What does it take for women entrepreneurs — especially women of color — to break through and thrive? Gayle Jennings-O'Byrne, CEO and founder of Wocstar, shares how she backs bold entrepreneurs and the lessons she’s learned along the way.

Episode Summary: In this episode of Founded on Purpose, Kt McBratney sits down with Gayle Jennings-O'Byrne, a trailblazing investor, founder, and ecosystem builder, to explore what it really takes to fund and support diverse founders. Gayle dives into the importance of owning mistakes, having hard conversations, and trusting your instincts. She shares her philosophy on "fessing up to your f*** ups," why ghosting is never the answer, and how scaling impact in venture capital remains one of her biggest challenges. From discussing how she plays—through cooking, cycling, and jigsaw puzzles—to navigating advice as both a mentor and mentee, Gayle offers invaluable insights on balancing the serious nature of venture capital with creativity and joy. She also reveals her deep belief in storytelling as a tool for systemic change and how it shapes her approach to investing, founder education, and media.

Key Takeaways: 

• Fess Up to Your Mistakes: Mistakes aren’t fatal—acknowledge them, learn from them, and move forward. 
• Difficult Conversations Matter: Avoiding hard discussions only prolongs discomfort. Addressing issues head-on leads to clarity and resolution. 
• No More Ghosting: Whether in investing, partnerships, or leadership, communication is key—just say yes, no, or that you need more time.
• Scaling Impact is Hard But Necessary: The real challenge is not just funding great founders but changing the entire system that supports them.
• Play is Essential: From cooking gourmet meals to solving puzzles, making space for joy fuels better decision-making and leadership. 
• Advice is a Practice: Taking advice is a skill—be selective, consider the source, and be intentional about seeking mentorship. 
• Storytelling Drives Change: Media and narratives have the power to reshape perceptions, unlock opportunities, and foster human connection. 

Mentioned Links and Resources 

• Connect with Gayle Jennings-O'Byrne and Kt McBratney on LinkedIn
• Learn more about Wocstar
• Building and/or investing with purpose? Sign the Pledge!  
• Subscribe to Founded on Purpose
• Explore other initiatives from Renew VC