Kaytranada played his highly anticipated set on January 5, 2025, brought to Cape Town by the Milk and Cookies team. Their first collaboration with Kaytranada dates back to 2015, making this a full-circle moment for everyone involved.

The concert was a resounding success, with fans flocking from across Cape Town to witness Kaytranada live – a truly once-in-a-lifetime opportunity. Rumors of a major headliner coming to South Africa in 2025 had been circulating online, with many journalists confirming the Milk and Cookies Festival and Music Week on October 31, 2024. Shortly after, Kaytranada took to Instagram to announce his South African tour, including stops in Cape Town and Johannesburg.

The festival itself was a spectacular display of the best the Cape Town music scene had to offer, culminating in Kaytranada's headline performance. From GQOM to Afrohouse and House music, there was something for everyone. 

However, the concert was not without its drawbacks. Many fans complained about the parking situation, with some not reaching home until 3:00 AM despite the show ending at 11:00 PM. This led to criticism of the festival organizers.

On the eve of their Johannesburg show, the Milk and Cookies team sat down with me to discuss the Cape Town festival and set the record straight. This is their story, raw, uncut, and honest.

"I lead marketing for Milk and Cookies, encompassing social media, advertising, publicity, assets, and all things marketing-related," shared Chase Freeman at the start of the interview.

Jhordan joined shortly after, introducing himself and sharing his role: "Cape Town was amazing! The people are incredible, and the weather is fantastic. The show itself was truly exciting. I think people had a really good time, aside from the parking situation (laughs). But from the actual experience, we received very positive feedback. We are working on making improvements to ensure the Johannesburg concert is even better. My role is head of sponsorships and general relations. I deal with brands and sponsors, connecting the dots behind the scenes whenever possible, whether it's artist liaison or anything else. Thank you for this interview; I truly appreciate you taking the time."

I began by asking Chase what it takes to bring an established act like Kaytranada to South Africa. "I can speak to that. Kevin, our head of logistics and production, handles bookings as well, but he's not here right now as he's on-site. We've been producing shows since college in 2009. We noticed a void in the events scene back then. We were very young and ended up producing a show for Wale, realizing that it was different from simply throwing a party, which is how we started. We learned the concert industry, and there's a formula to it. It involves understanding the artist, their management, their agents, and cultivating strong relationships with venues. On top of that, having a community is paramount – that's the cornerstone for us, building a community. We're not just here to produce shows, but to bring people together. That's the essence of the Milk and Cookies brand – fostering a diverse community through a diverse range of music. We're not just here to do shows, but we're here to bring people together. That's what the Milk and Cookies brand stands for – bringing together a diverse range of music and a diverse group of people. We grew up and came together in college, realizing that we have similar tastes, but they were diverse. That's why we built the festival to cater to people like us who enjoy R&B, Hip-Hop, House, EDM, and Afrobeats. Those are primarily the genres we work with, from Funk to Soul. For us, the foundation of building a festival lies in production and cultivating strong relationships with artists, which requires time and effort. We've been fortunate to be early or on time with certain artists – our platform is about music discovery. We brought Kendrick Lamar in 2011 when he released 'Section 80,' J Cole on the 'Warm Up,' Wiz Khalifa, Jack Harlow, and Summer Walker. It just kept growing – Kaytranada headlined our first festival in 2015. So, this is truly a full-circle moment for us, bringing him here to South Africa after ten years. But we could only achieve this because we've worked with him throughout his career. I believe the ability to accomplish something like this is a significant milestone in festival production."

Doing anything in the music industry is never easy, often presenting numerous challenges. I inquired about the challenges the team encountered while building Milk and Cookies into what it is today. "It's a business, so you have to navigate the process of building a business, raising capital, and hiring the right people. The good thing is that all four of us are brothers – we stuck together throughout this. Even when faced with significant challenges, we persevered because we love what we do. I don't think we would still be in business if we were just doing this for a job. We stuck together because we knew what we wanted to accomplish. Our goal was always to expand our brand and one day reach the scale of a Coachella. For us, it was about overcoming all the difficulties. They say that ten years is a kind of tipping point. After establishing our other company, Atlantic division, Milk and Cookies was formed in 2015, so it's been ten years. Every business faces challenges – it's about having the bandwidth and the belief. When you have a vision and see others give up, you're just one opportunity away from your big break. For us, expanding globally and moving here has been well-received. We've actually noticed a lot of similarities between our situation in Atlanta specifically and Johannesburg, as well as Cape Town. The similarities between the music, the renaissance – you see Gunna and Tyla collaborating on songs. There's a genuine connection between Atlanta and South Africa. Even things are happening between our governments, like exchange programs – it's truly inspiring to see that bridge and that connection being built. I hope to see that grow even further, and that's an ethos we want to continue to build," Chase shared enthusiastically.

Jhordan shared his perspective when I asked if they ever thought they would reach this point in their careers. "The short answer is yes. You never know what form it will take. We always envisioned our work being global. We always had this vision of connecting with other communities beyond our reach or the communities we thought were beyond our reach. I think a significant part of what we do is intuitive, much like music itself. There's a certain magic to music. There's a reason that music created by a child in a rural part of the world can resonate with someone else across the globe – it's not like the song can physically travel, but it's a frequency. I believe that a significant part of our brand is connecting with people and communities that share that same vibration and energy. We always felt we could take this thing really far. We made some changes years ago to our entire management team and ownership structure, which allowed us to truly spread our wings. I don't think we specifically knew we would land in Cape Town and Johannesburg. But we knew we were flying somewhere. I couldn't have asked to land the plane anywhere better than these two cities – Cape Town and Johannesburg. We've fallen in love with Cape Town, with all its energy and beauty, the people, the environment, and the culture. Similarly, we've fallen in love with Johannesburg, which is a completely different culture, right? The nightlife is crazy. And we see ourselves in both of those things. To answer your question, yes, we envisioned a bigger picture for ourselves, and we still envision an even bigger one now. I don't think it's up to us to decide where it goes next. Part of that is simply staying aligned with the right energy and alignment."

Before coming to South Africa, Chase and Jhordan had the opportunity to hear stories from friends and family about the rich history of South Africa. "Chase and I probably have different answers, but I think we can both share. From my perspective, I had an uncle who worked in international banking. He worked across the continent in Zambia, Zimbabwe, and had some experience in South Africa. He was the first person I knew personally who did things on the continent, and I also have a cousin who lives in Senegal who opened a school there. I think Africa was much closer to me than it was for many other Americans, at least when we didn't have exposure to it. With all the depth that the African continent possesses. When it comes to South Africa, this is so random, but I had an ex-girlfriend who went to a school Opera had opened here. After college, she was the next person I knew who had exposure to South Africa and told me how beautiful it was. I had these little moments throughout my journey where it became clearer and clearer. Our other partner, Kevin, who isn't on this call, wanted to come for his birthday, and I don't know his reasoning, but he really wanted to come to South Africa. Once he came (neither Chase nor I were on that first trip), they went to Durban, Mpumalanga, Cape Town, and Johannesburg and saw so much. After that, the picture of what South Africa was like became much clearer. Kevin shared that it was beautiful, Amapiano music is a vibe, the parties were great, and he felt a real connection between Johannesburg and Cape Town in significantly in different ways. The idea of South Africa became clearer after that. 

When I came here personally, I would go to restaurants, hear the music, and meet people. I then realized that this is the vibration I live my life on, even back home. For me, it was a natural affinity, and I kept getting closer to it without even realizing it. The other part for me is that we live in Atlanta. There is a twin cities link between Atlanta and Johannesburg, as well as Atlanta and Cape Town. The fact that our mayor even flew out here for an emergency trip in December speaks volumes. That whole relationship really stemmed from the connection between the Mandelas and Andrew Young, which is also rooted in the civil rights movement in the States and the end of Apartheid in South Africa. For me, there are so many ties between all these cities, with so many layers of depth that I can understand and appreciate. I think that’s why we’re able to connect with the people and the cities—not that we know everything, but we are still learning more. We do feel something in the air that makes us feel connected,” Jhordan shares as he waits for Chase to answer the question.

“A decent amount of what Jhordan just spoke about, but also I have a family friend who stays in Ethiopia. The first time I came to Africa, I went there. He managed Teddy Afro and worked with the Marleys. He always said I should go. He would often speak about many countries in Africa. For a while, I was telling him where our career was going and what we were trying to do. He was just so passionate about it. He was probably the first person who said it was a no-brainer to come to Africa because there’s so much to do here. He was really active in the space. Before Kevin came (who spoke about it for a full year), this was around COVID in 2020, and there weren’t a lot of tourists around. He had a different type of experience. Like Jhordan said, the connectivity between the music and the renaissance—if you think about Atlanta and Johannesburg, these are places with a strong community of creators and business people who build their own things. We work and collaborate with each other, and it’s very similar. If you go to Atlanta, you’d say it feels like home because we all have similar missions when it comes to building our creative scene. It’s massive; you can see it bubbling up now, and this is just the beginning. That was probably my first two introductions.” Chase added. 

As we discuss the music scene in South Africa, Chase spoke highly of the growth that has taken place in the country. “It’s amazing. On our side, Afrobeats came first. Then, after that, we saw Amapiano making a massive entry. There are Amapiano parties in every city. So when people ask us if we listen to it over there, we’re like, ‘Yeah!’ I go to these events to get a sense of South Africa when I’m not here because I miss it so much. Even the scenes from R&B, Hip-Hop, and House are growing as well. We love it so much. That’s why we want to celebrate all types of music. Our festivals are a bit different compared to others. We don’t just put on a lot of artists; we celebrate DJ culture a lot. I don’t think a lot of festivals celebrate the DJ. It’s always about the headliner. You don’t have to do that to bring people out. We want to dance and have a good time. We don’t always want to just stare at an act and watch them perform. That’s not what we’re trying to do, especially after COVID, where you can find an affordable ticket knowing that you’re going to meet cool people, and no one is staring at their screens. The reason our lineup is all DJs is because we’re celebrating DJs and putting them on another platform. We want them to perform with international acts that people love and celebrate. In turn, the DJs get a bigger spotlight. There are a lot of DJs, but there are so many great ones we want people to hear. We made sure to include people you may not know. At a Milk and Cookies festival, there will be artists you might not know unless you’re super tapped in. We want you to come and become a fan of someone new. That’s one of our goals in setting up our lineups and bringing diversity to the sound. DJs are a great way to do that because they can play whatever they want. We’re very attuned to the sounds they play. It’s a multi-genre experience every time.”

Jhordan elaborates on the research behind curating the DJ lineup, the preparation involved, and their focus on discovering Surreal Sessions. “That’s a great question. I was actually going to dive into that. A big part of it is that we want to tap into the culture wherever we go. We want to make sure it’s done authentically. A good portion of our team is actually from South Africa. We’ve been coming here for the last four years now. This year, we’ve come about three times. We wanted to understand the people and the culture well—what the style is, what the vibe is, and what’s next. We heard a lot of people saying they’re ‘over Amapiano,’ but there aren’t many Afrohouse or Afrotech acts. The sound is evolving here because people have been on it for so long. When we went after our lineup, we empowered our team members, Amirah and Kevin, to build up the lineups under Kaytranada. We knew we couldn’t just tap into the underground scene and understand who’s emerging. So we needed people who really knew that and who would be part of our team for the entire project. On the music curation side, they had a big hand in it. Our trip back in September took us to Bridges Academy, where we met Vincent and Loyd, who own Therapy. They explained the DJ culture here and told us how long Surreal Sessions had been around—they’re legends here. As we became closer with them, we knew we had to include them in our lineup. We heard their sets and instantly knew it was exactly what the lineup needed. We knew it would also translate well to our international guests, who haven’t heard some of these sounds. The talent here is incredible. We also wanted to expose our international friends to authentic sounds. We had about 400 Americans on the ground in Cape Town, so many of the parties were American-themed, even though they were happening in Cape Town. We wanted our festival to show people what Cape Town really sounds like, and that was really important. We had a second stage at the beach where we showcased more emerging acts. Again, the program was a joint effort. It wouldn’t have sounded the way it did if we’d done it alone. That’s always part of Milk and Cookies’ strategy—tapping into the culture and understanding where it is and where it’s moving.”

On the marketing side, Chase  shares the incredible work Darryl Hardy has been doing to ensure the concert’s visibility. “My good friend, DJ, who lives in Johannesburg, is a publicist. He has a team. I was watching the emails come in, and people were asking how we got their emails or if it was a scam. We had to make sure Kaytranada’s team understood how important it was for him to post about the concert as part of his world tour so the people of South Africa knew he was coming. We knew that questions like, ‘Is this real?’ would arise. DJ is our publicist, and he’s amazing. He was the one who did the research and went deep into the cultural ground and the larger outlets so they could hear our story. That was really important because if you’re coming into a place where nobody knows you, telling your story is key. We want people to know we’re here for the long haul, with good intentions, and we want to provide something really special, as opposed to just coming in and leaving. Some people have this sentiment, and we don’t want to be that. We love it here and aimed to make everything as affordable as possible while bringing in an international, Grammy-winning act. The tickets were significantly cheaper than on the rest of the world tour.”

As the interview wraps up, the Milk and Cookies team reflects on their future plans. “I think we can both touch on this. One thing we didn’t mention is that Milk and Cookies has a week of programming and panels, which is also super important to us and our brand. Mentoring youth and ensuring there’s information for people is key. We’ve had mentorship sessions, and the future for us is bringing back the Milk and Cookies festival week and continuing to have this conference and festival style where it’s free. You can go to these events, get information, and connect with people. In the U.S., events like these often cost a lot of money, which can block you from growing as an artist, entrepreneur, or businessperson. Our goal is to create something everyone can access, with real opportunities. I don’t know what’s in store fully, but we’re taking it day by day and seeing how the cookie crumbles. We’re excited because there’s so much we can do, and I think that’s what excites us. On our side, we see some of the acts who live here, so we’re familiar with them. It’s hard to just sell people on a conference, but if you bring something cool with it, the interest will be there,” Chase concludes.

“The music week is really the bigger vision for us in all of this,” Jhordan adds. “The concert is the most exciting thing, but the music week programming extends to panels, writing camps, and mixers. That’s where we see ourselves diving deeper into the culture and making connections between the U.S. and South Africa. We have a whole team here involved with the programming that’s not involved with the festival. It’s being led by Craig King, who has writing credits from Aaliyah to Chris Brown and Kanye West. He already has connections here in Johannesburg because he brought Usher here a few years back and even TI. The idea is how we can introduce students to the music industry and expose them to things that have worked well for us in the U.S. As Black Americans, we’ve had to fight for success in certain ways. If we can help the culture here move past some of those hurdles faster, we want to do that. South Africa is having a huge moment right now—many TikTok trends come from here. Uncle Waffles did Boiler Room, and that set was one of the craziest I’ve seen. That’s how I met her and her team. Tyla won the first-ever African Grammy. There are so many levels of talent here, and so many jobs that kids don’t even know about in the music industry. We want to expose them to that. You don’t have to be an artist—you can be an agent, a lawyer, an accountant, even a stylist. There are many ways into the industry, and we want to help expose that. We do a similar program in Atlanta around June as part of Milk and Cookies Music Week. We had Flo Milli perform and various panels with people from the Recording Academy. So we wanted students in Atlanta to know the same thing. Eventually, we want to bring students from Atlanta to  Cape Town and Johannesburg for Music Week and vice versa. We’ll see phenomenal results as we continue that over the next couple of years,” Jhordan shares excitedly.

As Milk and Cookies gears up for its Johannesburg festival, they share their vision, cultural identity, and how they plan to connect the three cities of Atlanta, Cape Town, and Johannesburg through sustainable music develop

For more on Milk and Cookies, read my interview with  Greg Burton who deals with brand management and nightlife, as well as Chase and Jhordan below:                                                                                                                                               

Daniel: How was the festival for you? 

Greg Burton: On my side, it was a great experience. I spoke to a few people from general administration, VIPs, friends, and family. Everyone had a great time despite the track situation. Outside of that, the music was great—the DJs were amazing, and all the sets they played were on par with the experience. We will try our best to repeat what went well and amplify anything that needs improvement. But it was good in my books.

Daniel: What was the highlight of the festival for you?

Greg Burton: My highlight was the community and seeing the passion for music you guys have compared to the United States. There was no beef or altercations—just good vibes. The crowd and atmosphere were my highlight; it was good to see.

Daniel: What was your highlight of the weekend?

Chase: For me, it was the music program. The mentorship sessions with management and songwriters were incredible. Everyone who joined seemed to get a lot out of it. They kept coming up to us and sharing that they had never seen anything like this before, that it was needed, and asking us to do something like this again. I got to speak to kids with their own clothing lines or even up-and-coming DJs. We were all in artist management, so we were able to shed light on things and give them advice. We could also give them direct contact and let them know they could message us. We’re all mentors and have mentees. That would be my highlight—to make sure people are heard. It’s not easy to break into the music industry. As people of color, we are making things, but don’t always own it. The fact that we can be founders of our company and have a platform to utilize for good is huge. We only champion positive music on Milk and Cookies lineups. You won’t find anything that would be destructive to our community in our lineup.

Daniel: What was your highlight, Jhordan?

Jhordan: I would say the panels as well. Because when you do these panels, you don’t know what the reaction will be. You don’t know if people will show up or if they’ll really care. The level of engagement that everyone had who was there was incredible. We had five sessions, and we had people stay for six hours. That’s a whole work shift or a whole school day. They stayed the entire time, engaged. That was incredible to see.

For more on the production side of Milk and Cookies, read my interview with Kevin Reese below:                                                                                                 

Daniel: What goes into the production of a festival like this?

Kevin: I think it first begins with the artist you're working with. Different artists have different technical needs when it comes to production. Some need a bigger stage, and some need a smaller stage. But it all starts from there. After that, you get into your actual suppliers. You have different loading days with the various suppliers, whether that's fencing, LED walls, toilets, marquee tents, or parking structures—all those things. This is obviously packed into months of planning as you interview different suppliers who will be building on-site. It’s a very long and tedious process.

Daniel: What was your favorite set or show that you worked on?

Kevin: I would say it was the set that we did last year, probably for sentimental reasons because it was our first major festival back after Covid. We did it for ourselves, and we did it for the city of Atlanta. There was a point in time when we thought the business wasn’t going to be around anymore. For us to build the event and bring the brand back to life was important. This one is also special as well. We are in South Africa, and we are building between both sites for about 20,000 people, which is exciting and stressful at the same time.                                                                                                                                                     

 Daniel: How do you deal with that stress?

Kevin: Day by day (laughs). You can’t think about it too much; you just have to keep moving.                                                                                               

 Daniel: It can be very stressful, like you shared, but what is that thing that keeps you going?

Kevin: We've been building this since we were 20 years old. I think what keeps me going is being able to look back at what has been accomplished and what the road ahead looks like. Every time you have a "level-up" moment, where you make it to another country and get to do something big, that’s what you’re building your brand and personal story on. For us, this is a legacy that we are building for our future families. So that’s what makes it worth it for me.

Daniel: What was your highlight of the weekend?

Kevin: Watching Kaytranada go up on that stage. When the headliner goes up, it’s like a climax moment. You get to see the artist and the fans interact with them—someone they’ve been waiting to see for months. All of the anxiety gets released, and you can enjoy the moment as a fan.                                                                                                                                                                         

 Daniel: What was the experience like working with the suppliers that you did?

Kevin: It was good. I would say that the biggest difference between doing something here and doing something back home in Atlanta is the difference in people. The people who helped us put together this event—we wouldn’t have been able to do any of this without the people we’ve met. Our new South African family, I could say. They’ve really come in clutch and introduced us to a lot of people, which has translated into what’s been built.