Anita Bennett and Kevin E. Ross talk marketing and music

Kevin E. Ross of Two Guard Media Group and Anita Bennett of Anita on the B Side - Photo Credit: Courtesy of Anita Bennett
Kevin E. Ross of Twoguard Media Group and Anita Bennett of Anita on the B Side (Photo courtesy of Anita Bennett)

With the advent of social media, marketing has taken a different tack. The ability to reach out to millions is a reality; however it is still challenging. The right mix of branding, hard work and execution make for a winning project and team.

We spoke to the owner of Twoguard Media Group, Kevin E. Ross, and Anita Bennett of Anita on the B Side who have come together to form a marketing and promotion powerhouse in the city of Chicago. We discussed their experience and some of the reasons what they do works and how they will continue to win.


Tell us who you are and what you do.

Anita: My name is Anita Bennett, my company is Anita on the B Side. My career began as a radio personality. I developed, produced and marketed my own radio show call Anita on the B Side. I was able to work with various artists as a consultant. We create media and promotional opportunities through banding and strategies that I help to develop. These opportunities came about because of my radio show. My work also led me to do freelance consulting for the Shrine, which was one of the most popular music venues in the city at the time.


Kevin: I am a 30-year music industry veteran. My concentration for the last 20 years or so has been in radio promotion and marketing. I take the artists and the records to radio, get them airplay and also get the artist exposure in the marketplace to support that airplay. You can’t sell records just by playing the song on the radio, there are other parts to it. My job is to bring a marketing and promotion component to it. I moved to Chicago in 1996. My first assignment was with Motown Records where I worked with 702 and Boys II Men.

My biggest most influential label job I had was with Capitol Records where I was able to work with Tyrese, Tamia, Anita Baker, Avant and a number of other artists. I saw that the industry was moving more towards the independent artists so I decided to start my own company. My concept was that independent artists are going to need the same structure and tools that signed artists need. Since I had the experience and relationships, I took that and started my own business as a consultant and my first client was Dallas Austin. Dallas had an artist named Sammy and took his record “Come With Me” to the top five nationally on Billboard.

Both of you are extremely skilled at what you do. Why did it make sense for you to collaborate?

Kevin: I was introduced to Anita by Joe Russo, who was one of the owners of the Shrine. What impressed me about Anita was her hustle and her drive. She is rare. She was able to secure major artists on an internet radio show. That is not easy to do. Our personalities matched and we got to become great friends and it was very natural for us to partner.

Anita: What impressed me about Kevin is that he is so personable and free with sharing his experiences in the music business. He invited me to a few of the events with his artists and our personalities and talents seemed to mesh. It’s very organic and there is a mutual respect that is very rare in this industry.

What does a regular day look like for you when it comes to your business?

Kevin: My day starts off hoping I don’t have to jump off a building at the end of it. I try to wake up around 6 or 7 a.m. I’m on emails right away. One of my mentors told me that if you send an email to someone at 2 in the morning that your email will be the first thing they see in the morning. So I try to wake up as early as possible to send emails, text people and get to them as early as possible. We work to secure partnerships and relationships with many different companies and labels.

Anita: My day can be full of adventure and I try to go about the day with my hair still remaining intact. I am accustomed to being a workaholic and a self proclaimed perfectionist. The morning starts off with meditation and I get my mind ready for the rest of the day. I send emails, make phone calls and getting caught up for the day. On event days, I reach out to the venues and the artists just to make sure everything is set up properly. I don’t like to leave things undone. We don’t panic, things come up, so I try to anticipate best case scenario and worst case scenario. That’s what our strength is. We always have a plan, A through Z.

I like that you say that you don’t panic. Take a moment to talk about how you deal with challenges when it comes to what you do.

Anita: In this business at any given moment things can happen. There are always going to be challenges. The better prepared you are the better suited you are. In this business you have be able to stay composed and stay poised in the event of the unexpected. You have to be able to maintain and produce in a fast paced high stress situation. There have been many times things didn’t go as planned but because of organization and great communication we can move in the midst of it and make for a great event and experience. We keep a positive attitude and we make sure that our guests are well maintained and taken care of.

Kevin: The calling card for our brand is that we are problem solvers. In order to be problem solvers you have to be able to identify what those problems can be before hand and that helps us out a lot. The first question we ask are where are you strongest and where are you not so strong. Then we come in and shore up where you are not so strong. That’s part of why we are able to deal with so many different situations. There is a large spiritual component with us as well. Nothing is ever the end of the world. Everything is a learning experience, good or bad. It’s an opportunity for you to learn, grow and get better the next time around.

Talk about some of your highlights.

Kevin: I would say we did real well when we did Chrisette Michelle’s listening party. We only had less than a week to put that together and that was successful. What I am really impressed with is how Anita secured El DeBarge with the circumstances we had to labor under. Also securing a venue like City Winery, which is traditionally very independent is really big this early in our partnership.

So what’s next for you?

Anita: Well El DeBarge is coming to City Winery on Aug. 2 and we are very excited about it. We have had an overwhelming response to the event and we are looking forward to future events that we are planning. We are also looking to get into production through television and film.

Kevin: We want to bring something to Chicago that we feel is missing. We want people to see us as brand ambassadors for something different and feel the human element of what we do. We also want people to meet the artists and learn something new. Expect to have an experience when you come to something we do.

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