Chapters 28 through 30 of Angel by Jason Calacanis offered a dose of reality that I believe every entrepreneur and future investor needs to hear. These chapters focus on the harder, less glamorous side of angel investing—the emotional turbulence, difficult decisions, and long wait for returns. As someone preparing to launch my own ventures and maybe one day even step into the role of investor, this section reminded me that perseverance, emotional intelligence, and long-term thinking are just as critical as financial capital.
In Chapter 28, Calacanis shares how the excitement of the first year can quickly give way to tough decisions. Startups that once looked promising now need more money, and it’s up to you to decide if you’ll bridge the gap or step away. This made me reflect on how hard it can be to let go of something you believed in—especially when people are involved. I appreciated Calacanis’s honesty about the emotional toll, but also his clarity: not every startup is meant to survive, and it’s not unkind to make strategic choices. That’s leadership.
Chapter 29 really spoke to the emotional endurance this space demands. Calacanis encourages readers to maintain balance and perspective, even in the face of setbacks. That resonated with me personally, not just as a businesswoman, but as someone navigating life’s uncertainties with faith. I’ve learned that failure isn’t final and that every disappointment carries a lesson. It was encouraging to read that angel investing isn’t about getting everything right—it’s about staying in the game and noti letting losses shake your confidence or values.
Chapter 30 reframed how I think about success. I used to associate startup success with big money moments, but this chapter helped me understand that most great outcomes happen through acquisition. Calacanis emphasizes the importance of knowing from day one how your startup might be valuable to others down the road. That’s a perspective I want to adopt in my own ventures—thinking not just about how to build something amazing, but how it might fit into a broader system and provide value beyond my vision.
These chapters were a necessary reminder that angel investing—and entrepreneurship—isn’t always easy or linear. But if you can manage the ups and downs, stay emotionally grounded, and think strategically about long-term outcomes, the journey can be absolutely worth it.
EmpowerMe Life 