Darren Roberts was born in Santa Cruz, Trinidad & Tobago, and migrated to the United States in 1998 to pursue higher education. He earned a Bachelor’s degree in Accounting from Bentley University and a Master’s degree in Finance from the University of Phoenix. After spending 15 years with McDonald’s Corporation in leadership and consulting roles across the Boston and New York Metro Regions, Darren transitioned into ownership in Pittsburgh, where he became a McDonald’s Owner/Operator in 2016. Today, he proudly owns and operates four McDonald’s restaurants in the Pittsburgh market and has served in key leadership roles, including four years as Chair of the Black McDonald’s Operators Association (BMOA) for Pittsburgh.
Deeply invested in Pittsburgh’s communities, Darren is passionate about creating opportunity, supporting cultural initiatives, and giving back locally. He has been a longtime supporter of Juneteenth celebrations and community events in Pittsburgh, while also maintaining strong ties to Boston and his hometown of Santa Cruz, Trinidad. Darren has been married to his wife, Lisa, a Boston Police Officer, for 30 years, and together they raised two college-educated children. His vision remains focused on growing a strong Pittsburgh-based business while uplifting communities through mentorship, youth empowerment, and service.
Darren Roberts: A Black History Month Conversation on Business, Purpose, and Pittsburgh
Q: You were born and raised in Santa Cruz, Trinidad & Tobago. How did your upbringing there shape your mindset around hard work and opportunity?
Mr. Roberts: Growing up in Santa Cruz, Trinidad & Tobago instilled in me the values of respect, strong family ties, and the belief that hard work truly pays off. Education was always emphasized, and I was surrounded by a close-knit community where neighbors supported and looked after one another. That sense of collective responsibility and encouragement shaped my character in lasting ways. Many of the lessons that guide me today came from that village environment, and I remain committed to supporting the growth and development of youth there.
Q: What led you to immigrate to the United States, and how did those early years influence your ambition and resilience?
Mr. Roberts: I came to the United States in pursuit of greater educational and career opportunities. I earned an associate degree in Accounting from Roxbury Community College, a bachelor’s degree in Accounting from Bentley University, and a master’s degree in Finance from the University of Phoenix.
During college, I joined INROADS, which provided internships with Fortune 500 companies. Those experiences introduced me to corporate culture, professional expectations, and the power of networking and mentorship. It was during this time that I began setting clear life goals and building the resilience needed to achieve them.
Q: You spent 15 years working in various leadership roles at McDonald’s before becoming an Owner/Operator. Why was it important for you to fully learn the business before pursuing ownership?
Mr. Roberts: I always knew I wanted to own a business, and I’ve long been passionate about the food industry. My career with McDonald's allowed me to gain leadership experience across finance, operations, training, and technology. That broad foundation gave me a deep understanding of the business and confirmed my desire to become an Owner/Operator.
I also sought hands-on restaurant experience by working alongside Owner/Operators Jeff Brewster and Jim Roberts, who mentored me and allowed me to learn directly inside their restaurants. When I first applied for ownership, I was turned down because I did not yet have the required capital. Instead of giving up, I doubled down on my career, savings, and investments while studying franchising and business ownership more deeply. In September 2016, I finally achieved my goal and became an Owner/Operator in Pittsburgh. My wife Lisa, my children Britney and DJ, and the community I grew up in were all major sources of inspiration and motivation.
Q: You held roles spanning finance, operations, technology, and training. How did that breadth of experience prepare you for owning and operating multiple restaurants?
Mr. Roberts: That range of experience gave me a strong and confident start as a new business owner. My financial background helps me focus on profitability and growing market share, while my operational and training experience supports team development and execution. Expanding my organization has brought both successes and challenges. One early hurdle was relocating to Pittsburgh without an established local support network, which required me to quickly build relationships and credibility in a new market.
Q: Becoming a McDonald’s Owner/Operator is highly competitive. What did it take—professionally and personally—to reach that milestone?
Mr. Roberts: It required clear goal-setting, strong mentorship, and a willingness to invest both time and resources into professional development and networking. I worked diligently to build the financial foundation necessary for ownership and sought guidance from experienced Owner/Operators and advocates within the system. Just as important was the unwavering support of my family—my wife Lisa, my children, and my extended family—who believed in the vision and stood by me throughout the journey.
Q: What were some of the toughest challenges you faced in transitioning from corporate leadership to entrepreneurship?
Mr. Roberts: The transition was both exciting and challenging. I moved to Pittsburgh with no local roots, no permanent housing, and no established support base. My last day as a McDonald’s corporate employee was September 15, 2016, and my first day as an Owner/Operator was the very next day. I lived in a hotel for the first month while building my business from the ground up.
Another major challenge was shifting from a corporate perspective to full financial responsibility as an owner. While my corporate experience was invaluable, managing every financial obligation firsthand required a new level of fiscal discipline and decision-making.
Q: Today, you operate four McDonald’s restaurants in the Pittsburgh market. What does success look like for you at this stage of your journey?
Mr. Roberts: Success means developing my employees and showing them that they can achieve more in life by setting goals and staying focused. I see my role as a mentor, especially for young people, helping them understand the value of education and the opportunities available through our restaurants. From a business perspective, success also means continuing to grow profitably, increasing market share, and creating future leadership opportunities within my organization.
Q: As one of the few African American McDonald’s owners in Pittsburgh, what does ownership represent to you—especially during Black History Month?
Mr. Roberts: Black History Month is a meaningful time to reflect on the sacrifices and achievements of those who paved the way for opportunities like mine. Ownership represents both progress and responsibility. I feel a deep obligation to succeed so that my children, my family, and the young Black employees I work with can see what is possible through perseverance and hard work.
Q: Why is Black ownership within major global brands like McDonald’s still so important in 2024 and beyond?
Mr. Roberts: Black ownership in global brands is important not only for representation but also for economic impact. It helps address wealth gaps, supports job creation, and strengthens local communities. Owners who understand the unique challenges of underserved communities are often well-positioned to provide employment, mentorship, and community investment. Representation within major brands also sends a powerful message to future generations about what is achievable.
Q: What advice would you give to aspiring Black entrepreneurs who may feel discouraged by the barriers to entry in large-scale business ownership?
Mr. Roberts: Don’t be discouraged. Seek out mentors and connect with organizations like the National Black McDonald's Owners Association, where experienced Owner/Operators are willing to share guidance and encouragement. The process can be challenging, but mentorship and preparation can make a significant difference.
Q: You’ve emphasized creating career pathways for your employees. Why is mentorship and workforce development such a priority for you?
Mr. Roberts: Mentorship and workforce development are important because they help employees recognize and take advantage of the opportunities available to them. I want my team members to stay focused on growth, build confidence in their abilities, and use their skills and knowledge to advance both professionally and personally.
Q: Community involvement has been a consistent part of your journey—from Juneteenth events in Pittsburgh to back-to-school initiatives in Boston and Trinidad. Why is giving back non-negotiable for you?
Mr. Roberts: The communities where I operate have strongly supported the McDonald’s brand, and giving back is a way to show gratitude and partnership. For the past eight years, I’ve supported Juneteenth events in Pittsburgh, which promote community unity and economic empowerment. Supporting causes that matter to our customers and neighborhoods is an essential part of responsible business leadership.
Q: Your annual back-to-school event in Trinidad is deeply personal. What does it mean to reinvest in the community where your story began?
Mr. Roberts: As a former student of Santa Cruz R.C. School, giving back to that community is very personal. These events help students and families prepare for the school year while fostering community spirit and recognizing young people as future leaders. We also provide motivational talks to encourage students to strive for success. It’s important to me that they have a real opportunity to reach their full potential.
Q: How has your family supported you throughout your journey, and what role do they play in your continued success?
Mr. Roberts: My family has been my greatest source of strength. My wife, Lisa, a Boston Police Sergeant nearing retirement, has been my strongest advocate and strategic partner as we build our family legacy. My daughter Britney, a professional educator focused on special needs students, is a strong supporter of the business and spends time with me in Pittsburgh. My son, Darren Jr., a graduate of the University of Miami with a degree in Economics, worked in the restaurants during his summer breaks and gained valuable financial and operational experience. He currently works in hedge fund compliance in Miami and hopes to join the family business in the future.
Q: Looking ahead, what do you hope the future holds for Black McDonald’s owners and for the next generation of entrepreneurs coming behind you?
Mr. Roberts: I hope future Black Owner/Operators continue to have a level playing field and equal opportunities for success. Black Owners must understand what they are getting into and seek out advice to insure they will achieve financial success.
Q: When people see your story, what do you hope it inspires them to believe about what’s possible?
Mr. Roberts: I hope my journey shows that with perseverance, education, mentorship, and faith in yourself, it is possible to achieve goals that may once have seemed out of reach.