Given Riley Wallace’s long tenure as a music journalist, his lack of a formal journalistic education comes as a surprise. Like many in this industry, becoming a freelance writer and author wasn’t a specific path for Wallace; he initially focused on becoming a musical artist, utilizing the connections he made to start a music-sharing platform called AAIHIPHOP for the new tracks he, his crew and other artists were putting out. The site earned a few big hits and a year later, in 2015, he took the plunge and sent an email to XXL Magazine’s then-deputy editor Vanessa Satten.

“I never thought about it again. I wasn’t even sure she had gotten it,” he shares, admitting that he wasn’t sure of the publication’s email format and just typed several variations in the email’s BCC field. One of them must have been the correct email address, however, because six months later, he received a response from Georgette Cline, XXL’s editorial site director. His first assignment was a best-of list for Queen Latifah’s 46th birthday, and, as someone who had been reading the magazine since he was a teenager, Wallace recalls an aura of fascination and charm surrounding the surreal experience.

“I came to understand that my [non-traditional] path was my brand.”

He took great advantage of his involvement with XXL, which allowed him to share his treasure trove of hip-hop knowledge. Eventually, he became a contributor to HipHopDX and Exclaim!, where he continues to drop facts about some of hip-hop’s best records, pen album reviews and interview artists that are changing the game. And with almost a decade’s worth of work as a music journalist under his belt, it was almost natural for Wallace to lean towards the idea of writing a book.

He toyed with the idea for years, and his early affinity (and later, an admitted obsession) for producer interviews served as the cornerstone for his upcoming book, From Boom Bap To Trap. He offers up the 312-page work as the ultimate catalog and reference source to hip-hop’s most revered producers, where even the tiniest details and connections are meticulously listed out. “I wanted to create a repository of the greatest producers in hip-hop, one that laid out the origins and essential works in their catalog, making it easy to get these great origin stories without having to put in a lot of work — because learning about the culture shouldn’t be a chore,” he explains. “Even more significant than that, I wanted to leave a stamp. It’s not my life’s work by any means, but it’s a path that will define the next leg of my career and life.”

In three words, how would you describe your job to someone who isn’t familiar with the music industry?

Always in motion.

Can you run us through a day in your work life?

I’m currently dedicating my focus to album reviews and editorial content. On any given day, I listen to an album repeatedly and comb every detail, search for story ideas or create content. You could also catch me transcribing something on a good day; this is built around other things in my day-to-day life, though, like being a father.

I’ve been getting into the swing of my current workflow since finishing my book. During the time I spent on the illustrations, manuscript and then layout (which I completed just over two months ago), I was active to a degree, but more or less consumed with that process — rabbit holes and endless research. This past summer, I put my foot back on the gas more consistently.

“My best pieces have always been organic and the result of me getting obsessed with something.”

Can you tell us the story behind your most interesting interview?

At this point in my life, that is extremely difficult to pin down. I’ve published several thousand pieces between all the platforms I’ve ever contributed to. I did some of my most personally exciting pieces between 2018 and 2020, after which time HipHopDX shifted its focus slightly.

For example, I interviewed Kurt Nice, who filmed the iconic cypher with DMX, Big Pun, Mos Def and Canibus. I did an in-depth interview with J. Armz, the NYC DJ behind the iconic How To Be An MC instrumental mixtape series that, more or less, helped define an era — long before YouTube “type” beats were a thing. I interviewed Strange Music rapper X-Raided months after his 26-year prison sentence ended; his story is incredible.

My best pieces have always been organic and the result of me getting obsessed with something. The common thread of many of my more memorable ones is that they weren’t influenced by trends or clicks but rather preserving culture.

Can you guide us through the process of getting a book published?

My book drops at the end of this year — finally! But, as you may have gathered from how I got my first gig in this industry, the process has been mainly by the seat of my pants; the result of simply being open to blessings and rolling with the punches. In this case, my publisher had been looking to transition into music books and, in a search for authors, had come across me on Twitter. I had been feverishly looking for an agent at that exact time. When I saw them follow me, I sent a few messages, and about two months later, we were planning the Kickstarter campaign, which we ultimately funded.

The journey isn’t over, but the ride so far has offered me a lot of learnings that will make my future in this sphere brighter.

For starters, you need a solid idea. This book wasn’t brought to the publisher [Hamilcar] in a finished state. It came out of conversations with them, amalgamating ideas. After fleshing out the concept, we looked at comparative books to determine the audience size. I then crafted a detailed proposal that laid out my vision, defined what I brought to the table (based on my audience, network, etc.) and even included illustration samples.

What I’m getting at is that a lot of time and research went into getting the conversations to turn into a relationship — all of this was before I even wrote a word. It’s easy for writers to focus on angles without thinking of the business around it; pitching a book is like pitching a company to an investor. How can they benefit?

I had come from an independent, self-published book, so it was eye-opening to realize how much went into getting a book from ideation to actual physical bookshelves — and how many moving parts are at play, from agents to distributors.

“It’s easy for writers to focus on angles without thinking of the business around it; pitching a book is like pitching a company to an investor. How can they benefit?”

What’s been the most fulfilling (and most difficult) part of writing the book?

It was the most challenging thing I’ve ever done; it’s a project that, despite planning, seemed impossible. I distinctly remember the soul-crushing feeling I got after checking my “pages left” counter and seeing how high it was after weeks of work. Also, the format made it more complicated. I couldn’t crawl into a rabbit hole and pour myself into one story/narrative. There was rabbit hole after rabbit hole, hour and endless hours of consuming and digging.

Having completed it, I’m a slightly different person. I’m not a runner and have never been lucky enough to experience that runner’s high that runners brag about, but I have now gotten to feel the book writer’s high, and it’s made me want to dedicate myself to doing more.

I’m late to the parade, but I’m glad I made it.

Would you say that there’s a more rigid path to becoming a music journalist in comparison to other careers in the industry, or is it just as flexible?

I’m living proof of its flexibility. But that flexibility should not be confused with simplicity; it’s an insanely competitive industry.

Did you always know you wanted to have the career you do now, and did school play any part in inspiring you to this path?

I wasn’t bred to do this and didn’t explicitly set out with this as a goal. I lacked the journalistic educational background that many of my peers had. I’ve suffered from imposter syndrome many times in my career. But, I came to understand that my [non-traditional] path was my brand. I started writing about hip-hop because the culture was so deeply rooted in my timeline that it felt natural.

“With the rise of AI, the human workforce will shrink… The possibilities are endless as GPT-4 improves, and we eventually move toward GPT-5. An element of soul and humanity can’t be faked, though.”

What are the necessary first steps someone should take to enter a career in music journalism?

I’ve had the opportunity to see many young writers glow up. I’ve even had a few interns that have gone on to be great. I have always advocated for having a voice and a vision. No matter where you go, you’re still you — not the platform you write for. Social media has enabled young people to build audiences and find themselves independently.

That’s one thing, and the other is to create — a lot. The easiest way to find your vision and voice is to create, fail, learn, evolve and grow. If you’re blessed enough to have the drive, desire and vision at a young age, make it your academic focus. I wish I’d started younger.

What lessons and/or work ethics did you only pick up after working in the music industry?

Maintaining relationships and taking chances. However, some of my wildest interviews and editorial opportunities happened in this field due to going to bat on behalf of PR reps I believed in. Helping them land media is helping them win, and those PR relationships you form get you exclusives, get you top of mind for stories and get your albums in advance. Whenever I’ve found myself burnt out or at a low point, I’ve consistently been able to rely on my relationships to hold me down with a great interview to pitch or an advance copy of something to get me back in the mix (even if they didn’t know it).

What was the biggest challenge you’ve had to face so far, and how did you overcome it?

Burnout is real, and it slapped me very hard around the time COVID hit; I’m an older writer and have been active throughout many shifts in the music landscape. The feverish pace, the doom spiral of news cycles, plus dealing with grief while the world was seemingly melting was too much. I honestly lost the composure I needed to get back at it.

One of the biggest things I did in 2020 was self-publish a book of my best pieces from 2019. Doing that not only gave me the initial book bug by introducing the idea that a year’s worth of work could fill a book but also reminded me of what I’d done so far.

It was a case of just meditating on my work. As writers or creatives, we often don’t stop and revel in our work. Stories are old the moment they go live, and it’s always on to the next. I found myself as a result of losing myself.

“The easiest way to find your vision and voice is to create, fail, learn, evolve and grow.”

What is one thing about your job that most people would find unexpected or surprising?

It can be incredibly nerve-racking. A piece rarely goes out that doesn’t make me nervous, especially reviews. I often envy the anonymity a writer with a pseudonym could once enjoy. Nowadays, a heavy-handed take could get you flamed online.

It’s weird because my voice reads way more confidently than it sometimes feels.

Is there a secret to career longevity in this industry?

Being open-minded, maintaining your voice and never staying complacent. There is a lot of innovation and change right now, so knowing your strengths and finding ways to create a lane for yourself is powerful.

What does a day off look like for you?

Hanging out with my wife and two daughters.

How do you see your job evolving with the music industry in the next five years?

With the rise of AI, the human workforce will shrink. I have no idea where it’s headed, but how we do things now will profoundly change. The possibilities are endless as GPT-4 improves, and we eventually move toward GPT-5. An element of soul and humanity can’t be faked, though. I am holding on to that.

Stay tuned for more features with music industry professionals — from managers to sound engineers, stagehands and others; the people who make the music world go round without standing behind a microphone.