ANGEL 25-27: Execution, Relationships, and Communication

Chapters 25 through 27 of Angel by Jason Calacanis provided a powerful reminder that angel investing isn’t just about picking the right startup—it’s about what you do after you say “yes.” These chapters really emphasized the importance of execution, relationship-building, and consistent communication. As an aspiring founder, I found these lessons both practical and thought-provoking.

Chapter 25 outlines the exact steps an investor should take after deciding to invest. From securing legal documents and pro rata rights to wiring funds and scheduling follow-up check-ins, this chapter reminded me of how important it is to be organized and intentional. I liked how Calacanis encourages investors to act professionally and with care—not just for the sake of documentation, but to show the founder that they’re serious about the relationship. As someone who’s working to build trust with others in business, I know how far that kind of thoughtful follow-through can go. It’s not just the money—it’s the effort and consistency that matter.

In Chapter 26, Calacanis flips the perspective and speaks directly to founders. He encourages transparency and mutual respect, reminding founders that angels take on real risk—often before anyone else believes in them. That really resonated with me. I want to be the kind of founder who respects that early faith and doesn’t go quiet when things get hard. The idea that angels should be treated as true partners—not just bank accounts—really aligns with how I view meaningful business relationships.

Chapter 27 drove home the point that consistent communication is everything. I’ve always believed in the value of strong communication, but this chapter made it clear that regular updates aren’t optional—they’re essential. Calacanis explains that silence breeds uncertainty, while a short, structured update can reinforce trust, give investors the chance to help, and create long-term alignment. As someone who values connection and clarity, I see how this discipline could be a game changer—not just for keeping investors informed, but for staying accountable as a founder.

These chapters reminded me that the best investment relationships are built on professionalism, honesty, and consistency. It’s not just about getting the money—it’s about maintaining the trust, energy, and transparency needed to grow something great together.