What does it really take to raise capital when you’re not coming from the traditional finance world? In this episode of UNMASKED: The Capital Raise Files, Alan McLaren sits down with Eric Vest, Founder & CEO of Yellowwood and Founder & Managing Partner of Y Capital, to unpack what more than 30 years of building, growing and selling technology companies has taught him about people, technology and capital. In this episode, we explore: ➡️ Building credibility when entering the capital markets as an operator ➡️ The role of relationships, trust and reputation in raising capital ➡️ Finding the right investors and building a strong cap table ➡️ What Eric learned from nearly 350 investor conversations ➡️ Why going from zero to one can be the hardest part of a capital raise Eric shares the realities of raising $15 million, what surprised him along the way, and how his experience as an operator, investor and entrepreneur has shaped the way he approaches capital, technology and growth. _______ UNMASKED: The Capital Raise Files: Real stories from CEOs who have raised capital, so other leaders can move through the process with more clarity, confidence and fewer wasted rooms. In this special series of Unmasked: The CEO Files, we sit down with CEOs and founders who have actually lived through a capital raise to uncover what happened behind the deck, the numbers and the polished story. Why was the money needed? How did they approach the market? How many investor rooms did it take? What questions created pressure? Where did trust form, and where did resistance show up? Most importantly, what would they do differently if they had to raise again? Because raising capital is never just about the business opportunity, the financial model or the pitch deck. Investors are evaluating the leader in the room, too. How clearly can a CEO communicate under pressure? Can they build trust? Can they respond when challenged? And how does the way they show up influence the outcome? The Capital Raise Files goes beyond fundraising advice to explore the lived experience of raising capital, giving CEOs and founders practical insight they can take into their own investor rooms. If you’re preparing to raise capital, considering M&A or moving toward an IPO, these are the real stories worth hearing. We’re researching why some capital raises move quickly in fewer investor meetings while others drag through extra meetings and follow-up. If you’ve raised capital, we’d value your input. It takes under a minute and all responses are aggregated and never attributed.