The first three chapters of ANGEL by Jason Calacanis were insightful and motivating—especially for someone like me, a budding entrepreneur just beginning to develop her ideas and build a foundation for the future. In Chapter One, “Someone Else Was Supposed to Write This Book,” Calacanis introduces the book by placing his story and knowledge in the larger context of the American dream, the changing job market, and the urgency of escaping the “matrix.” He explains that the world is shifting, and we need to be ready for the changes ahead. What I really appreciated was how he framed this book as a way to teach readers not only how to survive the changes that are bound to come, but how to ride them out on top. That mindset alone is empowering. He made it clear—if he could do it, then I can too, with hard work and proper knowledge. That lit a fire in me, and from the start, I felt encouraged and hungry to learn more.
In Chapter Two, “The Brooklyn Grinder,” Calacanis breaks down the idea of risk in investing and entrepreneurship. He asks, “Is angel investing gambling?” and follows with stories that show how angel investing is really about taking informed risks, betting on people and ideas before they’re fully proven. He talks about his journey in the Sequoia Scout Program and taking a chance that ultimately paid off. His words—“No gamble, no future”—stood out to me. In life, and especially in entrepreneurship, it’s about taking risks and sometimes getting uncomfortable to eventually get comfortable. He also shares how he used to dream about the life he has now and how angel investing changed everything for him. What I found really impactful was the Yoda quote he used: “Pass on what you have learned.” That’s exactly what he’s doing in this book—giving us the knowledge, tools, and mindset to follow a similar path. He wraps the chapter by speaking to “real outsiders,” acknowledging his own privilege as a white male born in New York City and recognizing the systemic challenges faced by marginalized groups in America. That hit home for me. As an African American woman, I often feel like an outsider in spaces like business and investing. But he wrote this book to be a playbook for people like me, to help level the playing field—even if he doesn’t have all the answers. That moment of honesty and empathy made me respect him even more.
Chapter Three, “What is Angel Investing?” helped me better understand the basics of angel investing and what makes angel investors different. They’re the ones who come in early, when a founder is still figuring things out—still searching for product-market fit and probably hasn’t made a single dollar yet. But they take a chance because they see potential. A true “angel” is someone who believes in you and what you’re doing, even if there are no tangible results yet. That’s the kind of support every entrepreneur needs at least once in their life. Reading this made me reflect on where I am right now. I’m still developing my ideas, gathering data, and trying to get things off the ground. But this chapter reminded me that before anyone else sees the vision, I have to. I need to be the one who sees all the ways my business can go right. I need to be my biggest fan, because when people see how much I believe in it and invest in it, they’ll want to believe too.
The “no risk, no reward” theme carried through this chapter as well. The author even shared how he invested in Uber early, before it was obvious whether the company could scale or even make money. But he believed in the founder and personally loved the product. That reminded me that angel investing is not just about the business, but about the person behind the business. That’s encouraging because I want to be someone who others see as worth betting on—not just because of my idea, but because of who I am and what I bring to the table.
Lastly, Calacanis touches on the difference between angel investing and “boring,” safe investing like low-fee index funds. He explains that the life of an angel investor—and also an entrepreneur—can change dramatically if you’re willing to “suspend fear, squint a little, and focus not just on what could go wrong, but what could go right.” That stuck with me. Yes, it’s important to prepare and plan, but it’s even more important to focus on the solution you’re creating and the impact it could make. That’s what I want to hold on to as I continue building my business ideas.
These first three chapters reminded me that I have what it takes. They pushed me to dream bigger, believe more, and act boldly. This book is not just teaching me about angel investing—it’s reminding me that the future belongs to those who are willing to bet on themselves and take the first step.
I even came across a platform called Angel Investment Network, which allows entrepreneurs to pitch ideas and connect with potential investors. I hope sharing this resource can be helpful to someone else who might relate to my journey or is looking for new ways to gain traction and visibility.
EmpowerMe Life 
Aamiya,
Your reflection makes me want to read this book! One aspect that stood out to me was a common theme throughout your reflection of empowerment, if someone else can do it, I can, too! How encouraging and what a way to draw a reader/entrepreneur in!
I also was drawn to “no gamble, no future” and “betting on people and ideas before they are fully proven.” If nobody took a chance on opportunities, on potential, on thoughts, on people, we’d have a boring world. So many ideas have come to fruition because someone took a chance and believed in that person and their thoughts and ideas.
Not only do others have to believe in us, we have to believe in ourselves. You even mentioned before anyone else sees your vision, you have to see it first. Often in life we focus on what could go wrong. I love how you flipped it around and are holding yourself accountable to focus on what could go right! And yes! Your belief and passion will be contagious to others and they will follow suit.
I also agree with you that taking risks and being okay with being uncomfortable can lead to comfort. This is a pattern it seems for every part of our lives, so it just makes sense, it would be a part of being an entrepreneur, too!
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Hey Jenny!
I’m really glad the reflection resonated with you. That theme of empowerment—“if someone else can do it, I can too”—has been such a mindset shift for me, especially as I continue learning what it really takes to step into entrepreneurship.
I love how you expanded on the idea of taking chances—on people, ideas, and potential. You’re so right! The world would be a lot less creative and innovative if no one took that first leap of faith. And yes, it truly starts with believing in ourselves before expecting others to buy into our vision. That’s been a lesson I’m constantly learning and relearning.
Thank you for your encouragement and insight—it means a lot! I’m excited to keep growing alongside you this semester.
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Hi Aamiya,
What a powerful and inspiring reflection—thank you for sharing so vulnerably and passionately. Your post perfectly captures the spirit of the first three chapters of ANGEL and adds such an important voice to the conversation. As someone who works in the grants and funding space, your thoughts really resonated with me, especially around taking informed risks and believing in people early—before all the proof is there.
What struck me most was your insight about needing to believe in your own vision first, before anyone else will. That mindset—of being your own first “angel”—is something I’ve seen play out in many successful ventures. Whether you’re applying for a grant, pitching an investor, or launching a new initiative, the conviction and clarity you bring to the table are what draw others in. It’s not just about the idea; it’s about the person driving it. Your reflection shows you already understand that deeply.
Your mention of Calacanis recognizing his privilege and addressing the realities that marginalized entrepreneurs face was also a highlight for me. That kind of acknowledgment, while not a solution in itself, opens the door for broader inclusion and empowerment—especially when paired with real tools, resources, and encouragement like this book seems to offer. I’m so glad it lit a fire for you—your voice absolutely belongs in these rooms.
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Hey Freddy!
I’m really glad my reflection resonated with you, especially coming from someone who works directly in the grants and funding space. Your point about being your own first “angel” beautifully sums up what I was trying to express. That internal belief is such a powerful foundation, and I’m learning more each day how crucial it is to lead with conviction before anyone else can buy into the vision.
I also appreciate you highlighting the part about privilege and inclusion. You’re right—acknowledgment isn’t everything, but it is a start. When books like ANGEL combine awareness with actionable guidance, it opens real doors for people who haven’t traditionally had access to these spaces. Your encouragement reminded me exactly why these conversations matter—and I’m grateful to be part of a community where our voices, stories, and ideas are truly seen and valued. Thank you so much for your kind and thoughtful words—it truly means a lot to me!
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Hi Aamiya,
I posted a comment previously but it didn’t seem to post so if you receive a message twice that’s why 🙂
I really enjoyed reading your reflection—your passion and drive came through so clearly, and it was truly inspiring. I especially connected with your takeaway from Chapter Three about believing in your own vision before anyone else does. That mindset is so powerful and something I’m reminding myself of constantly as I build my own ideas.
I also appreciated how you highlighted Calacanis’s honesty in acknowledging systemic challenges. That moment really stood out to me, too. It made the book feel more inclusive and intentional, like it really is meant to empower people like us to take bold steps forward. And that “no risk, no reward” theme? It’s such a great reminder to lean into the unknown with confidence and preparation.
Thanks for sharing the Angel Investment Network resource—I’m definitely going to check it out. Looking forward to hearing more from your reflections!
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Hey Bridgett!
Thank you so much for your kind words—I’m really glad the reflection spoke to you! And no worries at all if the message posted twice—I appreciate you taking the time to reach out either way.
It’s so encouraging to hear that you’re also working on building your own ideas and reminding yourself to believe in your vision. That’s honestly one of the most important things we can do—trusting the seed we’ve been given, even before it fully blossoms. I’m glad that part resonated with you too.
And yes, Calacanis’s honesty about systemic challenges really did shift the tone of the book for me. It made me feel reassured that there’s space for our voices and experiences in this world of entrepreneurship—and that we can take risks, build strategically, and still stay grounded in who we are.
Let’s keep encouraging each other throughout this semester!
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