What Does A Female Rapper From Trinidad & Tobago Need To Do To Make It As A Musical Isle-preneur in 2020?

My appearance on Trinidad & Tobago Television last week was facilitated by none other than powerhouse talent Sophie Guillaume.  Sophie is one of those unassuming people that you will never know has more talent in her pinky than most people have in their entire bodies.


Sophie had a dream of being a rapper.  She has performed on every local stage you can imagine.  From Siparia to Crown Point Sophie’s lyricism is known and respected all over the country.  But there is just one major problem: People don’t know what to do with a female rapper from Trinidad & Tobago (worse yet one from Tobago).


Even though two of the Top 5 female rappers in the world can lay indisputable claim to Trinidad & Tobago roots, we still are unsure of how to make females in any musical genre go viral here in Trinbago.  Recently, Sophie sat down with me for a a little pow wow and I wanted to share with you some of the key points of our discussion.


What’s the blueprint for a female rapper (or any musical Isle-preneur) from Trinidad & Tobago to make it in 2020?  Become self-aware about what type of music she absolutely loves doing.  Create a plan for her own self-motivation so that she creates and distributes content every day without relying on external motivation.  Have the self-discipline to follow that plan every day for the next two years.  Nurture the self-control and patience required to understand that nothing fruitful is going to happen for the next two years. Implement your monetization framework from day one.


Understanding what needs to be done is one thing.  Read on to get the details on how this actually needs to be executed and what you need to do to make sure you get paid.



Self-awareness is having a deep understand of who you are as a person, as an artist and most importantly as a communicator.


As a person

As a person, you have likes, dislikes, strengths, weaknesses.  A good many things go into the understanding of you and your personality.  The problem is that most people don’t take the time to know that person really well.  And because we don’t take the time to know ourselves very well we tend to accept the version of ourselves that other people see.


That’s not to say that what others experience from our personality are inaccurate.  The version of you that other people believe they know doesn’t have all the information, facts and experiences that you have.  So while someone might say, “You’re an awesome singer!”  They will not know that you actually hate singing and have a passion for rapping.


The reason for you to get clear on you as a person is because it will inform your entire strategy.  And you don’t want to build your entire strategy around something that you yourself don’t like.  Or something that someone else told you you should do.


As an artist

The same thing goes for being an artist.  As a hip hop junkie I cannot tell you how many interviews I’ve seen where rappers, R&B artist and anyone who has been signed to a label says, “With my first album, the label really took the lead but on this second album I took over the reigns and decided on the direction and the sound.”  And while many people would think that that’s why the artist’s second album doesn’t historically perform as well as when the label handles it.  Let me stop you there.  That doesn’t necessary follow.  If an artist starts taking control of their music from the beginning and the label’s job then becomes a simple matter of funneling and channeling the art to the people who like that type of sound then you would have way more happy artists and listeners to the music too.


But labels are going after making the most amount of money and recouping their investment on a project.  Traditionally that has meant going for mass appeal.  Segmenting the market down to 5000 people who love over 30 female rappers also doesn’t sound as appealing or lucrative.  It’s much easier to offer an artist with mass appeal.


But for an independent artist who is self-aware and understands themselves enough to know the type of music they want to create and who it is for, the possibilities are endless. The difference between knowing that you are a hip hop artist versus knowing that you’re a 90s hip hop lyricist is huge.  Hip hop is getting older which means the demographic is also getting older.  That older demographic who grew up with hip hop is resistant to many of this new style hip hop and mumble rap as they call it.  They prefer it as it was in the 90s.  And there is nothing wrong with that.  It just means they’re looking for and willing to pay for a different type of music. And if 90s hip hop is your sweet spot then bet on yourself and your talent and go all in.


As a communicator

If you are an artist you are probably closer than most to knowing if you are a great at communicating via writing, video or voice.  If putting pen to paper is your thing then that needs to be the corner stone of your execution plan.  I am a writer so almost every piece of content I create begins with writing before a video, a podcast, or anything is created.


Knowing your communication styles gives you a superior advantage with distribution.  Probably the biggest secret about the music industry is that there are no longer any gate keepers.  That is true regardless of if you are in the US or on a Caribbean island like Tobago.  The internet has reduced the role of the middle man between the artist and the listeners.  So you can take your talent direct to consumer by creating the content and then distributing it yourself.  Whether you decide to put all the written lyrics up on a blog.  Or create a Spotify podcast to release your songs complete with commentary about the headspace you were in when you created it.  Or whether you decide to do YouTube videos about the song with some dope visuals.


Whichever you decide – and you should probably be doing all of those depending on how badly you want to make it – the starting point is understanding yourself as a communicator.  Then you can capitalize on which ever ones are your strength and then create a game plan for supporting the areas you’re not as strong in.



Understand that you need to find your motivation from within.  Forget external motivation.  Stop waiting for the inspiration to come to you.  When you are self-aware and know what makes you tick or turns you on, then your reliance on external motivation becomes a crutch.


Making it is going to require that you absolutely love the process.  That you have a drive to make songs more than you need oxygen.  That you want it so bad absolutely nothing keeps you from it.


External motivation is like listening to radio for inspiration, or hanging out with friends until the lyrics come together.  Or binge watching a Netflix series to stimulate your creative process.  That’s all well and good for people who have the luxury of a having the attention of the masses and industry heads.  But that’s not you boo.  You trying to do something unprecedented.  Something that hasn’t really been done before.  So you’re going to have to hustle.  And you don’t have the time to wait until the inspiration comes.  You need to create so that the inspiration finds you working not on down time.


The last two pieces of the puzzle, self-discipline and self-control, may seem like they’re the same thing but you’ll see how they are different sides of the consistency coin.



Once you are self-aware and self-motivated it’s time to make a plan of consistent action.  A plan of action that can be executed daily to let the masses, the industry, the universe know that you want this so bad that you’re not going to wait for it to come to you.  You’re doing something about it and chasing it.  Hard.


Everything you want is on the other side of consistency.  But most of us are unsure exactly how to get it.  So here’s what it is.

  1. Identify 10-12 themes you want to explore with your music. Almost like a music hit list. Which is a numbered list of songs you would want to create. This takes power away from the excuse that you have to try and figure out what you want to sign about.  Give yourself the greatest advantage by creating a hit list that you can select any one to make songs from.  This reduces your reliance on external motivation.


  1. Simplify the music creation process into 5 action steps that you can easily do without having to rely on anyone else. Most artists overcomplicate this. For instance, an artist might say, but I don’t have a studio.  Well let me stop you right there. Recently Da Baby revealed in a Gary Vee interview that he created his record smashing album in a hotel room.  It’s 2020, no need to get fancy when recording a song could be as simple as whipping out your phone.  Is it going to be the most amazing sound quality?  No.  But more important than sound quality is getting your art out there.


  1. Simplify the distribution process to 5 action steps. In years gone, distribution for an independent artist might have meant standing up on corners or heading to the mall and haggling passers by to listen to your music. This process has now gone digital.  Almost every person in Trinidad & Tobago.  The Caribbean.  the world has a smart phone.  And what’s even better you can easily access them with your smart phone.  So once you’ve created your music, you publish it to the 5 platforms that matter.  For an artist that means Youtube, Tik Tok, Linked In, Instagram, Facebook.  Added to that you post it to your podcast and your website.  To get a gold star, an artist can then spend the rest of the day connecting with content creators across these platforms offering their music for free use in YouTube videos, IG videos, etc.



  1. Rinse and repeat for 2 cycles of 365 days no matter what. Wake up each morning and slavishly pick a theme, create the music, distribute the music. Every day without fail.  Without a missed day.  Without a “Oh, I’m sick today guess I’ll do it tomorrow.”  Without a “my Grandma died I guess I’ll do this after the funeral.”  Basically without any excuse.  That’s where the self-discipline comes in.


Let’s see how self-control factors into this.



This blueprint is one that requires patience.  Haters will say this sounds like hard work and they’d be right.  Every female rapper you can think of that has had any type of success had to first be committed.  Don’t judge me, but on a recent episode of Love and Hip Hop (the original New York series) lyrical queen Remy Ma revealed in a chit chat with hip hop legend Fat Joe that she was tired of fighting.  Tired of the grind of churning out an album.

What she was saying made complete sense.  She just had a baby.  She was on parole after her stint in prison.  And unlike other female artist her forte is lyricism which takes a helluva lot more thought and energy and time to pull together than simply putting on a thong to get your music played on the airwaves.


Fat Joe’s response?  You better lock yourself in a room, 24 hours a day like the old days and create no matter what.  Facts.  Truth is that we can complain all day but the truth remains that it’s either you’ve done it or you haven’t.  Black or white.  Two choices.


Give yourself two good years of patience executing the action plan.  You would be stunned by the body of work you’ll be able to produce.  In awe of the types of opportunities that will find you.  Taken aback by how far taking charge of your situation takes you.


Be prepared for absolutely nothing to happen in that time but be grateful to stay the course on the plan if something does.



Getting the creation and distribution part down is one part but what about making money?  Before we continue you must understand that he who holds his breath the longest wins.  That means that the longer you are able to go without monetizing or asking your community for money, the larger you stand to make in the long term.




You want to get paid now.  And that is understandable.  So you can create live show events that people have to pay to attend.  But you have to have a framework for doing this.


  1. Use social media as the the introduction to you and your music. Remember social media is noisy so don’t try to sell people right there. Instead, use social media, your podcast, your website to drive traffic to a private place for you to build a buying relationship with persons who sign up for your email list.


  1. To get people on your email list you want to give them a gift. For instance, you can create artwork for a t-shirt that best embodies your brand and give that away free.  You can give them access to never before released songs or some sort of item – preferably one that doesn’t take significantly extra work out of you to produce.


  1. Email every other day to nurture that relationship with your fans. When you are building a relationship with your people especially in the beginning, the more touch-ins you can have with your people the better. So be as hands on as possible.  The more exposure to you the better.


  1. Have a way to accept money. This could be directly on your website using Stripe or Paypal or you might have someone other way of accepting money that is convenient for them to pay.


  1. The reason you want to email your list daily is so that you can get paid daily. No email should leave your computer without a link to purchase. Doesn’t matter what you are selling.  How are you going to make money if you don’t ask the masses to buy.  The cool thing about this is that when you make it really big and become a huge successful artist your tribe is already accustomed to purchasing from you.  You don’t have to  now think about how you’re going to flip them from free to paid because you been doing it.


That my lady is how you move from talented artist to paid musical Isle-preneur


Female musical Isle-preneurs should know that there is just as much opportunity for you out there as there is for any dude.  And contrary to pre-internet where you had to rely on some label insider, radio personality or promoter to put you on, your talent mixed with work ethic is more than enough.


So good luck Sophie.  Be so grateful that you lived to see a time when musical Isle-preneurs don’t need to wait.  The best way to show that gratitude is to execute on a plan that makes it work for you.