It’s mere days before Christmas, and Paycom Center is unusually quiet. 

The arena — home of the Oklahoma City Thunder, the reigning 2025 NBA champions — typically holds 18,000 roaring fans, but today, you could hear a pin drop. Yet even in silence, the Thunder’s accomplishments speak loudly. Division title banners hang proudly from the rafters. Scan past those banners and across the empty arena, and three words in bold orange and blue come into focus: Committed. Community. Together.

That trifecta isn’t just the glue that keeps the Thunder ahead of the competition — it’s the ethos of Simon Gebrelul’s ISLA Management. Since launching ISLA in 2018, Gebrelul and his co-founder, EK, have proved that a powerhouse management company can be built on a foundation of friendship — at least when the friends in question are some of the biggest stars in sports and music today, including Thunder superstar and reigning NBA MVP Shai Gilgeous-Alexander and Grammy Award-nominated, multiplatinum singer GIVĒON.

“My clients are my friends,” says Gebrelul, 34. “I met some of them playing video games early on when I was 16, 17, 18. You go hard for the people you care about. I’ve gotten in front of huge companies and burned relationships because I was standing up for clients. When you love them that much, the relationship with whatever brand doesn’t matter. I’m going to live or die on the sword with my client. You lose that when you try to become more of a company than a family.”

An avid sports fan, Gebrelul always dreamed of working in the NBA. He managed basketball players independently in the mid-2010s on a day-to-day basis but felt pulled toward something more. “[Basketball] was my first love,” Gebrelul says. “That’s where I started a lot of my business relationships. But I always had an admiration for the music space. I had friends making music at the highest levels, and artists and producers would lean on me for advice for their music and beats. I saw a lane on the music business side, so I entered that world first.”

With a roster of just music clients initially, Gebrelul has led with a family-first approach — he’s never recruited clients, nor does he plan to. In fact, he and EK met through a mutual friend at a party in 2017. At the time, EK worked in banking, and she saw that while Gebrelul “had all the tools to be great,” he needed “a bit more structure and formality in how he was operating.” She quit her job to co-found ISLA with him, and now sees the value in its family atmosphere. “Simon forced me to look at things through his lens by leading with love, compassion and doing things for the people you love,” EK says. “Sometimes that means putting them ahead of yourself, and sometimes even ahead of the business.”

“Sports and music are huge parts of the culture,” says Gebrelul, sitting alongside Gilgeous-Alexander and GIVĒON center court at Paycom. “There’s so much overlap in both of those worlds. It’s not easy to make them coexist all the time. Sometimes it comes across inorganic, but if you do it the right way, you can bring the best of both worlds together.”

Gebrelul met Gilgeous-Alexander in 2016, when he was just a teenager with hoop dreams playing at Hamilton Heights Christian Academy, a high school with a nationally recognized basketball program in Tennessee. Their first in-person meeting occurred when Gilgeous-Alexander was representing Team Canada during the FIBA Americas U18 Championship. Finding that they shared both lofty ambitions and a fondness for childish humor, their bond deepened over time when they started working together during his rookie year with the Los Angeles Clippers. A turning point for Gilgeous-Alexander’s career came in 2019, when he was traded from the Clippers to the Thunder — and morphed into a full-fledged superstar.

Last year, Gilgeous-Alexander — long known in NBA circles simply as “SGA” — had a historic season. The four-time All-Star won his first MVP award after leading the Thunder to a league-best 68 wins, a franchise record. His nimbleness and lethal midrange skills helped him average 32.7 points per game en route to an NBA championship and his first scoring title.

As he racked up those accolades over the past year, Gilgeous-Alexander has quietly redefined how a reserved athlete (albeit one with modelesque presence) playing in one of the nation’s smallest markets can position themselves in mainstream media. In tandem with his client’s rise in the NBA, Gebrelul says he took a “highly intentional and carefully curated approach” to building his off-court portfolio, staying “disciplined in our willingness to say no” and securing brand partnerships for Gilgeous-Alexander with everyone from AT&T and Converse to Audemars Piguet and YSL Beauty.

“I’m 27 years old. There’s a lot of games to be played, a lot of game to be learned,” Gilgeous-Alexander says. “That’s my motivation. I would be wasting the opportunity if I didn’t see how good at this game I could become. Wherever that takes me, it takes me. It’s taken me places so far, I’d say.”

Athletic excellence has translated to impact off the court for Gilgeous-Alexander, who’s now a part-owner of the newly renovated TD Coliseum in his hometown of Hamilton, Ontario. Following a renovation led by Oak View Group, the venue reopened in November with a concert by Paul McCartney and currently hosts both concerts and home games for the professional box lacrosse team the Toronto Rock. As a kid, Gilgeous-Alexander used to travel to Toronto with his younger brother and mother to attend concerts; now, he has helped to bring mainstream music back to Hamilton itself as an investor in the venue, with artists like Nine Inch Nails, Charlie Puth and GIVĒON slated to perform there this year. Last August, Hamilton offered its prodigal son the key to the city and named a street in his honor.

“Music has always been a huge part of my life,” Gilgeous–Alexander says. “I want this arena to be a place where artists feel excited to come through, where fans don’t have to leave the city for world-class shows, where some of my friends who are musicians can perform and where we’re truly investing back into the local economy. This is about creating opportunities and putting Hamilton on the map in a bigger way.”

ISLA’s influence, too, extends well beyond the hardwood. In 2018, Gebrelul met R&B artist GIVĒON at the home of his longtime collaborator Sevn Thomas, a producer who also happened to be a Gebrelul client. Known for his baritone voice and understated bravado, the musician immediately stood out to Gebrelul, EK and Gilgeous-Alexander, who was present the night they all met.

At the time, GIVĒON was working as a server at Bubba Gump Shrimp in Long Beach, Calif., and walking dogs while quietly honing his craft alongside Thomas. With Gebrelul in the fold, GIVĒON continued to work toward his breakthrough opportunity — and his patience paid off when, in 2019, he landed a deal with Epic Records; in March 2020, he appeared on Drake’s “Chicago Freestyle,” which became his first Billboard Hot 100 entry.

Even amid the uncertainty of the COVID-19 pandemic, his career quickly picked up momentum: His 2020 single “Heartbreak Anniversary” became his first top 20 Hot 100 hit as a solo artist, and he secured his first chart-topper in 2021 as a featured artist on Justin Bieber’s “Peaches.”

Last July, GIVĒON released his second album, Beloved, debuting at No. 8 on the Billboard 200. A deeply felt R&B album rooted in heartbreak, solace and hope, for which Thomas produced on every track, the project was inspired in large part by the work of iconic Philadelphia Sound pioneers and production duo Gamble and Huff. Beloved was nominated for a best R&B album Grammy, and last November GIVĒON sold out New York’s Madison Square Garden.

“I used to always tell the story of how I was a server, but now I’ve been in music longer than I was a server, so I can’t even say that story anymore,” says GIVĒON, now 30. “I used to be like, ‘Can you believe that it worked out?’ Now it’s like, ‘Bro, you can’t keep saying that story. We all know it worked.’ ”

He’s now one among many marquee names in hip-hop and R&B on the ISLA roster, along with producers and songwriters like Thomas, Boi-1da, OZ, Jahaan Sweet and, in his capacity as a producer-songwriter, Grammy winner Leon Thomas (who just took home two awards as an artist at the 2026 ceremony). OZ earned a No. 2 debut on the Hot 100 with Drake’s “What Did I Miss?”

“Those guys are massive hit-makers in their own regard,” Gebrelul says of that pool of behind-the-scenes talent. “We manage a really special group and they’re obviously a lot more low maintenance. They’re at the point in their careers where they can be selective with who they work with, which is probably the No. 1 blessing as a producer.”

And with ISLA thriving in both sports and music, Gebrelul feels like his own blessings are coming together. “In my first year of music, I got Forbes 30 Under 30 and Billboard 40 Under 40,” Gebrelul says. “Even though my first love was sports, I’m now able to exist in these worlds simultaneously — and at the perfect time.”

Shai and GIVĒON, how has Simon helped shape not just your careers, but the way you think about career longevity and legacy?

GIVĒON: When I met Simon and Sevn Thomas, I was still a server. I was kind of antsy about everything when it came to deals and how everything worked. I wanted to do things right away. The biggest thing Simon taught me about longevity was building up your leverage. That comes with quality, being patient and having some business acumen, too.

Gilgeous-Alexander: Simon came to my life as a friend first, and our relationship was organic. I had an approach on the court that I hadn’t really homed in with longevity and being professional. He showed me how to take that approach on the business side of life. From there, everything skyrocketed. He unlocked a bunch of doors that I hadn’t even seen. He changed my life.

GIVĒON: He’s a wizard.

Simon, what’s the hardest part of managing superstardom across two industries where the pressure, pace and public expectations sometimes differ?

Gebrelul: It’s two different types of pressure. In Shai’s field, he’s on the court and that’s where his results come from. I can’t really [influence] that. Whereas in GIVĒON’s world, it’s more subjective. You got to have more input. You got to think about your rollout, the creative and how the songs sound because music is subjective. Your whole circle at the table can say, “This is a perfect album,” but if the world doesn’t receive it like that, there’s nothing we can do.

Both [Shai and GIVĒON] make it real easy by being amazing at what they do. They love their craft.

Gilgeous-Alexander: I’d think it would be easier for Simon because [for him] it’s the same standard to reach success no matter what you’re doing, and he holds you to that. We’ve gone into deals and Simon will think higher than what I would think about myself, and I’m a very confident dude.

GIVĒON: [When it came to my record deal], I thought it was a nice number and then [Simon] 10x’d it. That’s why I’m also able to take time with my creative process, because we don’t say yes to anything and everything. We’re financially healthy.

GIVĒON, you’ve checked major career boxes already, from earning multiple Grammy nominations to selling out Madison Square Garden. From a competitive standpoint, what still drives you?

GIVĒON: I want to do a full arena tour. That’s one of the main things that drives me, just because the quality of the show could be higher for each and every city. The MSG show, we added a couple more pieces, so I want everyone to get the same experience all across the board. And I want a Grammy. Please. I’m at eight nominations now. I would like one, please. (Laughs.) (GIVĒON lost out in the best R&B album category to his ISLA mate Thomas.)

Gebrelul: Shai actually met GIVĒON the same time we did. He was a rookie on the [Los Angeles] Clippers. Me, Shai and EK were chilling and were about to pull up at Sevn’s house. I think Shai just finished a game and GIVĒON was there and that ascension kind of happened at the same time. Shai was a rookie in the NBA, and Giv was [starting out] too.

Also, he was one of the artists that I called “COVID babies.” There’s a couple of artists that popped during COVID that didn’t have a live experience. His first festival performance was Lollapalooza, main stage. He kind of had to jump right into the deep end with Lollapalooza, Wireless, Coachella and Met Gala. It was a quick ascension.

Shai, you just had the kind of season most players chase their entire careers, winning MVP, an NBA championship and Finals MVP. How do you stay motivated after a year like that, and what’s left for you to chase?

Gilgeous-Alexander: I always say this: When I was a kid, I picked up a basketball to see how good I could become. My goals and aspirations were on a list — and were things that happened along the way — but my final [goal] has always been seeing what I can become. I’d like to think I’m far from that.

You’ve drawn Michael Jordan comparisons over the past year because of your style of play
and success. How do you balance the weight of those comparisons with your desire to define your own legacy?

Gilgeous-Alexander: I’d be lying if I said it wasn’t flattering. Being in conversations with a guy like that — who is the face of basketball — is pretty insane. Honestly speaking, I don’t really love them just because he’s three-peated twice, what he did for the sneaker business — and everything he’s been to the game — I think it’s a disservice to compare me seven years in to what he’s been. So, I don’t love them, but I appreciate them. That’s what I’m after, that’s what I’m chasing, and that’s what I’m striving for.

What does being ONE OF the best in R&B and music look like for you right now, GIVĒON?

GIVĒON: As much as there’s similarities between sports and music, that’s one of the things I don’t compare. I look at it more like a garden — there’s different types of flowers that are there. Some flowers are going to be bigger than others; it’s just a different thing, especially knowing that my sound is just a cocktail of all the music I grew up listening to.

People are comparing my upbringing to someone else’s upbringing and my personal stories to someone else’s stories. So, I don’t actually rank [myself], but there are technical abilities that you could rank, like how well you put on a show, how well you tell a story [and] your uniqueness. I will say if we’re going off technical and not just subjectiveness, I feel like I rank among the top.

Simon, how do you feel about R&B today?

Gebrelul: I feel like there’s been a resurgence in R&B — not to dis the genre because I don’t think it’s ever been dead. I don’t even like when they say, “R&B is back.” Objectively speaking, there’s been a resurgence the last couple of years. I think it’s in a great space. So many great, foundational R&B artists. Some of the older artists are still dropping music that resonates with a lot of people. A lot of artists are dipping into R&B and are dropping R&B projects that aren’t R&B artists first, like Drake with the [$ome $exy $ongs 4 U] album. Then, you have a lot of new R&B artists on [the come up]. Accessibility is at an all-time high. You can get a mic and make crazy melodies and you’re an R&B artist at that point, right?

Who was on your playlist in 2025, Shai?

Gilgeous-Alexander: I listen to four artists religiously: Giv, Drake, [Lil] Yachty and Justin Bieber. Two rappers and two singers. Those are my defaults. And then I just mix rappers in every now and then. If we’re on the plane, the vibes are a little different. So I have to work the room and not just play what I want to play. (Laughs.)

Gebrelul: Shai and GIVĒON are very notorious for being early on artists. That’s what I appreciate most. Shai’s list is super mainstream, but he has that layer of him like Giv. They’ll listen to artists, and we’re like, “Who’s that?” Three months later, [they blow up].

Simon, what was the preparation like on a day-to-day basis when GIVĒON was on tour and Shai was gearing up for an NBA season?

Gebrelul: It was a lot. We do a great job of staying together. I remember during the Western Conference Finals [in May 2025], and Giv had his Billboard playback in New York. EK stayed with Giv. I was [in Oklahoma City] the day Shai won Western Conference Finals MVP. I couldn’t miss that moment. We do a good job of trying to be everywhere together but also realizing that Giv is an artist — he moves around a lot. He has a great team that corresponds with us on the highest level and if there’s any type of hiccup, it gets corrected right away. Shai is a hooper, so he has his literal team around him. So it’s not like we have to be there in that regard.

What’s the toughest internal battle each of you has faced in your careers so far, and how did you overcome it?

GIVĒON: I can start by saying how the ascension was so quick. I was always aware of my ability and talent, but as I started to break through that ceiling, at a certain point it becomes impostor syndrome. You have to walk around like, “Yeah, I can sell out MSG in presale”; otherwise, you’re going to make yourself smaller than you actually are.

Gilgeous-Alexander: Telling people no and standing for what I actually want. By nature, I’m just a very laid-back guy. I live my life, do what I’m supposed to do on a daily basis and take care of who I need to take care of. In the past, I’d just go with the flow and not really care. If it wasn’t massive or detrimental [to me], I would let it slide. I was being taken advantage of because of my passive personality. I’ve just grown to understand the people that I want around me — whether I tell them no or yes — will just clear the room for the people that you really want around you. That will make life simpler in the end. Simon and EK have helped me with that tremendously through this process. I’ve definitely grown in that area the most.

GIVĒON: Simon will definitely tell somebody no.

Gebrelul: That’s definitely my favorite thing, but for me, I think my No. 1 battle since I started has been complacency. It’s something that’s not front-facing, because as a manager, you can’t show that, especially when you’re preaching to clients not to be. (Laughs.)

EK would tell me that I’m not where I should be and I would look at her crazy kind of in the beginning of my career. When you look back at it, you’re like, “You weren’t that crazy.” It’s easy to be complacent when you’re young and you meet a certain level of success. It’s kind of human nature to be a little bit complacent, but that’s why there’s a small percentage of people who touch greatness. It’s a different gear you have to kick into to erase complacency.

What does accountability mean to the three of you?

Gilgeous-Alexander: The truth at all times. That’s how I’d sum it up. No matter what, no matter how it’s going to make you feel, it’s always the truth.

GIVĒON: I’m a little more emotional. I wear my heart on my sleeve. Sometimes, I’d need to go away and write it out. Then, I’ll look at it objectively. I get stubborn.

Gebrelul: That’s a good question because that’s “the artist” versus “the athlete.” Shai can take the harsh truth, but he’ll dish it too.

GIVĒON: I need something sugarcoated.

Gebrelul: It’s not even sugarcoated. [GIVĒON] might be super defensive when he first hears it, but he’ll sit, let it register and be like, “You know, you’re right.” That’s the biggest difference between the two worlds in terms of accountability.

GIVĒON: (To Gilgeous-Alexander.) I don’t know how you develop that. Sometimes I’ll watch some of your postgames before I go on [stage].

Gebrelul: Shai’s postgame [interviews], he’ll take accountability for things that were legit not his fault. (Laughs.) He’s overaccountable. It’s good to be at fault, sometimes.

Shai, where did you get this thick-skinned mentality from?

Gilgeous-Alexander: My parents. We couldn’t come home and make excuses for whatever it was. Whether we got in trouble at school or played badly at a tournament on the weekend, everything was, “Did you do what you could control?” That’s all that they cared about. That’s what was taught to me and my brother at a really young age.

I remember coming home from a basketball game [with my cousin] and we could lose by 20. Both of us can have like 20 and 15 [points] at 9 years old — which was like 40 [then] — and it was our faults being the best players on the team. Things like that are instilled in us now. Heavy is the head that wears the crown.

Simon, when you think back to when you started ISLA, is this what you envisioned?

Gebrelul: Yeah, for sure. Shai has the hottest sneaker out right now [in collaboration with Converse]. A basketball sneaker you can wear off the court. GIVĒON just sold out MSG. He’s turning into an arena artist. He’s growing in his own regard.

Our team has to be bigger to support both things. I don’t think scaling means adding 10 more clients or 15 new managers. I get a lot of DMs, but growing comfortably is more my goal. Individual growth for everybody is more important than adding a bunch of people. ISLA is a very family-oriented company. My clients are my friends.

This story appears in the Feb. 7, 2026, issue of Billboard.