What does it really take to raise capital, scale a technology company, and build lasting enterprise value? In this episode of UNMASKED: The Capital Raise Files, host Alan McLaren sits down with Kyle York, Co-Founder, CEO and Managing Partner of York IE, to uncover the realities of fundraising, venture capital, and building enduring technology businesses. Drawing on his experience scaling Dyn from $3M to $100M in ARR before its $600M acquisition by Oracle, Kyle shares candid insights from both sides of the capital table. They explore what investors really look for, why founders matter more than ever, the importance of capital efficiency, navigating leadership transitions, and why raising money should be about building a better business—not simply chasing the next funding round. In this episode, discover: ➡️ What investors really want to see in a startup pitch. ➡️ Why enterprise value matters more than fundraising milestones. ➡️ The realities of venture capital and investor expectations. ➡️ How to scale teams, navigate governance, and prepare for growth. ➡️ Why founder-market fit and execution can make or break a company. ➡️ How to build a successful business without losing sight of your values. Whether you're a startup founder, entrepreneur, CEO, technology executive, or investor, this conversation offers practical advice on raising growth capital, scaling strategically, and building a business that lasts. Connect with Kyle York and York IE: 🌐 Website: https://york.ie 🔗 Social: @YorkGrowth | @KyleYork20 🔗 Connect with Kyle on LinkedIn: https://www.linkedin.com/in/kyork20/ 📚 Check out Kyle's E-Book, "How to Become the CEO of Your Career" here: https://york.ie/wp-content/uploads/2019/09/York_IE_Become_the_CEO_of_your_career.pdf _____ 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. Click here: https://tally.so/r/68yyZB If you are interested in the findings let us know at alan@strataoriginals.com 🔗 Connect with STRATA Website: www.strataoriginals.com LinkedIn: https://www.linkedin.com/company/80453987 Subscribe for more candid conversations with the people behind the capital, companies, and decisions shaping the entrepreneurial ecosystem.
