Chapters 21 through 24 of Angel by Jason Calacanis sharpened my understanding of what it truly means to invest with discipline and integrity. These chapters moved away from the emotional and instinctual side of angel investing and leaned into the processes and practices that protect both the investor and founder. As someone who’s an aspiring entrepreneur and potential investor, I found these chapters incredibly grounding.
Chapter 21 highlights the importance of timing, pro rata rights, and understanding valuations. What stuck with me most was the reminder that just because a startup has potential doesn’t mean it’s the right time to invest. Learning to evaluate traction and weigh the risk against the timing of the deal is a skill I want to continue developing. The emphasis on securing pro rata rights also opened my eyes to how easily investors can lose their position in future rounds. I hadn’t realized how strategic those early terms really are.
Chapter 22 discusses the value of writing deal memos. I loved this part because I already journal and reflect in other areas of my life, so applying that same mindset to investing made perfect sense. Calacanis makes it clear that deal memos aren’t just about documentation—they help you be honest with yourself and your reasoning. This reminded me that clarity of thought is just as important as confidence. I want to be someone who doesn’t just follow a gut feeling but can articulate why a decision makes sense.
In Chapter 23, Calacanis talks about the art of saying “no.” I really appreciated this one. Whether you’re an investor, a founder, or just someone navigating relationships, how you decline an opportunity matters. I’ve learned in my own journey that clear and respectful communication goes a long way. Saying “not yet” instead of ghosting or overpromising shows maturity and keeps the door open for future opportunities.
Chapter 24 introduced the due diligence checklist, which was practical and eye-opening. As an entrepreneur, it reminded me of how important transparency and documentation are. If I want someone to invest in my business, I need to be organized, honest, and ready to back up my claims. On the flip side, in the role of an investor, I see the importance of doing my homework. Diligence is protection, not paranoia.
Altogether, these chapters reminded me that angel investing is both a people game and a precision game. It’s about heart and strategy—being thoughtful, careful, and honest on both sides of the deal.
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