Hey New H2O!

My name is Thomas and I’m a rapper from Hawaii.

Some of you may know me better by my rap name, Illtalian – but more than likely, you’ve never heard of me. If you’re reading this, though, you’ve probably heard of some of the people I’ve worked with (1k Phew, Swift, Gemstones, Je’kob, Big Juice, Spechouse) or am working with now (KJ52, Joey Jewish, Haley Joelle). How have I, an admittedly unknown rapper from a small island in the middle of the Pacific, managed to work with Grammy winners, Billboard chart-toppers, and some of my own personal heroes?

Well, it didn’t happen over night.

Trust me, the list of rappers I haven’t worked with is just as long.

I’ve been rapping for over a decade now, but only in the last few years have I started to find success when approaching other rappers for guest features. Below are a few of the things I’ve learned not to do when asking someone to rap on your song.

Pay attention and see if you can learn from my mistakes.

Do NOT just hit them with a random link to your mixtape/single

Believe it or not, messaging a rapper (or tweeting, or DMing, or emailing, etc) a link to your SoundCloud without warning or context will not suddenly make them want to work with you – no matter how fire your mixtape is.

While there is a time and place to share your music, and even though you should include your social media profiles (we’ll get to that in a sec), the beginning of your message is not the place to do it. Rappers have people constantly bombarding them with links to songs and social media pages, trying to get feedback, shout outs, follows, or features.

The bigger they are, the more it happens. Seeing a link in their DMs is probably just going to trigger some PTSD memory of a crazy ‘fan’ trying to break into their house at 3AM, screaming “I’M THE NEW LECRAE BOI CHECK ME OUT,” and they will delete your message without hesitation.

Instead of that, try your best to be friendly and professional. Introduce yourself and explain why you’re contacting them. It’ll immediately separate you from ninety percent of the other struggle rappers that hit them up, and even if they ultimately turn you down, you’re less likely to have permanently burned that bridge with them. Which brings me to my next point…

Do NOT forget to include all of your relevant information

Here’s the other side of the coin – though you shouldn’t just spam them with links to your music, you definitely should include a couple samples of your work.

No offense, but your favorite rapper probably hasn’t heard of you, and they’re going to be understandably hesitant before agreeing to hop on your song.

We’ve all made the mistake early on in our careers of agreeing to be featured on someone’s track without properly researching them, and those memories haunt us. This is more than just a talent thing, though that’s important, too. For all we know, you could be a Satan-worshipping racist asking us to feature on your new track, “Hitler was Dope.”

Help us make sure you aren’t crazy, and that what you rap about will at least be somewhat in line with what we believe and stand for.

Tell the rapper a little about yourself – not a novel, but the highlights. Any other artists you’ve worked with, maybe some awards or achievements (but only if they’re relevant), perhaps your involvement in ministry or the vision for your music, etc. The point of this is not to brag or flex, or even necessarily impress; you just want to paint an accurate picture of yourself, your music, and the level you are currently operating at. Many rappers actually want to invest in up and comers, but they have to choose who they pour into carefully.

Save the rapper from having to do all this research himself (because, let’s face it, he’s probably too busy to to that anyway), and it may play out in your favor.

Do NOT hit them up for a song they have no business being on.

Seriously, guys. If the rapper you’re approaching is a very poetic, spoken word, heavy-theology kind of MC, you probably shouldn’t approach them about your new Trap song.

And if they are very open about their faith, you probably shouldn’t ask them to write a hook for your song glorifying drugs and sex.

Take two seconds to research the person you’re approaching, because otherwise you’ll seem like you just want to capitalize on their fame, and care little about their art.

That’ll get you turned down fast, and will hurt your chances of collaborating in the future. This one is simple, y’all: when approaching a rapper for a feature, make sure they fit the track.

Do NOT stalk/harass them on social media

Whether they got your initial email, or it’s taking so long for them to respond, or for any other reason, don’t bother them.

Rappers are busy people; more than likely, rapping is not their only job. It may be one of two or even three careers the artist is balancing, and if they’re married and have kids? Forget about it.

That’s in addition to the tons of other people who are constantly approaching them for shows, promo, advice, and (of course) guest features.

When you add in the fact that not all artists have managers/agents to help them handle the workload, you can see why it might take them awhile to get back to you. Don’t worry, they saw your email; if they are interested, they’ll respond when they can. A polite, professional follow up is fine, but give them time.

You’re probably not at the top of their list, and constantly pressuring them to hit you back will only drop you further down that list, if not get you knocked off altogether.

And now, for my final tip…

Do NOT ask them to rap on your song for free.

Believe it or not, most rappers aren’t rich, and music is expensive.

Studio time alone can cost you anywhere from $50 (on the cheap side) to $250 an hour to record. And if the rapper in question is lucky enough to have their own setup, between costs for the recording software, laptop, microphone, and soundproofing their booth, you’re looking at an investment in the thousands.

That’s not even considering all of the other expenses accrued by MCs, including buying or making beats, marketing their projects, travel and airfare, booking venues, and any guest features they might have paid for themselves.

Plus, due to the advent of streaming, their revenue stream is greatly diminished, and the little that remains is split between distributors, producers, co-writers, and labels.

These guys need to eat too!

By asking someone to feature for free on your song, you are telling them that you do not value them and you do not value their art.

If your budget is limited, be upfront about it from the beginning – there’s no shame in working within your means. Don’t be afraid to admit you can’t afford them right now but you hope to be able to make it happen in the future.

You’ll earn their respect that way – and once in awhile, if they see something they like in you, they may even be willing to work something out. Maaaaybe.

Oh, and also, please don’t ask if you can rap on their song. Remember: you’re the one coming for a guest feature – not the other way around.

What do you think? Let us know @newh2o

Author Bio: Thomas Iannucci (rap name: Illtalian) is an award-winning rapper, author, and poet from Hawaii. Rapping since 2008, his music has won or been a finalist in many prestigious music competitions, most recently receiving a finalist slot in the 2016 National John Lennon Songwriting Competition, in the Hip Hop category. Thomas has collaborated with many well-known rappers and producers, including 1k Phew, Gemstones, Big Juice, Je’kob, Swift, and Spechouse, and his new album “Makana” is out now.

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