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Nationally recognized coach, author, influencer and brokerage leader Jemila Winsey went from homelessness to top-producing, award-winning Realtor through a combination of resilience, purpose and passion. She has spearheaded initiatives through the Houston Black Real Estate Association and the National Association of Real Estate Brokers (NAREB) to honor excellence among Black real estate professionals.
“Public recognition of Black Realtors’ achievements has given other Black Realtors inspiration to be mega-successful, expand into luxury, launch large production social media and video campaigns, live out loud, and come out from behind the curtain and take center stage,” she wrote last year in an Inman op-ed.
Find out how this Houston, Texas, Realtor puts her two decades of expertise to work for clients and for the agents she influences.
Broker Spotlight: Jemila Winsey
Name: Jemila Winsey
Title: Co-founder and broker
Experience: 24
Location: Houston, Texas
Brokerage name: ERA Legacy Living
Rankings:
- No. 1 Black-owned brokerage in Texas by production
- No. 2 Black-owned brokerage in the U.S. by production
- 2023 Inc 5000 — No. 23 in Texas, top 5 in Houston
- Real Trends top 1.5 percent brokerages in the U.S.
Team size: 55
Transaction and Volume: $2 billion in combined sales volume and 3,000+ transaction sides
Awards:
- INC 5000 (2022)
- Real Trends – America’s Best (2021 and 2022)
- NAREB Top 100
- Houston Business Journal Top 25 Teams
- Houston Business Journal Women Who Mean Business
- Houston Association of Realtors Top 20 Realtors
- RISMedia Industry Trailblazer
- Multiple production-based awards from franchise affiliations, including Hall of Fame honors
Professional and board affiliations (past and present)
- Vice Chair, Fresno Tax Increment Reinvestment Zone (TIRZ)
- Texas Realtors Board of Directors
- Texas Realtors Strategic Planning Committee
- Houston Association of Realtors, Board of Directors
- Texas Realtors, Regional Vice President
- Board Member, Big Brothers Big Sisters
- National Association of Realtors (NAR) – Business Issues, At Large Member
- National Association of Realtors (NAR) – Federal Technology Issues, At Large Member
- Texas Realtors, Professional Development Committee Member
- Texas Realtors PAC (TREPAC), Board of Trustees
- TREPAC Budget Committee Member
- Houston Black Real Estate Association Board Member
- Chair, HAR Fort Bend Political Affairs Advisory Leadership
- Chair, HAR Fort Bend
- HAR MLS Committee Member
- HAR Technology Committee Member
- HAR HRIS Committee Member
- HAR TREPAC Committee Member
What 3 things should readers know about you and your brokerage?
- Industry leaders with heart: ERA Legacy Living proudly stands as the No. 1 Black-owned Brokerage in Texas by production and is ranked among the top 1.5 percent of brokerages nationwide. But what truly sets us apart is our focus on building a collaborative culture where our agents feel supported, celebrated, and empowered to thrive. Success is a team effort, and we rise together.
- Excellence rooted in care: We blend cutting-edge technology, unmatched expertise and a heartfelt commitment to excellence. For us, it’s more than just numbers — it’s about creating life-changing opportunities for our clients and fostering a family environment where our agents feel valued and motivated to bring their best.
- Community and culture first: At ERA Legacy Living, we’re not just building careers — we’re building a family. Through mentoring, celebrating milestones, and championing diversity, we’ve cultivated a culture that prioritizes personal and professional development. Our agents are more than partners — they’re part of a legacy focused on growth, support and lasting impact.
What’s your top tip for freshly licensed brokers?
Focus on building a strong foundation with your team and operations. Prioritize cultivating a collaborative and supportive culture where your agents feel valued and empowered to succeed. Develop systems that streamline processes and ensure consistency, but don’t lose sight of relationships — your agents are your greatest asset.
Always lead by example, stay open to learning and never underestimate the power of mentorship and coaching within your brokerage. Never focus on headcount, and lose the ego so you can pivot when you need to.
Remember that building a brokerage is a marathon and not a sprint. The journey may feel thankless at times, and it will probably be one of the hardest but most rewarding things you will ever do in your career. Real leadership in real estate is about balancing vision, strategy, and heart.
Tell us about a high point in your brokerage career
One of the most memorable high points in my career was being honored with the Houston Business Journal Women Who Mean Business award, alongside ERA Legacy Living, earning a spot on the Inc. 5000 list and the Greater Houston Black Chamber Pinnacle Award. These accolades represent more than recognition — they solidified our place as true business owners beyond just real estate, showcasing our strength and impact across industries.
Getting there wasn’t easy — it took resilience, vision and an unwavering commitment to excellence. We focused on building a business rooted in sound systems, innovation and a people-first culture.
These awards validated that our hard work had not only elevated our brokerage but also positioned us as leaders in business, entrepreneurship, and community impact. It was a moment that reminded me that every setback was setting us up for this level of success.
What’s one thing you wish every agent knew?
Success in this game isn’t about luck — it’s about consistency and focus. Too many agents are chasing shortcuts, but the not-so-secret sauce is the long game. This is where greatness lives.
Day in and day out, you’ve got to show up, even when it’s hard, even when the results aren’t immediate. Stop getting distracted by what someone else is doing. Lock in on your vision, focus on the fundamentals, and stay relentless.
The agents who win big in this industry aren’t the ones who sprint — they’re the ones who pace themselves, who build relationships, who master their craft. Play the long game like your legacy depends on it, because it does.
Don’t just work to close deals; work to create impact, to build something so solid that it can’t be shaken. Consistency is the bridge between where you are now and where you want to be — so cross it every single day.
Tell us about an epic fail you’ve experienced since you’ve been a broker
Fear can cripple an organization. I learned this the hard way when I hesitated to remove individuals who were toxic to our brokerage. I allowed fear — fear of backlash, fear of instability — to hold me back. But here’s the truth: when you let fear dictate your decisions, you give people the power to become bigger than the vision and legacy you’re building. That’s dangerous.
When I finally stepped up and made the decision, it was transformative. Removing those individuals didn’t break us; it freed us. It realigned us with our core values and demonstrated to our team that no one — no matter how influential — can be allowed to compromise the greater purpose.
The moment I chose vision over fear, it revitalized our culture, strengthened our unity and gave us the clarity to build something even greater. Leadership is about making the hard calls, knowing the legacy you’re building is worth more than any temporary discomfort.
