First of all, you can’t. I know it’s a popular idea, and everyone thinks they’re two seconds from fame in the Youtube generation, but no. Stop trying.

But if you must do it, if it’s your calling, or at the very least, you feel like it, then do it right. Follow this advice and you may do better than terrible.

Care About Stuff

One rapper on the street, Fine$e (yes, with the dollar sign) was selling his album for five bucks. After an impromptu rap battle (he insulted my hat) I was impressed and bought it. Beat a hamburger, after all.

I have it playing right now. Because it’s terrible. It’s hilarious. This street rapper of clear talent recorded this on a camera-phone while under-water by the sound of it. And he only put in one take, clearly: you can hear stutters and mistakes around. That’s not terrible in a freestyle, but in a recorded session where you can edit and try again? Unforgivable. Don’t do it.

Don’t Bother Friends

Friends aren’t the ones you need to persuade; it’s strangers who, if you’re any good, need to like you. Selling music to friends is like selling your girl-scout cookies to your parents. Don’t do it.

Love It

You have to love rap to rap well. It has to be something you’ve done for a while, done to impress friends, done when it stopped impressing them, done when they asked you to stop. It has to be a labour of love that your happy to do for free, because, guess what? You will. You’re not making money, so enjoy it for free. An angry rapper, furious at the money he isn’t getting from his angry rap is never going to succeed.


If you want to succeed, you can’t lay back and not care, spitting freestyles here and there. That’s what I do, but I don’t want to succeed; I enjoy it as a hobby.

Max Gredinger of is more than a hobbiest. He isn’t a rapper but he cracks the list by default. A manager and hip-hop writer and blog-head, he’s a hustler in the P.Diddy sense and I mean that mostly as a compliment. If you could bet money on people, I’d have put quite a bit on him. And that’s because the man has ambition, not in the narrow sense of the word but in the applied “I manage actual bands at the age of twenty” type sense. And that’s because he’d research. He’d call people and ask questions, shoot off dozens of texts. He had hundreds of ideas and he’d share them all. Some worked. Some didn’t. But a hustler knows that action even misplaced is better than inaction.

Just how much of a hustler is he? He has me hyping him up without asking, when I haven’t seen him in years. That’s a hustler.

Be Good and Do All of This

Lastly, I rapped with this guy for a bit on the same radio show and he blew me away. His name was Justice, (currently J’You) and he handed me his C.D. Now, I get handed C.D.s fairly often by aspiring rappers, and I don’t listen to most. Some, I listen to once. His, I had on repeat.

J’You followed the crucial lessons. He hustled, hitting up radio shows and small gigs, handing out C.D.s for free instead of hoping for the occasional short-term dollars. He cared, producing his music at near professional quality and securing talented features. He put out enough free music such as  This that by the time he had an actual album selling I was eager to give him my money.  And I wasn’t some random friend of his who was obligated to like him: I was a stranger he won over with talent. I was a believer because he was good and he did all the advice.

That’s ultimately what it’s about. That I could keep an amateur rapper on my iTunes shuffle and not skip his tracks when they came up: that’s respect and that’s talent. On my iTunes he wasn’t competing with other amateurs; he was competing with Jay-Z and Tupac, Billy Joel and Nirvana. He might not be as good, but at the very least he beat Kid Cudi. And shouldn’t that be every rappers dream?


To refresh: listen to J’You, Kam Royal, and read Hold My Coat. And follow this advice. The world doesn’t need more rappers, so if you want it, do it well. The world isn’t going to cut you slack.

Also stay on the lookout for my first mix-tape, SOLID GOLD TANK. I’m sure I’ll make millions.