With nearly three decades of entrepreneurial experience, Maja Sly has mastered the art of strategic business pivots, building successful ventures across beauty, real estate, and coaching while empowering other women to achieve extraordinary success.

The beauty industry taught Maja Sly her most valuable business lesson: everything that glitters isn’t gold. But after nearly three decades as an entrepreneur, she’s learned to spot real gold in unexpected places—from empty salon chairs during economic downturns to undervalued real estate opportunities that others overlook.

“I’m not afraid to fail,” Sly says matter-of-factly. “The biggest thing that I attribute to any amount of success is that I’m not afraid to try.”

This fearless approach has propelled the Alabama A&M University graduate from working as her uncle’s assistant at age 13 to becoming a powerhouse entrepreneur with an impressive business portfolio. Her ventures include Walk-In Weaves, Pretty Hair Now, and PrettyTech Inc. in the beauty industry, alongside her real estate brokerage and Pretty Powerful University coaching platform. Today, through her Pretty Powerful University platform, she’s helping entrepreneurs across all demographics navigate the complex landscape of business ownership. Her success comes at a time when Black women entrepreneurs represent one of the fastest-growing business demographics, with Black women-owned companies increasing by nearly 20 percent between 2017-2020.

The Art of Strategic Business Pivoting

Sly’s entrepreneurial journey reads like a masterclass in strategic pivoting. After graduating college with a finance degree and briefly considering Wall Street, she chose to follow her instincts back to the beauty industry. For nearly a decade, she operated a traditional salon, but it was her willingness to step away that ultimately led to her biggest breakthrough.

“I left the beauty business for 18 months in 2008,” Sly recalls. “I closed my first brand of stores and pivoted to real estate with a booth rental salon model. When I came back into the beauty business, I had never seen Black women’s hair look so bad in Atlanta.”

That observation sparked the creation of Walk-In Weaves, one of her most successful ventures. But the path wasn’t conventional. Initially planning to purchase a franchise, Sly visited existing locations and identified gaps in the market approach.

“My grandmother used to always say, ‘If you don’t like the way something’s done, then do it yourself,'” she explains. This philosophy became the foundation for her approach to business opportunities.

Numbers Don’t Lie: The Finance-First Approach

What sets Sly apart from many entrepreneurs is her unwavering focus on financial fundamentals rather than passion alone. With her finance background, she approaches every venture through a numerical lens.

“I’m not worried about anybody’s passion around here. My pockets fund my passion,” she states bluntly. “The businesses that are the least sexy make the most money.”

This mindset proved transformative in the beauty industry. “I didn’t make my first million dollars in beauty until I went to a commission-based model. I didn’t make my first million in beauty standing behind a chair. I needed more people to do the work so that I could generate the seven figures.”

Her analytical approach extends to her coaching methodology. When working with clients, Sly immediately examines their financial data to identify problems and opportunities. “It’s very easy to find the problems in someone else’s business because I just follow the numbers,” she explains. “I could look at their numbers and see who was stealing at what location.”

Turning Setbacks into Stepping Stones

Sly’s success story isn’t without its challenges. Her willingness to discuss failure openly provides valuable insights for aspiring entrepreneurs facing their own obstacles.

“My failures have been how I’ve been able to be more successful because in every mistake I’ve learned a valuable lesson,” she reflects. “And those lessons allowed me to get paid for my mistakes because I’m going to teach you how not to make them.”

This perspective shaped her coaching philosophy when she launched Pretty Powerful University. After appearing on the reality show “Cutting in the ATL,” viewers began reaching out for business advice, leading Sly to formalize her coaching approach.

“I wasn’t going to be on the phone for you to waste my time because most of the time people take your information and they don’t apply it,” she explains. Her solution was to create a structured discovery process with a fee attached, ensuring serious commitment from potential clients.

Building Legacy Through Impact

For Sly, success extends far beyond financial achievement. Having chosen not to have children, she’s channeled her nurturing instincts into mentoring other entrepreneurs.

“My legacy will be left based on the people that I’ve impacted, not from children,” she says. “I can make a bigger impact on other people’s lives because I don’t have children. Most people have to pour into their own family so much that they don’t have enough time to help multiple people.”

This mission-driven approach influences her current projects, including plans to expand her real estate business into affordable housing. “Affordable now is not low income,” she clarifies. “Affordable is someone who is making between $50,000 and $100,000 a year, being able to find a place that they can own versus renting.”

The Power of Uncomfortable Growth

Sly’s advice for aspiring entrepreneurs centers on embracing discomfort as a pathway to growth. Her recommendations are both practical and philosophical:

• Surround Yourself with Like-Minded People: “You need other people that are more successful than you. You need to be able to put yourself in situations that you have to get comfortable with being uncomfortable.”
• Think Beyond Comfort Zones: “If you think you’re going to be comfortable being an entrepreneur, I tell people go to corporate. If you only want to make $100,000 a year, do not be an entrepreneur.”
• Embrace Strategic Risk: “You have to be willing to do it scared. You can’t think that everything is going to work out how you want it to on paper. You have to be willing to be nimble, you have to be willing to pivot.”

Beyond Beauty: Building a Diversified Business Empire

Sly’s business acumen extends far beyond her beauty industry roots. Her current portfolio demonstrates the power of diversification and strategic expansion. Walk-In Weaves revolutionized affordable hair services, while Pretty Hair Now and Pretty Take carved out unique niches in the competitive beauty market. PrettyTech Inc represents her expansion into technology solutions, and her real estate brokerage has generated multiple million-dollar deals.

“I’ve opened insurance agencies. I’ve opened a medical facility,” Sly notes, highlighting the transferable nature of entrepreneurial skills. “Everything is transferable. I just packaged them all in one place and showed other people how to do them.”

Lessons from the Beauty Chair

Perhaps most importantly, Sly’s years in the beauty industry taught her invaluable lessons about human nature and business relationships that transcend any single sector.

“Once you touch a woman’s head, she trusts you with anything,” she explains. “I was the keeper of all secrets. I knew that abuse didn’t look one way. Poverty didn’t look one way. Abandonment didn’t look one way.”

These insights inform her coaching approach today, helping her connect with clients on a deeper level and understand the full context of their business challenges.

The Road Ahead

As Sly continues to expand her influence through Pretty Powerful University and her real estate ventures, she remains focused on creating systemic change within entrepreneurship. Her mission-based approach to affordable housing represents a natural evolution of her commitment to solving problems while building profitable businesses.

“I don’t have to actually go after anything anymore,” she reflects on this phase of her career. “I need to really see how many lives I can impact with all the things that I know now and how I can make my life better and the people around me lives better.”

For entrepreneurs of all backgrounds facing the challenges of business ownership, whether systemic barriers, funding obstacles, or market uncertainties, Sly’s story offers both inspiration and practical guidance. Her journey proves that with strategic thinking, financial discipline, and the courage to pivot when necessary, extraordinary success is not only possible but achievable. For Black women entrepreneurs specifically, who continue to face unique challenges including lower loan approval rates and limited startup capital, Sly’s success serves as powerful proof that these barriers can be overcome.

“Anything that I ever wanted to do, I don’t have a lot of regret because it was something that I truly wanted to do,” she concludes. “And if I failed or it wasn’t successful, I found my win in it. Whatever you focus on grows for sure.”

In an entrepreneurial landscape where Black women continue to break barriers and build businesses at unprecedented rates, Maja Sly stands as proof that with the right mindset, strategic approach, and unwavering determination, there’s no limit to what’s possible.