Empowering Change: How Gayle Jennings-O’Byrne and Wocstar Are Elevating Women of Color in Business

Gayle Jennings-O’Byrne

Women of color entrepreneurs are finding a powerful ally in Wocstar, a groundbreaking initiative led by the CEO, Gayle Jennings-O’Byrne. With a focus on fostering sustainable growth and resilience, Wocstar offers comprehensive business strategies, financial guidance, and continuous learning opportunities through its specialized Wocstar Academy.

Gayle has been instrumental in propelling Wocstar beyond a mere business support network to a vibrant movement reshaping leadership landscapes. With an impressive career spanning over three decades on Wall Street and roles in technology, philanthropy, and professional speaking, Gayle’s multifaceted expertise has profoundly impacted the trajectories of countless women-led initiatives.

Beyond her corporate achievements, Gayle is carving out a niche as an educator and influencer through mediums like her podcast “VCs off the Record” and her teachings at Wocstar Academy. Additionally, she’s also the co-founder of Ally Capital Collab, an initiative addressing systemic capital-raising challenges faced by women of color fund managers.

Check out the full interview with Gayle below.

How did the concept for Wocstar first come about, and what inspired you to focus specifically on women of color entrepreneurs?

Gayle Jennings-O’Byrne: I started Wocstar because I was excited about building a sisterhood of entrepreneurs—especially for women of color and diverse teams.

I saw incredible women around me developing new products and growing their companies, but they remained seemingly invisible to the world in too many ways. I also recognized that, traditionally, black women have been undervalued as founders, inventors, or entrepreneurs – despite all that women of color have to offer and all that we have accomplished. I was frustrated with the status quo and that lack of recognition, so I decided to do something about it.

Black women have a long history of innovation, yet the market and society haven’t fully embraced their accomplishments, despite benefiting from them. I decided to make a difference. I did that by spotlighting these women, lifting them, investing in them, and helping them be seen! I wanted the world to see how unique, worthy of investment, and critical our sisterhood is to the economy and to creating the future.

My alliance of intelligent, experienced, well-traveled, knowledgeable, and informed black women with strong opinions and feelings were no longer willing to be invisible. We got excited about what our sisterhood was doing in technology, science, sustainability, media, and consumer-enabled tech.

Given your extensive experience across various industries, how do you think your background has shaped Wocstar’s approach to supporting women entrepreneurs?

Gayle Jennings-O’Byrne: With 30+ years of experience in financial services, technology, and international relations, I have decades of knowledge to impart. I am eager to share it all, so I mentor in many ways, through Wocstar Ghetto Film School Entrepreneur Academy, where I do one-on-one office hours with entrepreneurs, with tips and tricks in my LinkedIn newsletter, or via my podcast, VC’s Off the Record with Gayle Jennings-O’Byrne.

I hope my legacy will be the people I have mentored. I want them to know they are enough.

My mission is to also be an alternative to the usual suspects in the VC world. That’s another reason I do my podcast: We have real conversations about what it takes to go into a meeting, pitch a VC, and get your bag.

The New York Times recognized you as one of the “10 Women Changing the Landscape of Leadership” in March 2021. How has this recognition impacted Wocstar and your mission?

Gayle Jennings-O’Byrne: It was a very humbling experience that has kept me grounded in the work and my purpose. Receiving the honor was also a big validation to myself, my community of women entrepreneurs, and the market that investing in women is indeed important and imperative to grow the economy and create wealth.

It also got me thinking about our work not for the individual, day-to-day activities but for addressing a system-wide issue of how to allocate capital to the best opportunities, generate wealth and financial independence for a broader population of investors and business owners, and restore human dignity, equity, and equality in finance.

Can you discuss a success story of a woman entrepreneur who has benefited significantly from Wocstar’s support?

Gayle Jennings-O’Byrne: One standout success story is Chef Saidah Farrell, the visionary founder behind Joy Craft Cocoa. Chef Farrell is a graduate of the Wocstar Ghetto Film School Entrepreneur Academy, our digital course aimed at helping diverse entrepreneurs refine their abilities to raise capital, along with honing their storytelling skills.

Through Wocstar Academy, she clinched a $40,000 victory at a pivotal pitch competition. She received practical, action-oriented advice by maximizing our free office hours with industry experts. The key tips and tricks she focused on included shifting her language when talking about her business to project greater confidence. This encourages investors to support your business.

I always say it doesn’t matter what you say; it matters how you say it. These insights proved invaluable, and she ultimately won her pitch competition. We’re incredibly proud of Chef Farrell and hope to continue supporting her. We at Wocstar will continue on our trajectory of teaching female founders and diverse teams the skills necessary to grow a successful business.

Wocstar Academy offers specialized classes for entrepreneurs. What are some key skills or knowledge areas that these classes focus on?

Gayle Jennings-O’Byrne: We emphasize to entrepreneurs enrolled in Wocstar Ghetto Film School Entrepreneur Academy that preparation is key to success—fundraising isn’t merely about soliciting funds; it’s about orchestrating a strategic campaign that leverages your network.

The eight-week course provides the knowledge and preparation required before embarking on fundraising initiatives. We also recommend substantial research and introspection. Business owners must make pivotal decisions regarding their business’s trajectory, including envisioning its growth, revenue streams, potential exit strategies, and scalability options, whether local or global, in advance of fundraising. Determining the precise funding requirement and assessing the strength of your staff are crucial first steps.

At Wocstar, we encourage founders to pursue diverse funding avenues beyond traditional routes. We advocate for small businesses to explore alternative funding sources, such as small business loans, grants, or more innovative approaches, such as leveraging pre-orders to secure a loan.

Lastly, understanding whether your business aligns with venture capital investment criteria—AKA determining if your business is “VC-backable”—is essential. A comprehensive fundraising strategy ensures entrepreneurs are well-prepared to make their ask.

How does Wocstar identify and select women entrepreneurs to support? Is there a particular industry focus, or is the support extended across various sectors?

Gayle Jennings-O’Byrne: Wocstar invests in the next wave of women-led boundary pushers & diverse teams that are building companies and technology that redefine how we will consume content and resources, work, learn, build wealth, and create a sustainable world. We focus on media, data, AI-enabled consumption, retail tech, fintech, green economy, and commerce.

Ally Capital Collab is an initiative you co-founded to address systemic capital-raising challenges for women of color fund managers. Can you elaborate on some of these challenges and how Ally Capital Collab is tackling them?

Gayle Jennings-O’Byrne: I aspire to live in a world where women invest in women, and men invest in women, not simply because they are women, but because it is a smart investment.

I want to see people being purposeful about spending their hard-earned money with women business owners. That’s what we do at Ally Capital Collab, and I hope those reading this will join us, support us, and become an ally. How? By helping us get the word out, and most importantly, donating on our website.

Ally Capital Collab is a group of female investment fund managers who believe we can rally people to help us improve access to capital and create a more inclusive financial future for everyone. Your support will help us educate people across the country about the benefits of investing in women.

Wocstar’s mission emphasizes creating wealth. Beyond financial support, how does Wocstar contribute to the personal and professional growth of the women entrepreneurs it supports?

Gayle Jennings-O’Byrne: At Wocstar, our commitment to creating wealth for women entrepreneurs extends beyond financial support. We believe in fostering holistic growth, both personally and professionally, by cultivating a vibrant community and sharing invaluable insights and resources.

Our ethos revolves around a shared sisterhood where women uplift and empower one another. Together, we recognize the transformative power of supporting small businesses and embracing diversity in entrepreneurship.

Central to our approach is creating a supportive community grounded in shared experiences and mutual encouragement. This network is a source of inspiration, motivation, and collaboration, nurturing personal and professional development at every step of the entrepreneurial journey.

Through Wocstar Ghetto Film School Entrepreneur Academy, we provide practical guidance and expertise to equip entrepreneurs with the skills needed to thrive in the competitive business landscape. Our classes offer comprehensive lessons on capital-raising strategies, effective storytelling techniques, and building a compelling brand identity. Our personalized one-on-one coaching calls and office hours offer tailored support to address individual needs and challenges.

Our ultimate goal is to champion and uplift diverse entrepreneurs in every possible way. Whether through community building, educational resources, or individualized mentorship, we are dedicated to empowering women to achieve their full potential and make meaningful contributions to the entrepreneurial landscape.

Investment and resources are pivotal to Wocstar’s support for boundary pushers and diverse teams. Can you give an example of a recent investment or resource allocation that has made a significant impact?

Gayle Jennings-O’Byrne: Wocstar recently received more than $2 million in federal funding, and we committed to matching that investment, ultimately reinvesting a total of almost $5 million back into North Carolina’s startup ecosystem.

At Wocstar, we know it takes significant capital to succeed, and we’re here to be that crucial support for North Carolina entrepreneurs. Our efforts are two-fold: not only will we be putting our money where our mouth is, we will also be offering Wocstar Ghetto Film School Entrepreneur Academy, our training course for entrepreneurs on how to raise capital and how to tell your story.

Our goal is to support North Carolina business owners in all aspects of their business, creating jobs and innovative technology along the way. Because when they succeed, so do we!

Looking towards the future, what are some of the goals and objectives you have for Wocstar in the next five years, particularly in terms of its growth and the impact on women of color entrepreneurs?

Gayle Jennings-O’Byrne: The goals that the team and I are working on center around three things. First, generate outsized returns for our Wocstar Fund investors by helping our portfolio companies grow and succeed. Second, scale the number of women we serve and the community of allies supporting women and underrepresented entrepreneurs. Lastly, increase and diversify income streams so that we are generating wealth for the team, our families, and our communities.

Lastly, is there a specific mantra, quote, or affirmation you hold close to your heart?

Gayle Jennings-O’Byrne: My mom taught me years ago that no one ever died from the word ‘no,’ so when I get told ‘no,’ it doesn’t hit me as hard as it may other people. That’s because I know, at some point, there’s gonna be a yes in my future.

Oftentimes, people of color, especially women of color, have been told no, but it didn’t kill us. It made us bold and resilient, and we must believe in ourselves and do for ourselves. I want to be that for all the women who have been told no repeatedly.

I want to live in a world where people and ideas are seen and trusted, and taken at face value, and we start with a yes. I wonder how much more efficient and innovative we would be if we genuinely allocated dollars, resources, and opportunities more equitably and did so without all the -isms and barriers we put in front of people.

That’s the world I think about, and that’s the world that I believe we are creating at Wocstar.

Learn more about Wocstar at: https://www.wocstar.com/

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Emily Sprinkle, also known as Emma Loggins, is a designer, marketer, blogger, and speaker. She is the Editor-In-Chief for Women's Business Daily where she pulls from her experience as the CEO and Director of Strategy for Excite Creative Studios, where she specializes in web development, UI/UX design, social media marketing, and overall strategy for her clients.

Emily has also written for CNN, Autotrader, The Guardian, and is also the Editor-In-Chief for the geek lifestyle site FanBolt.com


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