Masego’s touring in support of his debut album Lady Lady, a project that fuses elements of R&B, hip-hop, and soul into a sound he calls ‘trap house jazz’. Sometimes he sounds like Jamie Foxx, on other tracks he’s more like Gucci Mane—he’s a musical chameleon in rap and R&B. As we talk about Lady Lady, his viral hit ‘Tadow’, and the joys of travel, one thing becomes clear: Masego really loves this shit.

Hey Masego. You’ve been all around the world. How has travelling changed your perspective on life?

Touring the world combats ignorance, we all think we know about a place until we get there—something as small as me thinking everybody in Texas rides horses, or thinking of Africa as just a place, not as a continent, to then seeing South Africa and the other unique places there. There’s a bunch of other examples of thinking you know a place until you get there. I think going places also allows you to glean more culture and information and that spills back into the music.

Absolutely, travelling makes you realise how big the world really is. Any particular moment that realisation dawned on you?

I think in Shibuya Crossing in Tokyo, where you’re crossing the street alongside thousands of people. Or when they’re using brooms [in Tokyo] to shove you on the train so they can pack as many people as possible in. It helps you understand that it’s really hard to stand out in the world, because it’s so big.

Congratulations on Lady Lady. It feels like it’s an ode to the women in your life. How have your experiences with women influenced you?

I don’t think you can really choose what influences you, but when I’m freestyling or when I’m jamming with the band I always end up telling some story involving a woman. Whether it’s a conversation or a lesson learned, I just think that’s how it goes. Naturally, that’s what inspires me, and makes me want to excel.

“I don’t think you can really choose what influences you, but when I’m freestyling or when I’m jamming with the band I always end up telling some story involving a woman.“

It’s a pretty honest album. Was it hard to be vulnerable on wax?

Yeah, I feel like it’s easier to speak in riddles and metaphors, where you don’t wear your emotions on your sleeves. Then you see artists like the Erykah Badus of the world where they’re really just saying what they feel in a raw way, and the listeners just have to deal with it. I think just the courage to be a fully realised artist is a journey, it’s one that I’m still living.

What do you think you’ve learned about yourself on this journey of love that you take us through on Lady Lady?

I think I’ve learned how important it is to centre yourself. I used to have like option paralysis, where I feel like because I was travelling so much and seeing so many people that I thought I could never settle down. And true chemistry is rare, I really think like when you gel with someone physically, mentally and spiritually it’s a rare thing, so you’re less troubled by the “what ifs” in life. Another thing I’ve learned is that I’m moody, and that being alone helps me, in terms of creating and understanding myself. Also, love in general in the terms that unconditional love is what you’re trying to get to. I feel like we’re introduced to shallow love early on. Like, where you have to look good and always treat me right— a love that always lines up and a love where we’re always good friends. But I think you get that kind of unconditional love from a family member, and you try to find that same energy in a mate essentially. It took me a while to understand that, because before I was like “We gotta’ look good, and if not, let’s just find somebody that looks good!” But when I stopped trying to find that shallow love, I started to grow up.

As an artist that is so invested in the creation of music, does it ever make you feel disheartened that—and I feel this way—it’s as if music can be distilled down to simple streaming numbers on a computer?

Sometimes it does get frustrating, I think in the beginning mainly. Because in 2015 I was trying to outsmart the system. I’d be like “I’m gonna email every blog’s blog, and follow this person that this other person follows” and it was all these calculated tries to get attention. But, I think when I really tapped into making my best art, it kind of got easier, and I surrounded myself with the business people that enjoy the numbers and enjoy utilising what I do naturally and profit off it—in a pure way. I feel like compassionate business is the best business. And by no means is it easy, there’s tons of craziness going on. But I feel like you need to keep pure in making your best art and things will get easier, because people will gravitate towards it, and because it feels like everything is an advertisement these days. Like, sometimes I get upset with how much brands control how artists move. Like I don’t know if you’re wearing this outfit because you like it or because the brand paid you some coins to wear it. You know, that’s what I try to get away from.

“When I stopped trying to find that shallow love, I started to grow up.”

It feels like in fields like music and even journalism sometimes, that the only way to get paid is if some corporation sponsors it.

It’s one of those things where it’s like “Damn! The only time I get to get paid is when I partner with someone that has all this money?” But yep, that’s how it is.

Did you ever have the opportunity to go the major label route, and if so, what made you want to avoid it?

I mean honestly, I’ve never felt a sense of community when it comes to that. Like, back in the day, when I was 16 or 17, I’d get jealous of artists that had like 30 people waiting on them hand and feet to curate their career. But for my journey, considering my music wasn’t cookie cutter and didn’t fit into one category, it made sense to just make my own money. And it has got to a point where there are fans that are powering that lane where I can just do my own thing. Again, not an easy route, but I think there’s more happiness tied to it. Because I know a lot of signed, wealthy artists that are just not creatively fulfilled. I want to do everything I want to do, and I couldn’t do that without my own lane.

When I was researching for this interview, I got really interested in your hometown. What’s it like growing up in Newport News?

It gets a lot of its character from being a military town. It’s a place where you meet somebody from overseas early on in your life, and you kind of get a little bit of that feeling where there is something more out there. Even my father working at the military base in Newport News resulted in him coming home with atlases and stories of places he’s travelled, but other than that man, I don’t know what else to tell you about Newport News (laughs). I know some cool people there, but there isn’t a huge musical base there, which in a way is a good thing because it made me want to travel. If I was in L.A, I think it would become intimidating seeing Hollywood everywhere I go and it would make me question the possibilities of making it. But being from a town like Newport News, I didn’t know what the possibilities are, and I was the only saxophone player I knew. A place like that makes you think differently.

“I know a lot of signed, wealthy artists that are just not creatively fulfilled. I want to do everything I want to do, and I couldn’t do that without my own lane.”

Is your music at all influenced by your surroundings?

I was talking to a friend in London, and his chords sound like the weather there. I asked “Why do you keep making these minor sad songs?” and he said, “look at the weather, it’s Gotham City out here”. L.A has a certain sound to it too because there’s so much sunshine. So, yeah, weather impacts me a lot, as well as the architecture of building and nature, and that’s why it’s such a good thing to travel. Like people don’t know where I’m from or where the music is created. It’s a little thing from here and another little thing from over there, and travel is the epicentre of why the music is so eclectic. It has influence from everywhere.

It seems like that applies to other artists from Virginia as well. You’ve got people like Pharrell, Timbaland, Pusha T and Missy Elliot that make music without boundaries. What is it about Virginia that makes it different from other places in America?

I don’t see that sense of community in Virginia that I see in places like Atlanta where it’s like “trap is our thing and this is what we do.” It’s more like having a blank palette that you can colour any way you see fit. And it’s resulted in Timbo sounding a way, Missy sounding a way, man, even D’Angelo is from Virginia.  

Do you ever feel pressure to live up to those names?

Nah, you’ve got to live your own journey. There are times where I’ve been jealous of other artists success, but I feel like we’re really good at making it look like it was easy to get here. Like Instagram is just a highlight reel. And when I learned that, I just decided to let myself live my own journey. Because someone may make it look easy online but could have been doing it for 10 years. Just keep building and you’ll be alright.

“Instagram is just a highlight reel. And when I learned that, I just decided to let myself live my own journey. Because someone may make it look easy online but could have been doing it for 10 years. Just keep building and you’ll be alright.”

The term ‘trap house jazz’ is an interesting one you coined to describe your music. Why do you think the sounds of trap and jazz go so well together, and how have these genres stood the test of time?  

There was a guy named David Connelly, and we were just having a jam session and he came up with the term. He said “this is like some trap house jazz” because it had an elegance to it, the chords we chose were always sensitive and emotional, and I just loved drums that knock. In terms of those genres standing the test of time, there’s something about drums that dictate movements. Drums make an artist who they are— you know an artist based on what beats they hop on. Bass and drums always move people, you can change the chords and cadence around but the fundamental is the drum work and those middle sections. I don’t know the science behind why that works, but I think life teaches me that you go on trips, you clean your room, you make love, you eat, you cry, and there has to be background music for these activities. It’s like with movies— we have all these movies out and they still use things from the 70s, 80s and 90s. There are certain aspects of things being so pure that they stand the test of time.

Congratulations on ‘Tadow’ hitting 100 million views on Youtube. That song is interesting to me because it seems rooted in a simple, fun jam session between friends. Is that something we’ll see more of in your music?

Yeah man. It’s funny, yesterday, here in Melbourne, can’t remember where I was, but I remember hearing just the high hats from ‘Tadow’ from a store nearby. I immediately thought “Hey! They’re playing Tadow!” I just knew it from the high hats. I’m going to do more of that where you can always hear a piece of that music and it just sticks with you. I love that sticky sort of music where no matter where you hear it you can instantly recognise it, and all the new music has something like that. I want to make more music with FKJ as soon as he’s done creating in the Philippines.

So, what’s next for Masego?

I have to recalibrate. I gotta go somewhere with some good weather with my band and make some good music, eat some good food, and be thankful for all the good stuff.

You can stream Masego’s debut album Lady Lady here. 

Photography by: Gina Nero 

Photography Assistant: Courtney Owen