Jeff Pearlman

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Reggie Williams

#290
The founder and CEO of one of hip-hop's biggest websites long dreamed of following Russell Simmons' entrepreneurial path. Here's a blueprint for chasing your goals—and capturing them. POSTED January 3, 2017

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Here’s a compliment I’ve never before paid to a Quazer: I struggled to find pictures of Reggie Williams.

That’s a rare thing in 2017, when everyone and their mothers are on Facebook, Instagram, Twitter, Snapchat. Hell, I can dig up photos of my great grandfather; of your great grandfather; of your great grandfather’s great grandfather. But Reggie Williams, head of one of America’s top hip-hop websites? Well, the pickings were slim.

But, if you think about it, that’s an insanely cool thing. I’ve known Reggie for nearly two decades, and it’s always been about the dream, not the celebrity. His dual loves of hip-hop and entrepreneurism are the driving forces of his career, and the reason why—after lengthy stints at MTV and BET—he now runs the fantastic (and funkily named) Ambrosia for Heads.

Here, in the magical 290th Quaz, I talk with Reggie about the beauty of hip-hop and the pursuit of greatness; about a very short Phife Dawg and a very old Jay-Z and Eminem. One can visit the site here, and follow its Twitter, Facebook and Instagram existences here.

Reggie Williams, man of, oh, six images, you are the Quaz …

JEFF PEARLMAN: I’m gonna throw a weird one at you. So I’m a longtime Tribe Called Quest diehard. Love them, love the music, love the inventiveness. I did not, however, love the recent album. In fact, I initially hated it. Then I kept listening—over and over. Before long I couldn’t get enough. I wonder, as a guy in music, why you think this happens? And can we properly judge the greatness or shittiness of music after one listen? Is it even possible?

REGGIE WILLIAMS: I love that question. I think the answer is “Yes” and “No.” There are lots of songs that are instant hits. I felt that way about Macklemore’s “Can’t Hold Us Down,” a song I heard and posted 18 months before it broke, Pharrell’s “Happy,” another one that I loved several months before it caught fire, The Weeknd’s “Can’t Feel My Face,” an instant smash, and several other songs. I think the songs we instantly like tend to be more simplistic. That’s not a bad or a good thing. It’s just a thing. I’ve found that the music I go back to for years and decades, however, tends to be more complicated and does require more time to properly process. I believe, in those instances, the artists are creating work that goes against the grain of what is popular at the time, and it takes some time for the ears to adjust. One of the best examples of this, for me, is D’Angelo’s Voodoo album. His Brown Sugar album was one of my favorites of all-time, so I had incredibly high expectations when it was released. It was wildly different than what I expected when I first heard it—dirty and dissonant—and I was not enthralled, immediately. Like a fine wine, however, it opened up, and, to this day is always the first album I play when I get new speakers, headphones, etc., to test how good they are.​

J.P.: You’ve worked for MTV, for BET. You’ve had a long and successful career being employed by big outfits, knowing a good check would come regularly, knowing there’d be perks and a company holiday party and flights to here and there and there and here. So why did you decide to start your own site? Was there a moment of definitiveness? And how terrifying was the move?

R.W.: I’ve been working toward having my own company since 1992. I had a picture of Russell Simmons on my dorm wall during my first year in law school, with a quote from him about owning your own business. I knew I wanted to run a multimedia business–music, film, television–and the question was whether it would be via climbing the corporate ladder to the top or starting my own. The people I admired, like Russell, David Geffen, Jay Z and Sean “Puffy” Combs all had their own, so I always suspected that would be the ultimate route. Even when I was in the corporate environment, I found myself in entrepreneurial roles, like doing MTV’s first ever digital video streaming deals and helping transform BET’s Music Programming department from videos to full lifestyle programming around music and comedy. In many ways, running my company, Ambrosia For Heads, is just the culmination of what has been a two-decade long journey. It’s been more of a progression than a specific moment of definitiveness. The move definitely requires a huge level of courage. Beyond the obvious financial sacrifices and implications, there’s the fear of public failure and the inability to recover. In time, however, you see that the difference between success and failure is often a matter of perspective.

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J.P.: You started your first hip-hop site, nurules.com, right around the turn of the century. It didn’t last long. Why? What did you learn from the experience?

R.W.: They say “timing is everything.” In my case nuRules was both several years too early and some months too late. My belief back in 1999 was that the Internet would become the ultimate pipeline through which all media was delivered–audio, video and editorial. For audio and editorial, that’s already true and for video (TV, movies and short form), it’s well on its way. Back then, however, only 10 percent of US homes had broadband penetration, so it was way too early for an entire business to be built on that distribution pipeline. At the same time, a lot of the money that was invested in that digital entertainment space was funded a year or so before I got nuRules up and running that November 1999. By the time 2000 hit, the first Internet bubble was bursting and we were about to get hit with a massive crash, compounded by the attacks of 9/11. The biggest thing I learned, however, was that we have far more control over “timing” than I knew then. The key to any business is to stay up and running. Whether you do that by hook or crook, grit or guile, if you’re able to stay in business long enough and have a sound idea and strong team, you can wildly increase your chances of getting to a point where the timing aligns with you. With AFH, we’re able to do an amazing amount with an incredibly lean team and we’re currently self-sustaining. We’d like to grow and will need additional resources to do so, but we’re built for the long haul.

J.P.: I have a theory, and it comes from my observatory and participatory viewpoint as a white person in 2016. Namely, I think a large percentage of whites interact with blacks while thinking, “How am I supposed to do this? Are there things I should say to sound informed and empathetic? Is there a way I need to be? To come off?” Not all of us (I truly don’t have this in my head), but a good number. My question for you—are you aware of this? Are most of your non-white friends? When you’re talking with a white guy who’s overthinking interaction with a black guy, are you overthinking what the white guy is overthinking about what you’re thinking? (that was a fun sentence)

R.W.: I actually think we all have far more in common than we do differences. I believe the basis of any relationship is finding commonalities upon which we can build a rapport and from there the interactions can take many twists and turns. We get caught up in beliefs about groups of people, but those beliefs often fade, or are at least subordinated, when two individuals come face to face. There’s a reason why common ice breakers when people first meet are conversations about the weather, sports, kids, jobs and, sometimes politics. Those are things to which, whether we agree or disagree, many of us can relate. Maybe there’s an added layer of discomfort initially when the interaction is between members of different races, but, as long as the two people are relatively open-minded about people from other races, I don’t think the interaction is any more stilted than it would be with two strangers of the same race meeting for the first time at a cocktail party. I think that’s a roundabout way of me saying I think you’re overthinking it.

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J.P.: I have a weird, untested theory, and it’s this: Hip-hop allows its artist to hang around far longer in the mainstream than pop, rock, country. I mean, Jay-Z, Eminem, Kanye, even Nelly—guys in their late-30s/early-to-mid 40s who are still commercially viable. Am I wrong? Right? And why?

R.W.: I think the people you named above are outliers. Generally, in all genres of music, most artists have a very short shelf-life. Stars have 1-2 years, if that, of being hot and then they never reach that level again.  I’m immersed in hip-hop, so I see how vast the turnover is from year to year. For every Kanye West, there are a hundred artists who had a hit song or two and then are nowhere to be found. If you look at the charts from five years ago, you’d be amazed at how few of those acts charted this year. There are even less so from 10 years ago. Every genre has its titans, though. In pop, for example, there’s Rihanna, Beyonce, Bruno Mars, Katy Perry, Adele, Taylor Swift and the two Justins. Even Britney Spears remains relevant 15 years later.

J.P.: How do you think hip-hop is embracing homosexuality? Can a rapper still use “faggot” or “homo” in a song and be commercially embraced?

R.W.: Like with the country overall, hip-hop’s acceptance of the LGBTQ community and understanding of related issues is layered. On the one hand, there are most certainly a number of hit songs with derogatory terms in the lyrics, and it’s disproportional. On the other hand, you have an increasing amount of gender-fluid artists like Young Thug, Young M.A. and Jaden Smith. Perhaps the greatest example of the complexities and nuances is Tyler, The Creator. He is a staunch supporter of openly gay members of his Odd Future collective, like Frank Ocean and Syd Tha Kyd. Yet, he’s also quick to drop the “F” word and say other things many would think are derogatory in his music and conversations. It’s complicated.

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Reggie with, oh, someone.

J.P.: What’s your work day like, soup to nuts?

R.W.: My work day never stops. The Internet is a 24/7, 365 day cycle, so most of my waking day, I’m typically working on something AFH-related, or thinking about it. I usually wake up between 7:30 and 8, check my phone and then do a cardio workout. Even while I shower, I’m listening to hip-hop news, to get the latest and greatest. From there, my team and I have a virtual writers room where we are constantly vetting content, stories and angles throughout the day. I intermittently check emails, but I try to avoid having those control my day. I deal with way too many of our tech issues than I’d like, so that takes up a fair amount of time, and I’m constantly scouring the web, social media, YouTube, etc. for stories. Generally, I’ll have a few calls and, on a fair amount of days, I’ll have meetings, interview an artist or producer, attend a showcase or something like that. I often do a quick workout with weights in the late afternoon/early evening to clear my head and re-charge, but typically I’ll watch an interview or listen to a podcast during that time, looking for stories. At night, it’s similar, though things settle down a bit. I typically go to bed between 1 and 2 am.

J.P.: You’re closer to 50 than 40, and I always find the aging thing fascinating with people like us, who work in funky fields that often cater toward youth. Do you have any internal fight to stay young? To remain relevant? Is it increasingly hard to care about the same things, say, a 17-year-old hiphop head cares about?

R.W.: You know, I just heard a quote by Quincy Jones, as relayed by producer Terry Lewis. It goes, “You’re only as old as your ability to accept and process new things.” I fully subscribe to that. I’ve worked with some people in their 50s who would absolutely exhaust most people half their age, and I know some people in their 20s who seem ready for retirement. It may sound cliche, but I truly do believe that age is a mindset. I bet you no one under 40 ever said that…:) In terms of the music, some of my favorite artists of all-time became popular in the last five years, and I have a saying that the “Golden Age” of hip-hop is from 1978-present. I think it’s all a continuum. There’s terrible hip-hop from the 90s, great hip-hop in the 2010s and vice versa.

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J.P.: Greatest moment of your career? Lowest?

R.W.: I’ve been truly fortunate to have more magical moments than I can remember. I think that’s common when you love what you do. Right now, I’m literally working the hardest I’ve ever worked in my life, and it’s for no pay to me. I feel lucky everyday though. One highlight is seeing Prince perform in a room of about 25 people and then speaking to him for a bit, after. That said, I’m hopeful the greatest moment is still yet to come. The lowest was definitely when I realized that we had to close down nuRules. That day actually led to a tattoo …

J.P.: I just watched an interview with Q-Tip on the Daily Show—and he was wearing sunglasses indoors. You’ve dealt with many celebrities. I’ve never, ever, ever understood this. Are people trying to look cool? Do most people think it is cool?

R.W.: That’s funny. I think people do it for many reasons. For some it’s a fashion statement, for others it’s shield. Sometimes people just had a rough day … I’ve learned not to read too much into it.

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QUAZ EXPRESS WITH REGGIE WILLIAMS:

• Number of times in your life you’ve been compared to/asked about former Clipper Reggie Williams or former Dodger Reggie Williams?: Hilarious. Only a couple of times for Clippers’ Reggie Williams. As a kid, people used to ask me often if I was related to Reggie Jackson … go figure. The best is I once attended a conference with Bengals’ Reggie Williams. That created ALL SORTS of confusion. Nice guy, though.

• Five reasons one should make Indiana his next vacation destination: 1. Donut Bank—Best donuts I’ve ever had in my life, to this day; 2. Nice is the default attitude for most people; 3. Holiday World—One of the greatest amusement parks in the world–the largest wooden coaster and the largest water slide–with the shortest lines you’ll ever experience at a park of that scale; 4. My mom and dad; 5. Did I mention Donut Bank?

• Celine Dion calls. She wants to invest $100 million into the site, but you have to change your name to Al B. Sure and get a tattoo of Gary Coleman across your forehead. You in?: What you talkin’ ‘bout, Willis?

• Five greatest short rappers of your lifetime: Tupac, Kendrick Lamar, Phife Dawg, Lauryn Hill, Too Short (in no order)

• Rank in order (favorite to least): bluebirds, Pointer Sisters, Real Housewives of Orange County, Mookie Wilson, Bronx Zoo, Keith Van Horn, Jewish brother in laws, Amelia Earhart, Stacey Dash, Kyrie Irving, Little Shop of Horrors: I’m so excited to start with Pointer Sisters that it stops there.

• Why ‘Ambrosia’?: Ambrosia was the food for the Greek Gods. We try to serve up the best for Hip-Hop Heads and the best food for thought. Ambrosia for Heads.

• One question you would ask Vince Ferragamo were he here right now?: Does he think he’d be on Fox NFL if he’d won Super Bowl XIV instead of Terry Bradshaw?

• In exactly 19 words, make a case for the music of Carrie Underwood: After thinking about this, I don’t think I would be able to do that even if I tried hard.

• This is a song I absolutely love. Wondering what you think: I’m a bit of a Tupac purist. He’s one of my favorite MCs of all-time, so, for me, his catalog stops after Makaveli.

• Why haven’t you taken more of a public stance on the Braves signing Bartolo Colon?: Googles Bartolo Colon with the left hand* *Tweets about him with the right*

• Who was your favorite Brady kid? Why?: Sadly, I can’t remember a single episode of The Brady Bunch. What was that question about age, again?

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Once again, Jeff Pearlman has produced an exhaustively researched, elegantly written book that re-creates one of the most colorful and memorable teams of the modern era. No basketball fan's bookshelf will be complete without it.

— Seth Davis, author of Wooden: A Coach's Life