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Diplo (@diplo) is everyone’s favorite celebrity rebel. Born Thomas Wesley Pentz, known as Wes to his close friends, the musical mastermind has garnered immense success and worldwide recognition by staying true to himself and playing by his own rules. Veering off the traditional trajectory for music industry rise, Pentz first made his splash on the scene through his own form of rebellion as he unapologetically shied away from traditional label protocol and multilayered levels of communication, instead reaching his fans directly and releasing music on his own terms.

“I got really lucky with my management,” he recalls. “They knew I was kind of a punk and let me do things on my own. My original manager actually worked for me for free for a few years because he was like, ‘This guy really doesn’t give a s***. He’s just putting out music and leaking his own songs and selling mixtapes on his own.’ I would go to a freaking warehouse in New York and ship to Turntable Lab or drop them off at Kim’s Video in my car, and he just realized I was a big DIY guy.”

While he self-deprecatingly laughs at his old ways as we chat, it’s clear he was well ahead of the game—actually serving as a pioneer in the new-world music industry by following the single-release-dropping mentality versus album-release business model.

“At the time, the main goal was to put out an album and be front row at Target. There was so much power in the major label machine, but people eventually caught on to using the internet to take matters into their own hands,” he notes.

Continuing to make a name for himself as a worldwide phenomenon, Pentz dedicated his time and energy into his group Major Lazer, as well as his own brand under Diplo for years, run through his Mad Decent record label. While Mad Decent is still growing and thriving, more recently he’s turned his attention to his new Higher Ground label, which focuses on deep underground house music, serving as a return to his roots and a celebration of pure, original dance music.

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“I’ve been really good at building my business for the last couple of years for Mad Decent with my brands as Diplo and Major Lazer and finding projects to build from the ground up. We did the Mad Decent Block Parties for a while, which was awesome and had a really cool community. But for the last two years, I’ve been building the Higher Ground party, which is similar to what we did with Mad Decent, but more of a big house party vibe,” he shares.

“We started the parties, and I think our last one in San Francisco was the biggest one we’ve ever done, with all different stages built around these underground DJs. The crowd is different than I’m used to, and it was cool. So we’re continuing to build on that brand—we’re actually throwing the next party during Art Basel in Miami.”

For 2022, he’s working on a house project, and later in the year, there’s a lot more music to come that will showcase a completely different side of his musical depth. Whether it’s house music, EDM or even country, he’s proven his musical prowess excels in all different genres.

“It was kind of a joke at first,” Pentz recalls of the release of his first country album in 2020. “I even changed my name as Thomas Wesley because it’s my first two names, and that’s the way country guys do it. But it blew up and ended up going gold and did billions of album streams, so it’s funny, when you think about Diplo you think about house DJs playing Vegas, but the country album was actually the bestselling solo project I’ve ever done.”

Following the same mentality, he entered the country scene—which has a long history of hard-set guidelines and radio guards—by going against the grain and making his own rules.

“There’s rules you have to play with the major labels in country music because it’s so old-school and you typically take years to work your way up, and I was like, ‘I’m just a DJ dude and I’ve got a bunch of friends on a record.’ No country radio station played any of my songs, but we streamed everything instead of relying on the old guard of Nashville, and people there were like, ‘Wow, this Diplo album really made a stink,’ realizing you can be a little different and be crazy. Now Nashville is changing as a city, as is the industry, and it’s becoming super cool and inclusive. They’re embracing streaming, the songwriters and personalities are getting better, and there are gay country singers, singers of different races, and it’s really revolutionizing.”

Achieving so much of his success by savvily utilizing the digital networks and social media like TikTok and YouTube, Pentz has been able to capture the younger generation through one simple upload.

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“The Latin music industry does this particularly well, with artists like Bad Bunny, for example, or in rap, Lil Nas X. They understand the internet so acutely, and their brand becomes so much more real. You can interact with fans and they see what you’re doing. It’s real and tangible,” he explains.

“Lil Nas X literally knows how to wreck the internet with content and get people excited about it. Kids don’t want to wait in bed for a pop album to drop. They want to scroll through their phone and run through things they see and like. The power is back in the hands of the 17-year-old kids and not the major labels. That is great. Teens know how to shake things up like the Wild West, and the TikTok world is having a huge hand in this.”

Keeping in theme of putting power into the artists’ hands, Pentz, like many others, entered the NFT world earlier this year. He partnered with his childhood friends—who also happen to be one of the most famous and cutting-edge artist collaborators on the global scene right now—Samuel Borkson and Arturo “Tury” Sandoval III behind FriendsWithYou. With a history that dates back to middle school years in South Florida, Pentz, Borkson and Sandoval collaborated on a 10-part series to create an animated Cloud 10 series featuring FriendsWithYou’s famed little cloud motif set to a soundtrack created by Diplo.

Diplo with Sam Borkson and Tury Sandoval of FriendsWithYou; Diplo wearing: Louis Vuitton pants, louisvuitton.com; stylist's own tank.

As two worldwide creative forces coming together, Diplo and FriendsWithYou is the perfect representation of the famed artists’ brand ethos, which centers around the concept of friendship, positivity and bringing joy to others through art. Whether music or art, both Diplo and FriendsWithYou achieve this concept to the highest level of ingenuity.

“We were literally in middle school as bad kids, getting sent to detention and playing football together. I didn’t realize my life would be so intertwined with these guys 30 years later,” recalls Pentz.

“When the crypto scene exploded and NFTs came into the space, Tury and I were immediately trying to get involved. And when Wes called us up and said, ‘Yo, I want to do something really special as my first intro into this thing,’ it was the perfect opportunity,” says Borkson. “He made a mixture of video sounds and story lines that took our little cloud character on a deeper journey into this space—sort of like the beginning of a video game that we created with Wes.”

“He’s obviously such a homie,” Borkson continues. “Aside from being our friend, he’s been a great supporter of our art, buying crazy pieces and sharing our stuff with all kinds of artists. We have mad love for Wes.”

As a true creative, Pentz’s passion for the arts is indicative outside of the music realm with his growing personal art collection. As a loyal guy who values friendship first, he originally got into collecting through his personal connections, which then turned into a true love and appreciation for the craft.

“I originally got into art by wanting to support and purchase from my friends, like Sam and Tury. For the most part, I’d say my taste centers around a lot of pop art and punk kind of stuff, which is primarily because I grew up doing a lot of graffiti. Nothing serious, but I like the idea of tagging and writing things in random places. Growing up in South Florida, I actually met so many creatives who helped introduce me to this world,” Pentz shares.

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“I wouldn’t say I’m a huge collector because that is a full-time job. But I really enjoy it and I’ve been lax on my collection, just finding things that I love. I have some Warhol pieces and Keith Haring, Raymond Pettibon and even a lot of historical documents like flags from countries, old letters from people like Thomas Jefferson to Gandhi. For me, art should make you feel like, ‘Oh, this is something I love,’ that brings an emotion out of you. If you love it, that’s all that matters because it makes you feel good.”

That notion is precisely what has driven the FriendsWithYou brand to its global recognition and appreciation. With a refreshing philosophy centering on joy and positivity, it fills a void that many people are looking for in their lives.

“Their art feels like they regurgitate all the things that were in our childhood. They make it so even though there’s violence and s***** things in our day-to-day lives, it’s a silly and happy escape. They create a beautiful picture of all our memories. I’ll never forget it; they did my sons’ birthday party before they turned into art moguls with fine art and a Netflix TV show and made it the coolest thing ever. They did all the goody bags and decorated the space for all the kids. It was awesome,” he recalls.

This was particularly special to Pentz, as the single most important element of his life is his family, with three sons, Lockett (11), Lazer (7) and Pace, his 1-year-old. Taking after their wildly creative dad, the two eldest boys are already musicians in-the-making.

“Fatherhood so far has been amazing because I’ve had great mothers of my children. It’s so cool to have grown-up, awesome kids, but as they grow it’s becoming trickier because they need so much more and I always want so much more for them. I want them to be the best they can be as their brains are now developing,” he shares.

Diplo with Tury Sandoval and Sam Borkson of FriendsWithYou; Diplo wearing full Louis Vuitton look, louisvuitton.com; stylist's own hat and boots.

“They’re really good at music. I’ve kind of forced them into lessons every week. They play the drums amazing, and the piano. They play the guitar way better than me. I gave them a musical background, but they’re even better than I was at those things at, like, age 10, so I’m happy. And they love my music—they went on a trip with their friends camping and made the kids listen to all of my albums over and over again on the ride, so they support me. I think it’s going to come to a point where I may have to take less shows eventually, because they need me and look up to me, and it makes me so proud of them.”

With a balancing act of a booming and wild, jet-setting career, a passion for the arts and a growing family that he treasures, Pentz has miraculously been able to find the beat to his drum and tend to each element of his life, all the while serving as an icon for up-and-coming talent. While he likes to shrug it off as if he’s learning along the way, his rejection of following the norm and remaining true to himself may just be the golden ingredient to mastering the art of the all-encompassing Diplo machine—and we’re here to embark on the wild ride.

“I think one of the most important things to keep in mind is to dig deep within yourself and find out what makes you who you are. What is your name? What makes you so special? Figure it out. Look into yourself and tap into what makes you stand out apart from the rest. And don’t live by the rules just because you’re looking at what everyone else is doing—do your special thing, whatever that looks like, and people will appreciate that.”

Artwork by FriendsWithYou. Full Louis Vuitton look, louisvuitton.com; stylist's own hat and boots.

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