Regina Gwynn is revolutionizing the tech landscape for women of color as co-founder of Black Women Talk Tech, an organization dedicated to identifying, supporting, and encouraging Black women to build billion-dollar businesses. From her first tech startup TresseNoire in 2014 to being named one of the 100 Most Powerful Women by Entrepreneur Magazine, Gwynn’s journey exemplifies the resilience and innovation she champions. In this exclusive interview, she shares valuable insights on mentorship, team building, and navigating the challenges of entrepreneurship while discussing the upcoming 9th annual Roadmap to Billions Conference.
Why and how did you found Black Women Talk Tech?
Black Women Talk Tech started as an opportunity to create a community for women of color building technology companies. Myself and my co-founder, Esosa Ighodaro were both tech entrepreneurs, we had founded our own technology companies and understood very personally how challenging it was navigating the technology ecosystem. I had a beauty startup back in 2013-2014, here in New York City, and it was that experience where, raising venture capital, trying to find the right CTO, trying to understand how to develop a business model, that just hadn’t been developed before. There was no blueprint, and so trying to find other resources and access to those opportunities was what really prompted us to develop Black Women Talk Tech. We now educate, amplify and fund other women entrepreneurs through our Roadmap to Billions technology conference series, our recruiting events, as well as our pitch competitions and more.
What should young women understand about having a mentor in the tech business?
When I think about having a mentor, the first thing is having someone who’s willing to tell it like it is. You want to be able to have someone that’s going to not sugarcoat anything. This business is very tough, it’s very male dominated, and in the grand scheme of things you need to be able to do your job. A mentor should be able to help you understand that, and be able to position you to understand how well are you doing in your job first, and then be able to position all of the other pieces.
Specifically within technology, the challenge isn’t getting in, it’s staying in and so making sure that you’re finding those multiple mentors that you may need. You may need the technical mentor that’s helping you understand technically, how are you doing in your engineering role? Your UX/UI role, your project manager role, and then how are you doing in your relationship manager roles or your relationship manager skill set, so it can be done.
How important is understanding the language of technology?
I do think that there is some value to talking tech. It is that thing that oftentimes make people feel very intimidated. That was one of the things that was very intimidating to me. I don’t come from a technology background, I went to school for marketing. I am not an engineer by trade, didn’t go to school for it, and so that was something that felt very foreign to me.
The more comfortable you are in understanding this language the better you are able to communicate. I do think that it does help you navigate being able to move between different opportunities. It helps you identify opportunities when you can kind of translate the language, but also understand that the language is changing, the technologies are changing. So being up to date is also really really hard, because there’s a new technology coming out. I do think that there does need to be a baseline understanding of what’s going on, but also an acknowledgement that you’re not gonna know everything, and being able to say, Hey, listen! What is that? I don’t know what that is.
How important is it to know how to build a team?
Critical. I do think it’s absolutely critical to understand how to build a team. There’s a time to know how to lead a team, and then there’s a time to know how to be a part of a team. I think teams are what helps you scale your impact. So when you’re able to create a team that actually allows you to scale the impact of your work, that speaks volumes to your ability to show your success.
It’s also really hard when, unfortunately, you have the people on your team that can drag it down, and the people that will be the Debbie Downers, and the folks that actually can provide roadblocks and barriers to that growth, so it can be a very tricky thing to create teams that can help set you up to win and set you up to fail.
How should individuals approach failure instead of seeing it as something that defines them?
Failure is going to happen. I think that I have failed very publicly several times in my life and throughout my career, and so you definitely have to get used to failure. Understanding that not only is failure going to happen, it’s going to happen often, it’s going to happen publicly, but being able to put failure in a box and understand that it’s going to happen at this one moment and for this one project.
Knowing that failure is going to be an opportunity to learn, it’s going to be this one project, this one box, this one opportunity. You’re going to learn from it, you’re going to go to sleep, and then you’re going to move on, and it can be tough. It can definitely be frustrating, it can be disappointing, but you have to define the failure, not let other people define it for you.
What should entrepreneurs know about asking for funding?
Two things to always know, or two things to always be ready to answer should always be your numbers. What is your current traction? What type of return on investment should an investor expect? So in terms of margin or profitability, if someone were to give you half a million dollars, what type of return should they expect? Those are definitely numbers that you should be prepared to answer if an investor were to ask.
I also think, in terms of today’s climate, it really depends on the business, but particularly for businesses of color, it’s a very tough climate. The focus is green, and I think that a lot of investors and a lot of clients that we talk to are always going to be focused on the economic opportunity that has not changed.
Why should entrepreneurs attend your conference?
I think that, specifically for Roadmap to Billions, we have been very intentional about filling this conference with a lot of value. Let me start with the number one, education. This conference is packed with very specific workshop intensives that are meant to allow you to leave with literally learning something you’ve never learned before. We have two artificial intelligence trainings, such that you will leave learning how to build a custom GPT and learning how to build an Agentic AI bot.
You’ll also be learning master classes with venture capitalists, women venture capitalists on fundraising workshops. So how to raise capital, specifically for early stage startups. We also have VC office hours.
What we wanted to do this year was have a private off the record space for founders to be their whole selves. In this climate, we need that and conferences and in-person community spaces are needed at this very moment.
I think the last thing that was really important for us, and why we think conferences, specifically Roadmap to Billions, is important for this entrepreneur community is that we’ve been doing this for nine years. This is our ninth annual Roadmap to Billions Conference. We’re not new to this, folks. We have over 15 years of experience, 15 years of networks, 15 years of folks answering the phone when we call.
How do you keep moving forward and take care of yourself in a challenging environment?
Listen, it’s hard. I am not even going to lie to you. It is hard. James Baldwin says to be even mildly educated it is to be in a state of rage, it is hard to be in this world right now.
I think I just spend a lot of time with my family. I have a 2 and a half year old baby boy, he’s just the silliest baby boy in the world, and he is my heart’s joy, and he makes me smile literally every day, every day, and a lot of things just kind of melt away when he’s just running around, so that, I think definitely helps for sure, and he reminds me of just what joy looks like, and why I do a lot of things that I do.
I think that it’s not going to stay like this. It cannot stay like this, and I am not willing to let it stay like this, and I am free. I am not willing, and I do not accept where we are and what this is, and I think a lot of people feel the same way, and that’s also comforting, this won’t stay like this.
What are some keys to leveraging limited resources as an entrepreneur?
One of the big things that I think, if I had to do it again, I would absolutely advise more people to keep your full time job for as long as possible. I probably would have stayed in a full time job for at least two or three years longer than I did before going full time as an entrepreneur.
I think that also hiring, and we’ve done so many workshops on hiring, and we’re doing another one this year. I think that, definitely, hiring is the hardest part of entrepreneurship. Whether it’s your first full-time hire, whether it’s your part-time hires, whether it’s a 1099, whether it’s a W-2, whether it’s overseas hiring, but it is the biggest expense, your overhead will make or break your business hands down.
What’s the value of having a diverse team?
You want and need a diverse team, you want to be able to have the best of the best at all times, so wanting to have the best accountant, the best lawyer, the best marketing, the best operations, the best technology, the best whatever. You’re building a business, and you just happen to be Black. You’re building the best business, and he happens to be latino.
The diversity of thought is, yes, that does need to happen, and it’s critical, because it’s just as important at for any other business to have diversity of thought, because you want the best team for any strong economic bottom line, and you want that that level of excellence across every function, for sure.
What areas should entrepreneurs be looking at for future opportunities?
Climate, tech, environmental engineering, environmental technology. Let me tell you why. One thing that I discovered a couple of years ago was this idea of how much money is spent in trying to address the huge challenges we have in powering the world.
I’m not even talking the U.S., I’m not talking New York City or New York State, I’m talking the amount of energy it costs to power data centers, the amount of energy it costs to power quantum computing for artificial intelligence, the SpaceX computers, all of these things require ridiculous amounts of energy.
We in particular, Black and Brown communities in particular, need to be aware and need to be involved in how energy technology and how climate tech systems are being created, because otherwise it’s going to be created and then plopped right in our communities, and we will have no say in it.
