Q&A: Anita Bennett and Kevin Ross

Entertainment industry veterans Anita Bennett and Kevin Ross have made their individual marks in the Chicago market on a number of fronts. Bennett has worked in a number of areas in entertainment including hosting her own radio show entitled “Anita On The B-Side, in addition to running her own multi-faceted company of the same name. Ross is a 30-year music industry veteran who is currently the owner and CEO of Twoguard Media Group, a dual level company that houses TMG – Music and Brand Marketing as well as Twoguard Music Group, a boutique independent record label.

N’Digo recently sat down with Bennett and Ross to discuss their career origins, individual companies and some of the things they look to do in their newly formed partnership.

Did you have any early influences that made you want to be involved in the entertainment industry?


Anita – Yes, I come from a musical background. My father was a musician and toured all over the world opening for legends such as Chaka Khan and The Gap Band among others. My paternal grandmother was a gifted vocalist, whose vocal coach was jazz legend Dinah Washington. As a teenager, the late great BB King offered her a job to sing background for him but her father, a devout minister, would not allow his daughter to sing the blues. So needless to say, I’ve been around great music my entire life and it’s definitely influenced my career path.

Kevin – I fell in love with a record on the radio “Midnight at the Oasis” when I was 12 years old. I loved the way it sounded and made me feel, so I wanted to know why that was. After that, I began to study everything I could about the records that I bought, reading the backs of album covers, studying every aspect of the recording process, learning about the record labels and their personnel. My first two biggest influences were Berry Gordy and Don Cornelius. They knew what people wanted and they knew how to give it to them. They were cultural influences. I attribute “Soul Train” and Motown to where I am today

What was your first job in the industry?


Anita – I initially began my career in the hospitality industry. I worked for MGM-Mirage in Las Vegas and it was there where I learned how to develop contracts and handle multi-million dollar accounts. MGM Grand also taught me discretion, poise and how to create exceptional clientele (portfolio). I used these skills to create my radio show, “Anita, On the B-side,” which essentially blossomed into what I do today.

Kevin – My very first job was two record stores. Barney’s Records in Davis, California and Tower Records in Sacramento, California. My first industry job was for Motown Records in 1996.

How important do you believe mentors to be and have you had any mentors that made a big impact on your life?


Anita – I’ve been blessed with so many great mentors. However, my greatest influence is definitely my mother! She’s such a strong, and dynamic woman who still amazes me daily! My mom was a widow with four small children at age 35. Despite the difficulties, she gave us an incredible life. She never allowed me to make excuses and made it clear that failure was not an option! Other mentors include multi-Grammy-Nominated producer-songwriter Carvin Haggins, , who taught me the importance of licensing and making sure that I protect and own my intellectual property! Vince Bass and Joe Russo (who both are major influencers in Chicago) were candid with their knowledge. Finally, my business partner, Kevin Ross, shares his thirty-plus years of wisdom and experience quite often. So, I’ve been very fortunate.

Kevin – In my opinion, mentors are absolutely vital. My early mentors include Dr. Dave Ferguson and Ricky Lee Mensch, when I was an on-air personality in Sacramento where I grew up. Other mentors include Motown President Jeryl Busby , Sean “Puffy” Combs, Andre Harrell, Russell Simmons, Derrick Brown from V103, and George Daniels. My single greatest mentor is Craig Davis, a veteran executive I worked for at Capitol Records for four years. He is single-handedly responsible for the man that I am today both on a personal and professional level.

What can you tell us about Anita On The B-Side?


Screen Shot 2016-08-01 at 4.11.01 PMAnita– Anita On The B-side began as a radio show that I developed after co-starring on another radio show, “Life and the Public Figure,” on LR Media Group. Although I enjoyed being on-air, I found that producing and marketing is what really fascinated me. I was then able to enhance these skills when Joe Russo of The Shrine Chicago asked me to accept a job as a consulting, marketing and assisting with public relations. I then began freelance work with artist development, PR, talent booking, strategic marketing and promotions, while still producing events; thus, Anita On The B-side Consulting Group was created! I’ve produced events and worked with artists from various genres. They’ve included: Verdine White of Earth, Wind, and Fire, Charlie Wilson, Joe, Nas, Lil Wayne, Kem, Elle Varner, Marsha Ambrosius, Raheem DeVaughn, Chrisette Michele, and many more. I’m truly blessed to do what I love!

Tell us about Twoguard Media Group?


Kevin – Twoguard Media Group is a full service marketing and promotional company. It specializes in artist marketing, artist development, events, events planning, full service marketing and social media management, management, and consultation on all levels. It also includes Twoguard Music Group, which is a record label I founded and co-own with one of my artists Marwan (Soulflow). I’ve patterned TMG after another company made popular in the mid-nineties, Violator Management ,founded by a former Def Jam executive, Chris Lighty. Our goal is to provide the same services and development that are available to artists or brands that have access to resources on a major or national level. It is also designed to target social and cultural influencers in the market. I work with Chicago independent artists as well as major independent artists like Tyrese, Eric Benet, Tamia, Ginuwine, Joe, and others.

How did the partnership between AOTBS and TwoGuard come about and what the city of Chicago can expect from it?


Anita – The partnership between AOTBS and TwoGuard really developed organically from many conversations that Kevin and I had about what we felt was missing in the market. We both are passionate about what we do and we felt blending our talents to create something to filled that void would challenge us, yet be rewarding to both us and the market!

Kevin – I met Anita about 5 years ago. I was introduced to her by Joe Russo. At the time, as she was producing her own radio show while I was at Warner Brothers Records , and I fell in love with her hustle. I find very few people that hustle as much as I do, but she was one of them. She managed to get major artists to come do an interview with her on a non- terrestrial radio station. That takes a lot of work as well as relationships. We’ve become very good friends over the years and finally decided to partner with each other. Not only do we hold a great many of the same beliefs, but our skill sets complement each other. The concept for our merger is really hers.. Our goal is to provide quality entertainment. We want to provide the consumer with an experience, not just an event. We want it to be something different that they can remember for a long time, not just a week later. It’s more personalized, innovative, and more interactive.

What’s something people would be surprised to know about you?


Anita – People would be surprised to know that I’m very shy. I can be reclusive because I’m always in “creative mode” mentally. I’m also a part of one of the most incredible Level 1 Trauma teams in Chicagoland.

Kevin – I am a huge fan of this sixties cartoon “Speed Racer”. It’s a Japanese import that is poorly-dubbed and the dialogue is terrible, but it is considered a classic. I absolutely love the show

What’s your best advice for aspiring entertainment professionals?


Anita – If it’s your passion, go for it! It may not be easy and success may not come overnight, however, stay persistent! Also, listen more and talk less. DO YOUR HOMEWORK! Study the business, know the market, and trust your instincts! Finally, If it doesn’t feel right, don’t do it!.

1) Take your ego out of the equation. You will be able to learn and grow toward your success faster.

2) Stop worrying about what other people are doing and focus on developing your own brand in your own lane.

3) You cannot do this by yourself. And do not let money be an excuse. It is vital to construct your own platform and your own team in order to execute.

4) If you cannot find a way, make one

Favorite motto or affirmation?


Anita– Always put a little Love and a lot of GOD in everything that I do! It’s definitely been the key to my success thus far!

Kevin – “With God, nothing is impossible”

What’s next for Anita Bennett and Kevin Ross?


Anita – I have a series of books coming soon! I’m also developing a few projects for tv/film, among other things! I just want to keep challenging myself professionally and grow! When I leave this life, I don’t want to take my creativity and passion with me. It is my goal to leave it here for the world to enjoy for generations!
Screen Shot 2016-08-01 at 4.11.18 PMKevin – To further develop and execute the goals set forth for Anita and myself, to continue to build a platform that will break artists from Chicago & promote brands on a local, national and international scale. On the event side, I’m working on a real Soul music festival for Chicago. I’ve been able to place a couple of my artists songs in an independent film and I want to become more involved in that side of the industry. I’m also working on concepts for two music- driven shows that will stream on internet television networks. And of course, I want to continue to rep my city as hard as possible.

Anita On The B-Side and Twoguard Media Group-Music And Brand Marketing in conjunction with City Winery Chicago will present legendary singer El Debarge as he plays two shows on Tuesday 8/2 (7pm and 9:30pm) at City Winery in Chicago’s West Loop neighborhood at 1200 W. Randolph. For more information please visit www.citywinery.com.

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