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.