Gayle Jennings-O’Byrne, 51, a former banking executive, is a founder of WOCstar Fund, a venture capital fund that invests in women of color and diverse teams in technology.
Credit…Naheem Adio Kujenya

Did you have role models?

It all started with my mom, Thelma Bataille, who spent 30 years working in Silicon Valley. For me, she was one of those “Hidden Figures.” I grew up seeing women working with technology and science and computers. They were the women in our kitchen, chatting and laughing and complaining about things at work. Over the years, I heard the stories of innovative Black women in technology.

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How did you get started in finance?

After grad school at University of Michigan and time in Israel and Singapore, I moved on to Wall Street. I wanted to get in the game and be part of that world.

What motivated you to launch the WOCstar Fund?

I was at work in my office [at JPMorgan Chase & Company] when I got the news that I had cancer, and I thought, “I can’t die in this chair and at this desk without really having made an impact like the trailblazers before and those women like my mom.”

After I got over my fear of dying, I got this courage for living. And at that moment, I became bold and fearless to be a champion for the women I knew — women who looked like me.

You worked in mergers and acquisitions at JPMorgan. How was that helpful?

So much of investing is not solely picking companies and doing the due diligence, it’s also helping them build, so we can monetize and return capital to investors.

I’m now a middle-aged Black woman, and I have accomplished a lot in my career. I am now at an age where I can authentically give that to the start-ups.

Where are things now?

I don’t live in fear of where my next paycheck is coming from, how my mortgage is going to get paid. I’m at a point in my life where I can take everything I’ve done and put it toward those that I believe are worthy of investing in. It has become my why.

My sisterhood and I don’t always have a seat at the table, and we are not always invited into the room, but I’ve gotten real comfortable being a party crasher.

And just a little secret … the party is always better when my sisterhood and I show up.

What is the economic backdrop spurring venture capital demand from women founders of color, and what can be done to improve it?

The fundamentals haven’t changed: People love winners. Markets love winners. Money follows winners.

People need to put money where their mouth is. What is happening these days is there are too many press releases being issued by people and big corporations proclaiming their financial commitment to Black businesses or racial equity, but the dollars show up as marketing, sponsorship dollars or loans.

We need more checks to the Black businesses and new Black venture capitalists who are investing in Black, women-led, diverse companies and less headlines about people’s intentions.

What advice do you give other female entrepreneurs of color?

I always tell them be bold, be courageous and double your number. Whatever you are asking for, double it. You have choices, so look for investors who will build with you.

Be a problem-solver. Entrepreneurship is about being a problem-solver. Build things that are big ideas, that are going to change how we work and how we live and consume.

What has been the biggest challenge in your career?

I get noes every day. What is worse is the silence, or the nice “let’s keep in touch” and the pat on the head. Those cut deeper than the noes. At least with a no, you know where you stand. My mother always said, “Go ask. No one has ever died of the word no.”

And really, don’t tell my mom, but I’ve stopped asking. Now I’m inviting, and only inviting those that truly get it. Women and women of color are crushing it in the tech world and too many are going to miss out on sharing in our success.

What have been your greatest rewards?

My biggest reward is the people who have rallied around the fund since we launched. I am not alone in this. The fund is a network of allies and mentors. I love how we have raised the money. JPMorgan contributed the initial funding to what is now the WOCstar Fund.

Two of our initial investors were Caucasian men, who live in my neighborhood in New York City. It’s grounding to know I can see them in the grocery store, or the gym, and they don’t have shared experiences as me, or look like me, but trust me to know the best investments by people of color.

Finally, it’s the conversations with the founders. It is the mentoring. It’s the tough love. That’s where I get my joy and my energy.

What else interests you?

I love film and media and getting more women and people of color in media.

For many years, I’ve been involved in building the next generation of diverse storytellers and filmmakers. In the past, I have been on the advisory board of the Ghetto Film School and am still involved with them and the Bronx-based creative content house by its alumni called Digital Bodega. And now, I’m very lucky to get to have creative outlets like Southbox Entertainment, a film and television content studio where I combine creativity and capital, and serve on the board of the Nantucket Project Academy, which is a community of change-makers and powerful storytellers.

This conversation has been edited and condensed.

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By kerry