Sometimes the spirit of entrepreneurship takes hold of an ambitious child early. Take the case of realtor and businesswoman Nikki Lee. Though she was too young to know what the word “entrepreneurship” meant, she knew that there was no other way for her than to be her own boss. Already determined to forge her own way, Lee became a keen student of business and has been building and creating a lane of her very own ever since.
After attending Illinois State University on a track and field scholarship, Lee earned her Bachelor’s in Management and Marketing before spending time learning various aspects of business in her six years as a Brand Ambassador for Monster Energy drink. She would go on to work as a Key Brand Influencer for the Echelon Agency and alcohol brand manager while growing her first business, a hair extension brand called Hair Executives, which was launched in 2009.
Since 2019, she’s worked as a realtor with HomeSmart International and her brand, Showings In Stilettos, which works especially with first-time buyers and investors across the Chicagoland area to help make their home ownership dreams come true. The former athlete (and original member of the groundbreaking Lingerie Football League’s Chicago Bliss has come upon a full circle moment as the proud founder of the newly formed H3R Flag Football league, a platform created to empower women and girls through sports, leadership, confidence-building, and community.
N’DIGO recently caught up with the multi hyphenate businesswoman and mogul to learn more about her philosophy of her business approach, what drives her, and where she wants to take her brand.
N’DIGO: In your own words, who is Nikki Lee?
Nikki Lee: Nikki Lee is a visionary, a connector, a humanist and a woman deeply rooted in purpose. I’m a passionate real estate professional and a dedicated Chicago influencer who loves highlighting the beauty and opportunities within my city. Everything I do is centered around impact, ownership, and creating spaces where people can grow.
What are three words that family and friends would use to describe you?
Driven. Inspirational. Resilient.
What did you dream of being as a child?
As a child, I dreamed of being successful and independent. I didn’t always know what title that would carry, but I knew I wanted to build something of my own, create opportunities for others, and make my family proud. I’ve always been drawn to leadership and ownership — I just didn’t realize back then that entrepreneurship would be the vehicle.
How did you become acutely interested in becoming an entrepreneur?
I got locked in on entrepreneurship because I wanted total freedom — freedom of time, creativity, income, and impact. Real estate opened my eyes to what ownership really means. Helping others purchase property in Chicago showed me how transformative real estate can be for families and investors. That sparked something bigger in me — the desire to not just participate in business, but to build businesses.
Take us back and tell us about your first entrepreneurial venture and what lessons you learned from it?
My first entrepreneurial steps started with a hair extension brand called Hair Executives. I built a clientele selling hair out of the trunk of my car. I learned quickly that consistency beats talent when talent doesn’t work hard. I learned about rejection, resilience, discipline, and the power of relationships. Most importantly, I learned that your name is your brand — and integrity is everything. I had a solid run with that business; however, the explosion of e-commerce sites like Amazon took a large toll on my business. Years later, real estate was a natural progression based on my lifestyle and social circles.
Please tell us about your work in real estate with HomeSmart Realty?
As a real estate professional with HomeSmart, I specialize in working with first-time homebuyers and investors throughout the Chicago and surrounding suburbs. I’m passionate about educating my clients — especially first-time buyers — so they feel confident and informed every step of the way.
For investors, I focus on identifying value-add opportunities, helping analyze potential returns, and navigating deals strategically. Real estate isn’t just transactions for me — it’s about helping people build wealth, security, and legacy through property ownership.
Do you have a motto or philosophy you abide by in your business dealings?
“Lead with value, operate with integrity, and always think long-term.”I don’t chase quick wins. I build relationships. I believe reputation compounds just like investments do.
What’s something people would be surprised to know about you?
Maybe how strategic I am behind the scenes. While I’m visible as a Chicago influencer and community leader, I spend a lot of time studying markets, business models, branding, and growth strategy. Everything I do is intentional.
What’s the best piece of advice you have been given?
“Stay consistent — even when it’s not exciting.” That advice changed everything for me. Success isn’t built in big moments; it’s built in daily discipline.
What’s the best piece of advice that you can give?
Own something. Whether it’s real estate, a business, your platform, or your time — ownership changes your mindset. Don’t wait for permission to build the life you want.
Favorite quote or affirmation?
“Everything I build will outlive me.” It reminds me that I’m not just working for today — I’m building legacy.
What’s next for Nikki Lee? (Future Projects, Dreams, Goals?)
Expansion and impact. I’m focused on growing my real estate presence across Chicago, continuing to serve investors and first-time buyers at a high level, and scaling H3R Flag Football into a movement that young girls and women will be proud of. The vision is bigger than business — it’s about community ownership, economic empowerment, and creating platforms where women win. And we’re just getting started. 🚀
For more information on Nikki Lee, please visit her website at www.showingsinstilettos.com and across social media at @showingsinstilettos
