Why Your Dreams Need to be Bigger
with Regina Gwynn, Founder of Roadmap to Billions and Black Women Talk Tech
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.
Listen to Regina’s full story on Spotify, Apple Podcasts, or wherever you get your podcasts.
The Uplifters’ Web
Today’s opening is from
.Regina was nominated by Kymme Wlliams. Check out her wonderful story below.
Let’s keep rising higher together.
💓 Aransas
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