Ahead of His Time: How “Grouchy” Greg Watkins Leveraged the Power of the Internet Into a Successful Publishing Career

Starting as just a “one-man-band” in the realm of digital advertising, he has since empowered AllHipHop.com with comprehensive expertise in supply path optimization. 

“Grouchy” Greg Watkins is the co-founder of AllHipHop.com, a website that has been doing successful business in the music space since its inception in 1997. The site’s mission continues to be the same as it was then, a place to share news, feature articles, and any other pertinent content for people who make and enjoy hip-hop. 

Most importantly, the site has an incredible reach, which it achieves largely thanks to Watkins’ knowledge and expertise in the online advertising space. Leading up to his talk at PubForum in Coronado Island, California, we caught up with Watkins to learn more about his career journey and how he is helping others learn the ins and outs of ad tech. 

Music & Technology Paved the Way for Watkins’ Career

Watkins says he knew he was destined to be a part of the music industry since he was only three years old, listening to tapes on his parents’ tape recorders at home. When he was just a kid, he also began tinkering with technology. 

“My dad had an old reel-to-reel machine in his basement that he listened to music on. He had transistor radios that I would take apart and look at,” he says. 

As he grew up and began getting involved in music, he started a recording studio. Then he went to the Art Institute of Philadelphia, where he received an Associate’s Degree in Music, Business, and Audio Engineering. 

By 1996, Watkins was pressing records and having success selling those online to people worldwide. That’s when he registered AllHipHop.com, which he originally conceived as a way to sell records but quickly morphed into the hip-hop news site it is today, with the help of his long-time business partner Chuck “Jigsaw” Creekmur.

Watkins Was an Early Adopter of & Believer in the Power of the Internet 

Witnessing the evolution of communication through the web via early programs like AOL convinced Watkins that the Internet would be the way of the future. At that time, he began reading trade publications to understand the ins and outs of this new communication tool. 

“By ‘96 or ‘97, I don’t want to say I was a veteran of the internet, but I knew my way around. At that time, I knew HTML, how to code, and how to make websites. I saw it as a logical step when I saw people buying the music online, and how it reduced my overhead by having a direct-to-consumer relationship,” he explains. 

That direct-to-consumer relationship completely changed how Watkins and his team sold music and connected with their audience. He knew then that the internet would change how we share news and information globally. 

Awareness of the Internet’s Advertising Potential 

If you asked Watkins back when he launched his website whether he would be so involved in ad tech today, he says the answer would be both yes and no. 

“I’ve been reading the trades since ‘94, 95. I visited San Francisco. I saw Yahoo in its early days before they were even a worldwide known brand – I saw cabs riding around with ‘Yahoo’ on top and billboards around San Francisco. That blew my mind that an internet company was marketing in that manner. That opened my eyes to see there is an advertising business here,” he shares. 

Even so, the urban advertising system was basically nonexistent until the year 2000, which is when AllHipHop.com began to dive into the world of online ads. Watkins notes, “I helped launch our first ad server. I bought it off the Internet, ‘software as a service.’” He began launching ad campaigns, doing the creative, HTML, and tracking codes with a small team of sales reps. 

At first, the advertisers were direct-to-consumer marketers, but AllHipHop.com landed a campaign with the anti-smoking organization The Truth. The money from that campaign helped the website hire more writers and salespeople who did brand cold calling. This eventually led to some big fish advertisers like American Airlines and Pepsi. 

“I did know that the advertising business would be big on the Internet and that this would be a way to directly speak to consumers in a way that possibly had never happened in media history. When you’re dealing with television, it’s usually a one-way transaction. When you’re dealing with the internet, especially at the time, you could develop actual relationships with these consumers, depending on what type of ad campaign you’re running,” he notes. 

Understanding the Supply Chain Leads to Success

Watkins says his biggest advice for publishers looking to succeed in this industry is to understand the supply chain we are all a part of. 

AllHipHop.com started as a direct selling business, then it began dealing with ad networks. When programmatic started, the supply chain became more complicated and less transparent. 

Ten years later, the supply chain has become even more complex and even wasteful, up to the billions of dollars in terms of waste spent by brands and agencies. This is what Watkins says he will be speaking to at PubForum. 

“There are a variety of headwinds impacting our industry right now that will probably be issues for the entire ecosystem in the supply chain for advertising over the next two years. Those are going to be some of the things I’m talking about and telling publishers: what to look out for, and how to avoid bad actors in the space. I’ll also be giving some actual testimonials,” he says. 

Making Ad Tech a More Inclusive Space

The lack of diversity and inclusion in the ad tech space confounds Watkins. “One thing that has always surprised me is the fact that Black, Latin, and other minority-owned businesses still have this difficulty in the 21st century having their audiences respected. We have huge audiences, yet only 1 percent of ad budgets go to Black and minority-owned and targeted websites.” 

For his part, Watkins makes it a point to take time out of his busy schedule to speak to college students and mentor minority owners of small businesses.

“I speak at HBCUs (Historically Black Colleges and Universities) and colleges, in general to encourage the students to understand ad tech, one for the impact that it has on society and how we see ourselves, but two, there has to be human capital available for these companies to hire for change to happen,” he states. He believes it’s important to make sure these students know how low lucrative ad tech can be.

He also is involved with BOMESI, the Black Owned Media Equity and Sustainability Institute, which assists publishers with resources, grants, and training to help serve diversity, equity, and inclusion in the publishing industry. “I mentor a variety of these brands and some of their executives on what’s happening in the business,” Watkins says. 

To hear more about Watkins’ journey and his advice for publishers looking to succeed, make sure to attend his keynote speech, “Lessons From the Trenches: 25 Years as a Publisher Navigating Ad Tech,” at AdMonsters’ upcoming PubForum in Coronado, California on August 7.