How to Raise Capital as a Founder: Real Talk on Process, Story, and Grit

Raising startup capital is one of the hardest things a founder will do, and most people learn the hard way. In this episode, three founders who have collectively raised over $27 million share what actually works. Robin Cowie (Skillmaker.ai), Isaac Park (Keebler Health), and Lucy Shores Kosturko (Social Cascade) break down how to build a fundraising process, why the story you tell investors must be different from the story you tell customers, and how non-dilutive funding sources like SBIR grants can build the traction that makes venture conversations easier. They also get honest about the time cost of fundraising, the evolving expectations at each funding stage, and why the best companies of the next decade are being built right now. Recorded at Grep-a-Palooza 2026, sponsored by GrepBeat, and moderated by Anna Tharrington, corporate partner at Hutchison PLLC.

Founder Shares is brought to you by Hutchison PLLC.