Cindy Cowan A Powerhouse In The Entertainment Industry Shares Her Entrepreneurial Journey

Cindy Cowan pool

Cindy talks small business insights, celebrities and the upcoming Omni Cultural TV Fest.

Latin Business Today (LBT) chats with entrepreneur, producer and songwriter Cindy Cowan who co-founded Initial Entertainment Group (IEG) with Graham King in 1995, and it became the leading film production and foreign sales company. Her latest entity is Cindy Cowan Entertainment and Omni Cultural TV Fest. All photos property of Cindy Cowan.

LBT: Cindy please tell us a little about yourself, your background and family…Did they have an impact on your values and drive?

Our family was in the hotel business, The Diplomat, in South Florida. It was the home to many entertainers who would come and perform there throughout the years, such as Sammy Davis Jr., Liza Minnelli, Dionne Warwick, Diana Ross, Gladys Knight, and Bob Hope to name a few.

Because so many celebrities were always around, and the hotel was taking center stage as a premiere destination spot in Miami/Hollywood, my family became adamant that my sister and I had our own spotlight in which to shine. So, we began riding horses at a very young age. By the time I was 10, I had won my first world championship.

I have been extremely driven ever since.


Cindy's father and Roberto Duran

My father weighing in Roberto Duran to fight at the our hotel.


Cindy Cowan and President Ronald Reagan

Visiting President Reagan in his office. Notice the framed picture of me behind my head?


Cindy Cowan's parents, Liza Minelli and Sammy Davis Jr.

My mother and father announcing that Sammy Davis Jr. and Liza Minnelli were going to perform at The Diplomat.


Cindy Cowan and Gladys Knight

One of my favorites, Gladys Knight. She has known me since I was a baby.


Cindy Cowan and Joe Namath

Accepting the World Champion title from legendary football player Joe Namath.

My trajectory

After graduating college, I came back to Florida to work at my father’s hotel for a bit. I quickly became restless, so I moved to Los Angeles as a songwriter. I wrote songs for the likes of Sinitta, Engelbert Humperdinck and Howard Hewitt from the group Shalamar before getting into the film business

My parents never really wanted me to get in the business, they had seen what fame had done to their friends, and they were very protective.

Having grown up with the biggest stars though, I certainly wasn’t star struck when I arrived in Hollywood. After going to my first film set, I knew I had found my calling.

The drive I had learned from my youth coupled with my blind ambition to succeed paved a path for my future.

Jay Leno who performed at our hotel, now lives behind me in Los Angeles.


Cindy Cowan and Jay Leno

Featured with Jay Leno, who would later on become my neighbor in LA!


LBT: Please share some prior business successes and failures which honed your expertise to become one of the most influential and successful female producers in the entertainment industry. What skills did you acquire in business that prepared you for becoming a producer?

I started out as a PA (production assistant) on a film set. I had no idea what I was doing, I just knew I wanted to be in the business. One day, the company I was working for sent me to a set in Canada.

It turned out the producers were stealing money from the budget and needed someone to take the fall if they got caught. Well, I was the one to catch their scheme.

I called the bond company to report what I had found and befriended all of the actors, assuring them I would get the film delivered on time for them without the set being shut down. Little did I realize I had just reported my employer.

The bond company ended up protecting me and I became a hero to the actors and crew. Those relationships carried on when I launched my own company a few years later.

Honing a vision through preparation

I studied Psychology in college. I truly think that this knowledge, along with my gift of running a set in difficult situations, has made me who I am today.

I also studied the film market place. While most of my friends were off doing their passion projects, I wanted to make what the audience wanted to see and what I knew I could sell.

I had a way of networking with talent while never overstepping my bounds. I had a knack of getting to know agents and managers who became eager to help put my projects together.

In the 5 years I had my last company, we had either bought, financed or produced over 25 films. It was a grueling schedule that I am not sure I would want to repeat, as it compromised my personal life at times, but it paid off in the end and I am extremely proud of what I have accomplished.

LBT: Has the entertainment industry made progress in the acceptance women and minorities? Please share any examples of progress as well as ongoing challenges to achieve success in the entertainment industry.

The entertainment industry has really come a long way in the past few years when it comes to women and minorities.

It is almost fashionable right now to hire both. The “MeToo” movement shed a light on a lot of things and certainly unlocked many doors…and then of course came Wonder Woman, never did Hollywood think that a female director or star could carry a film that would rival all the boys

We all saw Black Panther, which blew our minds and was a commercial success. Both of these films changed the argument that these types of movies would never be accepted or have overseas value.

Now the door is open. Hollywood is making films such as Blackklansman, one of Spike Lee’s best, and Green Book, which won the Oscar this year for my friend Peter Farrelly.

Look at Crazy Rich Asians–our world is finally expanding.

I never saw being female as that much of a challenge though. I knew that because I was a girl the doors would open, the trick was to be smart enough to stay in the room once you got there.

The difference now is…I am not the only girl in it.


Cindy Cowan and Ricky Martin

My new neighbor, Ricky Martin.


Cindy Cowan and Enrique Iglesias

Love seeing Enrique Iglesias. My family has been friends with his dad Julio since I was a child.


Next: People that changed my life and the Omni Cultural TV Fest


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