How Producer & Director Alex Cirillo of New York Women in Film & Television Is Helping To Make the Entertainment Industry More Diverse and Representative


I spent the better part of the last decade dedicating my career to creating opportunities for women, people of color, and LGBTQ creators through my incubator and production company Big Vision Empty Wallet long before it was the cool thing to do. We created programs, ran labs, produced events, and partnered with festivals, distributors and financiers all to support creators and get their projects made and seen, and we had a great time doing it!

As a part of my series about leaders helping to make the entertainment industry more diverse and representative, I had the distinct pleasure of interviewing Alex Cirillo, producer of the new Derek Jeter docuseries “The Captain,” which premiered at the 2022 Tribeca Festival in June and will broadcast on ESPN on July 18.

Cirillo is a Producer, Director, and Vice President of the Board of Directors of New York Women in Film & Television, which advocates for inclusion in the media industry and supports women at every stage of their careers through professional development programming, networking opportunities, and funding. Past projects include SXSW Audience Award-Winner “The Light of the Moon” (Showtime), Sundance selection “One Cambodian Family Please for My Pleasure” (TNT), Sundance premiere “How to Tell You’re a Douchebag” (BET), and “Lez Bomb” (Netflix).

Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I was fortunate enough to take IB Film classes in high school so I knew from a young age what career path I wanted to pursue. I think the moment that solidified it for me, though, was when I was directing one of my first short films in 11th grade and one of the “actors,” who was really just another film student who had zero interest in acting, would get nervous every time I called action and totally clam up.

We had to shoot during the 40-minute class period, so I was quickly running out of time to get the shot. I kept rehearsing with him and he was nailing the rehearsals, so I whispered to the cinematographer to roll and I told the actor we were going to do one more rehearsal. He had no idea the camera was rolling, he nailed the scene, and we got the shot right as the bell rang. Afterward, my teacher Mrs. Tanklow told me I was a natural director, and that was all I needed to hear to know I was pursuing the right career path!

Can you share the most interesting story that happened to you since you began your career?

Well, that depends on your definition of “interesting.” I’ve been threatened by a woman with a machete, nearly trampled by an angry man on horseback, swarmed by locusts, and almost kidnapped all while developing projects in Costa Rica. I island-hopped through the Philippines on a helicopter, snorkeled at a pearl farm, and slept on a private island in a Swiss Family Robinson-esque treehouse with no locks on the door while screening a documentary I produced. But I imagine you’re asking about something more industry-related, so selling a series to a streaming platform that folded the following day comes to mind…

Through one of our Big Vision Empty Wallet programs, my producing partner Dani Faith Leonard and I worked with an incredibly talented writer, AJ Janakas, to develop a series that she created. Along with her representation, we set it up at a streaming platform that will remain nameless. They ordered a pilot script and series bible, which we all worked tirelessly on. After months of addressing notes from our point person at the streamer, who was a thoughtful and smart collaborator, they bought the show! We signed the contract and we were over the moon; we had sold our first series! The next day, we read in the trades that the streaming platform had folded. They would still be in operation, but would no longer be producing original content. And because they had purchased our series, they owned it and we couldn’t get it back even though they had no intention of making it.

That’s the abridged version, but we never gave up hope that we would get a series made. And now I can proudly say that the first series I produced, The Captain directed by Randy Wilkins, had its World Premiere at the Tribeca Festival on June 12 and will air on ESPN on July 18!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

My first internship during the summer after high school was working for a very cool, but very small, PR and event planning firm. I got to help plan and attend star-studded events at venues I wasn’t even old enough to step foot in, and the young woman who started the company always empowered me to take on big responsibilities. I have always been a very confident person, and her positive encouragement made me feel like I was way above my pay grade. I often handled RSVPs and the guest list, so I knew all the big musicians and music executives and felt like I was way cooler than I was.

One day I was chatting with one of the executives and the Ying Yang Twins at a G-Unit album release party, and I made a loud joke and slapped the executive on his big belly. Maybe this story is more cringeworthy than funny, now that I think about it…The executive brushed it off and wasn’t a jerk about it, but I knew instantly that I had totally crossed a line and I still cringe when I look back on it even though it happened nearly 20 years ago. I don’t know what I was thinking, but I should have kept my hands to myself and remembered that just because your superiors are nice to you does not mean you are on the same level as they are, and especially as a young person trying to come up, you always need to mind your place and be respectful.

Ok thank you for all that. Let’s now jump to the main focus of our discussion. Can you describe how you are helping to make popular culture more representative of the US population?

I spent the better part of the last decade dedicating my career to creating opportunities for women, people of color, and LGBTQ creators through my incubator and production company Big Vision Empty Wallet long before it was the cool thing to do. We created programs, ran labs, produced events, and partnered with festivals, distributors and financiers all to support creators and get their projects made and seen, and we had a great time doing it!

I have always aimed to make popular culture more representative of the U.S. population through the work that I produce and direct. My most recent series, The Captain, chronicles Derek Jeter’s journey as a five-time champion with the New York Yankees, but instead of simply retelling his story, we utilize his experiences as a vessel to tell a much larger cultural story about race, community, the media, and family.

Additionally, as the VP of Special Events on New York Women in Film & Television’s Board of Directors, I help the organization conceptualize their largest fundraiser each year, The Muse Awards, which celebrates the achievements of women in the industry and raises funding to support programming, scholarships, and initiatives for the 2,500 women in the membership.

Can you tell us a story about a particular individual who was impacted by the work you are doing?

I would never take credit for anyone else’s talent and hard work, but this question reminds me of a conversation I had with a friend and colleague the other day. She did some freelance work for me a while back, and when she gave me a quote, I told her she wasn’t charging enough. I reminded her to value her time and her talents, and not to be afraid to charge what she is worth. The right clients and collaborators would value and respect her, and have no problem compensating her what she deserves.

I didn’t think anything of that conversation at the time, but she told me the other day how much that stuck with her, and how it changed how she approaches dealing with potential clients even today. Sometimes it just takes someone else reminding you of our value to inspire you to elevate and grow!

As an insider, this might be obvious to you, but I think it’s instructive to articulate this for the public who might not have the same inside knowledge. Can you share three reasons with our readers about why it’s really important to have diversity represented in Entertainment and its potential effects on our culture?

  1. First of all, it should be this way already. It’s long overdue for us to showcase more than one POV as “normal”.
  2. Seeing cultural diversity represented in entertainment helps us all learn, grow, and be better people. There is more than one way to live life, and it’s important for us all to see the options out there so we can decide how we want to live our lives.
  3. It’s crucial for all types of people, especially young people, to see themselves represented and truly understand the world of possibilities out there for them to pursue. Through entertainment, we have the power to inspire and inform people. This world would be a much better place if everyone had equal opportunities and equal access to what life has to offer.

Can you recommend three things the community/society/the industry can do to help address the root of the diversity issues in the entertainment business?

On the most basic level, we need more diverse people in positions of power. And that only works if we begin by creating programs and opportunities to train people from the ground up, so once they rise to those positions of power, they are qualified and experienced decision-makers. And the good ol’ boys club culture of the industry needs to end, so the most deserving, hardest working, most intelligent people are the ones being promoted through the ranks, not just the people who look like those already in charge.

As individuals, what we all can do is speak up. Call out misogyny, racism, and xenophobia. Don’t allow it on your sets or in your workplace, and don’t perpetuate a culture that allows that harmful, negative behavior. Instead, hire a diverse team of kind and collaborative people with different life experiences. Your work and everyone on your team will be better for it.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leadership is all about establishing a culture where hard work is rewarded, your team feels safe and valued, and everyone is collaborating to create fantastic work and have fun while they do it. As both a producer and a director, I think leading by example is the best way to get your point across and foster the company culture you strive for. We work in an industry that isn’t 9 to 5, so if you aren’t willing to go the extra mile and put in the time and work as a leader, your team won’t be either.

That said, I clearly communicate my expectations up front in hopes of letting people know from jump what I expect of them and what the specific project will demand. It shouldn’t come as a surprise to them. I always do my best to hire the right people for the job, but we all fail to make the right hires sometimes, so we can’t be afraid to remove or replace the people whose work ethics, attitudes or skill levels do not match our needs and expectations. And just because someone is talented doesn’t mean they are the right fit for you. I have a strict “No Asshole” policy and am not willing to work with a rude or unkind person no matter how talented they are.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. Having a good support system is crucial. Your relationships with your colleagues, friends, and family will get you through difficult times, and make the good times that much more enjoyable. Value your relationships and make time for the people who truly matter.
  2. Be well-rounded. Work isn’t everything and you’ll be a better human being, artist, and collaborator if you have real-life experiences that shape and inform you. Take risks and have fun!
  3. No project or paycheck is worth compromising your core values as a person. Never forget who you are, but also don’t be afraid to grow. It’s important to evolve!
  4. You’ll learn more from your failures than you will from your successes. Don’t be afraid to fail. And don’t be afraid to talk about your failures because other people can learn from them too.
  5. It takes a lot longer to find success than you expect it will (or than I expected, at least). Keep fighting!

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Wow, this is a difficult question to answer! There are so many causes that are near and dear to me, but my mind keeps going back to something very basic: life is meant to be enjoyed and shared with the ones you love. A simple reminder to be kind and have fun could bring a lot of good to a lot of people!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I’m rolling my eyes at the amount of times I have used the word “empower” in this interview, but “Empowered women empower women” is a quote that drives me. The first time I heard it was when I was directing a commercial for Loacker and it stuck with me ever since. I’ve never understood the feeling of competition among women in this industry. It doesn’t benefit us to fight each other for one spot, instead, we should be fighting alongside each other to open up more spots for us all! If I hold back or diminish the women around me to make myself look better, it will be a very long road to make it to the top alone. If I instead uplift the women around me, I can be a part of a group of badass successful women who can elevate and support each other as we rise to the top together. Which option sounds like more fun to you?

This is why I have been a member of New York Women in Film & Television since I was in my first real job at a production company 15 years ago. The camaraderie, mentorship, sharing, and support among women has helped me tremendously throughout my career and I joined their Board of Directors to put myself in a position to do the same for my peers and the young women finding their way as filmmakers in New York. Lifting up other smart and talented women makes me feel empowered every day.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

Kris Kardashian. Seriously. That woman knows how to build an empire!

How can our readers follow you on social media?

Instagram: @Alex_of_AntAndAlex

Twitter: @MissCirillo

This was very meaningful, thank you so much!



Edward Sylvan CEO of Sycamore Entertainment Group
Authority Magazine

Edward Sylvan is the Founder and CEO of Sycamore Entertainment Group Inc. He is committed to telling stories that speak to equity, diversity, and inclusion.