Startup Fundraising Exposed: What First-Time Founders Need to Know

Raising capital for the first time can be an overwhelming experience for founders, filled with complex negotiations and high-stakes investor meetings. To help entrepreneurs navigate this challenging journey, FounderSquare & The Grey Journal hosted Ugly Talk: First-Time Fundraising last February 20, 2025, at the Microsoft Building in Times Square, NYC. The event offered raw, unfiltered insights from experienced founders and the investors who backed them.

Attendees had the chance to learn from Krishna Dosapati (Clockout), Vince Trost (Plastic Labs), and Michael Bervell (TestParty), as they shared their firsthand experiences in securing funding. The discussion provided valuable insights into the fundraising journey, covering essential strategies for closing deals, understanding what investors seek, and avoiding common mistakes that often challenge first-time founders. It was a unique opportunity to gain knowledge directly from those who have successfully raised millions.

We are thrilled to have been part of this incredible event as proud sponsors, alongside Redrob, a company equally committed to fostering innovation. Redrob empowers startups with access to over 200 million verified contacts, making networking seamless and efficient. Meanwhile, M&B IP Patent Firm specializes in data-driven patent strategies, ensuring groundbreaking ideas are well-protected.

Whether you’re preparing for your first funding round or refining your approach, Ugly Talk: First-Time Fundraising! provided invaluable insights and connections to help founders succeed. A heartfelt thank you to everyone who attended and contributed to making this event a success!