“I like short-term goals. I’m never thinking about a five-year or a ten-year plan; I’m always thinking, ‘What am I doing in the next year? What am I doing the year after that?’”
In the mid-1990s, Katrina Taylor’s short-term goal was to get her real estate license in sunny south Florida. Hip hop was finding its way into regular radio rotations as more audiences (and stations) across the country began to embrace the sound, but despite the contributions of trailblazing femcees like Queen Latifah and MC Lyte, the genre still remained more or less a boys’ club. The brash and braggadocious lyrics of Lil’ Kim and Foxy Brown in the latter half of the decade signaled the arrival of a new wave of women in hip-hop who proved that they could rap as well—if not better—than their male counterparts.
It was out of this era that rap icon Trina was born. Taylor was plucked from anonymity by fellow Miami rhymer Trick Daddy and made her debut on his 1998 breakout single “Nann,” delivering a guest verse filled with swagger and having the beauty to back it up. From there, she says, there was nowhere else to go but forward, and fast: she signed a deal with Miami-based label Slip-n-Slide Records and got straight to work on her first album.
Trina’s debut album “Da Baddest Bitch” celebrates its 20th anniversary on March 21st.
“Once [‘Nann’] came out, from there we were on tour for a year; in the midst of the tour, that whole year of 1999 I was creating this album,” Trina remembers. “I didn’t have that much time to actually do it; we were just working on the road as we go, and we just went day by day.” She would often pass up on partying after shows to hole up in her hotel room and focus on writing and finishing the album. “It was a lot of pressure because it was all on a short time frame, and I was going back and forth with different sounds with my voice and just trying to get things done that I wanted to actually make the album,” she recalls. In spite of the hectic work schedule, Trina looks back fondly on the recording process, calling it her “most vulnerable and most raw moment.”
Her debut album Da Baddest B***h hit store shelves that following March, and immediately put the whole music industry on notice: a new girl rapper had arrived, and she was coming for her rightful spot at the top of the heap. “Rap divadom has a new challenger,” Billboard declared. Critics praised her for being “as nasty as Lil’ Kim used to be” and crowned her “the new queen of randy hip-hop tales in which sex is a contact sport played by rival genders.” Da Baddest B***h was certified Gold by that November, and maintained a strong Billboard chart presence for nearly a year after its release.
Before she knew it, Trina was thrown into the life of a professional rapper, and began to set one short-term goal after another.
“Once the album came out, I didn’t come off the road for like two years,” she tells Forbes of the time. “I stayed on the road promoting the album and doing other records; in the midst of all that, at that time while the album was out I still had ‘Nann,’ then I had the Ludacris record [‘What’s Your Fantasy’] which was just as hot as the ‘Nann’ record.” It wasn’t long after Da Baddest B***h’s release that Trina began working on her next album, once again juggling touring and recording. “I was just all over the place at the same time.”
Trina recruited the likes of Missy Elliott, Kanye West, and an aspiring Miami rapper named Rick Ross to help create her sophomore LP. Diamond Princess was released in August of 2002 to favorable reviews and better chart performances than Da Baddest B***h. Trina’s star was on the rise, and hip hop fans in Miami and around the world were lucky enough to be watching it in real time.
Prior to Nicki Minaj’s debut at the end of the decade, there were very few female rappers who were actively recording and releasing new music. Hitmakers like Missy Elliott, Eve, and Lil’ Kim had released their last albums for the foreseeable future by the mid-2000s, leaving artists like Trina with all the momentum and motivation in the world to carry on the torch for women in hip hop.
Glamorest Life, Trina’s third album, continued her rising trajectory: the Kelly Rowland collab “Here We Go” became Trina’s first certified Gold single and highest charting song, peaking at number 17 on the Billboard Hot 100 in December of 2005. Her 2008 album Still da Baddest did even better, becoming her first to top Billboard’s rap and hip-hop albums charts and simultaneously pushing Trina into new sonic territory with R&B-tinged singles like “Single Again” and the Keyshia Cole-assisted “I Got a Thang For You.”
In the years after the release of her fifth album Amazin’ in 2010, Trina began to lay low and independently release mixtapes and EPs while making scattered TV appearances. In March of 2015, nearly 15 years to the day after the release of Da Baddest B***h, Trina signed a deal with hip-hop label Penalty Entertainment to create her own imprint. Rockstarr Music Group was born, and Trina’s transformation from entertainment figure to business mogul had officially begun.
By late 2017, Trina was prepared for her long-awaited return to the hip hop conversation. VH1 announced her as a leading cast member of Love & Hip Hop: Miami alongside Trick Daddy, and she released the candid confessional single “Overnight” in the lead-up to the show’s premiere. Cameras have been documenting much of Trina’s life in the years since: her and Trick’s disagreements over their shelved joint project, her various business ventures, and the loss of her mother last September, to name a few.
After a nine-year break, Trina released her sixth studio album The One in June of 2019 with all all-star list of guest appearances ranging from Nicki Minaj and Lil Wayne to Kelly Price and Rico Love. “It’s personal to me; I worked on it for six years,” Trina recounts. “I put a lot of effort and energy and time into it, and I actually executive produced it myself, so it meant the most to me because I’ve grown to that phase of my career and I became the person in charge, the CEO, the brand, the person who had to oversee everything else.”
Two months after its release, however, the album was pulled from streaming services over what Trina calls “bad business” with a former partner. She’s since regained total control of the album, which will be back in all its glory on March 30th; a deluxe edition with a few new tracks arrives that following Friday, April 4th.
Still, it was a long road for Trina to get to this point—not just legally and professionally, but personally. Despite the calls from fans reassuring her that they wanted to listen to The One again, Trina was discouraged that it had even gotten to that point in the first place. “I lost the love for wanting to put it back up… It was a very emotional process because for me, from an artist’s perspective, I was emotionally attached to the album,” she reflects, “but when I have a label and these people are looking at me as the boss, then I had to make a different decision—a strategic decision—of less emotions, more business.”
Beyond the heartbreak of having the project she worked so hard on be taken away from fans, Trina was more disappointed in letting down the collaborators she invited to take part in the album. “To me, it’s more about everybody that I had on the album—my features,” she says. “These were favors; we did this project together… Everybody who was on my album, that meant something to me.” On top of everything else, the album’s removal couldn’t have come at a worse time personally for Trina. “I stayed quiet through a lot of it because I still was dealing with my mom being sick, so it was a real shutdown moment for me.”
Now, Trina is back with much more than just control of her latest album: she wakes up early every day to co-host the Trick & Trina Morning Show on Miami’s 99 Jamz radio station, and is hard at work as the businesswoman behind Rockstarr Music Group and her Fashion Girl Boutique clothing and accessory line.
“I love that I can talk to the people; I love that I have the power and have the voice to say as I feel,” Trina says of the radio show. “I love that I’m able to understand [radio] more, because when you’re an artist you wonder what records are on radio and why records don’t get on radio, but being in radio, I get to understand that now and know how it works.” Being a hip hop radio host has also allowed Trina to invite artists like Fat Joe and K. Michelle as guests on the show, and learn new things herself in the process. “It’s good, for me, because I’m an artist and I’m able to hear from these artists and how they view and look at things from an artist’s perspective.”
MIAMI, FL – AUGUST 29: Trina performs at Jungle Island at Port of Miami Concert on August 29, 2016 … [+]
Trina has been able to incorporate these lessons—along with all the other knowledge she’s picked up along the way—into her management style as the head of Rockstarr Music Group. “I’m taking it one day at a time with these artists. It’s not like when I came out, it was a quick, fast buzz, where I did a record and I was the biggest artist in the game,” she says. “With these artists, it’s all about building that momentum, the brand, that fire… You could have a great song out today, but two weeks from now, there’s some new person out with another song and you’re not that memorable because it’s such a short attention span here and now in the new generation.”
As Rockstarr Music Group’s first signed artist, Miami-bred singer Nia Amber is learning these lessons from Trina firsthand on an almost everyday basis. “She’s amazing,” Trina smiles. “I believe in the artists; they have great music, and right now I’m focused on Nia.” Amber already has a promotional single out, but Trina teases the release of a “hit single” and a full-length project slated to be released in early summer. “I’m just excited,” Trina says. “I just want to see them win. The youth and the ones that are under me, the people that I’m putting on, I just want to see them do amazing job.”
Needless to say, having Trina as a mentor would be a godsend for any up-and-coming artist looking for real advice rooted in experience. Trina emphasizes the importance of “being true to yourself and figuring out exactly what it is you’re searching for,” but caveats that the music industry “is not a world of flowers and bliss.” Being yourself, Trina says, doesn’t mean that you can’t and won’t change who you are as an artist. “You can’t say ‘Don’t change,’ because every year I’ve learned something different. Every time I traveled out of the country or did different things or did a new record with an artist I loved, all of that is growth. All of that is different experiences.”
Among all her other business dealings, Trina still maintains her status as the crown jewel of the Love & Hip Hop: Miami cast, and emphasizes the truth of the situations she experiences onscreen as opposed to the scripted storylines that reality TV shows are often subject to. “This is real life; this is not for the TV,” Trina says. “For me this season, I showed what I was actually going through: the loss of my mom, the whole situation with my business partner that was dealing with me and my album, why my album got taken down… The good, the bad, the ugly, the hurt, the pain, all of it—you saw it, I lived it.”
With the 20th anniversary of Da Baddest B***h now in the books, Trina is busy working towards the short-term goals she’s set for the rest of 2020. “The whole end of  has been a disaster, so to even start off at the top of this year and have a refreshing desire to even deal with that, it’s a step forward,” she says thankfully. “That’s how I look at it. It’s music, it’s passion, it’s what I do, so I look at it all as a lesson learned.” Keeping a clear head as an artist is crucial when facing hardships like the ones Trina has faced in the last year, which is why she’s prioritized being able to channel her emotions into her music. “I look within myself and say, ‘I still have life,’ so I can breathe into the next phase. I just always think like that,” she muses. “I went in the studio and recorded a whole new project in two days… I’ve let go of the hurt of how I felt with [The One], which meant everything to me, so that showed me a light in itself.”
More than anything, Trina is grateful for the fire burning inside her that drives her love for what she does more than two decades into her career. “Every day is about growing and evolving, and each day I just take it one day at a time and embrace it as it comes,” Trina smiles. “For me, 20 years later, to be so inspired still, especially with the culture and the music, and then to be able to do things outside of that, it’s just an amazing feeling. I feel like I’ve grown into the person that I want to be.”