HipHopDX celebrated a significant milestone this year. It’s been 15 years since Sharath Cherian launched the publication out of his home in Winnipeg, Manitoba, Canada. Over that time, there have been five Editors-in-Chief, seven different versions of DX, and a gaggle of incredible articles written by a generation of talented journalists. The online journalism landscape has changed significantly. The Internet is infinitely more crowded. A decade and a half is impossible to document in one non-book-length conversation, so we’ve decided to provide an extended glimpse into the history of HipHopDX throughout the week. Over the coming weeks, we’ll release interviews with previous DX Editor-in-Chiefs as well as Cheri Media CEO and the founder of DX, Sharath Cherian. Each delivers a compelling peak into the publication’s legacy within a constantly morphing journalistic landscape.  

Up next, Jake Paine joined the DX team in 2007 and took over as Editor-in-Chief in 2008. Paine steered the site through arguably the roughest period in its 15 year history. The global economy had entered the Great Recession. Online journalism had officially entered the Blog Era. And HipHopDX was struggling through a site redesign that threatened to derail the publication. Oh, and three integral staff members were about to leave the company, as well. Few Editor-in-Chiefs of any medium scaled as many albatrosses as Rap journalism’s Quiet Giant. Jake Paine not only did so without downsizing a single staff member, but over his five year tenure, DX doubled in traffic, outlasted the “Blog Era” and cemented its reputation.

How Jake Paine Became Editor-in-Chief of HipHopDX


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HipHopDX: How would you describe your transition into Editor-in-Chief of HipHopDX? What year did it happen? How did it happen?

Jake Paine: I believe it was September 20, 2007. I took the job really without a title. ­I took the job because of a number of weird occurrences. It was serendipitous. The Senior Writer of DX at the time, Paul W. Arnold had been in talks with Andreas Hale. I had worked with Paul at AllHipHop, and I had known Andreas through HipHopSite and also DX and I was a big fan of DX. I ended up there in December of 2007 and transitioned from being with AllHipHop for nearly six years as a Features Editor. I worked really hard that first year with DX. Somebody who I’d also worked with closely was Melanie Cornish. Mel was the first person I knew who was writing for DX, and I remember meeting with her in 2007 in Times Square. She told me how DX valued writers in compensation, and really spoke on my behalf. In about August, it was six years ago this week, somewhere around August, Andreas decided to take a position at He had been the Editor-in-Chief at HipHopDX since 2004 or 2005. We were very much collaborative in the year together. It was definitely a system of checks and balances. But when he left, I became Editor-in-Chief, kind of like how the Vice President becomes President. I remember at the time, DX was a lot of business individuals who were very unsure of their titles. I said based on my experience, which was six or seven years in digital, we need to have titles. Not because I’m someone who loves credit, but at the end of the day we need to create that same system of checks and balances. So my first week in August of 2008 and my main objective at that point early on was just trying to steer the ship that Andreas and [Jeff Ryce] had kind of set over the previous six or seven years.

DX: Were you nervous?

Jake Paine: Actually, it was funny. I didn’t have time to be nervous, and really I wasn’t. I’m so glad that I had that buffer year to really learn the nuances of a site like HipHopDX versus my experience with AllHipHop. Every magazine, every digital space, every brand is so different, so is the audience and what they are looking for. That year really gave me an opportunity to transition into DX. If you were an artist on a major label versus an artist on an independent label, the difference meant nothing in terms of the treatment you would get in an album review or in the terms of a feature. One thing I always loved about HipHopDX is merit in terms of art and creativity stands on its own. So I went from a site like AllHipHop that was very aware of Blu & Exile and Below The Heavens to a site like DX where in 2007 was like, “This is the most important album of this year.” I went to a site like AllHipHop that really took Lil Wayne’s movement into strong consideration to a property like DX who didn’t pay it as much mind. I really had that year to iron out the wrinkles and understand that and find my fun and my rhythm. So to answer that question, by August, no I had no time to be nervous. I really remember getting off the phone after Dre had announced that he was taking on, I think his title was [Executive Music Editor Of Music] and I was like, “Wow this is how it goes down.” Just like any athlete or any politician, you just stay ready. For me, I didn’t have this 100 day list of everything I wanted to do with my complete vision I just kind of took it one day at a time. In all honesty, 2008, which was the year that Dre and I shared together as Editor-in-Chief, was one of the most important years in DX history.

DX: Why is that?

Jake Paine: Well that was the year I feel that we broke out of the shadow. I remember in January of 2008 sitting in a meeting at Asylum Records. Asylum doesn’t even exist anymore. A very respected publicist told us—I’ll keep her name out respectfully—that DX was a backpacker site. We were not taken seriously. Also at that time, you know this is before Twitter, before there is a social aspect, it’s all about brand. DX is not in New York at that point and had no presence in New York. So for us to be kind of a West Coast company with an Editor-in-Chief who’s living in Las Vegas, NV and an Editor in Philadelphia, PA we were really kind of, not fly by night but definitely more heard then seen. By the end of that year, I really believed that DX was kind of contending for the top spot in the Hip Hop media space. The numbers were starting to prove it, our advertising was strong, and artist whether it was 50 Cent, Lupe Fiasco, Game, Blu, they were all working with us or participating with us, which for me coming from my experience at AllHipHop where it was pretty much nobody short of Dr. Dre or Eminem that we couldn’t speak to, that was a major affirmation. I feel like 2008 gave DX the confidence that was necessary to weather the storm that was ahead in the next two years.

Why 2009-2010 Was HipHopDX’s Most Challenging Time

DX: Describe the storm that awaited in the next two years.

Jake Paine: Well, I feel like as any company that has multiple employees, we’re a corporate site. DX at that point had eight to 10 employees and you know we do have an overhead to keep. We do have advertisers. DX in its entire history has never altered a review rating or shown favorable support of an artist because they advertised. But I always admired Eskay at NahRight, because Eskay is not a fan of 50 Cent, and it never hurt his bottom line to say so. 2DopeBoyz has their reasons and they don’t need to post Lupe Fiasco tracks. When you’re a corporate site, you owe yourself to the culture. What was happening in 2009 and 2010 was sites like NahRight, 2DopeBoyz, TheSmokingSection, Unkut, CocaineBlunts, OnSmash, so on and so forth—YouHeardThatNew—that group came out and they had such authentic, unadulterated voices, that it was the blog era. Now at that point in technology, it was about who got the music, who got it first, who had great presentation and who had an authentic voice. For us being a corporate site working within the confines that we had to, it was kind of a challenge.

One of the major heroes of DX’s success that is so often understated is Shake, who is one of the 2DopeBoyz. Also Meka, who is one of DX’s loudest and most articulate voices as a blogger and as a contributing journalist in 2007, 2008, 2009. Those guys took their tremendous ability to 2DopeBoyz and left DX very vulnerable in a way that I feel like is natural progression. If some of the Cleveland Browns go on to start on the Baltimore Ravens and earn a Super Bowl very quickly, and you’re the Cleveland Browns and you have to start fresh. You already know how this equation goes. For us, 2009 and 2010 were very much about rebounding, weathering the storm, and trying to stay the course as a corporate Hip Hop site at a time where individuals were definitely contending and winning in the ring.

DX: What do you remember about the decision to remove the blogs?

Jake Paine: That was definitely a major challenge. I met you in December of 2009, so that would have happened in 2009. What had happened is DX had went through several redesigns between 2008 and 2009. Andreas very much to his credit had really cultivated the blogs. He found important voices like Meka, like Amanda Bassa, like Legend who is now with OnSmash. We had artists, too. We had Chamillionaire who would blog occasionally. We had Crooked I, Nino Bless, Sha Stimuli—dope artists that still are very active in the culture. Dre also had the relationships and the ability to motivate those people and kind of have dialogue with them on keeping their ideas crisp and fresh and so forth. I also need to include Andres Tardio who was also blogging and is on staff with the site today. It was never my decision to get rid of the blogs. Honestly that had to do with the redesign and allocating that space differently.

The bloggers all know this, but that was never my strength. I’m the type of dude that can work on a researched editorial, but I’m not the best at educated armchair opinion. And I hope and mean no disrespect in calling it that. But the beautiful thing about a blog is I can know everything about football. I don’t have to work for sports media, and I can publish my thoughts on football. What I’m more used to is being an editor, being a writer in the professional setting and kind of mining, working and crafting those ideas, which completely defeats the purpose of blogging. I remember when that six to nine months when blogging was still up, we had bloggers that were running interviews, and I struggled with that because I’m like, “Interviews should definitely be run through the site.” Which also kind of defeats the purpose of blogging that you can do anything you want. So to answer your question it wasn’t my decision, but it was a decision that I do feel that DX suffered a consequence for. I think DX celebrated its First Amendment. It always has, and you’re going to get that when you speak to J-23. DX was the one site that gave LL Cool J, I think it was half a star or one star for an album review. This is LL Cool J, one of Hip Hop’s greatest trailblazers. HipHopDX is a site that would have the courage to take pot shots in an interview with an A-List artist and DX really exercises First Amendment. So take those blogs away, especially with writers and thinkers as talented as that group was, our audience including ourselves let us know it. It was a major detriment only added to the tremendous rebound and tremendous hurdle that was 2009.

Shake, Meka & The Origin Of

DX: Dre talked about how Meka and Shake started 2DopeBoyz and then their decision to leave. He also noted that he had already left the site by then, so his details weren’t there. What are your thoughts on that? What do you remember about the origin of 2DopeBoyz and then the eventual separation?

Jake Paine: That was August of 2009. That was the very end. It’s funny we’re speaking now in August. When I got to DX, I had known Dre through just being colleagues and peers in the media. I had known of J-23 because I had really admired his courage and honestly. His opinion really resonated with mine reading his content. But it wasn’t until I was hired with DX that I got to know the intricacies. Shake, at the time I believe his title was Media Director, and Shake was truly one of the secret weapons of the DX’s success. I think that [Shake] is one of the reasons why DX exists today, and that has to do with a few different things: A very fierce work ethic. I pride myself on being able to work 70 to 80 hours a week especially in that time of my life. That first step that probably exceeded me was that Shake was there. Also I’ve never met anybody in all of my years covering music that had their pulse more on the hand of new artists. Years before I heard anyone else mention Kendrick Lamar, Shake knew about him. Tiron, Fashawn, Skyzoo—all of the artists that are making noise that are new in the last five years, new in terms of the media mainstream level, Shake was running their content on on HipHopDX. To the user, it was an incredible place to experience dope Hip Hop, the same way Kay Slay or DJ Skee and all these programs where you can depend on radio to hear somebody new. Shake made that with his position at DX with audio and video. He is also incredibly talented with his graphic design and Photoshop. He had a hand in more than I’ve ever realized in the years since.

When his day wasn’t occupied, he began a side project, which at the time I don’t think any of us paid any attention to. I mean it was designed for the fans of music that couldn’t get enough of it on DX. More than that—not to underplay or down play Meka at all—Meka is a phenomenal writer. Truthfully, Meka says and writes what so many people are thinking. He is a tremendous writer and also has that same pulse. Meka knows what’s going to be hot in 2016 and he’s very shy, and I think that makes him a better writer. The two of them created this project. I think it began in February of 2008, if I’m not mistaken. It had dope images, it was beautifully curated, and it wasn’t designed to compete with NahRight. It wasn’t designed to become what it is. But it was just this place that was kind of a West Coast Damascus for dope Hip Hop and it didn’t have to be exclusively West Coast. So they started that in early 2008 and by the summer of 2009 it had become so much of what it is today. Clearly they filled a major void in Hip Hop.

It got to the point where I think it was too demanding, and there was definitely some politics between Shake and Meka and owners of DX, and I was forced to mediate that for a few weeks…a few months. In the end, Shake and Meka had an opportunity to go full time at 2DopeBoyz, and they did. Now six Summers later, we can see what that meant. I don’t know about you, but to this day I still check 2DopeBoyz 25 times a day. I’m really happy, and I think that those two meeting at DX and Shake meeting J-23 at DX through the message boards if I’m not mistaken, it is such an organic story. That’s what happened, and it was massively hard to fill Shake’s shoes. Luckily I had experience with Kathy Iandoli at AllHipHop, who is somebody who is very much on the cusp of music on the come up. She is very well-versed in genres close to Hip Hop like R&B and EDM. I really give Kathy a world of credit because at that time she was unemployed at a full time level and took to DX in August of 2009 as our Media Editor, and that was one of the easiest transitions I’ve ever witnessed. I still feel like DX is a major destination for audio and video both for the established artists and the new. I love that the new site provides so much additional content than it ever did in my time on what matters in a song or what’s really at play in a video.

DX: How did Omar Burgess join the team?

Jake Paine: That’s a great question. Well when Dre left for BET in August of 2008, I was running the show so to speak myself for two months. I probably gained 30 pounds in that two months, and I probably lost three inches of my hairline. I’m kidding, but in all seriousness, it just wasn’t to be done. At that point DX as a team for that period of time was: me, Shake, Mike Trampe who runs our social media and had begun that year. It included a tremendous staff of news writers including Andres Tardio, Slava Kuperstein, Alliyah Ewing, Amanda Bassa, Anthony Springer Jr., some other folks, William Ketchum. We just didn’t have enough time. Omar was a writer, and I had worked with Omar at AllHipHop in 2005 and 2006. One of the people that got me integrated to DX, Paul W. Arnold, had introduced me to Omar way back. They had a previous connection from a mutual acquaintance and Omar, of all the people I’ve worked with at AllHipHop, Omar was my favorite. He was the one guy that could take any story. I remember him doing interviews with Pharrell. I remember him doing interviews with Yung Joc. I remember him doing an interview with I think it was Tha Alkaholiks. Omar’s an encyclopedia of Hip Hop knowledge and that showed in everything that he does and I think anything he doesn’t know he researches.

So Omar was working at that time at a non-industry job and wasn’t very happy with it. He was also doing freelance news for DX every morning as he had done prior to my being hired. At that time I really needed a reinforcement. I knew Omar’s work ethic. I knew his love. I also knew that Omar is—and I tried to look for this in any hire I made at DX—somebody who considers this his dream. Not somebody who’s out to be famous, not somebody who’s out to take Instagram pics with Dr. Dre, but somebody who really loves covering the culture and asking the right questions and just grasping what an opportunity this is. Omar Burgess is all of those things. So it was October of 2008, I still remember I was in a family member’s kitchen traveling and I called Omar to share with him that [Sharath Cherian] the owner of DX was on a three way call and offered Omar the job in October. I think he accepted before we even got to the terms of it, which was a recurring theme of DX hires. Omar is still there today, and he is the ultimate utility man. He’s like Charles Woodson, he can play both sides of the ball. He is incredibly aggressive. He speaks through his work ethic. Anybody that knows Omar knows that he’s shy, he’s not a media personality that pops on social media. He just speaks through his by line. So many times his by line isn’t related to what he is doing and honestly I feel like Omar’s another secret hand in DX’s survival and persistence and perseverance over 2009 and 2010. 

How Pimp C’s Passing Factored Into DX’s Most Impactful Era

DX: During your time as Editor-in-Chief, what is the most important story or the most impactful story in your opinion as you look back?

Jake Paine: I’ll always remember Pimp C dying. That was December 4, 2007. My date might be slightly off. Chad Butler was somebody I knew, not well, but I knew. I think within the last year of him dying I had spent time with Bun B and Chad and I remember that story. I remember that day and it was chilling. It wasn’t the first time something like that had happened. I interviewed and covered Proof from D12 quite a bit before his passing. There’s a bunch of artists and people that I’ve known throughout the industry that died suddenly but that day was really difficult. It came after a year that UGK had what I’ve considered to be the greatest comeback year in Hip Hop. “International Players Anthem” owned that year. Whether you looked at the charts and saw UGK’s number one album debut or you were just ahead and loved Andre 3000’s verse, UGK made everyone believe in the possibility of music in a time when CD stores were closing and Rhapsody’s format was changing and all of these crazy things were happening. I always, always, always, remember that story and Roberta Magrini who is UGK’s long time publicist and a long-time friend of mine. I talked to her that day and I remember writing that story. For me that is something that I will always remember and it was one of the most vivid DX memories. It still kind of gets me a little emotional to this day.

DX: Man I remember that too, that was a crazy time. It was a super crazy time.

Jake Paine: It was a wake-up call, too. No one wanted to come out and condemn lean or anything like that, but it was just really…there are moments in pop culture and entertainment when you know the party is over. They talk about the Hell’s Angels killing at Altamont at the Rolling Stones concert, and you knew that the Summer of Love was over. The Beatles breakup, and you know when that happened. Tupac Shakur and [The Notorious B.I.G.] getting murdered, The Source Awards, all of these moments when you know something beautiful is coming to an end. I think everything that was great about the early 2000s, the great comebacks, the great music, the great personalities, the amazing interviews, which Pimp C was never short on words for, it all kind of came to a screeching halt in 2007. I had only been with DX two or three months at that point. I will always always, always remember that.

Jake Paine’s Legacy As HipHopDX Editor-in-Chief

DX: What do you think your legacy is as Editor-in-Chief for the time that you ran the site? What are you most proud of?

Jake Paine: I’m really proud of weathering the storm. A lot of sites were never able to recover over that bump. There are a lot of sites that are not the same as they were in 2008 as they were in 2011. My goal with DX was to make sure that nobody got laid off, nobody got fired, and the coverage and the social media never suffered. I’m really proud of that, and I don’t think it’s something I ever put out there like that. I don’t think it’s something that I expect anybody to notice, but DX was something special long before I got there. I’m always the type of person that, what is it that Billy Martin said, “I’m not the biggest Yankee, I may not have been the best but I may as well have been the proudest.” I’m paraphrasing, but that’s how I feel about DX. Knowing what J-23 and Andreas Hale had done before me and knowing the standard they set as well as knowing that Sharath Cherian started the company back in 1998, 1999 and then there’s editors like Albert McCluster, these people that never get mentioned but because of my six years with DX, I know their bylines. I know the stories they did. I know the nights of sleep they must have missed, and their significant others that were upset with them because of it. I tried to maintain that standard as well as grow.

I really didn’t try to bring any to bias DX. There are artists in Hip Hop that I absolutely adore and couldn’t cover enough, and there are artists in Hip Hop that personally I cannot stand and I made a living covering. I tried to do all of those things in the interest of the culture. I never took a dollar from anybody under the table. I never tried to put myself over the brand, and I am really proud of that. There’s a lot of sites, a lot of magazines, and a lot of people just in the entertainment culture that can’t say the same thing, and that was a hugely special time. It’s funny because in two weeks it will be one year since I left DX, and that is always a special special, special time in my life that I wouldn’t trade anything for. I never say this to people, I took a pay cut to be at HipHopDX before I was ever Editor-in-Chief. I worked more hours than I did with my previous job at AllHipHop and I gave more of myself than I ever had than pretty much anything in my life during that six years. I’m really proud of what I’ve accomplished. I’m proud of what you’ve done. I’m proud that so many things that I had my hand in are still there and I’m proud of the things that have moved forward. It was definitely a time in my life and an opportunity and a call of responsibility. I was 24 years old when I became Editor-in-Chief of DX and I was 29 when I left DX. There’s not a lot of people that young that get an opportunity like that when they’re covering giants. From Kanye West tweeting that I wrote an incredible review, from my relationship with 50 Cent and my relationship with Game, to all of these tremendous experiences. Covering Kendrick Lamar early, covering Fashawn early, I’m proud man. I think that if you take DX out of the Hip Hop equation, Hip Hop is much more different than people realize.

DX: Looking back at 15 years of HipHopDX, what do you think about where the sites been? What comes to mind?

Jake Paine: I feel like DX will always stand up for the little guy. Not to say we did it either, but I woke up this morning and I turn on HipHopDX and see the Dilated Peoples’ Directors of Photography a 4.5 out of 5. Forgive me, but I don’t think anyone has the balls to say that. I’m not trying to throw shots but I’m just like, people are so quick to say that when it’s convenient or when it’s safe. But HipHopDX giving perfect album reviews and asking really difficult questions. There were so many times when Paul W. Arnold who I spoke of earlier, he would ask the ultimate ice water veins questions to anybody. He would ask it to AZ then turn around and ask it to Chamillionaire. DX had so much courage in media and I feel like that’s true today and I feel like DX still has this little brother mentality to it. We’re scrappy, we hustle, we always run to first base, and I feel like that’s something that’s always been true. That work ethic is definitely there. Hip Hop media, the first wall is broken now, we all know who personalities are the same way you know who your newscasters are and your news anchors. Anyone who’s investing in the visual presentation of the culture knows who’s at Vibe, who’s at XXL, who’s at DX, who’s at AllHipHop, etc. and I always think DX has that work ethic because you have to. It’s just embedded in the bloodline of this company, of this culture, and in this publication. That’s just something I understand through the ownership at DX, through Jeff, Andreas, hopefully me to you and everyone else who is part of that equation we’ve just got that grind. This sounds so cliché but having been sleeves rolled up, hands in the ground with it towards the six years that I was, I know that to be true.

Jake Paine Details HipHopDX’s Approach To Business 

DX: Last question, what was Sharath like as a boss?

Jake Paine: You know I always tell people—I don’t want compare myself too much to Kobe Bryant because I haven’t won any championships—but I came out of high school and I went right to AllHipHop in June of 2002. I was 18 years old, my voice still squeaks, I started with AllHipHop and later that year I had a job title. I learned so much from Chuck Creekmur (Jigsaw) at AllHipHop about how to write, how to talk to artists, how to maneuver the industry. That’s my mentor and that’s my big brother. By version of becoming whatever my title was at DX to being Editor-in-Chief of my last five, Sharath who is the owner and President of DX, he showed me the business. Not in a way that is Bob Dobalina sitting there twisting his mustache, trying to figure out how to make a million dollars off beef in the streets. But more so how to look at how to grow an audience. How to take this voice, how to take this brand, and I had fought so hard personally to uphold it out of respect to Jeff and Dre and the other writers that have been at DX. So to find a way to cover the culture with no fear or concern of who is who, who’s got all the money, who’s on what label, was a part of it. But through Sharath I learned to really see opportunities and understand how to make a Hip Hop site profitable. Not profitable that we all drive around in V12 Mercedes’ but profitable in a sense that no one got laid off. Sharath taught me that. He definitely challenged me. Anybody who knows Sharath or who works for DX knows that he will call you at 9:01PM on January 2 to get a draft for what the plans for the year are. I still laugh about that with Sharath today. Sharath will call you on your anniversary if he thinks an interesting story is happening. But he definitely made me more prepared for the corporate world. I’m not just a Hip Hop journalist. I’m a Content Strategist. I’m a Digital Developer. I’m all of these nebulous terms because of the crash course I got at DX and because of the trust that its ownership and executive team put in me. I’m better because of it even if there were times when I thought that it was wearing on what my objectives were and what my passions were. I’m forever grateful because I know how to navigate other industries and other higher stakes platforms than just this thing that I’ve loved since I was 10 years old.

DX: Anything else you want to say?

Jake Paine: I really want to say thank you to everybody. Whatever side of the ball you roll on, I want to say thank you. First of all to the artists that make the music that led me to this career path and the people that work with them to the managers, the publicists, the assistants, all of those people who have a dream and chased it, take the pay cut, work long hours, and do all this stuff because of it. On a bigger note I want to say thank you to everyone that I’ve worked with over the course of those six years, I’m sure there were close to 200 writers that I dealt with. And just thank you, your blood, your time, your effort, your passion is in the Stone Hinge of DX. The team that’s there now you have my respect, you have my admiration. There are so many people there that I’ve had the opportunity of working with in different capacities and I really do. I want to see DX live forever and continue its dominance and its further rise. I’m just forever grateful for the opportunity. Years from now I hope to sit down with my grandkids and hopefully they know that I did something cool with my youth.

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