Sitting in a cramped community centre in the heart of the 519, you can feel the friction between ambition and reality. It is the kind of space where the floorboards creak under the weight of oversized dreams. This is the headquarters for S.T.R., a collective of five young men who are currently redrawing the map of the local urban scene. Rak, I.G., M $wift, D Prince and C Milli are not just another group of kids with a SoundCloud link. They are a multi-hyphenate operation blending hip hop, R&B and streetwear into a singular community-minded engine.
But do not mistake their community spirit for a lack of edge. They are sharp, calculated and deeply aware of their position as role models in a corridor stretching from the 519 into the concrete sprawl of Toronto. Their annual backpack drives and empowerment initiatives are not just PR stunts; they are the foundation of a brand that refuses to leave its neighbours behind.
The origin story of S.T.R., or Sad Till Rich, sounds like the classic high school hustle, but with a more sophisticated design eye. Rak, the group's visual architect, started where most great ideas begin: in the back of a classroom with a pen and a notebook.
Rak says, "Sad Till Rich was first just an idea because I always liked drawing when I was in class and came up with a couple design ideas and S.T.R. was one that stuck with me, so I started showing some of my friends the first was Noah and I asked if this would be a sick design on some T-shirts, and he said ‘That’s crazy bro yah do it’ and then it started from one design to a bunch more and now we are dropping collections, so we are very happy to come this far and we plan to build it up a lot more and have a store for people to come and shop."
It is a refreshingly honest take on the birth of a brand. Most founders try to retroactively apply some grand philosophy to their first sketches. Rak just wanted to know if the shirts looked "sick." And they did. But the transition from a T-shirt line to a full-blown music collective required a different kind of synergy.
M $wift remembers the early pivot during their senior years of high school. He explains, "In Senior High School years, Rak came up with the idea of starting a music team/group since he had an interest in doing music later on at the time. Me being his closest friend doing music at the time recruited me to the movement. We both agreed on the name ‘SoundTrack Records’, after a month Rak rebranded the name to ‘Sad Till Rich’ Rak was thinking about more ways to market the team/group in fields of not just Music but also Clothing."
The rebranding from SoundTrack Records to Sad Till Rich was the moment the group found its soul. "SoundTrack" is generic; "Sad Till Rich" is a narrative. It captures the modern hustle culture that dominates the 519 rap scene—the acknowledgment of the struggle while keeping eyes fixed on the prize.
I.G. provides the timeline, rooting the empire in a specific place and time. He says, "S.T.R. was first started in 2016 inside Beal SS when Rak came up with an idea to make a brand called ‘SoundTrack Records‘. The name shortly after changed to Sad Till Rich. Rak went on to recruit his close friends in his city to build an empire and start a business. A thought turned into action and within the upcoming weeks, the first Sad Till Rich T-Shirt was made."
The transition from fabric to frequency happened naturally. In an age where every rapper has a merch line, S.T.R. did it in reverse. They had the gear before they had the singles.
Rak explains how the two worlds collided through shared history on the court. He says, "The clothing line was first starting to take off around my high school and a lil bit outside of it and me and I.G. played varsity basketball together so we had a really good relationship before any of this but he was just starting to release his music and he linked me up and said if you wanna promote your new clothing I’ll wear it in my first video and we linked up and had everyone in S.T.R. clothing on and then myself and I.G. knew we could turn this into a bigger thing then the clothing to and are boy M $wift was also doing music and he’s my good friend so he came and helped push us to where we are today and then we had brought on D Prince around 2 years and a half, 3 years and he’s been doing great with helping push our name and the brand. We are more family then a team."
This "family first" mentality is what separates S.T.R. from the transactional nature of the Toronto industry. They are not just collaborating for the clout; they are building a closed-loop economy where the fashion fuels the music and the music sells the fashion.
I.G. recalls the specific moment the records division became a reality in 2017. He says, "Sad Till Rich Records came into place in 2017 when I.G. who was in college at the time decided he wanted to try out making music, knowing Rak from basketball and staying connected I reached out with the idea of us collaborating, Rak makes the clothes, I wear them in videos and then we both get our names out at the same time. The next thing you know it, I.G.’s debut song ‘Ya.x4’ was getting a music video shot with everybody wearing the S.T.R. gear as promotion, this went on to be I.G.’s first hit single as a Sad Till Rich Records artist."
And there is a certain charm to that early hustle. Rak and Isaac’s relationship was forged on the basketball court, a space where teamwork is not a buzzword but a survival tactic.
Rak says, "Isaac and I played varsity basketball together so we had a really good relationship before any of this but he was just starting to release his music and he linked me up and said if you wanna promote your new clothing I’ll wear it in my first video and we linked up and had everyone in S.T.R. and then I.G. and I were knew we can turn this into a bigger thing then the clothing."
It’s a good feeling to know that people are looking up to us and we don’t take it for granted. Growing up in different situations made us all realize the youth need inspiration to do things that help them grow as people... Our youth is the most important people to build up and we intend on helping do so to the best of our ability.
But let’s talk about the aesthetic. Rak’s foray into fashion was not some high-concept pursuit of the runway. It was about the daily uniform of the 519 youth.
Rak explains his motivation. He says, "Since I was young I loved dressing nice and matching my shoes with my hats and shirts etc. I just liked fashion in a way so I started thinking instead of wearing all these other guys clothes I want to make my own and wear it just as nice or better. I wasn’t really expecting people to buy it at first. It was mostly for my brothers and I, but the way we wore it and matched our shoes with the shirts people started to like them and started asking me every day at school for a S.T.R. T-shirt, then I evolved to making tracksuits and more."
There is a technical critique to be made here. Moving from T-shirts to tracksuits involves a significant jump in production quality and supply chain management. Rak seems to have handled the transition with a DIY grit that is admirable, though the challenge for S.T.R. will be maintaining that "boutique" feel as they scale.
I.G.’s transition from the court to the booth is perhaps the most dramatic narrative arc in the group. Growing up in Windsor and playing at the college level, the pivot to music was a calculated risk.
I.G. says, "I grew up playing sports, but I’ve always had a passion for music. I was listening to it all the time to get my energy up before games. What made me take music seriously was my brother Zovie when he showed me a song he had done in a professional studio in Windsor. After I was introduced to my first professional engineers Ty Butler (TNB BEATZ) and Brandon Deriveau (M.A.D Recordings) it seemed as though the stars were the limit. After choosing to cut my basketball career short for the love of music I moved back to my hometown Chatham-Kent, and set up a cardboard box studio in my friend’s basement and recorded Basement Bars, my first EP. It’s taken down since, I didn’t even understand ‘Free’ beats didn’t actually mean free beats."
And that is the reality of the independent grind. The "cardboard box studio" is a rite of passage. His admission about the misunderstanding of "free beats" is a crucial moment of transparency. It shows a willingness to learn from the technical and legal pitfalls of the industry—a trait often missing in younger artists.
He continues, "I’m still learning to this day and don’t plan on ever stopping, those long nights leaving when the sun came up and driving home to poorly mixed songs are what made me, and I wouldn’t change the way it happened one bit."
While I.G. brings the grit, M $wift brings the lyrical focus. His influences read like a syllabus for modern hip hop excellence.
M $wift says, "For my Rap sound it would have to be Kendrick Lamar, Drake, and J. Cole. For my R&B sound it would be Tory Lanez, Bryson Tiller, PARTYNEXTDOOR, & Eli Sostre. Telling my story and what I want to manifest into reality is what gives me my drive as a Rap artist."
The Kendrick and Cole influence is evident in his desire to "tell a story." In a genre currently obsessed with vibes over verses, M $wift’s commitment to manifestation and narrative is a necessary anchor for the collective.
Then there is D Prince, the R&B vocalist who adds the melodic texture the group needs to bridge the gap between the streets and the charts. His background is unique, rooted in a spiritual discipline that translates into vocal control.
D Prince says, "I’ve had many different influences in my life especially for music such as, Chris brown, The Weeknd, Tory Lanez, Justin Bieber, Drake and more. A really big influence for me right now has to be Ali Gatie because we come from the same life and same background and he’s already breaking the charts. My sound is very different when it comes to music because growing up my family was very religious and would recite verses from my holy book every night and that kinda made me find my voice. I’d say my voice is unique because there’re days I make a track and can’t even believe that was me. Like it’s just so crazy and I’ve only been singing for 4 years."
The mention of Ali Gatie is telling. Gatie has proven that a kid from the GTA can go global without losing their cultural identity. D Prince is clearly aiming for that same trajectory, using his religious upbringing as a vocal training ground.
Behind every great collective is a producer who can translate their energy into sound. C Milli is that man for S.T.R. His approach is utilitarian and remarkably fast.
C Milli says, "I listen to all kinds of music, and like it all the time."
When asked about his workflow, his efficiency is almost startling. He says, "I try to have every beat done in at least 15 minutes but I can admit to spending at least an hour on a few beats."
Here is the critic’s take: 15 minutes is an incredible turnaround time, but it carries the risk of sonic repetition. While speed is essential for keeping up with the relentless release schedule of modern streaming, S.T.R. will eventually need to allow C Milli those "hour-long" sessions more frequently to ensure their sound evolves beyond the standard "type-beat" tropes.
C Milli cites the greats as his north star. He says, "I’ve always been into music, but I would say my inspiration is people like Dr Dre and Boi 1da."
The group is currently sitting on a mountain of unreleased material. The roadmap for the next year is aggressive, with solo and collaborative projects slated to drop.
I.G. outlines the plan: "My solo project ‘NightShift V.I’ EP, collab project HIGHFLYERS and Rak S.T.R.’s ‘Story Told Right EP’ are all in the current process of being released early 2021. M $wift has also been working on his debut album ‘Rose Boy’ and is projecting to release in 2022. D Prince and C Milli are hard at work releasing singles and producing for artists across Ontario."
But beyond the release dates and the fashion drops, the core of S.T.R. remains their influence on the younger generation. They are acutely aware that their success is being watched by kids who see them as a way out or a way up.
M $wift says, "It’s reassuring knowing that we have an impact on the youth who are and always will be the future. We do our best to promote a positive message that emphasizes that you can achieve whatever you want, if you put your mind to it. Coming from rough times and surrounded with negative influences we know how important positive guidance is from role models."
It is a heavy mantle to carry, but one they seem to wear as comfortably as their own tracksuits. They are not just selling a lifestyle; they are advocating for a mindset shift.
I.G. concludes, "It’s a good feeling to know that people are looking up to us and we don’t take it for granted. Growing up in different situations made us all realize the youth need inspiration to do things that help them grow as people so they can give back to the youth when they have the chance. Our youth is the most important people to build up and we intend on helping do so to the best of our ability."
And that is the definitive take on S.T.R. They are a collective that understands the value of the 519. They are not looking to escape their community; they are looking to elevate it. Whether they are handing out backpacks or dropping EPs, they are doing it with a level of intentionality that is rare in the modern scene. Keep your eyes on them. They are not just sad till they are rich; they are working until the whole community wins.
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