In this VCs Off the Record episode, host Gayle Jennings-O'Byrne sit down with Sydney Paige Thomas, Founder & General Partner at Symphonic Capital, to get real about what separates startups that secure funding from those that don’t.
💡 Sydney breaks down why a great idea isn’t enough, how execution sets winners apart, and why not every founder is meant to be CEO. She also shares her insights on the mistakes that keep investors from writing checks—including founders who don’t do their homework.
If you’re a founder looking to raise capital, an investor seeking fresh insights, or an entrepreneur navigating the VC world, this episode is a must-listen.
Hosted by
🎙️ Gayle Jennings-O'Byrne
Co-hosted with
🎙️ Victoria Byrd
Produced by
📍 Wocstar Media
In this episode of VCs Off the Record, Jonathan Hakakian, Managing Director at Soundboard Venture Fund, joins Gayle Jennings-O'Byrne for a real talk on what makes founders truly investable. Spoiler: It’s not just a great pitch—it’s how you listen, adapt, and execute.
Key Takeaways for Founders:
✅ Investors need a conversation, not a monologue—don’t talk endlessly.
✅ Saying you have no competition is a red flag. If there’s no competition, is there even a market?
✅ The best founders take tough love in stride—investors aren’t critiquing you, they’re evaluating the business.
Want to secure funding? Learn how to position yourself for investment the right way.
In this VCs Off the Record episode, host Gayle Jennings-O'Byrne sits down with Sergio Marrero, Managing Director of Blue Ridge Labs at Robin Hood Foundation, to discuss venture-building with purpose.
Sergio Marrero shares his unconventional path from engineering and DJing to venture capital. He breaks down what founders need to move from zero to MVP, why impact-driven startups thrive, and how Blue Ridge Labs supports founders.
If you’re a founder, investor, or changemaker looking for insights on startup acceleration, impact investing, and navigating the venture world, this episode is full of game-changing advice!
Hosted by
Gayle Jennings-O'Byrne
Co-hosted with
Victoria Byrd
Produced by
Wocstar Media
🔊 Listen now on VCs Off the Record wherever you get your podcasts!
In this VCs Off the Record episode, host Gayle Jennings-O'Byrne sits down with Jackson Feder, an investor at MetaProp, to explore the intersection of real estate, technology, and venture capital.
Jackson shares his unique path from launching a startup in high school to becoming a VC, the lessons he learned along the way, and how he evaluates early-stage investments. He dives into the future of PropTech, the importance of sustainability in real estate, and why founders need to think about market fit and execution from day one.
If you’re a founder looking to break into PropTech, an investor curious about the space, or someone navigating the VC world, this conversation is packed with insights on fundraising, deal flow, and what makes a great investor.
Hosted by
Gayle Jennings-O'Byrne
Co-hosted with
Victoria Byrd
Produced by
In thisVCs Off the Record episode, hostGayle Jennings-O'Byrne chats withRomeo Ortiz, founder ofProductStory Media, andChi Achebe, a venture capitalist atAchebe Capital.
Romeo shares how his background in filmmaking led him to brand storytelling, helping founders craft compelling narratives that connect with investors. He opens up about a$40K mistake that reshaped his approach to content strategy and offers insights on why authentic storytelling is critical for securing funding.
Chi dives into her journey from tech and social impact in Africa to launchingAchebe Capital. She discusses her investment thesis focused oncare, climate, commerce, and culture, how she bridges capital between the U.S. and Africa, and the power of culturally aligned investing.
Tune in for actionable insights, real founder experiences, and an honest conversation about the role of storytelling in venture capital, navigating the fundraising landscape, and driving impact through investment.
Hosted byGayle Jennings-O'Byrne Co-hosted with Victoria Byrd Produced by Wocstar Media
In this VCs Off the Record episode, host Gayle Jennings-O'Byrne dives into the intersection of biotech, planetary health, and venture capital with Sabriya Stukes, an investor in early-stage biotech companies.
Sabriya unpacks what it means to invest in human and planetary health, breaking down the deep connections between climate, healthcare, and innovation. She shares her unconventional journey from microbiologist to venture investor, detailing her work at SOSV and IndieBio, one of the world's leading deep tech accelerators.
This episode is packed with insights on how investors evaluate scientific startups, why diversity in STEM is critical, and the power of saying yes to opportunities—even when self-doubt creeps in. If you're curious about biotech investing, early-stage funding, or how deep tech is shaping the future, this one's for you.
In this VCs Off the Record episode, host Gayle Jennings-O'Byrne chats with Justin Huebner, author of Inclusive Investing, and Megan Gray, founder & CEO of Moment AI, about the future of venture capital, AI innovation, and what it takes to build a successful, venture-backed business.
Justin shares his journey from intern to published author, breaking down the power of inclusive investing and why diversity in venture capital isn’t just about equity—it’s a financial advantage. He explores the barriers that entrepreneurs of color face and how investors can unlock untapped potential.
Megan takes us into the cutting-edge world of artificial intelligence, explaining how large vision models are set to revolutionize healthcare, security, and transportation. She shares her experience navigating AI fundraising, the challenges of raising capital as a woman in tech, and why selecting the right investors is critical for long-term success.
Tune in for actionable insights, industry trends, and a candid conversation on the intersection of AI, venture capital, and diversity.
Hosted by
Gayle Jennings-O'Byrne
Co-hosted with
Victoria Byrd
Produced by
In this VCs Off the Record episode, host Gayle Jennings-O'Byrne chats with Mirit Lugassi, an investor at Laconia Capital, about funding early-stage startups and what it takes to build a venture-backed business.
Mirit shares her journey from operator to investor, breaking down the difference between market gaps vs. market demand, how VCs evaluate startups, and the key strategies founders need to secure funding. She also offers insights into Laconia Capital’s investment approach and how they help founders scale.
Tune in for actionable advice, insider knowledge, and an honest conversation on what makes a startup truly investable.
Hosted by
Gayle Jennings-O'Byrne
Co-hosted with
Produced by
In this VCs Off the Record episode, host Gayle Jennings-O'Byrne chats with Desiree Almodovar, a venture capitalist at Alley Corp VC, and advocate for underrepresented founders. Desiree shares her inspiring journey from leading advertising campaigns to investing in diverse, innovative startups through venture capital.
Discover how her unique career path shaped her approach to mentorship, her dedication to empowering founders, and her strategies for fostering diversity and inclusion within the ecosystem. Desiree opens up about the evolution of mentorship in the digital age, practical tips for founders seeking funding, and the importance of resilience in navigating entrepreneurship.
Tune in for actionable insights, inspiration, and an honest conversation about building authentic relationships in venture capital, supporting women of color, and driving equity in the startup world.
Hosted by
Co-hosted with
Produced by
In this episode of VCs Off the Record, host Gayle Jennings-O'Byrne chats with Victoria Kennedy, founder of Patternist and former product leader turned venture capitalist. Victoria shares her inspiring journey from scaling startups to launching a groundbreaking venture designed to align financial returns with social impact.
Discover how her background in product strategy shaped her approach to investing in diverse founders and solving societal challenges. Victoria opens up about the realities of fundraising, building a fund, and creating hybrid funding models that blend traditional venture capital with mission-driven investments.
Tune in for actionable insights, inspiration, and an honest conversation about reimagining venture capital, empowering women of color, and building innovative solutions that matter.
VC's Off the Record:
Hosted by Gayle Jennings-O'Byrne Co-hosted with Victoria Byrd Produced by Wocstar MediaIn 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. Resource:
Gayle's The Hill Article: Venture capital’s AI love affair: A bubble waiting to pop?
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!