Regina Gwynn, Co-founder of Black Women Talk Tech

Regina Gwynn is a driven entrepreneur, and the force behind the Black Women Talk Tech movement. In this interview with, she shares her personal journey and the inspiration behind her groundbreaking work, highlighting the highs and lows of entrepreneurship. She then discusses the challenges women of colour face in the tech industry, emphasizing the need to build diverse and inclusive communities for support and advocacy.

The conversation delves into the stark statistics of venture capital funding for Black women-run businesses, underlining the importance of alternative methods of finance.

Gwynn sheds light on the upcoming technology conference in Toronto, Roadmap to Billions, which will take place from September 29 to 30, 2024. The conference aims to foster collaborations and discussions on tapping into global markets.

She concludes with insights into Toronto's vibrant entrepreneurial ecosystem and provides a sneak peek into the highly anticipated event's powerhouse lineup of speakers and workshops.

Entrepreneurial journey and inspiration

First, thanks a lot for taking the time to do this. Second, I just wanted to get to know your journey—a backstory of your journey as an entrepreneur. I did a bit of research and found out that your dad and grandfather were both entrepreneurs. So, tell me about that and how you've grown up at the dinner tables, hearing about entrepreneurship, and how your journey has been.

Regina Gwynn:

Yes. Absolutely. As you just mentioned, I've always wanted to be an entrepreneur. My dad was an entrepreneur. His dad was an entrepreneur. I grew up in North Carolina. So, I was a country girl climbing trees and reading books, and my dad ran a recycling firm in Greensboro, North Carolina. And so, I was a firsthand witness to the highs and lows of entrepreneurship coming home. I saw when my dad was excited about securing a new client.

And then, you know, there are days where he loses a client. So, just kind of understanding that adventure, if you will, is a part of entrepreneurship. However, there is also the need to be really comfortable with risk and pivot multiple times. And so, while I knew I wanted to run my own company, I definitely didn't know what I would do. I played around with lots of ideas, and I had a lot of hobbies, but it wasn't until 2013 that I landed on an idea that would not leave me alone. You know?

I was on fire. I couldn't sleep at night, jumping up to take down notes and develop this model around technology, the intersection of technology and beauty. So, at the time, we were just now starting to get more familiar with on-demand technologies like Uber, FreshDirect, and Handy. I had the idea of creating a platform that allowed women to have a stylist come to them the way their car comes to them. That was the impetus behind launching my first startup called TresseNoire. We were the first on-demand, on-location beauty booking app for women of colour.

Black Women Talk Tech and empowering women entrepreneurs

We started in Philadelphia, Pennsylvania, and expanded across the country, and then COVID hit. That definitely impacted the business. But before that, I had started to really understand just how hard it was to build a technology business from an R&D perspective, from the technical talent that's needed, from the social networks, and from an environment that's very different from what we consider a lifestyle business like a restaurant or daycare or a laundromat.

Building a technology company requires a different set of skills and networks. And so, for women, and particularly women of colour, we didn't have that. So that's really the impetus behind creating Black Women Talk Tech. It was to say, okay, we recognize that these experiences and opportunities are out here, but they are being gatekept in a very meaningful and very serious way. And so, if you aren't getting a seat at the table, it's time to build your own table.

So, we focus on educating, amplifying, and funding women entrepreneurs. We've been building this community since 2017. We focus a lot of our efforts on our National Technology Conference. So, we host we've been hosting our flagship event, Roadmap to Billions, here in New York City for the past eight years — where we bring over 1,000 entrepreneurs and investors, technologists and tech professionals together to learn and network, as well as share resources.

And over the years, we would have so many people come from Toronto, and we'd have speakers from Toronto, and we've had investors, and we've had all of these folks come from Toronto. So, we're like, well, what's going on in Toronto? Why don't we go up there? And so, we started coming to Toronto about a year ago. I've been working with the DMZ at Toronto Metropolitan University. We hosted a conversation with founders and funders there last year. I was just in Toronto for the Black Innovation Summit they hosted recently, and then Collision. We've worked with each other and just really listened.

That was really why we thought that bringing some of our resources, network, and experience would be valuable to offer up as an exchange. Right? We see ourselves as resource matchmakers and can share these conversations and opportunities with our Canadian counterparts.

And so, what does that mean? How do we have a conversation about tapping into US markets? What does it take? How should we be thinking about things like company structure? Technology continues to boom everywhere. So, what are some trends that we're seeing? Can we compare and contrast what we're seeing versus what we might see here in Toronto? So yep. Those are some types of conversations we're gearing up for at the end of September. We've got many amazing speakers already lined up, and we have Dell for Startups as one of our sponsors.

So, it's going to be a great time.

Great. Well, I think Black Women Talk Tech has been attracting international attention since you started, you know, from Africa, the US, and Canada. So, tell me about this: why do you think you've been able to attract an international audience?

Regina Gwynn:

We've been able to attract an international audience because, fortunately or unfortunately, the challenges are still the same. Right?

As a woman and as a woman of colour, we find ourselves in these challenging situations if you will, or these challenging environments where we're always second-guessed. We're consistently underestimated. We're always undervalued. And that happens whether you're in New York or Montreal or whether you're in Joburg or whether you're in London. So the story ends up being the same, and then, ultimately, how we support each other is also the same. There must be a community involved.

There has to be advocacy, and there must be allies who help and support us. Our job is to find those resources and allies in every market we enter.

Venture capital funding for Black women entrepreneurs

There is a statistic that says that, as we know, a lot of businesses are started by Black women, but only 1% of venture capital funding goes into Black women-run businesses. How do you tackle such a huge gulf in terms of funding? Are you connecting with some venture capital firms or trying to? I know that it's important to build your own table, but are you also trying to develop links between, you know, the capital funding community to address this issue?

Regina Gwynn:

Absolutely. You know, we've definitely seen these terrible statistics, and we know even in Canada, the landscape is even worse, and just the amount of venture funds in Canada, so, you know, speaks to a part of the challenge. And so, while we always connect with the venture community, we invite them to our conference. We host an investor reception where venture funds come out and participate. However, what we also do is encourage alternative methods of finance. So, you know, we'll always have some workshops that speak to ways to generate revenue or funding outside of ventures because, unfortunately, these stats have not changed.

They have not changed in over a decade here. You know? There was a slight uptick after George Floyd. But, right now, the amount of venture funding going to Black and brown people is less than what was given before George Floyd. So, we're seeing an even larger retraction now than ever before. And so, the idea of continuing to knock on a door that does not open, you know, we like to, of course, as I said, continue to knock, but we're also knocking on other doors. We have conversations with banks about lines of credit and loans. I know that RBC in Canada provides an extensive loan program for women entrepreneurs.

We also look at grants and revenue-based financing. There are lots of different financing methods. Venture is only a tiny portion of the total. It's one of the smallest asset classes among all the financial products. And so that's part of the education, right? Because venture is sexy, and everyone wants to be venture-backed. There's a lot of value in venture money, but you do have to be prepared to understand how your business will change and how your company will change when you choose to accept funding.

Educational opportunities and financial awareness

So, speaking about educational opportunities, I know that the conference includes a number of workshops, panel discussions, and presentations. I mean, having spoken to previous interviewees about what you just discussed in Canada, we have some grants and loan programs. Some of them are tied with banks.

As you know, there is a historically problematic relationship between the Black community and banks, whether it's north or south of the border, where credit lending hasn't been where it should be. We know about the legacy of redlining and so many things that were set up historically to make it more difficult for Black people to obtain generational wealth-building funding opportunities from banks.

Some of the programs that have been set up in Canada, like the Black Entrepreneurship Fund and others, are creating awareness programs around credit building, tax filing, and so many other things. As you said, it is sexy to be an entrepreneur and get funded, but once you get the money, there is this whole management that needs to be taken care of.

Regina Gwynn:

Right. You know, I think that it depends. Like, there's a mixture of needing to get that support from the venture community but then also needing to grow and scale your business. So, you know, we also focus on that. You can increase funding, but ensure that your business model is sound, you have product market fit, and you're just making money. That's the most non-volatile money you'll ever get, which is just purely being able to generate revenue and build a profit margin for your company. So, how do we do that, and how do we educate our community about that?

What I'll also say is that our community is industry agnostic. So, there are times when we may focus on Fintech founders, education tech, or healthcare tech. How we build those businesses from a vertical perspective will also influence how we educate around them.

The Toronto entrepreneurial ecosystem

That sounds great. So, can you tell me a bit about your experience and what you've learned about the Black entrepreneurial community in Toronto? I know you've been up to TMU recently. So, from an outsider's perspective, how do you see the entrepreneurial ecosystem for Black founders in Toronto?

Regina Gwynn:

Yeah. Well, first off, I'm really excited about this community. So, for a couple of reasons. It is the Toronto ecosystem, and the Canadian tech ecosystem is where the US ecosystem was, let’s say, five years ago. Right? Just in terms of the size, the growth, and the expansion of products and services, there is what I think is really exciting. And then, in terms of the founders, I've also met a lot of deep-tech quantum computing enthusiasts. There's a lot of interest in tech.

The deep tech, quantum computing, and climate tech-type businesses that I've met really speak to how sophisticated the market is in understanding these billion-dollar market opportunities. So that's something that I really love. It's great that even though the ecosystem is more miniature, they're focused on, you know, the big whales. They're focused on these big markets instead of those in the US.

You see, we have everything. We've got beauty tech. We've got retail. We've got folks working on the most random things, which is totally fine and can also bring a huge opportunity. There’s a focused effort to really tap into the biggest markets possible in Toronto with the founder of Toronto that I've spoken to.

And the last thing I'll say is that there's definitely this immigrant focus. Right? So, you know, a lot of Toronto founders are either first generation or literally coming from the continent, coming from the Caribbean, coming from other countries, due to Canada's very open and established immigration policy. And so, there's that immigrant layer, from a cultural perspective, that can pose a challenge and an opportunity given that founders are creating businesses for their countries or their markets at home. Sometimes, a Canadian investor may not necessarily understand because it's not a Canadian market.

If you're Jamaican and creating a product for the Jamaican market, but you're talking to someone who’s a Canadian investor, it will be that much more important to do that translation, if you will. So that they really understand, you know, the value and the opportunity. So that adds a little bit of complexity, but it also means you’re a subject matter expert in an untapped market that no one's ever leveraged. That also gives these founders a huge upside. We've loved talking to so many founders of really cool companies, and we're looking forward to doing more.

About the conference

The conference will be held from September 29 to 30, so it will last two days. So, tell me a bit about the format, some speakers, and what we can expect from the event.

Regina Gwynn:

Yeah. September 29th and 30th fall on a Sunday and a Monday. On Sunday, we'll kick off with a welcome brunch at a Black-owned space. We're still nailing down where that will be downtown. That'll be an opportunity for us to welcome our attendees, get them excited, and start the networking and platform. Then, on Monday, September 30th, we'll kick off with the actual conference event.

There will be workshops focused on entrepreneurs and workshops focused on technology professionals. We wanted to ensure that we can have that dual-sided content because you could be an entrepreneur but still work full-time at Google or bootstrap your business to get another form of funding.

And so, one of our keynote speakers is coming to us from the US. Her name is Lauren Maillian. She is an amazing serial entrepreneur and investor. She has advised and invested in over 40 startups, and her portfolio represents over $5 billion in market capitalization. So, she will talk about tapping into US markets and what that means from both an entrepreneur and investor perspective.

We also have Giselle Mello, Managing Partner at Matr (matter) Ventures. She represents one of the few Black women-run venture funds in Canada, so she'll join us. Ishana Peck is the founder of data science, so we’ll talk about data structures and architecture.

She'll be joined by another technologist, Tashua Case, a founder and entrepreneur specializing in data architecture at Bluum. We'll also have Ashley Wright, who is the founder of Blacks On Blockchain and one of the top Crypto Educators in Canada. She'll moderate a few panels. And then I've missed someone or two people, but we’ll definitely have a fantastic lineup. We’re getting a few more folks involved ahead of our official announcement on July 6th.


Event: Roadmap to Billions

September 29-30, 2024
9:00 am - 5:00 pm

50 Carroll St
Toronto, ON
M4M 3G3

Secure your spot now and take your business to new heights!

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