Ever notice that the faces of founders of billion-dollar tech companies all look pretty much the same? Regina Gwynn has – and she's doing something about it. As co-founder of Black Women Talk Tech, Regina is flipping the script on what a tech founder looks like, helping Black women build the next generation of billion-dollar businesses. "When you think about a tech founder, you think of Mark Zuckerberg, Peter Thiel, Steve Jobs, Bill Gates," she notes. "They have a lot in common, don't you think?"

Named one of the 100 most powerful women by Entrepreneur Magazine and featured in Essence Magazine's top 10 women in tech, Regina's journey from self-described "mall rat" to tech mogul is reshaping what's possible. Through the groundbreaking Roadmap to Billions conference, the largest technology conference for Black women in the country, Regina and her team are educating, amplifying, and funding the next generation of tech leaders. But what truly sets Regina apart is her insistence that women think bigger. "Guys aren't thinking about making just $10 million," she points out. "We need to be thinking about how to build $500 million, billion-dollar companies."

Regina's approach to scaling impact while maintaining wellbeing offers valuable lessons for any woman building something meaningful. Her secret? Working smarter, not harder. "Your ability to produce output is directly correlated to your ability to scale," she shares. "Millions of people cannot be reached with one person working all the time. There have to be tools, systems, processes, and automation."

"Founder self-care is just as necessary as the pitch deck or the customer service strategy... If you aren't whole, if you don't have the mental, emotional, spiritual capacity to govern yourself, then where can your business go?"

5 Key Uplifting Lessons

1. Think Bigger Than You're Comfortable With: The path to real impact requires stretching beyond conventional goals. Don't settle for $10 million when you could build a billion-dollar company.

2. Choose Your Hard: Every path has its challenges. Whether it's building a business or going back to corporate life, consciously choose which "hard" aligns with your vision.

3. Delegation is Freedom: Learning to delegate – whether to people or to different time periods – is crucial for scaling and preventing burnout.

4. Small Tests, Big Learning: Start with small investments ($500-$1000) to test ideas and approaches. Learning what doesn't work is just as valuable as finding what does.

5. Community Creates Momentum: The power of network and relationships translates into lifting entire communities and changing the trajectory of what's possible for future generations.

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TUP EP 087

welcome to the Uplifters podcast. Today I'm [00:00:15] joined by Regina Gwen. Regina was nominated for our show by none other than the amazing. Kim Williams, who you probably fell in love with just like I did back in episode 25. Regina is the co founder of Black Women [00:00:30] Talk Tech, which helps Black women build the next billion dollar business.

So Before we get into all that juicy stuff, tell us about what you do.

We've hosted over 2000 entrepreneurs, technologists, investors and enthusiasts to come and learn about artificial intelligence. Let's learn about the metaverse. Let's [00:01:45] talk about productivity tools, access to capital, you name it. We design and we very intentionally curate both the programming and the audiences to make sure that we see women win.

You don't have to be an engineer to have a technical role. So getting the education out about career paths and opportunities is something that's super important as well as [00:02:30] amplify. You know, we want to change the idea of what a tech founder looks like. Because when you think about a tech founder, you think of Mark Zuckerberg, Peter Thiel, Steve Jobs, Bill Gates.

And so, part of the normalization of tech has to be normalizing the idea of who actually is thriving in tech, who's performing well in tech, who is, you know, killing it in [00:03:15] technology. And it's more than just white guys from Harvard and Stanford. We use technology. every single day. Well, you know, you turn over in your bed and you grab your phone and you're automatically plugged in whether it's a good thing or bad thing.

These are very real. Behavioral shifts that are happening. And so the opportunity to monetize those shifts from [00:04:00] again, starting your own company and or working for a company that is involved in this revolution also speaks to our focus on building generational wealth for black and brown communities. You know, we know that technology is the not [00:04:15] only the wave of the future, it is now and the top 5 trillion businesses are all tech companies.

Aransas: That is huge. What do you find is most [00:04:45] compelling in creating believers?

that women are important to the workforce, that people of color are important to the workforce.

They have higher valuations when they do reach investment. They provide higher profit margins. [00:05:15] companies that have diverse teams deliver stronger multiples. So the proof is in the numbers in terms of why diversity is valuable. Can't say that it always has mattered We don't want to get [00:05:30] into why diversity matters.

They're able to hit the ground running because they're well trained. They come from very strong backgrounds and experiences. We have a lot of women that [00:06:15] are transitioning, so they may come from finance into technology, or they may come from being a social worker. There's really no specific Path to land at a tech company.

Aransas: tech. That's so interesting [00:06:45] and so true for any entrepreneurial role, but also any innovation space.

Regina: You know, it's interesting because, so I never thought myself in technology for [00:07:15] sure., I grew up as a retail girl, fashion girl.

So my dad had a paper processing and like recycling plant. [00:07:45] I knew I did not want to do that, that I knew. That was not of interest, but figuring out what that was definitely took time. I worked at Macy's right out of college and added actually executive like training program like people [00:08:00] lose fight of how valuable those training programs are to give you like those basic foundational tenants of business.

ai

perspective on business as a whole, that no school necessarily helps you

Regina: Yeah. I mean, and at Macy's I was, had the chance to build brands. Like we launched Inc. International Concepts, um, which is I think still on the sales floor today.[00:09:00]

We're based in New York, but we host Roadmap to Billions in London and Toronto. We've hosted in Atlanta, Miami, Chicago, LA, every single market is different. And yet the challenge, [00:09:30] unfortunately, is still the same. The challenges that face women are still the same. I hope to be out of business at some point, would, would love, love, love that for sure.

And it's the only place that humans exist in the world that doesn't have rats. And it's because when rats were coming in the 60s, they were like, we're [00:10:15] not gonna deal with this. We're not gonna take rats. And they set up a system to block them at the border and create education because people in Alberta won't even recognize a rat.

that it is a possibility to have these divisions. And it, you know, it's a utopian idea for sure. And it's a lot [00:11:00] harder than even managing those pesky, highly reproductive rats. But when I think about it in those terms, it is exciting because you're right. This is, this is a problem just like the rats that exists the world [00:11:15] over, unfortunately.

Regina: Absolutely. Just as dangerous. Right?

Aransas: I would say more so, yeah.

Aransas: Yeah. And it is. It's incremental. And so for you, what energizes you [00:12:00] to keep going when you're facing such a hard time? gnarly problem.

Like we get Those testimonials and it just reinforces that we're on the right track [00:12:30] that we're doing what we need to do to get these women into the right rooms to get them the right opportunities to get them introduced to the right people. It's like I did that, right? Like, that's me. And I love being able to [00:12:45] see that power.

So the fact that we're even literally still here is a testament. to what we've been [00:13:15] doing and how we've been doing it. There's a lot to be said about the power of the community that continues to show up. They continue to support us. They continue to like our posts and respond to our emails and, you know, they say yes when we call [00:13:30] and those things really matter.

For sure. And it's not just the self care, right? It is creating momentum. It is Creating a [00:14:15] pathway for navigating the ups and the downs, both in business and in life. And so every time I hear it, I'm like, this, this is the secret. Like if you want to get something done, get some people. Absolutely.

But yes, no business is going to scale with one person. No business is going to scale with three people. Like you've got to have [00:14:45] a team to scale. And we specifically focus on technology companies because as I was mentioning with the top five companies. companies, literally the most valued companies in the world are all technology businesses [00:15:00] that requires scale.

It's like, Oh, we'll be okay if we, if [00:15:30] we have 10 million. And listen, we will be for sure. But guys are not thinking like that.

Regina: Yeah. So this May, this past conference we had, we literally had a panel called Big Tech Energy.

You know, I'm talking about decarbonization, space, electric vehicles, charging stations, the innovators, the [00:16:30] technologists, the startups that are focused on this, almost like overwhelmingly, not only white men, but just men in general. And the thing is, We don't know. We don't know. So if we knew and we had opportunity, then we [00:16:45] could at least get on the road.

Pun intended from our rat conversation. And [00:17:15] if you don't get out and like, just look around the corner, you'll just never know. And folks are out here making ridiculous amounts of money.

Absolutely. Which bias toward their needs and interest. And so if we diversify, who has the billions? Then we diversify who receives the benefit of the billions.

You

Regina: when burnout happens, okay, cause it's going to happen. So let's, let's just name from the [00:18:30] beginning that it's going to happen. So when it happens, your ability to recharge and overcome is correlated to the success of the business.

So the only [00:19:15] commodity or the only commodity, the only asset that you really have is your time and how you choose to spend that time on marketing, finance, operation, tech, whatever. So if you are not doing something [00:19:30] towards your business because you have burnt out, then literally your business stagnant. So it doesn't matter whether you have a pitch deck.

Aransas: Yeah. And so one of the things we we've talked a lot about on here is raising courage capital and the importance of that to starting any new [00:20:15] venture. But it's also interesting to think about your funding in essence as your own mental and physical and spiritual energy that you're able to invest.

is also key because once you've experienced it and you're in that, like, just brain fart like you're just in that, you know, that space where you just can't think and pulling yourself out, you can recognize the [00:21:00] signs the next time so that you don't get to that place again. And then there's also just like life happening.

Aransas: Yeah, I think as women, we, [00:21:45] the research shows that we tend to internalize stress, whereas men externalize it. And so men are more likely to get angry at someone or put that stress outward. Whereas women were like, okay, my family [00:22:00] needs me. My team needs me. My, And we're just like, I'll just take it all, pull it all in on ourselves and we internalize it as guilt and shame and stress and worry and fear.

Regina: Yeah, so two big things. Because [00:22:45] I know, like I, I know that I know that I know when I start to feel overwhelmed and can't make small decisions, right? Like something as simple as respond to this email that will take a minute, right? [00:23:00] It's one question. You can respond to that, and you can't respond to that one email, right?

Aransas: delegation.

Regina: And when I tell you delegation makes me feel so happy. It frees up my mind. And also delegate also means just not right now. You may not give it to someone, but you're [00:23:45] delegating it to a different place than it is right now. So I can delegate. 50 emails just to respond to by the end of the month, or they don't have to be responded to right now, or I can [00:24:00] delegate a task to my admin, which I will say game changer.

And then being able to say, okay, It's still going to get done because it needs to get done. It's just, it's not going to get done right now.

Right. But rather, these are my ways of working and this is how I protect myself so that I can continue working and make my purpose, my impact work sustainable in [00:25:15] the world. That's the essence of everything I'm trying to learn from all of you amazing guests on this show. It's like, How do you make this stuff sustainable?

Mm hmm. Because otherwise, we flame out fast.

Aransas: No one's dying. And no one's even [00:25:45] gonna notice most of the time.

Yep. Right? But we wear it as a badge. I haven't taken a day off in a year. That is not smart. That means I'm serious. But it doesn't, does it? It doesn't mean you're serious. No. It means you're short sighted.

Regina: Yeah.

Regina: Now, I wholeheartedly believe in working smarter and not [00:26:15] harder. If we can't figure out every hack, every shortcut, every AI tool, every outsource, because again, that is your ability to produce output is directly correlated to [00:26:30] your ability to scale. I don't care if you work every single day. If it's just you, Then there's no way of outsized growth, right, to reach thousands of people.

Well, now I'm

That should not be something we have to figure out all by ourselves. And [00:27:30] yet, it is largely, I mean, there are some amazing people who are helping me and supporting this work. And do I wish more people could hear your story here? Yes. Because I think the more people hear your story and these other women's [00:27:45] stories, the better off we will all be as a society.

Regina: For sure.

I am proposing, you [00:28:30] know, test new tools, be constantly learning, be constantly exploring to see whether or not it's a good fit for your business or not. When I talk to early stage entrepreneurs, I'm always surprised by how much money people are spending, and I spent that [00:28:45] much money, like I spent so much money trying to figure it out, and I tell everyone now, take 500.

Half the battle is just weeding out the stuff that is not relevant to you. And then the real work is the things that are relevant. What's the fastest, most efficient, most cost effective. I think

And so what you're saying, I think, is invest in [00:29:45] learning over everything else.

Right? Choose your hard. I was about to say it. Choose your hard. Like, I had a baby boy a couple of years ago, and so I've been trying to get the [00:30:15] weight off, like, get my mom bod together, and, you know, you gotta choose your hard. You wanna stay you know, with this mom bod or do you want a different mom bod?

Aransas: Yeah. And sometimes it takes [00:30:45] hard work to get to easy.

Regina: Thank you so much for having me. Really appreciate the time. [00:31:15] It's been really fun and went quickly, so yeah, hopefully more to come in the future.

I'll share links to Regina's work in the show notes and can't [00:31:45] wait to hear what it sparks for you. Thank you for listening to the Uplifters podcast. If you're getting a boost from these episodes, please share them with the Uplifters in your life and then Join us [00:32:00] in conversation over at TheUpliftersPodcast.

Music: Big love painted water, sunshine with rosemary. And I'm dwelling. Not [00:32:30] perplexing, though You find it ing.

Doo doo doo doo doo. Doo doo doo doo doo. Beautiful. I cried. [00:33:30] It's that little thing you did with your voice! Right? In the pre chorus, right? I was like. Mommy, stop it. I had to cry crying. Mommy, stop crying. You're disturbing the peace.