Ugly Talk: First Time Fundraising with FounderSquare and The Grey Journal
💰 What’s it really like to raise money for the first time?
You’ve built something great—now it’s time to fundraise. But between pitching, negotiating, and navigating the investor landscape, first-time fundraising can feel like a maze with no map. That’s where we come in.
We’re bringing together founders who’ve successfully raised their first round and the investors who backed them to share the unfiltered truth about the process. Expect real stories, hard lessons, and insider insights on what it takes to go from bootstrapped to funded.
🎤 Panel Speakers
Krishna Dosapati - Founder & CEO at Clockout.
Krishna is the founder and CEO of Clockout, an Evite-backed networking platform for Gen Z+. The platform was featured on 68 Fox News Stations, hit #22 on the App Store, and received 100,000 downloads in the last 6 months. Clockout is on track to $1M ARR this year has raised $1.3M from Evite Corporation, Gaingels, Baytech Ventures, and more.
Vince Trost - Co-Founder & CEO at Plastic Labs
Vince is the co-founder and CEO of Plastic Labs, a company on a mission to solve identity for the agentic world. He was the first graduate from the Data Science program at Penn State University and has spent his career building AI applications in education, data science infrastructure on Ethereum, and is now building Honcho -- a shared identity layer for LLM applications. His company has successfully raised $5.35m across 3 funding rounds to date.
Michael Bervell - Co-Founder and CEO at TestParty
Michael Bervell is the Co-Founder and CEO of TestParty, an AI-powered platform revolutionizing digital accessibility compliance. A Harvard Business School graduate and author of Unlocking Unicorns, he is a recognized leader in tech-driven inclusion. Michael’s work focuses on integrating AI into accessibility solutions, helping organizations reduce legal risk while building more inclusive digital experiences. $4m raised in February 2024 from Harlem Capital, Urban Innovation Fund, the National Science Foundation, and others.
Moderator:
Igor Volodin is a product management expert and mentor with over seven years of experience, currently advising startups through the Founder Institute and consulting on product strategy, MVP development, and growth. He has worked at leading tech firms and startups, successfully launching new product verticals and optimizing product processes from UX research to data-driven decision-making .
🤔 Why Attend?
Hear from both sides of the table: Founders who’ve raised, and the investors who wrote the checks.
Learn what works (and what doesn’t): Get insights on pitching, term sheets, due diligence, and closing the deal.
Avoid common fundraising mistakes: Discover the biggest red flags, negotiation pitfalls, and lessons founders learned the hard way.
🙋 Who’s coming?
Startup founders looking to raise their first round of funding.
Angel investors searching for the next ambitious founder with a big idea—and looking to expand their network.
Ambitious individuals curious about the world of venture-backed entrepreneurship.
💭 What to Expect:
This is an open, no-BS conversation about what it really takes to secure funding for the first time. Whether you’re gearing up for investor meetings or just exploring the fundraising landscape, you’ll walk away with practical insights and real-world takeaways.
🤝 Event Co-hosts
Founders Square is on a mission to uncover outstanding founders who are breaking boundaries, pushing innovation to new heights, and making a lasting impact on the world. We aren’t just choosing any founders—we’re seeking the boldest, the brightest, and the most inspiring. Each selected founder will be handpicked, pre-screened, and interviewed by our dedicated team, ensuring that only the most deserving stories make it to the top.
Grey Journal is one of the fastest-growing publications in entrepreneurial culture, we provide an insider’s view on innovative ideas, emerging trends, and the pioneering spirit that drives this journey. With readers across North America, GREY Journal has become a platform that encourages and equips the next generation of entrepreneurs. Join us as we explore the exhilarating world of entrepreneurship and reveal what makes it truly rewarding.
Ugly Talk In each UGLY TALK, we invite big hitters who are battle-tested leaders and founders in their perspective space to share their insights and lessons learned. Our moderator will ask the hard questions about the tough choices they had to make. Network with kindred spirits, uncover real-life lessons, and ignite your ambition. No BS, no fluff—just raw, down-to-earth insights from people who’ve been there, done that, and crushed it.
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