Chapters 14 through 17 of Angel by Jason Calacanis offered practical and powerful insights that go far beyond theory—they walk you through the mindset and behavior of an intentional, sharp angel investor. These chapters emphasized not only how to prepare for pitch meetings, but more importantly, how to evaluate people. As an entrepreneur, these chapters pushed me to think more deeply about how I show up in rooms, how I evaluate opportunities, and how I prepare others to see the value in what I’m building.
In Chapter 14, Calacanis shares some of his best and worst pitch meeting experiences, which helped normalize the process of learning through both success and failure. It’s not just about knowing what to look for—sometimes it’s about knowing what to avoid. The takeaway for me was that volume matters. Seeing a wide range of pitches builds instinct and discernment, and I realized this applies to me as a founder too: the more people I talk to about my business, the better I become at communicating my value clearly and concisely.
Chapter 15 stressed the importance of preparation. Calacanis recommends spending three hours per startup before a pitch, which includes product research, market understanding, and investor background. That level of dedication resonated with me. Whether I’m on the receiving end of an investment pitch or presenting my own vision, preparation is a form of respect—respect for the opportunity, the other person’s time, and the potential impact of the partnership.
Chapter 16 highlighted the importance of presence during pitch meetings. I appreciated how Calacanis talks about putting the phone away, being engaged, and letting the founder lead. It reminded me of how powerful undivided attention can be—something that can make or break trust in those critical first interactions. It also challenged me to be fully present in all meetings, not just as a professional habit but as a way to cultivate deeper relationships.
Chapter 17 was perhaps the most impactful for me: “You don’t pick billion-dollar companies—you pick billion-dollar founders.” That statement stuck with me. As someone who hopes to one day receive investments, it encouraged me to continue developing myself, not just my business model. Investors want vision, resilience, leadership. Those traits matter just as much, if not more, than the idea itself.
These chapters reminded me that angel investing—and entrepreneurship—is not just about metrics and numbers, but about people, preparation, presence, and potential. And that’s a space I want to grow in.
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