Inspirational Black Men and Women of The C-Suite: Stanford Oliver of DigiFlight & Camelot Secure On The Five Things You Need To Succeed As A C-Suite Executive

Cultivating Future Leaders: A diverse executive team is a role model for the next generation. When young people see successful executives who reflect their diversity, they are inspired to pursue similar paths. Furthermore, a company with diverse leadership will likely have a diverse internship program, which is crucial in shaping the leaders of tomorrow. By reaching out to a wide range of talent, the business contributes to its success and prepares a diverse, talented, and innovative workforce for the future.

I had the distinct pleasure of interviewing Stanford Oliver.

Stanford Oliver is President, CEO and Founder of DigiFlight, a technology services firm focused on cybersecurity, IT, aerospace and training to support government and commercial security, and Camelot Secure, a revolutionary new cybersecurity company. Stan is a recognized entrepreneur, technologist, aerospace, and cybersecurity expert. He has over 40 years of military, intelligence, and cybersecurity experience. Stan has held a variety of command and staff positions during his 20 years of military service as an Army Aviator and Blackhawk Helicopter Pilot to include the Army Staff, 101st Airborne Division, 1st Armored Division, U.S. Army European Command, 10th Mountain Division, U.S. Army Security Assistance Command,and the U.S. Army Test and Evaluation Command. Stan is a graduate of the Armed Forces Staff College and the US Army Command and General Staff College. He earned his bachelor’s degree in Mechanical Engineering from the University of Missouri at Rolla and an MBA from Boston University.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

As a young man growing up in the inner city of St. Louis, Missouri, I always had dreams bigger than the buildings surrounding me. The neighborhood was rough, but it was home. Boxing was my refuge. I idolized Muhammad Ali, and every time I laced up my gloves, I imagined myself floating like a butterfly, stinging like a bee. The discipline and rigor of training as an AAU boxer taught me much about perseverance and hard work.

I gave it all in the run-up to the 1976 Olympic trials. I dreamed of standing on the podium, the national anthem playing in the background. My journey ended prematurely, and the ring felt a world away.

That year, something was happening in the technology world. Bill Gates and Steve Jobs were laying the foundations for Microsoft and Apple. Inspired by their innovative spirit, I pivoted my dreams in a new direction.

I enrolled in the University of Missouri-Rolla in 1976 to study Mechanical Engineering. I knew this was the first step in harnessing the spirit of innovation I saw in Gates and Jobs. After five years of dedication, in 1981, I graduated with my degree.

I had a strong duty to my country and knew I had to serve. So, I joined the Army as an Aviator. As I flew Blackhawk helicopters, I realized I was at the forefront of another revolution. The technology in these machines was advancing rapidly.

I watched, as over the years, the Army modernized tanks, artillery, command and control systems and even started using unmanned aerial systems. The military was evolving, becoming intertwined with technology, and I was in the thick of it.

After serving my country for 20 years, I knew that my passion for technology was something I needed to pursue further. In 2002, I took the plunge into entrepreneurship and founded DigiFlight. My company culminated all the years of training, discipline, flying, and passion for innovation.

In DigiFlight, I found the perfect amalgamation of my dreams, experiences, and skills. It was here that I could contribute to the technological revolution, just like Bill Gates and Steve Jobs had inspired me to do all those years ago.

Can you share the most interesting story that happened to you since you began your career?

As the founder and head of DigiFlight, a technology firm making strides in the government sector, I experienced many challenges and successes. However, one event remains engraved in my memory, a test of resilience that reshaped my perspective on entrepreneurship.

The year was 2014, and like any other entrepreneur, I was enthusiastic about the prospects for my company. DigiFlight was deeply engaged with the intelligence community and other government entities, with around 80 employees diligently working on government contracts.

The winds of the challenge began to howl when a government shutdown was announced. Unlike previous instances, the intelligence community wasn’t spared. My heart raced as the news sunk in — all my employees were idle overnight. I feared the company would crumble.

Fortunately, DigiFlight had been performing well and had a cushion of financial reserves. The immediate impact was colossal, but the sustenance through the shutdown kept us afloat. With a determination that only an ex-boxer and Army Aviator could muster, I pulled my team together and reassured them that we would weather this storm.

The government eventually resumed operations, but the road to recovery was uphill and rocky. It took us six months to get our government contracts back in place. The shutdown was like a tremor whose aftershocks we felt for a staggering five years. During this time, I focused on rebuilding the business and ensuring my team’s morale remained high.

This tumultuous experience taught me the priceless lesson of being prepared for unforeseen challenges. A substantial cash reserve is akin to wearing protective gear in a boxing ring. It doesn’t make you invincible, but it gives you a fighting chance to stay on your feet when an unexpected blow lands.

Can you share a story about the funniest mistake you made when first starting? Can you tell us what lesson you learned from that?

I was eager to grow when I started my entrepreneurial journey, fresh from the army and working as a consultant with top-secret clearance from my basement. My neighbors were curious about my covert-like operations from home. My eagerness led me to buy out a partner’s business, but I made a hilariously naive mistake by not auditing his contracts. To my shock, I received a staggering $180,000 bill from the IRS for unpaid employee taxes by the previous owner.

In a frantic bid to resolve the situation, I had to hire a criminal lawyer, which surprisingly turned out to be a good move. However, my accounts were frozen, and the IRS put my house under lien, making my life feel like a suspense thriller in the eyes of my intrigued neighbors.

Reflecting, this funny and chaotic experience taught me the importance of due diligence. In business, it’s not just about taking leaps but ensuring that every step is well-calculated. This early blunder became a foundation for future wisdom, teaching me to be vigilant, meticulous, and prepared for the unforeseen.

Can you share three reasons with our readers about why it’s really important for a business to have a diverse executive team?

Enhanced Problem-Solving and Innovation: When an executive team is homogeneous, it needs more diverse thinking with different backgrounds, cultures, and experiences. By incorporating diversity, which goes beyond race and gender, you allow many perspectives to be brought to the table. This rich tapestry of ideas and viewpoints leads to more innovative solutions and efficient problem-solving. As mentioned, having females in senior key positions, for example, can contribute to faster and more effective resolution of issues due to the diversity in thought processes.

Positive Community Impact and Talent Attraction: A diverse executive team is beneficial not only for the business but also for the community at large. Providing opportunities to individuals from diverse backgrounds often results in a sense of gratitude and loyalty. These individuals will likely give back to their communities and alma maters, creating a positive cycle. Moreover, a company known for its diverse leadership is likely to attract top talent. Talented individuals, especially from underrepresented groups, are more likely to be drawn to a company that values diversity.

Cultivating Future Leaders: A diverse executive team is a role model for the next generation. When young people see successful executives who reflect their diversity, they are inspired to pursue similar paths. Furthermore, a company with diverse leadership will likely have a diverse internship program, which is crucial in shaping the leaders of tomorrow. By reaching out to a wide range of talent, the business contributes to its success and prepares a diverse, talented, and innovative workforce for the future.

More broadly, can you describe how this can have an effect on our culture?

Incorporating a mindset nurtured in the military, where individuals are trained to see beyond color or background, can profoundly benefit corporate culture. This approach emphasizes the reliability and competence of colleagues, especially in challenging situations, and fosters an environment where trust is paramount. Employees are instilled with a sense of belonging and reliability because they are valued for their skills and contributions. This atmosphere is conducive to building stronger bonds among team members, as they recognize each other’s inherent worth devoid of preconceived notions tied to ethnicity or background.

Furthermore, diversity plays a crucial role in facilitating efficient team dynamics. With a mix of experiences, perspectives, and problem-solving approaches, a diverse team is a powerhouse of creativity and innovation. When the corporate culture does not impose barriers based on color or background, it paves the way for uninhibited collaboration and the free exchange of insights among team members. This open communication leads to more agile and innovative solutions to challenges as the collective wisdom of diverse minds is leveraged to its full potential.

Moreover, a culture that does not discriminate based on color and actively embraces diversity inherently promotes inclusivity and mutual respect. The collaboration between individuals from diverse backgrounds within this environment breaks stereotypes and prejudices. As employees recognize that they can rely on one another regardless of their differences, a culture of mutual respect takes root. This leads to a more harmonious working environment and stimulates a learning culture where individuals are receptive to gaining insights from each other’s experiences and perspectives.

Can you recommend three things the community/society/the industry can do to help address the root of the diversity issues in executive leadership?

Engage and Recruit from Diverse Talent Pools: One of the first steps the industry can take is to actively reach out to diverse groups, such as historically Black Colleges and Universities, tribal organizations, Hispanic communities, disabled Americans, and woman owned organizations. Leaders need to engage with young people from various backgrounds personally, understand their aspirations, and recruit them. By bringing diversity into the staff right from the early stages, organizations can create a pipeline of diverse talent that can grow into executive leadership positions. Active recruitment and engagement show young individuals that there are opportunities for them, which can inspire them to pursue careers they might not have considered.

Invest in Economically Depressed Areas: Society and government can play a significant role by launching initiatives similar to the Marshall Plan but targeting tribal and economically depressed urban and rural areas. The government should consider reducing or eliminating tax overhead for businesses willing to invest in these areas. Doing so incentivizes developers to build and develop opportunities in often overlooked regions. Projects that allow students and young professionals to work and gain experience should be initiated. This not only revives local economies but also uncovers a reservoir of talent that can contribute to diverse leadership in the long term.

Foster a Mission-Focused Mentality through Mentorship: The industry needs to recognize the value of a mission-focused approach, akin to the military, rather than a purely monetary focus. Encouraging diverse teams to work together on accomplishing missions can instill a sense of purpose and commitment. Moreover, mentorship programs should be implemented emphasizing nurturing passion and dedication among young professionals, regardless of their background. By mentoring the passion in individuals, they are more likely to remain committed to their fields and ascend to leadership positions. This approach also ensures that executive leadership comprises individuals who are deeply committed to their mission and can lead purposefully.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leadership is closely intertwined with one’s understanding of success, and this perspective is influenced by notable figures such as Coach John Wooden, and Martin Luther King, Jr. Leadership is not about comparing oneself to others or striving to be better than someone else. While we can admire and learn from remarkable individuals like Michael Jordan, Roger Federer, Serena Williams, or Steve Jobs, it is imperative not to let their achievements define our sense of success or leadership.

Leadership is about utilizing one’s innate talents to the fullest and striving for personal excellence. It is about having peace of mind from the self-satisfaction of knowing that you put in your best effort to become the best version of yourself. This does not mean being the best compared to others but rather reaching your potential and continuously growing.

Moreover, leadership entails guiding and inspiring others to realize their potential. It’s about fostering an environment where individuals are encouraged to give their best and work towards their goals. A true leader understands that success is not a zero-sum game and that helping others succeed does not diminish one’s achievements.

Additionally, leadership encompasses a sense of responsibility and integrity. Leaders should act as role models, demonstrating honesty, empathy, and dedication. They should be committed to their personal growth and the growth and well-being of those they lead.

What are your “5 things I wish someone told me when I first started” and why.

Take Time to Find the Right People: Surrounding yourself with the right team is critical to success. However, finding those individuals is often challenging. It’s essential to exercise patience in the hiring process to ensure that the people you bring on board align with your values and contribute positively to the goals and culture of your organization. A strong, compatible team can be your most valuable asset.

Always Maintain a Cash Reserve: Cash flow is the lifeline of any business. Understanding the importance of never running out of capital is crucial, as recovering from a deep financial deficit can be nearly impossible. Always explore various means of raising capital and maintain a reserve to weather unforeseen challenges. Keeping a close eye on finances and ensuring enough cash to keep the business running is fundamental to long-term sustainability.

Be Passionate About What You Do: The complexities and challenges of running a business or pursuing a career demand unwavering dedication. It’s essential to be passionate about what you do because this passion will drive you to put in the necessary effort even when things get tough. It doesn’t feel like work when you love what you do, making it easier to stay committed and find fulfillment in your endeavors.

Be Prepared for Fierce Competition: The technology business landscape is highly competitive, and competitors will go to great lengths to gain an advantage. While it’s important to play fair, it’s also necessary to make tough decisions to stay ahead. Being strategically agile and understanding the competitive landscape is crucial in navigating challenges and ensuring your business remains viable.

Respect and Understand Different Cultures: Understanding and respecting different cultures is vital, especially in a globalized world where business often crosses borders. Employees must learn about various regions’ cultures, housing, food, and safety. Similarly, in industry, no matter whom you are dealing with, showing respect for their culture and treating everyone equally can build strong, lasting relationships. When you demonstrate commitment and professionalism and honor the diversity of your clientele, they are more likely to remain loyal and continue doing business with you.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

If I could inspire a movement that would bring the best to the most people, it would be a movement focused on revitalizing urban, rural, and tribal areas through technology and education, akin to a modern-day Marshall Plan.

Central to this movement would be the creation of Youth Centers of Excellence in urban, rural, and tribal areas, particularly those economically depressed or affected by outsourcing. These centers would be hubs for innovation, learning, and community engagement, where young individuals can gain skills and participate in cutting-edge projects.

Large technology companies such as Apple and Microsoft would play a crucial role in this movement. They would be encouraged to invest in these centers by providing coding projects, technology resources, and mentorship. This is not just about charity; it is about recognizing that investing in talent in these areas benefits the companies in the long run. Tech giants have traditionally sought innovation abroad, but this movement emphasizes that there is untapped potential right here in the US.

Moreover, this would allow companies to create a self-sustaining improvement cycle within these communities. As more young people acquire skills and become involved in meaningful projects, they will likely inspire others to follow suit. This upskilling and engagement attract more investment and opportunities to the area.

Another facet of this movement would be incentivizing industries to believe in the domestic workforce and commit to keeping jobs and investments within the country. Lessons can be learned from cities like Detroit, which suffered when industries pulled out. Enterprises need to realize that investing in American communities, particularly the youth, is sowing seeds for a more prosperous and stable future for all.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

One of my favorite life lesson quotes is by Steve Jobs: “The people who are crazy enough to think they can change the world are the ones who do.” This quote resonates deeply with me, as it encapsulates the essence of ambition, innovation, and the power of belief in driving change.

In my life journey, this quote has been particularly relevant. Growing up in St. Louis, Missouri, with dreams of becoming a professional boxer like Muhammad Ali, ambition fueled me. Though I didn’t make it to the 1976 Olympic trials, my undeterred spirit led me to find inspiration in what Bill Gates and Steve Jobs were doing with Microsoft and Apple. Their groundbreaking work fascinated me and instilled in me the desire to make an impact in technology.

The boldness in Steve Jobs’ words served as a reminder that it’s often those who dare to dream big and have an unwavering belief in their abilities who shape the world. As an engineer, an Army Aviator, and later the founder of DigiFlight, I found that embracing this mentality allowed me to innovate and contribute to the technological advancements I was passionate about.

I also hold close to my heart the wisdom in John Wooden’s quote, “There is no substitute for hard work. Worthwhile results come from hard work and careful planning,” and Jim Collins’ words, “Greatness is not a function of circumstance. Greatness, it turns out, is largely a matter of conscious choice and discipline.” These quotes and Steve Jobs’ collectively shaped my leadership, innovation, and entrepreneurship approach.

By combining the audacity to think big with the dedication to work hard and the discipline to make conscious choices toward greatness, I navigated the challenges and complexities of my career. These quotes served as inspiration and guiding principles in my pursuit of excellence and positive change through technology.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

I would love to have a private breakfast or lunch with Martin Luther King Jr. He was a man who was not just educated but was at the top of his game — a true genius in every sense. Dr. King’s mission is incredibly inspiring: his life’s mission wasn’t about personal gain or making money but about uplifting an entire culture, fighting for racial equality, and ensuring that people are brought together in the spirit of freedom and mutual respect.

I would like to understand the depth of his conviction and the reasons behind his chosen path. Despite his numerous challenges and personal risks, Dr. King remained steadfast in his commitment to civil rights. His eloquent speeches and writings, such as the Letter from Birmingham Jail, are a testament to his intellectual prowess and unwavering dedication to justice.

As someone with a Ph.D. from Boston University, he could have chosen many other paths, but he chose one that was laden with difficulties because he had a vision of something better for all. I would love to delve into his thought process, understand what motivated him every day, and learn how he managed to maintain hope and strength in the face of adversity.

Having a conversation with Dr. King would be incredibly enlightening and deeply humbling. His life and work remind me of the power of conviction, the importance of standing up for what is right, and the impact one person can have in shaping history. His example is a testament to the ideals of leadership, selflessness, and the pursuit of a greater good, timeless values that continue to inspire generations.

How can our readers follow you on social media?

https://www.linkedin.com/in/stanford-oliver-6b72242/

https://twitter.com/stan_digiflight?lang=en

This was very meaningful, thank you so much!