VCs Off the Record with Gayle Jennings-O'Byrne

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 ⁠

⁠⁠⁠⁠⁠⁠⁠Wocstar Media⁠

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 by

⁠⁠⁠Gayle 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.

Hosted by

⁠⁠⁠Gayle Jennings-O'Byrne⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Co-hosted with

⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠Victoria Byrd⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Produced by ⁠

⁠⁠⁠⁠⁠⁠⁠Wocstar Media⁠

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

⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠Victoria Byrd⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Wocstar Media⁠

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

⁠ ⁠⁠⁠⁠ ⁠Victoria Byrd⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠Wocstar Media⁠

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

⁠Gayle Jennings-O'Byrne⁠⁠⁠⁠⁠

⁠⁠ ⁠Victoria Byrd⁠⁠⁠⁠⁠

⁠Wocstar Media⁠

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.

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