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VCs Off the Record with Gayle Jennings-O'Byrne
Wocstar Fund
51 episodes
1 week ago
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"!
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Investing
Business
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All content for VCs Off the Record with Gayle Jennings-O'Byrne is the property of Wocstar Fund and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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"!
Show more...
Investing
Business
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Tough Love & Smart Investing: What Founders Need to Hear w/ Jonathan Hakakian
VCs Off the Record with Gayle Jennings-O'Byrne
40 minutes 17 seconds
7 months ago
Tough Love & Smart Investing: What Founders Need to Hear w/ Jonathan Hakakian

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.


VCs Off the Record with Gayle Jennings-O'Byrne
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"!