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VCs Off the Record with Gayle Jennings-O'Byrne

VCs Off the Record with Gayle Jennings-O'Byrne

Written by: Wocstar Fund
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About this listen

Real talk with real investors. This podcast is for founders, startups, and investors seeking brutally honest insights about raising capital and investment funds. Have you ever tanked an investor meeting or made a bad investment? Well, we talk to some of the top investors, venture capitalists, and women who have raised money for their startups so that you get some real answers on how to nail a pitch, secure your bag, or rebound from rejection! Join our host Gayle Jennings O’Byrne, co-founder of the Wocstar Fund and champion for female entrepreneurs, as we go “off the record"!Wocstar Fund Economics Personal Finance
Episodes
  • Fundable Startups, Execution & VC Reality Checks w/ Sydney Thomas, Symphonic Capital
    Mar 26 2025

    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

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    38 mins
  • Tough Love & Smart Investing: What Founders Need to Hear w/ Jonathan Hakakian
    Mar 19 2025

    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.


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    40 mins
  • How to Build Startups That Drive Real Change with Sergio Marrero
    Mar 12 2025

    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!

    Show More Show Less
    40 mins
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