VCs Off the Record with Gayle Jennings-O'Byrne

In this episode of VCs Off the Record, host Gayle Jennings-O'Byrne chats with Dawn Kelly, CEO and founder of The Nourish Spot. Dawn shares her inspiring journey from corporate marketing to creating a thriving wellness brand rooted in Southeast Queens.

Discover how a personal health journey and a pivotal idea sparked The Nourish Spot along with Dawn's commitment to generational wealth, and the power of leveraging community support. Dawn opens up about overcoming challenges, embracing confidence, and scaling her business with purpose.

Tune in for actionable insights, inspiration, and a heartfelt conversation about resilience, community, and entrepreneurship.

VC's Off the Record:

Hosted by Gayle Jennings-O'Byrne

Co-hosted with Victoria Bert

Produced by Wocstar Media

As the year winds down, hosts Gayle Jennings-O’Byrne, CEO of Wocstar Capital, and Victoria Bert, Chief Content Officer at Wocstar Media, share actionable insights to help founders, entrepreneurs, and dreamers prepare for a powerful 2025.

In this mini year-end episode, they dive into the art of reflections and road mapping to set meaningful goals for the new year. Hear Gayle's top strategies for business growth in 2025. Plus, Gayle and Victoria discuss exciting plans for a new book and journal tailored to female entrepreneurs and diverse teams.

VC's Off the Record:

Hosted by Gayle Jennings-O'Byrne⁠

Co-hosted with Victoria Bert

Produced by Wocstar Media

On this episode of VCs Off the Record, host Gayle Jennings-O’Byrne sits down with Josh Tanenbaum, a visionary whose career bridges entrepreneurship and finance. From founding LOCAL VIBES to managing partnerships at Rebalance Capital, Josh shares how his journey shaped his approach to impact investing. Tune in to hear candid advice on balancing financial returns with social impact, avoiding common investment mistakes, and scaling impact-driven startups. Whether you’re a founder, an aspiring VC, or just curious about the world of impact investing, this episode is packed with insights you won’t want to miss!

VC's Off the Record:

Hosted by Gayle Jennings-O'Byrne⁠

Co-hosted with Victoria Bert

Produced by Wocstar Media

In this episode of "VCs Off the Record", Gayle sits down with Benny Lorenzo, Managing Partner of Aspira Capital Management and a pioneering force in venture capital since 1996. From his roots in the Dominican Republic to earning degrees from Cornell and Harvard Business School, Benny shares his remarkable journey and insights on securing funding in today's competitive landscape. With over four decades of experience spanning IBM, AT&T, and growing a hedge fund from $35 million to $350 million, and investing in a #unicorn company! Benny brings a unique perspective on what it takes to succeed. Don't miss this illuminating conversation with a leader who's dedicated to both business excellence and community service, as he shares practical insights for the next generation of founders and investors.

In this episode of "VCs Off the Record", Gayle sits down with Megan Ruan, General Partner at Gold House Ventures, an early-stage VC dedicated to supporting multicultural Asian Pacific-founded startups. Gold House is renowned for its in-house accelerator, whose 115+ alumni have collectively raised $2 billion since 2020. Today, Megan dives into the big question: how did they manage to raise so much capital so quickly? She explains how Gold House’s mission to unify and uplift the Asian Pacific diaspora has created a powerful draw for both investors and founders. Don’t miss this inspiring conversation about the role of connection, culture, and shared purpose in driving innovation and raising capital.

In this episode, Gayle Jennings-O’Byrne goes off the record with Kenneth A Goodwin Jr. , Managing Partner of Jeanensis Ventures. Known for his deep expertise in blockchain, fintech, and digital transformation, Kenneth shares his approach to cash flow management, building partnerships, and the importance of trust and reputation when seeking venture capital. He offers practical advice for founders on creating sustainable revenue models and why it’s critical to have a solid foundation before asking for investment. Tune in to hear how his journey, influenced by his upbringing and values, has shaped his career in VC and digital assets, and discover why he believes venture capital is about more than just writing checks. This is a must-listen for entrepreneurs who want to build businesses that last.

Gayle's The Hill Article:

VC's Off the Record:

Hosted by ⁠Gayle Jennings-O'Byrne⁠⁠

Co-hosted with ⁠Victoria Bert ⁠

Produced by ⁠Wocstar Media

In this episode, we break down why investing in BIPOC, LGBTQ+, and other underrepresented founders isn’t just the right thing to do—it’s smart business. We discuss the real, often overlooked, financial opportunities tied to investing in these communities, the statistics behind the funding gap, and why businesses led by diverse teams have the potential to outperform in the market. Businesses led by inclusive teams aren’t just good for society, they’re good for the bottom line. Join Gayle Jennings-O'Byrne as she goes off the record with Jackson Block, CEO of LGBT+ VC. Jackson is leading initiatives to close the gap for LGBTQ+ entrepreneurs, while working to educate and engage new generations of investors in the process. Our conversation highlights the critical importance of allyship in investment spaces and tackles the complex intersections of race, gender, and identity in entrepreneurship. Tune in for a candid conversation on how inclusive investing can drive both change and profits.

In episode three of ⁠VCs Off the Record⁠, Gayle Jennings-O'Byrne dives into what makes a great idea—and what makes it profitable. She explains that innovation isn’t just about novelty but building a “better machine.” Joined by designer and product developer ⁠Marc Littlejohn ⁠of ⁠Littlejohn New York⁠, Gayle and Marc discuss the nuances of entrepreneurship, from crafting a compelling elevator pitch to turning an initial concept into a fully realized product. Marc shares his insights on storytelling, the impact of ⁠Wocstar Academy⁠, and advice for entrepreneurs building their vision from the ground up. Plus, VC ⁠Alex Chung⁠ from ⁠Chai Ventures⁠ shares what her company is looking to invest in next.

VC's Off the Record:

Hosted by Gayle Jennings-O'Byrne⁠

Co-hosted with Victoria Bert

Produced by Wocstar Media

In this episode of VCs Off the Record, Gayle Jennings-O'Byrne opens up about the realities of rejection—what it's like to tell founders "no," why she approaches it differently, and how it has impacted Wocstar. Jesse Middleton, General Partner at Flybridge Capital Partners, known for his expertise in building platforms and communities, goes off the record to share insights into pitching to venture capital investors. He offers valuable guidance for founders navigating the startup ecosystem, ranging from what Jesse looks for in new investments to advice on when not to use ".ai" in your company's name and what he likes to call the "Pied Piper effect" in entrepreneurship.

Season three of VCs Off the Record with Gayle Jennings-O’Byrne kicks off with a conversation between Gayle and Erica Duignan Minnihan, Founder and General Partner at Reign Ventures.

Gayle shares the story behind the start of Wocstar with CCO and Creative Director Victoria Bert, revealing the motivations that led her to create a female-forward venture capital fund.

Erica and Gayle go off the record, sharing their wealth of knowledge about the VC world. Erica discusses her extensive career, future investment insights, and valuable advice for founders on what to do—and what to avoid—when pitching to investors.

You won’t want to miss this!