Breaking Barriers, Building Business: Tasha Jones’ Inspirational Story

• With a strong passion for learning, Tasha enlisted in the US Navy where she refined her personal and professional identity.
• Tasha leveraged her experience to build a thriving business that prioritizes growth and social impact.
• Outside of work, Tasha’s interests include singing, being outdoors, and listening to audiobooks.

1. Tell us briefly about your childhood, and describe some pivotal moments that have influenced you both personally and professionally?

I grew up in a small town in central Florida with a large, supportive family. We were a close-knit bunch—my mom being one of ten siblings—so there were always cousins around. Everyone knew each other, and there was a strong sense of community.

As a child, I strived to make my family proud. I aimed for good grades and excelled in athletics. I remember teaching myself Swahili in first grade after being inspired by a PBS show. I have an early sense of curiosity and belief in endless possibilities.

I faced overt racism in the U.S., as common for someone from the South. Due to this, I learned how to analyze people’s intentions and behaviors to avoid and mitigate conflicts. These experiences, coupled with a loving and supportive environment, shaped my personal identity. I learned that failure isn’t final unless you stop trying.

When I was about nine or ten, I borrowed my grandfather’s lawnmower to mow lawns and earn money for icy cups. This early entrepreneurial experience, though unrecognized as such at the time, set the stage for my future endeavors. In high school, I worked as a waitress at Steak ‘n Shake. This experience taught me valuable lessons about customer service and understanding people’s behavior. After high school, I chose to enlist in the United States Navy as an Intelligence Specialist. This role suited my analytical skills and ability to synthesize large amounts of data to make accurate assessments.

In the Navy, I read extensively, evaluated situations, and used various techniques to understand and forecast events. This training enhanced my natural analytical abilities and built the foundation of my career.

2. What exactly is the commission of Twenty39 and how do you ensure that your work aligns with your mission?

Our mission for Twenty39 is to help organizations operate efficiently and adapt capabilities to improve performance and decision making. From a business perspective, this means promoting growth and readiness. We also aim to create access and opportunities for small businesses, communities and those who have been disenfranchised. 

I am intentional and strategic about resource allocation and hiring. As we grow, I partner with veteran-based organizations, second-chance programs for previously incarcerated individuals, and support mothers returning to the workforce. We also want to combat biases against immigrants by ensuring their skills and talents are recognized and utilized. 

Our core mission aligns with strategic growth, succession planning and community support. We partner with organizations like Great Explorations to introduce youth to various career opportunities. This initiative helps them visualize potential roles and develop coping skills to navigate adversity effectively. 

We also connect with professionals in organizations like NASA and the FBI to locate mentors with similar backgrounds to inspire and guide the youth. My personal experiences, like growing up with a father in prison, help me relate and show them that their circumstances do not define their future. By sharing our stories, we help them see that success is attainable, regardless of their challenges.

3. How do you measure the impact of your initiatives?

To measure the impact of our initiatives, I use several approaches. I am involved in organizations like Citrine Angels and Iron Butterfly Foundation. Citrine Angels focuses on women investing in women, addressing the gender disparity in investment where women receive less than 2% of funding, with women from ethnic backgrounds receiving even less. Iron Butterfly Foundation aims to bring women’s stories to the forefront through media, expanding from its origins in the Iron Butterfly Podcast, which highlights women in the US intelligence community.

The impact of these initiatives is measured through:

1. Verbal validation: Feedback from individuals who benefit from our programs provides immediate insights into our impact.

2. Monetary metrics: Success can be quantified through financial achievements, such as successful training programs, investments, and the ability of companies we support to secure additional funding rounds.

3. Community and company impact: We evaluate how our investments and efforts create healthier environments and opportunities within the community. This includes observing how supported companies give back and create opportunities for others.

4. Ripple effect: I look for a cascading impact, where the benefits extend beyond the initial recipients. For example, if one person helps another due to our influence, and this positive behavior continues, it demonstrates a widespread effect.

5. Behavioral change: We hope our efforts lead to positive behavioral changes in individuals and influence how they handle future situations more constructively.

4. What are some of the biggest challenges that you faced in your career and how you managed to overcome them?

One of the biggest challenges in my career has been dealing with internal struggles, compounded by external factors like systemic racism. It is a pervasive issue in this country, particularly impacting opportunities for Black Americans in environments like government contracting and business ownership.

A significant part of this challenge is the constant need to consider how my actions and behavior will be perceived. For instance, if I express frustration or assertiveness, it might be interpreted differently in comparison to a white or Asian woman doing the same. This stereotype acts as a burden and significantly influences how I am seen by others, which impacts my professional interactions.

Internally, I’ve had to manage my mental health and maintain emotional stability. This involves being kind to myself, properly attributing blame, and not taking responsibility for things beyond my control. I was raised to be a giver and to avoid creating issues, which has influenced how I respond to challenges.

Overcoming these issues required developing emotional intelligence and consistently applying it. I’ve learned to process external biases without internalizing them, and to focus on what I can control.

5. How has your leadership style evolved, considering the various experiences and trends you’ve encountered?

Initially, I didn’t see myself as a leader and led more intuitively. I believed in leading by example–showing and doing–rather than asking others to do what I wouldn’t do myself. This approach helped my team follow my lead naturally.

Over time, my leadership style evolved to include more decisive and descriptive actions. As I moved into higher roles, I realized the importance of delegating and providing detailed instructions to ensure everyone understood the importance of goals and worked cohesively toward them.

While my style remains collaborative and intuitive, I’ve grown more aware of the need for clear communication and guidance. Leadership, to me, is about service—serving those who depend on you, and ensuring they have the support they need to succeed.

6. How was your experience of working with federal agencies and the government?

I’ve had the privilege of working with several three-letter agencies, and the experience may not align with common perceptions. Contrary to common expectations, government work involves a diverse array of people from various backgrounds, each bringing unique skills, motivations, and perspectives to their roles. It’s akin to any other office environment in many respects.

However, what sets government work apart is its mission-driven nature. Whether you’re in intelligence or another sector, there’s a profound sense of purpose in knowing your work contributes directly to national security, economic stability, and creating opportunities for people—often in ways that aren’t immediately apparent. Conversely, some responsibilities can limit opportunities in certain areas.

My favorite aspect of working in government is the tangible impact on larger societal goals. Whether you’re helping to safeguard lives or shape policy that affects communities, every role ties into a broader mission. This dynamic nature varies across agencies and roles, but it consistently offers a unique perspective on public service.

7. How do you maintain a balance between your personal and professional life?

Honestly, I think it’s a myth as I don’t think true balance exists, especially for entrepreneurs. I focus on recognizing when I’ve been working too intensely, and then realizing that I need to pull back and spend time with my family.

The notion of portrayed balance is unrealistic. People imagine a perfect routine where you wake up looking great, make breakfast, exercise, attend meetings, take care of your family, and still have time for everything else. Whereas, the reality is different as there are times when you miss events or can’t be the perfect parent, partner, or friend because you’re focused on growing your business.

If you’re an entrepreneur, you can’t always do it all. If you choose to be a homemaker, you might be amazing at it, but you will be less than stellar at taking care of yourself or running a business. There’s always a trade-off, and sometimes it’s your personal time and well-being that take the hit. You might be a great homemaker, entrepreneur, or friend, but internally you might be struggling, and that’s often the easiest part to hide if you’re strong.

Balance is subjective and depends on individual perspectives. For me, I don’t have the traditional balance, but I manage things in a way that works for me and my circumstances.

8. Where do you find your passion and hobbies integrating into your daily life?

I grew up in a family of singers, so singing is a big passion of mine. While I don’t perform publicly, I do find immense joy in singing and exploring music. It’s my go-to activity when I need to unwind or de-stress; music has a calming effect on me.

Another interest of mine is being outdoors, though I’m not the adventurous type who seeks encounters with wildlife. I enjoy seeing my husband tend his garden, watching flowers bloom, or simply taking a quiet walk in nature. These activities help me recharge and reconnect with myself.

Lastly, I’ve found a love for audiobooks because I struggle to find time to sit down and read. Listening to audiobooks allows me to absorb new information and enjoy a good story while doing other things like walking or gardening.

These activities provide me with moments of relaxation and personal fulfillment amidst a busy schedule.

Tasha Jones’ diverse experiences have shaped her into a tenacious and analytical professional. She leads Twenty39 with a mission-driven mindset, focusing on strategic growth, community support, and creating opportunities. Her story is one of resilience, life-long learning, and dedication to making a positive impact.