ANGEL 18-20: Knowing Your Why -The People Behind The Business

Chapters 18 through 20 of Angel by Jason Calacanis were some of the most insightful for me as an entrepreneur. These chapters really dig into the importance of discernment, intentional listening, and being able to tell the difference between a passionate founder and a persuasive fraud. I appreciated how these chapters shifted the focus from flashy ideas to what really matters: the people behind them.

Chapter 18 introduced four foundational questions to ask every founder: Why this business? How committed are you? What are your chances of succeeding? What does winning look like? These questions seem simple, but they’re incredibly revealing. As someone who’s building a mission-driven business, I reflect on how I’d answer these myself—and how important it is that I can communicate those answers clearly. This chapter confirms that the “why” behind a venture is just as important as the product or service. Investors want to know you’re not just chasing a trend, but that you’re deeply committed to solving a real problem.

In Chapter 19, Calacanis goes deeper—literally. He emphasizes the importance of asking thoughtful, sometimes personal questions that reveal more about a founder’s character and background. I really connected with this because I believe in building genuine relationships, not just transactional ones. Understanding where someone comes from—what their parents did, how they think about money, what keeps them up at night—can tell you more about their potential than any pitch deck ever could. It made me think about the ways I can better show up in those conversations with authenticity and vulnerability, both as a founder and as a future investor.

Chapter 20 struck a cautionary tone: “Founder or Fraud?” Calacanis dives into the fine line between vision and exaggeration. It’s not always about intentional deceit—sometimes founders believe their own hype without having the data or plan to back it up. That really hit home for me. As someone who’s hopeful and optimistic by nature, I have to remember that good intentions don’t always equal good business. This chapter made me think about how I want to stay grounded in truth and transparency, even when I’m dreaming big. It also gave me a deeper respect for the investors who do their due diligence and ask the hard questions.

Together, these chapters emphasized that the heart of angel investing isn’t just in spotting big hits—it’s in understanding people. And that’s something I want to carry with me as a founder.