How one entrepreneur turned risk-taking into a business philosophy that transformed DC’s lottery operations

Emmanuel Bailey doesn’t believe in comfort or security. To him, they’re myths.

“Without movement you die,” Bailey explains with the conviction of someone who has lived this truth. “The biggest risk to whatever your goals are and what your plans are is indecision, is status quo, is being comfortable.”

This philosophy has guided Bailey through a remarkable 25-year career spanning finance, banking, and lottery operations management. From his beginnings as a bank teller to becoming CEO of Vital Services Contractors (VSC), a company that has successfully managed Washington, D.C.’s lottery system and on-the-ground operations for over a decade, Bailey’s journey offers powerful lessons in entrepreneurship, leadership, and community engagement.

From Branch Manager to Entrepreneurial Leader

Bailey’s professional journey follows an upward trajectory that seems inevitable in retrospect. After turning down a management position at IBM that would have essentially placed him in “a grand word for mail room,” he instead chose to become a branch manager at Citizens Bank of Maryland—a position he describes as “the most insecure position I have ever been in.”

At just 20-something years old, Bailey became both the youngest branch manager and the only African American among 122 branches. The stakes were high: “There was no progressive discipline. It was either you met your numbers or ‘let us show you the door.’”

This high-pressure environment taught Bailey to embrace discomfort and uncertainty—traits that would later define his entrepreneurial mindset. Rather than seeing this challenging situation as a drawback, he recognized it as an opportunity to “learn the financial system” and “understand the code that they didn’t teach me in school.”

The Leap from Corporate Security to Entrepreneurial Risk

After establishing himself at Citizens Bank, Bailey later secured a position at Fannie Mae as Chief Diversity Officer and Vice President of Human Resources. Yet despite having reached an enviable level of corporate success, he felt the pull toward entrepreneurship.

When asked what motivated him to leave the security of Fannie Mae, Bailey’s answer reveals his driving philosophy: “I thought, and I’ve always thought, that you have to challenge yourself.”

This challenge materialized in 2009 when Bailey founded Vital Services Contractors (VSC), a Washington D.C.-based firm specializing in central gaming systems and technology for government-sponsored lottery gaming systems. Since 2010, Bailey and VSC have provided operations management and administration services for the DC Lottery .

Bailey’s success didn’t come easily or overnight. He shares a pivotal story about pursuing a government contract at the Department of Energy after receiving his 8A license under the SBA program. After a year of persistent follow-ups, he finally secured a meeting with a contracting officer—only to be told he had no chance at getting work.

“You just got your 8A license. There are a dime a dozen 8A companies. You have no experience. You’re not going to get a contract here,” the officer told him bluntly.

Instead of reacting with anger or dejection, Bailey asked what made other companies successful. He thanked the officer and left. Months later, while boarding a plane to the Bahamas for the July 4 weekend, Bailey received a call from that same officer requesting help with an urgent $1,200 job that other companies had declined.

Bailey canceled his vacation, completed the job flawlessly, and three weeks later was awarded a $4.5 million contract.

“Most people stop when they hear the word ‘no,’” Bailey reflects. “The most consequential, devastating killer of particularly small businesses, minority business that has ever been invented is the word ‘no.’”

Industry Recognition and Achievement

Bailey’s contributions to the lottery industry have not gone unnoticed. In 2020, the North American Association of State and Provincial Lotteries recognized him with its Powers Award. In the nomination, D.C. government officials described him as “far from the stereotypical executive” who “ensures that the DC Lottery is operable every day and that our business remains viable for the long-term future.”

In 2024, VSC was recognized as the Operations Management Company of the Year by CIO Applications Magazine for its “industry expertise and unparalleled results.”

The Government of the District of Columbia has repeatedly praised Bailey and VSC, noting they are “extremely satisfied with VSC’s overall performance, their commitment to the success of the DC Lottery and their positive and cooperative approach to problem-solving and project execution.”

Beyond Business: Community Commitment Without Expectation

Despite his business success, Bailey remains deeply committed to giving back to D.C. communities. He has donated hundreds of thousands of dollars to various local organizations supporting programs like school sports, arts departments, educational support, and health services.

Bailey believes in giving back to communities that have contributed to his success, regardless of whether it benefits his business. “I’ve lived a life where people have taken a lot from me and my family and given us nothing in return. And I’m never going to operate that way,” he states firmly.

This commitment extends to his business partnerships. He requires joint venture partners to allocate budget for community giving. “If I’m benefiting from a community, I think it’s my obligation to make sure that… if I can prevent someone from living the life that I lived and work and live in the circumstances I lived in, and I don’t do it, then I think I don’t deserve to be successful.”

The Bailey Blueprint for Entrepreneurial Success

Emmanuel Bailey’s career offers valuable insights for aspiring entrepreneurs, particularly those from underrepresented communities. His approach combines persistent relationship-building, embracing discomfort, empowering others, and giving back without expectation of return.

For those navigating government contracting, Bailey’s experience highlights the importance of persistence. He notes that 90 percent of companies with 8A licenses never win a single federal government contract because they stop at the first rejection.

“Most people spend the largest portion of their life waiting and wanting rather than planning and doing,” he observes. “And nobody is going to give you anything.”

Bailey’s journey from bank teller to lottery industry leader demonstrates that with persistence, strategic risk-taking, and a commitment to lifting others, entrepreneurial success is possible even in the most challenging environments.

For entrepreneurs looking to make their mark while making a difference, Emmanuel Bailey’s story provides both inspiration and a practical blueprint for turning challenges into opportunities and success into significance.