Ana Sierra's Women's Basketball League Tips Off; Unites Female Hoopers

The Ana Sierra Women’s Basketball League has tipped off its eighth season. Learn how this New York native is proving to Chicago that grassroots women’s basketball leagues can be successful, profitable businesses.

On October 27th, the Ana Sierra Women’s Basketball League kicked off its eighth season. The ASWBL began back in 2015 and is currently run by a one-woman show– Ana Sierra herself.

In 2019, Sierra was let go from her corporate job and made the nerve-wracking decision to take on a major career change. She decided to pursue her own business full-time, a pro-am women’s basketball league, and officially step into the world of entrepreneurship.

Ana was only eight years old when she fell in love with the game of basketball. She grew up in the Bronx and was exposed to neighborhood pick-up basketball at a young age.

While Ana admits the games were mostly male dominated in NYC, she was still able to find a strong women’s basketball community. It was the outdoor basketball environment that served as a cornerstone for Ana’s high school and collegiate basketball career.

After completing her academic and athletic pursuits at West Virginia State University, Ana moved to Chicago in 2010. She immediately sought out similar outdoor neighborhood runs that she found in the Bronx, but she quickly realized the culture she was seeking was scarce in Chicago.

Sierra shared, “When I came to Chicago, I started looking for ladies that played ball, but I couldn’t really find that.”

Ana still wanted to hoop and craved a consistent outlet to play ball with her fellow female hoopers. After five years in the windy city, Ana took the initiative to create the environment she had been seeking. “I knew I had to take the initiative and build the culture myself,” said Sierra.

In 2015 Sierra launched the ASWBL, running the league part-time as she balanced her corporate job— eventually pursuing the league full-time in 2019.

The league is a melting pot consisting of mothers, women from overseas, current hoopers, and women who want to be exposed to basketball— all are welcome.

“I wanted to create an environment, a family, an organization that is solely for women and girls,” remarked Sierra. “And when you come to the ASWBL, you can count on the fact that you are going to see other women that look like you.”

Ana wears many hats; she is the league commissioner, team captain, organizer, player, and accountant.

There are around 60 women who play in the ASWBL across six teams. This year the season began at the end of October and will run for just over two months. Games take place on Tuesday and Thursday nights in Lawndale, Illinois, at the UCAN gym on 3640 W. Fillmore Street, and tickets are $10 for adult entry.

UCAN serves and impacts over 21,000 at-risk children, youth, and families across Illinois. They strive to build strong youth and families through compassionate healing, education, and empowerment.

Building a grassroots women’s basketball league is not an easy task, and successful leagues can be hard to find.

So what makes the ASWBL a successful, growing semi-professional basketball league?

There are two underlying factors behind Sierra’s success: Ana’s ability to successfully apply her corporate knowledge and learnings to her own operation and prioritizing the energy and support she receives from friends and family.

Sierra credits her former corporate position for giving her the discipline and high-level knowledge she needed to be an entrepreneur. But her new role came with some surprises.

“In my corporate role, I was working for someone else, and the jobs were given to me with clear expectations,” said Sierra. “My entrepreneurship journey is very different. I must decide and prioritize what needs to get done. I must be able to speak and articulate what I need to others.”

“I wear a different hat every day. Some days I need to be in the shoes of a player and ask myself: What are the things I would expect if I were to play in my own league? What do I want ‘Her’ experience to be? Other days I need to be the commissioner of the league and operate at a higher level— making large decisions and putting my ask in at a larger table.”

Sierra values the versatility the ASWBL requires of her. “In corporate America, you work one job and know what you have to do: it’s the same role every day, and you experience monotony. Now I am a different person every day. I have to show up in a variety of ways, and that is what allows me to be in tune with all sorts of different individuals.”

Sierra also proudly admits that while she is a one-woman show, the league would not exist without the help of her friends and family. She encourages local entrepreneurs and small businesses to set up tables alongside the court and promote their products. It is a win-win for everyone.

This year's opening night at the far east wall of UCAN’s hunter green and yellow gymnasium, Terrance Robertson slowly pieced together a table filled with a variety of tacos and hot sauces. He stood in a navy blue letterman jacket with a smile on his face. “I am here for the women,” Robertson stated proudly. “The world doesn't always support women’s sports, so that’s why I want to be here. I got to show my support.”

Robertson runs a small black-owned catering business that he built from the ground up in 2017. He has been supporting the ASWBL for the entirety of the league's lifespan, selling a variety of foods courtside at ASWBL games.

Robertson specializes in jerk chicken and steak tacos, as well as some soul food. His love for cooking came from watching his mother and grandmother cook as a young boy.

Born and raised in Lawndale, Illinois, Robertson said, “I met Ana 12 years ago when she was working her corporate job. She is a very down-to-earth, kind-hearted person, so I knew I had to support her basketball league. We support each other.”

It is people like Terrance who help keep the ASWBL going. Sierra’s friends and family pitch in to keep the league afloat.

Ana has recently expanded her operation and launched sneaker drives, mentorship programs, and basketball clinics for female youth.

Ana’s youth clinics aim to inspire young women and offer them the exposure and opportunity to play ball at a young age.

The impact the ASWBL is having on young women in Chicago is evident. Michelle Perry and Emma Van Donselaars, two young girls on ASWBL’s Team Elite, are excited about what this upcoming season has in store.

Perry has been playing in the league for three years now; however, this will be Van Donselaars’ first run. Van Donselaars said, “I am super excited to make new friends and compete. I can’t wait to get a taste of Chicago basketball and tear it up on the court with my girls.”

Pictured: Team Elite’s Michelle Perry (left) and Emma Van Donselaars (right) smiling with the WNBA Official Game Ball

The ASWBL is making large strides in the realm of Chicago women’s athletics, but there is more work to be done.

Sierra believes there needs to be more support and comradery for female hoopers. “Support comes in many different ways,” Sierra explained.

“It doesn’t always have to be monetary support. We all need to think of more creative ways to engage our world with women in the WNBA, other female Pro-Ams—honestly every scale of women’s basketball.”

If you are interested in supporting Ana and the ASWBL, you can reach her via Instagram. And be sure to stop by the UCAN gym this season to catch a game and support women’s basketball.

As we finished our conversation with Ana, she left us with this important reminder, “We have to be able to speak up because no one will do it for us, and we need to bring other women along with us. Together we must collectively strategize how to bring that next female forward— that's how we are going to make the deepest impact.”

Updated January 22, 2023