Hip-hop industry legend, artist advocate, Rap Coalition founder, OG; these are a few of things we can use to describe Wendy Day.

After using her life savings to start up the not-for-profit Rap Coalition in March of 1992, Wendy has continually been a guiding force in the industry for artists.

As one of the most important business people in the rap game, Wendy has had a crucial hand in numerous deals, including the groundbreaking Cash Money-Universal deal which gave the fledging New Orleans label complete ownership of their music – something Wendy has always focused on.

Over the years, she’s worked with more legendary artists, including Eminem, Young Jeezy, Master P and plenty more; helping them negotiate fair deals and teaching them the inner workings of the game.

Stop The Breaks had the honour of interviewing Wendy Day and as expected, she had plenty of jewels to drop. Check out the interview below where she talks about her motivation behind helping rappers, opportunities for indie artists in today’s music scene, the Birdman-Lil Wayne drama and more.

Independent hip-hop artists pay attention, you’re about to get schooled!

1) I first heard about you when I read Dan Charnas’s book The Big Payback: The History of the Business of Hip-Hop and realised just how important you have been to the rap industry. I’d love to learn more about your motivations behind helping hip-hop artists for all these years.



*blush. Thank you for the kind words. I started listening to hip hop in 1980 when it first started (I’m old). I love the energy and passion in rap music. I’ve watched it shift, change, and grow over the years into what it is today.

In 1992, I decided I wanted to give back to the artists some of the happiness their music brought me, so I started Rap Coalition, an artist advocacy organization for rappers, DJs, and producers. I started by pulling artists out of bad deals.

Then I started getting artists into good deals; I played a role in Master P’s deal at Priority in the 90s, helped Eminem get signed and helped negotiate his deal at Interscope, shopped and negotiated the Cash Money deal at Universal.

I helped Do Or Die and Twista put out their first releases and then negotiated Twista’s joint venture with Atlantic, shopped the Trill deal for Boosie and Webbie back in ’05 ( I didn’t negotiate their deal at Asylum/Warner, however, because I felt they could get a better deal elsewhere), and negotiated David Banner’s deal at SRC/Universal.

With the influx of 360 deals in 2005, I began consulting artists on how to make money without a major label. I believe independence and “do it yourself” are the key to succeeding, and are certainly more profitable.

Signed to major labels, artists are lucky to get 15% of sales (after they pay back the majority of expenses) and 70% of their own show money. Independently, they control how much they and their investors make. Truth is, it’s easier to find an investor than a record deal.

2) At the moment the music industry in general is pretty much like the Wild West with successful independent rappers like Nipsey Hussle viewing it as the gold rush of our time. What sort of opportunities do you see the current music landscape presenting to indie artists?

Provided artists understand how to succeed, and how to monetize their music, the gatekeeper is no longer! Anyone with talent, grind, motivation, and a budget can survive.

From music sales, streaming revenue, merchandise sales, sponsorships, licensing deals, shows, touring, etc, savvy artists can build a nice career to support themselves and their families.

Since the gate keepers are gone, the playing field is wide open. Today, the only thing stopping a talented artist from succeeding is the lack of understanding of how all of this works. It’s easy to get fooled into thinking it’s easy and that one knows how to succeed, but it’s not easy and the paths are not obvious.

3) With all your experience helping rappers get fair deals, what do you see as the most common mistakes up-and-coming rappers are making in their career?

The lack of knowledge and understanding of how the industry really works are the biggest pitfalls for artists. Most rappers think all they need is a few features by known artists, some Worldstar video posts, MTV or radio spins, and they’ll blow up.

Nothing could be further from the truth. Some folks think they don’t need any money because a label will “discover” them. I haven’t seen that happen in the 23 years I’ve been doing this. Understanding how the industry works is key. Especially if you want a successful career in music.

4) The Cash Money-Universal Records that you helped orchestrate is legendary in the rap game. What leverage did Cash Money have that enabled them to command such a lucrative deal?

Cash Money had sold over 31 releases over a six-year period of time. Those releases sold anywhere from 5,000 CDs to 25,000 CDs on each release. When I was in the midst of shopping their deal, I helped them sell 75,000 CDs on a release by expanding their marketing area into the Midwest from the south. Once they had a large buzz in the south and in the Midwest, the rest was easy.

They were able to parlay that regional success into a $30 million distribution deal, where they could keep 80% of the income. Most new artists get to keep 15% of sales after they pay back all of the money spent on marketing and promotion. So to get to keep 80% AND own their own masters was amazing!

5) How do you feel about the Baby and Lil Wayne drama?

I’m saddened by the Baby and Lil Wayne drama. It’s the end of an era. But knowing how Cash Money has payment issues, I’m surprised this didn’t happen sooner.

6) Like you said, this marks an end of an era for Cash Money? After all, if Wayne splits and takes Drake and Nicki with him, that’s 3 of their flagship artists off the label.

Not only is it three of their flagship artists but it’s the only three artists that really matter in terms of sales and notoriety. It appears, from the court papers, that Young Money is jointly owned. It will be interesting to see how this all plays out.

The value today is in the YMCMB brand, not the Cash Money brand. Truth is, in the past decade, getting signed to Cash Money has seemed more like a career death sentence than anything.

7) From a business point of view, who do you think are the top hip-hop artists doing it at the moment?

I think on the business side Tech N9ne is one of the top artists doing it– he’s independent and he’s just killing it. He and his partner, Travis, made the Forbes list last year at $30 or $40 million!

I think we have a lot of artists in Atlanta that are doing exceptionally well financially, both with shows and with releases. I think Houston is about to make a resurgence. They have some really great new artists coming up.

On the major label national scene, I think Nikki Minaj is doing an awesome job of building an empire. And of course Jay-Z.

I think the money and influence today is in tech, and the really smart artists will go over to the tech world and space. On the artistic side I think Kendrick Lamar is doing a phenomenal job. He’s bringing it back to the importance of talent and skills and the fans seem to agree. I think this will continue to impact him greatly on the business side!

Thanks so much for letting me voice my opinions. If anyone wants more information about what I do or my consulting services they can find a ton of free information at www.WendyDay.com. It’s an industry that’s a lot of fun, once you know what you’re doing. Thanks, again!

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Written by Hao Nguyen
Stop The Breaks is an independent music marketing company focused on showcasing independent hip-hop artists. Our goal is to help motivate, inspire and educate independent artists grinding around the world. We provide branding, content marketing, social media, SEO and music promotion services.