Grounded in Black Excellence

This week, Terri Winston sat down with Chicago News Weekly to share her journey from Chicago’s West Side to becoming a successful entrepreneur, community leader, and change agent. She attended Howe Elementary before moving on to Charles A. Prosser Vocational High School and later transferring to Jones Commercial High School in the South Loop.

Her passion for business was sparked by her teacher, Ms. Cooper, whose impeccable dress and professionalism left a lasting impression. Inspired by that example, Terri knew she wanted to enter the corporate world.

In eighth grade, her mother was diagnosed with multiple sclerosis. Terri took on a caregiving role, helping raise her siblings. Rather than leaving home for college, she stayed in Chicago, attending Robert Morris University and later completing an accelerated business management program at National Louis University. Though she had opportunities to study elsewhere, she felt a deep responsibility to her family. “My conscience wouldn’t let me leave my mom,” she recalls. “I always worked while managing school responsibilities.” Her mother, a constant source of encouragement, instilled in her the confidence that she could achieve anything she set her mind to.

After college, Terri landed a job at Midway Airlines, where she worked as a gate agent. The role not only provided a paycheck but opened the world to her. “I worked 16-hour days, slept, then boarded a plane and explored for 48 hours before returning home to do it all over again,” she remembers. She spent seven years balancing work, school, and travel until Midway Airlines shut down in 1991.

With her siblings grown and her mother’s blessing, she seized the chance to travel even more, visiting New Orleans, San Francisco, the Bahamas, Jamaica, and Acapulco—experiences that broadened her perspective and fueled her ambition.

MCI

Midway’s shutdown in 1991 left Terri without an income, so she applied for a sales representative position at Mobile Communication, a telecommunications company in Schaumburg, a northwestern suburb of Chicago. “I was a West Side girl who had to drive to Schaumburg daily, forcing me out of my comfort zone,” she recalls. “But the bonus? I discovered the art of making deals. I enjoyed sales—I was good at it.”

Terri has always considered herself a trendsetter, so selling pagers to everyday customers and introducing them to the latest two-way models aligned perfectly with her mindset. One day, a customer recognized her talent and told her, “You have incredible sales skills. You should focus on mastering the art of sales—you’re a natural. You’re attractive, yes, but your real gift is persuasion. That talent is worth money.”

That comment stuck with her. When the same customer returned days later, he reaffirmed his belief in her potential. “You really should get into sales,” he said.

“That was twice that he recognized my natural ability,” Terri reflects. “And while he mentioned my appearance, he never asked for my number or flirted. That meant more to me—it was about my talent, not just how I looked.”

Encouraged by this and eager to grow, Terri seized an opportunity at MCI, a global leader in marketing innovation and, at the time, the second-largest long-distance telephone company in the U.S. after AT&T.

MCI gave Terri the experience of managing commercial accounts while working alongside graduates from top business schools. “As I mingled with them, I could still hear my friend’s words—‘You’re good at this.’ So every day, I channeled my teacher, Ms. Cooper. I dressed impeccably, armed myself with knowledge, and went out to make sales. And I exceeded my quota. My accounts spoke for me.”

SALON SENSE

Terri recalls how one of her accounts, ShopTalk Magazine, a Black-owned hair trade publication once owned by Chicago-based Soft Sheen Products, was bought by an English company. Recognizing her sales talent, the new owners made her an offer.

Just like that, Terri transitioned from telecom sales to magazine sales. She started as a sales rep, and within 45 days, her stellar performance earned her a promotion to Vice President. This role gave her direct access to major players in the beauty and haircare industry—brands like L’Oréal, Johnson & Johnson, and Carol’s Daughter. Since ShopTalk was based in London, its reach spanned across Europe.

“My gift is that I’m a brand maker. I’m a connector,” Terri says. Naturally, she became a favorite in the industry, receiving invitations to exclusive business soirées, lunches, and even gifts.

But behind the scenes, ShopTalk was in financial trouble—a fact the owner kept hidden. Terri continued excelling in sales and building relationships, unaware of the storm brewing. Then, the façade cracked. ShopTalk was going out of business.

At an event, she met someone who would change her future. While exchanging information, he said, “You need to come work with my employer to help improve his credit.”

Terri was loyal to her role despite the magazine’s struggles, so she countered, “Actually, you should meet my boss—maybe you can help him get the company back on track.”

Her new acquaintance took the meeting. Soon after, he called her back with a blunt warning: “The company’s going bankrupt. You need to figure out what you’re going to do. Don’t go down with the ship. And believe it or not, you can do this on your own.”

Terri was taken aback. “Do what?” she asked.

“People associate the magazine with you because they know you. You should seriously consider launching your own magazine.”

Doubt crept in. “I can’t run a magazine company. I’m not rich. I don’t have family money, no one to write me a check.”

To her surprise, he responded, “I’ll help you.”

The idea seemed foreign, and a thousand thoughts ran through her mind. She turned to her mother—the person she trusted most. Her mother reaffirmed the lesson she had instilled in Terri since childhood: “If you choose the entrepreneurial route, you will succeed if you want to succeed. You can do whatever you put your mind to.”

Terri’s voice quivers slightly as she recounts this moment. ShopTalk had officially shut down. It was gone. Poof. She told her mother about the suggestion to start her own magazine. By then, her mother had been battling multiple sclerosis for 20 years.

When Terri introduced her new business partner to her mother, he reassured Mrs. Winston that he would look out for her daughter.

“From that moment, we were business partners, moving forward together,” Terri says. “The rest is history—filled with all the head trips, questions, and doubts that come with starting something new, especially the nagging thought: ‘How am I going to pay my bills? What do I really know about entrepreneurship?’”

Fortunately, her business partner was knowledgeable in the areas she wasn’t. He gently guided her, starting with an essential step: incorporating her business.

“That day, he handed me my articles of incorporation, a phone number, a computer, and, most importantly, his unwavering support,” Terri says.

Initially, she thought she’d work from home. But to her surprise, they drove to 730 N. LaSalle. After exiting the elevator on the third floor, she followed her partner into an office space. The room was nearly empty—except for a printer.

Then he said, “Congratulations, this is your Salon Sense office.”

And just like that, Salon Sense was born. Terri launched her Black hair and beauty magazine with a laptop, a cell phone, and a printer.

“It was magical,” she says.

Ninety days later, she published the first issue. The launch party was held at the Hyatt Regency McCormick Place, celebrating the achievement of “a Black boy from Cabrini-Green and a Black girl from the West Side who turned their skills into reality.”

Terri hit the trade shows and market circuits, distributing Salon Sense internationally before the digital magazine boom. She built upon her established relationships with brands like L’Oréal and Luster from her ShopTalk days. The magazine skyrocketed from Chicago to Atlanta, Detroit, London, Paris, Vegas, San Francisco, Jamaica, Barbados, and New York, publishing six times a year.

Her traction in the industry propelled her into the company of media giants like ESSENCE, EBONY, BLACK ENTERPRISE, and UPSCALE. She mingled with influential figures like Earl Graves, Linda Johnson, and Susan Taylor.

Even as she signed two-year advertising contracts, she remained realistic about the financial ups and downs of running a business. “As a small business owner, you need contingency money for slow periods," she says. "You must be able to sustain yourself.”

Fortunately, she had a financial safety net in her business partner. “He was my foundation,” she says. “Even though I never spent his money, I always had that security blanket.”

Since Salon Sense had an international presence, Terri traveled extensively, teaching young entrepreneurs about financial literacy, business ownership, and wealth-building. She introduced workshops like “Are You Bankable?”, emphasizing the importance of owning land, buildings, and creating a solid business plan.

She worked three days a week in Chicago and spent the other four traveling, expanding her brand with initiatives like “Barber Boot Camp” and “Color Camp” to educate and empower the beauty industry.

Though she wasn’t a stylist or colorist, she learned the techniques to communicate effectively with professionals. “I invested in my business,” she says. “Black hair salons should never have gone bankrupt, but we allowed outsiders to infiltrate and dominate the market. At the time, I didn’t realize I was on a hit list. The Koreans were plotting to buy my company. The only reason they didn’t was because the market crashed.”

As the economy took a downturn, Terri took time to regroup and recalibrate. But she was far from finished.

The Chicago DefenderAs Obama worked to rebuild America’s financial stability, Terri took on a role at The Chicago Defender for the first time as part of the sales team, aiming to enhance the paper’s market value.

At one point, the publisher asked Terri to assist a staffer in collecting outstanding payments. He told her, “I need you to help me accomplish this.” So, she transitioned from sales rep to accounts receivable.

Terri recounts the circumstances that led to her first departure from the paper. As a salesperson, she worked on commission, so her first question was, How am I going to be paid for collecting overdue money? From that point on, she says, “I met every day with the Real Times CFO. He called me at 9 a.m., noon, and 4 p.m. like clockwork—because I was bringing in the money.”

During those conversations, he revealed something surprising: “You should have been the publisher in the first place. You have publishing experience, but the Defender's publisher had nothing—not even editorial experience.”

Shortly afterward, the company let the publisher go and brought in Cheryl Mainor Norman as Vice President of Real Times and Publisher of The Chicago Defender.

“That same man I had helped collect a million dollars in outstanding billing turned around and questioned Cheryl about why my sales numbers weren’t as strong as before,” Terri recalls. Cheryl had no idea what was going on behind the scenes. The CFO made it seem as though Terri was being overpaid because she hadn’t met her sales quota—without ever informing Cheryl that she had been reassigned from sales to collections.

Consequently Terri was released, based on false reporting. A few months later, after Cheryl discovered the truth and learned more about Terri’s background, she realized how valuable she could be to the team. Cheryl rehired her.

“Cheryl recognized what I could bring to the table,” Terri says. “That’s why I came back—to help her. But first, I consulted with my business partner, and he said, ‘Why not? Money always helps you get where you’re going’... and we had plans.”

“Under Cheryl’s leadership, I had the freedom to do what I do best—network, transform relationships, and turn them into revenue,” she continued

Terri began with politicians, knowing they always need positive publicity. “The first person I brought to the table was Kim Foxx. I heard her campaigning for State’s Attorney on the radio and thought, The Defender can help make that happen.”

“I invited Kim Foxx to the office and introduced her to Cheryl. Then you (Kai) did your editorial magic, and the editorial board endorsed her. And guess what? We had a winner. We were the first to endorse her, and Kim Foxx will tell you that.”

After that, The Defender became a magnet for politicians who wanted the paper’s support. “One by one, they filled that huge conference room—some of them had never even been to the then-110-year-old Chicago Defender office. It became a hub where they could share their initiatives and seek support when needed.”

With her marketing expertise, Terri also helped revamp The Defender’s two biggest events: Women of Excellence and Men of Excellence. “Those awards became the ones to receive—and they still are today, based on what we established,” she says.

She also helped elevate The Defender's presence at the Bud Billiken Parade by launching the high-end VIP viewing party. “That VIP party didn’t even exist until we made it happen,” she recalls. “Those were the hottest tickets in Chicago. ‘How do I get a ticket to the Bud Billiken VIP stadium?’ Aldermen, state congressmen—even the Speaker of the House—wanted to be there.”

Terri reveals her secret as a salesperson: “The buyer never knows they’re being sold something. And the other salespeople never see me selling.”

Many people had forgotten about The Chicago Defender. “I know that Terry Winston and Hiram Jackson’s Vice President had a whole lot to do with turning that image around—breathing new life into a forgotten, iconic brand.”

Then, at the end of 2016, the bubble burst. The executive leadership left the paper, making the front page of Crain’s. They moved into a new office and launched Chicago News Weekly, which began as a curated news platform on Facebook. Gaining popularity it maintained its following and published its firt printed issue in Septemebr 2022. Today Terri Winston is a Vice President at the paper.

Q Lounge and the Fire BrigadeFinally, Terri shares the beginning of the current chapter of her life. Money was always a reality—it always is. This time, when she and Quention discussed the future, he suggested she work for herself. That’s how the not-for-profit Black Fire Brigade was established.

He had recently purchased an empty building that had once been an Irish social club. Everything was green—the floors, the ceiling, the walls, the bar, even the toilet.

“I had to Google ‘brigade’ to understand what I was getting into,” Terri recalls. Quention made it clear that this wouldn’t be a drinking hole but a place with purpose. Then he announced he was retiring from the Fire Department—but he had a plan. “I’ve got a goal, and I’ve got a short window,” he told her. “I want to leave my legacy behind, which means I need to train my replacement.”

Terri’s thoughts raced. How long can I do this? But then Quention listed everything she had done throughout her career, emphasizing her role in empowering and connecting Black people. Terri received her assignment: build the brand. She and Quention defined their roles—her job was to shape the brand around a firefighter and to find young people who could one day replace Lieutenant Q.

Since 2018, they have recruited young men and women from the South and West Sides to become first responders. “We mentor them, train them, purchase their uniforms, and prepare them for firefighter training,” Terri explains.

She breaks it down: “The first phase is getting into a department, and to do that, you have to pass the test.”

But Terri soon learned that young Black candidates often failed the firefighter test, making them doubt their own abilities. The solution? Flip the playbook. Instead of waiting for them to fail, they began training candidates before they reached the department. By removing the key obstacle in advance, they ensured that when these young people arrived, they already had the necessary certification.

“That was the game changer,” Terri says.

Their training sessions filled with eager youth. They sent students to school, tutored them, drilled them, and prepared them to pass the national test—one that allowed them to work anywhere in the U.S. But the challenge was making firefighting appealing to Black youth.

“It has to be exciting,” Terri explains. “Otherwise, you lose them, and they miss the opportunity. At the end of the day, it’s about the basics of life: Will I enjoy what I’m doing? Will I be attractive enough to get the girl or the guy? Will I make enough money to buy the car, the bling, and the big house? That’s the sexy.”

She likens it to teaching hairstylists financial planning—owning their property, building their own salons, and expanding into supply stores. “It’s all about community building and legacy,” she says. “So here I am again.”

She paints a picture of their future: “If they go to EMT school, then Fire Academy, and finally paramedic school, they graduate with a paramedic certificate and can earn $70,000 to $80,000 a year—without a college degree.”

But Terri doesn't stop there. “We teach them about money management, life planning, investing, and living comfortably," she said. "We give them the map to success.”

Now, Terri proudly says, “We have kids in the Chicago Police Department, the Chicago Fire Department, and fire departments across the Chicagoland area. We’ve sent them to Houston, New Orleans, and beyond.”

Then came COVID-19. Like everyone else, they faced massive challenges—just as they were preparing to open Q Lounge. Terri admits she knew nothing about running a lounge. “But like I always do, I learned,” she says. “I understand business, even if I don’t know the specifics of every industry. So I took the time to learn, and we pushed through.”

She recalls the moment vividly: “I picked up the lounge license on Wednesday. On Thursday, March 14, Mayor Lightfoot shut down the city.”

That was one of the most difficult seasons of her life. With the city shut down, she had two businesses but no way to generate revenue. Meanwhile, insurance, taxes, utility bills—everything was due.

Slowly, they pulled it together. They opened and unveiled a cigar lounge patio. Their target market? First responders, city, state, and county employees. “You never know who you’ll see in that lounge,” she says. “And again, the revenue from both Q Lounge and the Black Fire Brigade helps pay tuition and buy books for our kids. Q Lounge is a blessing. We’re not wealthy—we use that money to support our youth.”

Terri sums it up: “When you know your job—my job is business and marketing—you can go anywhere and start a company. I went from sales rep to magazine owner, from working at the nation’s oldest Black-owned newspaper to running a not-for-profit and now a lounge. Because I am grounded in Black excellence.”