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The Chicago Sky Foundation Scored by Investing in Small Women-Led Business Owners – Essence

rmtsa by rmtsa
July 1, 2025
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The Chicago Sky Foundation Scored by Investing in Small Women-Led Business Owners – Essence
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The Chicago Sky, home to many legends, including the inevitable Angel Reese, just triple-dunked when the foundation congregated last week by providing the keys to economic freedom amongst an audience full of women business owners. Though no WNBA ballers were present, the foundation showed true sportsmanship by uplifting the Chicago community with a team of four women leaders who embraced future entrepreneurs willing to provide for their community. 

Photo Credit: Emma Falk Via The Chicago Sky

Former NBA player, veteran WNBA coach, and executive director for the Chicago Sky, Awvee Storey, praised the intentionality behind pouring into the league and small women-owned organizations since taking over the program almost a year ago. 

“These ladies humble the hell out of me, and understanding the importance of what they do on the court and what you do in the community, he expressed.” 

Storey highlighted the foundation’s key pillars: economic development, health and wellness, youth education, and women’s empowerment. By doing so, the Chicago Sky Foundation welcomed prospective leaders to enjoy an evening dedicated to exponential growth and womanhood. 

Moderator and ABC News anchor, Jasmine Minor, affirmed to the group that they “make up the fabric of the city.” The Emmy award-winning journalist complimented the eight cohorts and the remaining audience, stating their businesses provide advocacy for change in the community. She directed everyone to repeat, “I am proud of me,” as a reminder of the intentionality each woman poured into their establishments.

BIPOC Women Leaders Breaking Barriers In Nontraditional Circumstances

Minor introduced panelists Anna Valencia, Nicole Lee, and Melissa Conyears-Ervin. The three powerhouses provide communal and economic value to Chicago’s residents. Valencia is the second woman to hold the position of City Clerk. Lee is the first Chinese-American woman to serve as the 11th District Alderman. Conyears-Ervin is an Englewood-born and Westside-raised native who climbed the corporate ladder that now serves as Chicago City Treasurer. Each woman solidified their stance in politics by breaking barriers, optimizing their expertise, and contributing to society. Valencia was inspired by civic engagement as a college graduate during Obama’s first presidential campaign. She got involved in the campaign since Obama sparked her interest in electing the first African American president. Despite being a helpful force to change our democracy, she noticed a lack of women leaders as she climbed the political ecosystem. 

Photo Credit: Emma Falk Via The Chicago Sky

“I saw less and less women in the room. I said, ‘That has to stop,’ she expressed to the group.”

Conyears-Ervin’s dedication to serve Chicagoans is “rooted in purpose.” Raised by a single mother, her core values were fighting for the “underdog.” Though growing up in a predominantly Black, marginalized neighborhoods, Conyears-Ervin’s nonlinear path gained her a seat in local government. She rejoices in her position in public service; however, understands the complexities of being a woman leader.  

“We don’t know the energy that we feed off of one another, because we’re all going through the same thing,” she said. “What motivates me is you. My adoration for women is through the ceiling, because I know each and every day what you go through.” 

Photo Credit: Emma Falk Via The Chicago Sky

Lee is the first Asian-American and the first woman to serve as the city councilwoman for the 11th ward. Historically, the 11th ward was overlooked by her white counterparts. Lee’s identity sparks generational changes in a segregated city. During her campaign, she recanted a time when two Asian-American middle school girls recognized her—a moment she describes as impactful and a notion to “rewrite the script”. The single mom of two dreams of diversifying her city. These changes start with representation—a role Lee partakes in with communal strides. 

“I didn’t think that in my lifetime I would see somebody that looked like me serving on the city council, representing our community. I just didn’t see it. Shame on me for thinking that,” she confessed. 

Dismantling DEI Challenges As a Woman Business Owner

Minor informed the panelists that small women-led businesses suffer major roadblocks due to current DEI policies. Alderwoman Lee advised holding elected officials accountable, being active in local chambers of commerce, and staying current on current legislation to avoid citations. Conyears-Ervin reveals she’s fought the same DEI challenges for years. However, she gains momentum fighting inequitable defiance from the people she represents. 

Photo Credit: Emma Falk Via The Chicago Sky

“Some people just use the terminology of diversity, equity, and inclusion as terminology. For me, it’s my lifestyle. For me, it’s how I live every day,” she said. 

The city’s treasurer motivates businesswomen to lead with authenticity and a “discerning spirit.” Valencia believes the power of local government, community, and networking ensures a fruitful future for attendees looking to upgrade their businesses and access capital. She says four percent of venture capital is invested in women-founded companies nationally. She calls for innovation and a secure network for success in women-led foundations. 

“We’re not going back where the husband signs a credit card for you. We’re not going back where you can’t get your own capital funding for your businesses to scale up,” she said. “There are ways to keep moving forward, even in the time that we’re living in.”

Being Unapologetic And Standing on Business 

Minor noticed women don’t ask for resources, especially for resources they want, as opposed to men. An entrepreneurial spirit takes courage and profound adaptability for a business to scale. 

Photo Credit: Emma Falk Via The Chicago Sky

Lee advised the group to be straightforward and authentic and to maximize their time. Conyears-Ervin recalled indefinite microaggressions as a Black woman in the leading financial department. Despite misconceptions about Black women’s temperaments, she remains unapologetic in boardrooms. 

“Hold on to your power, because your finances, economics, that’s power. I knew that I was holding a checkbook, so whether you liked it or not, I’m going to hold you accountable. Why? Because, as I said earlier, I represent the people,” she said. 

Photo Credit: Emma Falk Via The Chicago Sky

Valencia practices collaboration, not competition, as the remedy to women’s empowerment. She believes women should create a space to combine ideas, which will equate to success. 

“We have to take care of one another; no one else is coming to save us. We’re here to save ourselves,” she said. 

Effectively Building Brand Recognition with Purpose and Preparation

Diane Primo, CEO, marketing magnate, and communication innovator, served as the keynote speaker. To Primo, self-investment is the foundation that balances women-led businesses. The award-winning public relations founder describes herself as a “wealth of knowledge,” since she’s applicable in every business sector. From starting as an Avon saleswoman to leading billon-dollar divisions, Primo recognizes each businesswoman performs “Olympic level entrepreneurship.” She detailed that consumers not only buy products, they buy your name. 

“First rule of business, visibility builds trust,” she said. “If people don’t remember your name, they won’t remember your what you offer.” 

Also, Primo states business constitutes meritocracy—a room most women aren’t allowed to fill. Fighting for you value, voice, and visibility is reclaiming your right and waiting for that right is a loss. Her mantra includes repeating your name several times, being the brand and not just the owner.

“Do not let others define who you are. Control it. Decide what it’s going to be, and tell it as often as you can—as many places as you can,” she said. 

Time is money, and she says, “underpricing is not humility.” The business leader thinks undervaluing solution-based products is sabotage than actual value. She emphasizes to perceive cash flow as oxygen since profit is power. The strategist continued by saying to launch any business before it’s developed and not hold back. She says “failing fast” is the key not procrastinating and solve business opportunities. Lastly, Primo advises the audience to lead with uniqueness and invest in the most valuable asset—yourself.

“Self investment isn’t intelligence. It’s infrastructure. Your business will never outgrow your leadership. So invest in you.”



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Tags: BusinessChicagoEssenceFoundationInvestingOwnersScoredSkySmallWomenLed
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