As part of the Morning Lazziness series about empowering women who encourage and do incredible things with their ideas in society, I had the pleasure of interviewing Gayle Jennings-O’Byrne.
Gayle Jennings-O’Byrne is CEO of Wocstar Capital, and co-founder of the Wocstar Fund, an early-stage venture fund that invests in the future of consumption and innovation using a female arbitrage strategy — we are a fund that invests in the future of consumption and innovation using a female arbitrage strategy — women of color tech entrepreneurs (“WOCstars”). Gayle (pronounced: Gay-lä) was named “10 Women Changing the Landscape of Leadership” by the New York Times, March 2021. She is the host of “VCs off the Record”, and instructor at Wocstar Academy. Gayle co-founded Ally Capital Collab, an initiative with women of color fund managers to address systemic capital-raising challenges.
Gayle has over 30+ years of wall street, technology, philanthropy, training, and professional speaking experience. She is a former mergers and acquisitions banker at JPMorgan. She led the capital/planning effort for the Cinema High School, 1st public high school of its kind. She began her career at Sun Microsystems.
Can you share the story behind your journey as an entrepreneur? What inspired you to start your own business?
I know firsthand that raising capital as a Black woman entrepreneur, or anyone that isn’t in the mainstream, can feel like breaking into a boys’ club. So many incredible female entrepreneurs are developing new companies, but too often, we’re left with empty promises and a ticket to the next accelerator while the tech bros cash in.
We’re here to change that. I started Wocstar because I wanted to disrupt the status quo and build a sisterhood of entrepreneurs. My alliance of founders and investors with a clear vision for the future and big, bold ideas are rewriting the narrative, one investment at a time.
Here’s what we found out about Gayle’s daily routine, followed by an exclusive Q+A.
What challenges have you faced as a woman in the business world, and how have you overcome them?
As a woman in business, we’re constantly being underestimated. But—that’s not always such a bad thing. Because when I come prepared, give 110%, and exceed expectations, there’s no better feeling than surprising someone with who you are.
How do you balance your professional and personal life as an entrepreneur?
Balancing my personal and professional life means setting firm boundaries and sticking to them. It’s a constant practice, but I always remind myself of my “why”—my family, my team, our investors, and the entrepreneurs. I prioritize family by putting away the laptop, ignoring emails, and muting notifications to fully engage with them. After all, tomorrow isn’t guaranteed. And for the sake of my team, investors, partners, and the entrepreneurs we support, I make sure to prioritize self-care, sleep, and exercise. Without balance, I’m no good to anyone. Trust me, a tired, grumpy, stressed version of me is not a good thing.
What strategies have you found most effective for networking and building connections in your industry?
When it comes to networking, I treat every connection and relationship like a flower. Start with a good foundation of values and goals; then water, nourish, and care for the relationship if you want it to bloom and flourish. Instead of seeing people as what they can do for you, see the human being behind the business card or the LinkedIn profile. Cultivating authentic relationships takes time and patience but proves to be more fruitful than superficial networking simply to get ahead. I’m always asking, “how can I be a blessing or help to someone else?”
How do you approach mentorship and seeking guidance in your entrepreneurial journey?
I encourage everyone to stay curious. I’m just naturally inquisitive and genuinely interested in people and their journeys. So much of what there is to learn lies in the journeys of others. The best lessons are not in books, but inside folks you come across everyday. Sharing stories not only nurtures empathy but also deepens our understanding of the world, and that’s what’s helped me on my business journey. I love me some Wendy Williams. Just imagine if we all started a conversation with “How you doing?” and we really, really listened to the answer.
Can you talk about a specific setback or failure you’ve experienced in your business, and how you bounced back from it?
Rejection is simply redirection! Wocstar recently encountered a setback when a bank, which had initially pledged a multi-million dollar investment, withdrew its commitment unexpectedly.
Another investor had already agreed to invest contingent on the bank’s commitment, so when the initial bank retracted its offer, we lost the second investment as well. That’s $5 million dollars that we could have invested in companies! It sucks to lose that capital. But it’s the perfect example of that old saying—when one door closes, another one opens.
This March, we were selected along with nine other minority and women-led venture capital firms to collectively invest $32 million in North Carolina. Vice President Harris announced the funding, which has been made available through the U.S. Treasury Department’s State Small Business Credit Initiative (SSBCI), at a personal visit with us in North Carolina. So check us out, because we are looking for innovative startups in North Carolina and across the country in whom to invest. We are actively investing and writing checks! We’re on a mission to invest in, grow, and stimulate the economy.
In what ways do you prioritize diversity and inclusion within your company or startup?
We prioritize diversity and inclusion every way we can — not just because it is the right thing to do, but because it is our “secret sauce.” We invest in diverse teams and underrepresented entrepreneurs, because it is profitable! They are creating innovative solutions and solving consumer problems.
Here’s just three (3) things we at Wocstar do that you can do, too! Starting TODAY, put your money where your mouth is by investing in women of color entrepreneurs, supporting diverse vendors, and serving as a connector of people in your network.
How do you stay motivated and resilient during tough times in your business?
I stay motivated and resilient by spending time with founders and investors — they give me energy. If you stay focused on the end user, customer, client, or your “why,” it’ll keep you grounded and motivated, and you’ll learn a lot about what they really need.
What advice would you give to other aspiring women entrepreneurs who are just starting out?
Be a problem solver. Create solutions people will pay for. Whether you’re a rideshare app like Uber, an edtech startup like Possip, or a document redaction tool like Redactable, success lies in solving real-world problems. Exceptional problem-solvers with value-add earn not just customers, but their loyalty.
Can you share a memorable success or milestone that you’ve achieved in your entrepreneurial career?
I’m proud of the team and the culture we are building – they really are Wocstars. They get up each day and give it their all, not because of me or their deadlines, but because of our shared focus and mission. Money and material things are not enough to inspire and motivate people. It’s not just about the hustle; it’s about feeling the love for the work, the ‘why,’ and the folks we’re serving.
