on the scene. Together with rapper and lyricist Eddie Dee, they fleshed out a track, adding the sound of gunning motors in the introduction along with Yankee’s rapid-fire verses and, atop Luny’s thumping, aggressive beat, that earworm of a refrain that sounded like a schoolyard taunt.

“The verse was so simple and easy to remember,” recalls Yankee today. He’s sitting in the library of the Palacio Provincial, a newly opened hotel in a 19th-century building in the heart of trendy Old San Juan — a 10-minute drive but a lifetime away from that old Villa Kennedy apartment. “People looked for a hidden meaning: Was I talking about alcohol, about drugs? But that track is completely literal.”

However his audience interpreted it, “Gasolina” turned out to be the fuel that reggaetón, and Yankee, needed to explode. The track became the second single from 2004’s Barrio Fino, Yankee’s third album on El Cartel Records, the label he’d created three years before. Distributed by Universal Music Group (UMG) imprint Machete, it debuted at No. 1 on Billboard’s Top Latin Albums chart — the first-ever reggaetón album to hit that spot — and stayed there for 24 weeks, ultimately becoming the top Latin album of the 2000s.

With it, Yankee irrevocably altered the sound and business of Latin music, not only propelling the rise of a genre that today is a global phenomenon, but quite literally building it from the ground up. He set the standards for everything from how reggaetoneros dressed to how their music was created to the way the genre’s biggest artists negotiated collaborations and song splits. Along the way, he introduced a DIY, independent business model — in which he financed his own recording, marketing and promotion; licensed out only distribution; and, most significantly, kept ownership of his masters — that has become a blueprint adopted by many of today’s top-selling Latin acts.

“[Daddy Yankee] was, and is, an inspiration for me, not just musically, but also as a visionary of the entertainment industry and a great advocate of our genre,” says Ozuna. Anuel AA matter-of-factly calls him “a legend” who “paved the way for many of us. We all started from the bottom, but he started from zero, when the genre didn’t even exist. That’s something only the greats can do.”

And Yankee hasn’t just stayed relevant; he has stayed on top, with six No. 1s on Top Latin Albums; a record 73 entries on Latin Airplay and 84 Hot Latin Songs hits since “Gasolina,” including the record-shattering, paradigm-shifting “Despacito” alongside Luis Fonsi. “He was at the forefront of the two most important shifts in Latin music,” says Jorge Mejía, president/CEO of Sony Music Publishing Latin America and U.S. Latin, of those two tracks. (Sony just renewed Yankee’s global publishing deal.) “Before ‘Despacito,’ the notion that Latin songwriters could collaborate on a world stage was not commonplace.”

Karol G says that partnering with rising acts is something she learned directly from Yankee. “You never perceive the guy as old because he collaborates with the hottest acts but also with the hottest new acts,” she says. “It’s something new artists are grateful for.”


Yet even as his reach has expanded to a global stage, much has stayed the same for Daddy Yankee. Over the years, he has continued to release his music on El Cartel through distribution deals with different labels. His 2007 bilingual album, El Cartel: The Big Boss, was distributed by Interscope because “they gave me the best deal,” he told Billboard at the time. It debuted at No. 1 on Top Latin Albums and a respectable No. 9 on the all-genre Billboard 200 chart, yet for his next studio album, 2010’s Mundial, he chose Sony Music Latin as distributor, and then Capitol Latin for 2012’s Prestige — again citing “the best deal” as his main reason for the switches.

At 46, he is still boyishly handsome, his buzz cut accentuating smooth skin and chiseled features. He’s lean from working out during the pandemic, wearing a white T-shirt, track pants and just the right amount of bling — chain, bracelet, ring and watch in matching platinum and diamonds — to exude self-confidence, not pretense.

He still lives in Puerto Rico, not just because it’s his home, but because it allows him to “stay in touch with the streets.” He still works with much of his day one crew, including publicist Mayna Nevarez and producer Luny. And he’s still married to high school sweetheart Mireddys González — who’s also his manager, CEO of El Cartel and an entrepreneur in her own right with over a million Instagram followers.

González (who declined to be interviewed) is widely known to wield broad influence over her husband’s career — which Yankee freely admits. “She’s the boss. She has always been the boss,” he says with a smile. (Later, I’ll catch the two of them chatting on the hotel balcony, Yankee whispering in her ear as her hands encircle his waist, as if they’re still teenagers.)

But final say on everything comes down to Yankee himself. “His attention to detail is unmatched,” says Simran Singh, his attorney for the past five years. “He looks at everything. He studies music today as he did 20 years ago — the numbers and the metrics, and he’s thinking about everything from the marketing side way before he releases a song.”

Why Daddy Yankee Is Still Reggaetón's Big Boss
Ambush T-shirt, Hudson Jeans pants, Y3 shoes, Richard Mille watch, David Yurman jewelry and Cutler + Gross sunglasses. Jai Lennard

Video director and graphic designer Carlos Pérez witnessed that first-hand back in 2004, when Yankee tapped him to design the marketing and visual strategy for Barrio Fino. “It took us like three days, him going line by line and asking, ‘What is this?’ ” recalls Pérez, who also still works with Yankee. “Finally, he said, ‘I want it all.’ Everything cost about $30,000 — not including the video. It wasn’t cheap for the time or for an independent artist. But he just said, ‘Can you break it down into three payments?’ He wanted marketing and the identity at the level of any of the top hip-hop artists.”

That strategic savvy is still evolving as Yankee prepares to release his 10th studio album, and his first since 2012, this fall on El Cartel but under a revamped global distribution deal with UMG — one that falls directly under the purview of CEO Lucian Grainge and UMG executive vp Michele Anthony, with Republic Records providing marketing and promotion. The deal — which Singh describes as “astronomical,” though neither he nor Yankee will disclose its value — also includes a partnership on a documentary about the history of reggaetón, executive-produced by Yankee and funded and produced by UMG, which will soon begin shopping it to streaming platforms and studios.

“Daddy Yankee is that rare artist who actually shapes culture and changes the world through his music and ideas,” says Anthony. “By elevating reggaetón into a global phenomenon, he helped fuel the explosive crossover popularity of Latin music. Through his music and entrepreneurism, he has created new business models and a platform that has launched the careers of many of today’s new artists.”


The agreement was crafted last year amid the height of the pandemic. Yankee, distributed by UMG since the 2012 Capitol Latin deal, still owed the company several singles. But rather than simply delivering those, he proposed a full album under a new deal — with UMG rather than Universal Music Latino.

“Fans are finally ready to listen to a full album on streaming platforms,” says Yankee. “We need to create a moment, and what better people than Sir Lucian and Michele Anthony to do so? Republic has a sense of [Latin] culture, and they have a lot of Latinos in their teams. [Universal Music Latino] was my distributor, but everything else, I did on my own. Now, UMG, they’re my partners.”

Though the album’s tracklist is still a work in progress, it includes the single “Métele Al Perreo” (released Sept. 2), a fast-paced vintage reggaetón track with a video paying homage to the Puerto Rican town of Bayamón, where Yankee trains daily at a boxing gym. And it will also include, as usual, collaborations with big names and up-and-comers alike. Yankee’s always on the lookout for the next ready-to-break star, as he once was — like hardcore rapper Eladio Carrion, with whom he recently paired up on a track.

“I’m supporting him and I’m embracing what he’s doing because I recognize the importance and cred of the artist that comes from the streets,” says Yankee. “My goal always was to create an urban culture, in Spanish, that would get recognition. And thank God, I’m approaching my fourth musical decade, and I’m seeing the results.”

Why Daddy Yankee Is Still Reggaetón's Big Boss
Daddy Yankee photographed on Aug. 5, 2021 at Palacio Provincial in San Juan. Jai Lennard

When did you decide to make music your career?

I had no other options. I had a daughter, so I thought, “I have to sing, otherwise how am I going to support this child?” The issue was, I was kicking off a career in a genre that didn’t exist yet. It was reggae, and it was rap, but it wasn’t reggaetón. Reggaetón culture started with us, in 1990, 1991. We started to release music and play in all the housing projects. And they started to pay us, little by little. We had a DJ and a turntable, and we used the same mic as the DJ, and they’d pay us $20, $50, $100.

What convinced you it could work?

We got our start singing in fiestas patronales [patron-saint celebrations common in Puerto Rico] at the housing projects. We had zero support or marketing and we were always the hit of the party. That’s when I realized we had something powerful in our hands. Plus, people were coming by to buy my cassettes. We were hot in the streets. Other people didn’t get it, but I did, because I’d been a big fan of ’80s rap – Run-D.M.C., LL Cool J — since I was a kid, and the same thing that had happened with rap was happening here, with us.

The new crop of reggaetón artists all say you are their inspiration, both musically and businesswise. The fact that you own your masters is always mentioned. Why did you take that route?

No one wanted to sign me. I tried. Honestly, no one believed in the music, period. They thought [reggaetón] was a fad. They’ve been telling me I’m a fad since 1990. They’ve been telling me to retire since 1990. I took Barrio Fino to EMI and Universal but they weren’t interested in that kind of music. Their offer was they’d pay me $10,000 or $15,000 to release it but they’d keep the masters. By then, I’d already released Elcangri.com [in 2002] and I had personally paid to manufacture 50,000 copies that I distributed on my own. If I’m getting $5 per album, and I sell 50,000 albums — $10,000 doesn’t add up. I knew, from the moment I started to manufacture the albums, that I wanted to grow, but I didn’t have the distribution system to reach everyone.


Were you doing this entirely on your own?

Yes. So when I went in to negotiate, I said, “I’m willing to be your partner. I need you to distribute my product and put me everywhere.” And they said no: “We don’t only distribute. We sign artists, and your music doesn’t sell.” That’s the mistake people make when they sit behind their desks and they’re not in the streets. That taught me to always stay in touch with the streets. Circumstances change when you grow as an artist and lose that anonymity and you’re not able to go out and connect with your environment. But here in Puerto Rico, I mingle with people, I go to the beach, I see how they consume music, I pay attention, and it allows me to create.

Early in your career, before you made your own albums, you recorded mixtapes and compilations. Did you cede those masters?

Yes. At that point I did, because we had no sense of the music industry. I didn’t know what a master was. When I put out Elcangri.com, I didn’t have to concern myself with anything because I was my own boss and it was my songs and my lyrics. I would pay for the beats, and that’s it. I made the investment, and everything else was for me. I didn’t even have ASCAP. We didn’t know we got royalties from airplay. Prior to [Barrio Fino], everything was verbal agreements, handshakes, song exchanges. Now, everything requires a contract [and monetary compensation]. Barrio Fino changed not only the culture, but the business model.

When you talk about the “business model,” you mean that on the one hand, the business was professionalized with contracts and agreements. But on the other, it was a new model in which you kept your master recordings — correct?

It was adopted not only by reggaetón acts — I have rockers, salseros come to me and ask: “How did you become your own boss?” Dude, because I had no choice. If no one wants to sign a talented kid today, he records himself, produces himself, writes the songs and engineers the album. He creates his own opportunities. I had to create my own opportunities and it became part of my DNA.

Why Daddy Yankee Is Still Reggaetón's Big Boss
Daddy Yankee photographed on Aug. 5, 2021 at Palacio Provincial in San Juan. Jai Lennard

You built your career performing. Today, some new acts have hundreds of millions of streams before they ever perform live…

That’s what I mean: Right now we have elevators, not stairs. And in music, you have to take the stairs to navigate the highs and the lows. Most of these kids talk to me, and what I see is they can’t deal with failures. They worked, they learned how to use Pro Tools and they exploded. They haven’t gone through a process. So when they hit that hard patch, which happens to all of us, how will they work through that? This generation doesn’t have the tools that are vital for longevity.

What advice do you give them?

Man, what I’ve always learned through the years: Go to the studio and do your best work. Music is what will speak for you and what will really connect with your audience. Social media is incredible but it doesn’t bring you revenue. Instagram doesn’t bring me revenue. If I owned Instagram, I’d post all my content there. But Instagram doesn’t pay me for my content. Neither does Facebook, Twitter or TikTok. YouTube pays me. And Spotify and Apple. Those are my allies. I release music, I give you content and your platform grows — but so does mine.

I’ve heard that when you work on a collaboration you have a fixed percentage you ask for, regardless of who it’s with or the number of artists involved. Is that true?

Yes. This is a hard topic to broach with artists, because they often know so little about the music business. The way I explain it is, “Papi, I’m not asking for more than I’m worth. Now, you want me on your album, I like to collaborate, but I don’t like to give away what’s mine. So, is the master yours? No? Then, from the onset I’m working for someone other than yourself. I’m not working for you, my colleague, but for whoever owns you, your boss. I’m a boss, I’m not an employee. You can’t ask a boss to work for another boss. You want to collaborate with me? I’m happy to do it, but remember I don’t need to do it.” I do it because I like the artist, or I really like the song.


Have you ever paid someone upfront to record with you?

Yes. When I’ve had to pay someone for the respect, I’ve done so. “I’m worth so much” — OK. I’ve always understood an artist’s value. If we collaborate and you charge me X, that’s fine. Most of my collabs are exchanges, but remember, there’s a very fine line there. What if my song works, but yours doesn’t? Hopefully both tracks work, but that’s not always the case, and I get that. I get that you have a value that you need me to cover so that in the end, we’re all in a good place.

But the business is flexible, and I’m flexible in many areas. I understand that sometimes, we’re talking about cultural moments rather than simply chart position. “China” [Anuel’s hit featuring Karol G, J Balvin, Ozuna and Yankee] is a good example. I saw it as a song that was important for the genre. When we do these collabs with many artists, there are times when [I’ve agreed to divide splits] in equal parts, because it’s important for the genre. Cultural vision is what has allowed me to take a big-picture approach versus simply focusing on the hit.

You’ve never had a traditional manager. Why?

In the past few years, Raphy Pina has stepped in as a partner. He helps Mireddys with the management, but I never had a manager per se. I had management offers and agency offers but back then, they didn’t understand Latin urban culture [Yankee is now represented by WME]. Agencies didn’t even have Latin divisions. Now they do. I got invited to Coachella [years ago], for example, and the pay was ridiculous. They kept saying, “It’s Coachella.” My reply was: “Get educated on what my value is, and who my fan is.” I was already playing [arenas like] Madison Square Garden and Staples Center, you get me?

Well, it took many years for reggaetón to be accepted not only in the mainstream U.S. market but also in countries like Mexico and Argentina. What role did you play in that?

I like to say I took the bullets. I wanted people to understand my essence, where I come from, what I represent. But at the same time, I wanted to take my culture to the very top. I can’t tell you there was a formula. Reggaetón was initially only known on the East Coast. When I released Barrio Fino, the West Coast didn’t get it. I’d go to Los Angeles or Mexico and people knew Daddy Yankee, but they didn’t know what reggaetón was. I had to take the culture with me everywhere so it became permanent instead of fizzling out like other genres where artists simply promote themselves. When I did promotion, I talked about all the artists in my album: “This is me. But this album also features Zion & Lennox, Plan B, Ivy Queen.” I had to play their music and say, “This is them. This is reggaetón.”


Your current album falls under your longtime Universal distribution deal. What would you have done if you weren’t under that contract?

Right now, being an indie is great, but if you don’t have a long-term major partner, you’ll be eaten up alive, because each platform is out for their own interest. But personally, if I didn’t have the former distribution contract, I would release my music independently on all platforms.

Don’t get me wrong: Major labels aren’t going anywhere. They have the power of their catalog, of hundreds of artists, and platforms need that content. A person like myself, who has leverage, can close deals directly with all the platforms and make more money. But, definitely someone indie will explode, or they’ll negotiate a release directly with Spotify and Apple, for example.

What new acts do you like?

All of them. I’m 100% pro Bad Bunny. I think what he’s doing is really important, and I support him to the millionth degree. Ozuna is a hard worker. [Anuel] brings the street and street swag with him. I really admire Balvin’s dedication, and he has been a pillar in bringing a new wave of music from South America. I like what Rauw [Alejandro] and Sech are doing. Maluma has extraordinary branding, and he’s underestimated. I love what Karol is doing.

Why Daddy Yankee Is Still Reggaetón's Big Boss
Alexander McQueen coat, Rag +Bone sweater, Givenchy pants, Pierre Hardy shoes, Richard Mille watch. Jai Lennard

It’s an exciting — and profitable — time for Latin music right now. What challenges still need to be overcome?

Paradoxically, the advantage and disadvantage is the same: We have the opportunity to be on one-on-one terms with fans, but fans consume you. They demand so much that the challenge artists have today is: How long can I last? I believe there’s a fan base that truly listens to and enjoys the music, and there’s a disposable fan base that’s simply looking for the next new thing and doesn’t allow the music to create experiences in their lives.

We [older acts] had the opportunity to create lifelong fans — not only me, but rock bands, balladeers and salseros who fill stadiums. They don’t have the same streams the younger generation has, but they sell more tickets. These younger artists have amazing numbers because they have amazing tools at their disposal, but I’d have done the same. I can’t be a resentful OG.

Now that it has become so big, is there any danger of the genre becoming disposable?

No, no. That’s why I never left Puerto Rico. I understand global music, but our roots are really important. That’s our identity, and we can never lose that identity. And I don’t think we’ve lost it. There are a lot of kids doing it, but they’re flying under the radar. That’s why you see so many of us recording with them, because we recognize the importance of the culture, even if the streaming numbers are not there yet. Right now, there are so many colors to choose from in our music. From reggaetón to trap, tropical, urban tropical, everything is working. It’s just about doing it right.

Why Daddy Yankee Is Still Reggaetón's Big Boss

This story is one of Billboard’s two 2021 Latin issue covers, dated Sept. 18, 2021. To read the other cover story on Karol G, click here.