What makes a venture investment a true home run—and why is it so hard to find those opportunities?

In this episode of High Stakes, Paige sits down with Sean Glass (entrepreneur, investor, and founding partner at Ayuda Partners) to unpack the mechanics of venture capital decision-making. Together, they explore:

• Why venture returns rely on power-law outcomes
• The importance of market size and market dynamics when evaluating startups
• The pitfalls of messy cap tables, notes, and SAFEs and how they can derail a deal

Sean also shares insights from his own entrepreneurial journey, including raising capital in tough markets, achieving outsized returns for early investors, and building conviction around companies that can define entirely new categories.

Whether you’re a founder raising capital, an investor honing your thesis, or just curious about how VCs make high-stakes decisions, this conversation is packed with hard-won lessons from both sides of the table.