Dr. Shakkiah Curtis has created a sanctuary for the Black community
Late on a Friday evening in February, the lights at Tailer Nicole Wine and Cupcakes glowed warmly against the winter dark. Inside the cozy lounge tucked within Madison’s Black Business Hub, dozens of people lingered, raising glasses in tribute to a beloved local man whose life they had gathered to celebrate. There were cupcakes and wine, of course. But more than that, there was connection. No one seemed in a hurry to leave.
That moment is exactly why Tailer Nicole exists.
From the beginning, owner Dr. Shakkiah Curtis envisioned more than a wine bar. She set out to create a space where luxury meets genuine community and where every guest is invited to belong. Every detail is intentional. Rhythm and blues music hums through the speakers. The walls carry rich tones and artwork that reflect the beauty and complexity of Black culture.
“The atmosphere is jazz and Harlem inspired with a big city L.A. vibe,” Curtis said. “Everything is curated to celebrate Black culture and create a place where people feel at home and safe.”
Curtis developed the concept and hired a trusted team to manage day-to-day operations in Madison while she remains based in Milwaukee. Though Tailer Nicole feels effortless, its foundation was built through grit.
Born and raised in inner-city Milwaukee alongside five siblings, Curtis once imagined her future far from home.
“I was a rebellious and angry girl,” she said candidly. “Then I had a child at 17. I could never NOT provide for my daughter. She forced me to focus on creating a better future.”
Curtis enrolled at Tennessee State University, earning a bachelor’s degree in English. For the first time, she found herself immersed in an environment where Black excellence was visible and abundant. It opened her eyes to what was possible. She began to see a different version of herself—one shaped by ambition rather than limitation.
After college, she returned to Milwaukee and opened two small clothing boutiques. The ventures were fueled by creativity but hampered by financial inexperience. Within a few years, both closed.
“I learned the hard way,” she said.
Instead of retreating, Curtis leaned into education. She earned her MBA from Cardinal Stritch University and later completed a Ph.D. in business administration and management from Colorado Technical University. What began as an “I’ll show you” mindset evolved into a mastery of research and strategy that would underpin her future endeavors.
“I’m an advocate for continued education,” she said. “It has provided opportunities and experiences that have changed my life. It has put me in rooms where I never imagined I belonged.”
One of those rooms was at Starbucks, where Curtis landed her first major corporate role. She credits the company, and its former CEO, Howard Schultz, as her “first business class.” The position allowed her to travel and expand her professional network. She imagined staying for the long haul.
Then COVID-19 changed everything.
Curtis lost her job in Schaumburg, Illinois, and returned to Milwaukee expecting a temporary reset. Instead, it marked a turning point. She joined Gener8tor, supporting tech-enabled business growth, and discovered a side of Milwaukee she hadn’t known before—one filled with innovation and opportunity.
“There was a big difference between the inner city that I knew and city life,” she said. “When I saw Milwaukee’s good parts, I wanted to be a part of it.”
After a year, she accepted a role with the MKE Tech Hub Coalition, where she helped build technology ecosystems by connecting entrepreneurs with resources and innovation opportunities. Her experience with entrepreneurs sparked new ideas.
She launched The Pink Hustle Consulting Firm to create sustainable systems for women’s advancement and business growth. She founded Her Fitness Finances LLC to integrate financial literacy and wellness strategies. She also opened Spinn MKE, Milwaukee’s first luxury indoor cycling studio owned by a Black woman—blending hip-hop, community and holistic health into a vibrant fitness experience.
Yet even with multiple ventures underway, she seized another opportunity in Madison.
While working at MKE Tech Hub, Curtis connected with leaders affiliated with Madison’s Black Business Hub, including Urban League of Greater Madison President and CEO Dr. Ruben Anthony. Their conversations centered on what the Hub needed.
“When I lived in Madison briefly before, I couldn’t find culture and community,” Curtis said. “I knew this was something the Hub needed to offer.”
From those discussions, Tailer Nicole Wine and Cupcakes was born—named for her oldest daughter, now in her 20s, whose birth transformed Curtis’ life trajectory decades earlier.
Open Tuesday through Saturday, Tailer Nicole offers wine, spirits, mocktails and desserts alongside charcuterie boards and specialty pizzas. But its menu is only part of the draw. The lounge regularly hosts special events and themed celebrations—from Super Bowl watch parties to Valentine’s Day soirées to Black History Month events highlighting Black winemakers.
“Our wines are made by Black winemakers, and our cupcakes and partners are Black-owned businesses,” Curtis said. “Everything creates a culture of Blackness.”
Each week brings its own rhythm. Wednesdays focus on networking. Thursdays invite guests to game night. Fridays turn into karaoke celebrations. Saturdays feature unlimited mimosas and lingering brunch vibes. Conversation starter cards sit on tables, prompting discussions that range from professional aspirations to childhood memories. Strangers leave as collaborators. Casual meetups turn into friendships.
“It’s a place to relax with your friends and make new connections,” Curtis said. “So many individuals come in just for the community. It’s about creating moments that nurture your soul.”
Curtis speaks with pride about her team in Madison, the staff who carry her vision forward daily and ensure every guest feels welcomed. Their leadership allows her to remain present in Milwaukee with her younger daughter while continuing to expand her entrepreneurial ecosystem.
At the heart of everything she builds is a quiet but persistent mission to challenge statistics and redefine narratives.
“I always want to fight the statistic of being a teen mom,” she said. “I’m creating a blueprint, paving the way, so my children have no limitations.”
Still, Curtis is quick to acknowledge that success is never solitary. Her daughters, life partner, mentors, staff, family and friends form the foundation beneath her ambition. Community is her focus.
On that Friday night in February, as laughter mingled with music and glasses clinked in remembrance, Tailer Nicole fulfilled its purpose. It became a sanctuary, where people stayed after hours, held together by shared memories and shared space.
In the end, that is the through line of Curtis’ journey from a determined 17-year-old mother searching for stability to a visionary entrepreneur. Tailer Nicole provides a standing invitation to come inside, stay awhile and find community.
